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Article(id=1218555557049454594, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1218551191416525698, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2017-1224, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1512662400000, receivedDateStr=2017-12-08, revisedDate=null, revisedDateStr=null, acceptedDate=1514908800000, acceptedDateStr=2018-01-03, onlineDate=1768455884467, onlineDateStr=2026-01-15, pubDate=1518364800000, pubDateStr=2018-02-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1768455884467, onlineIssueDateStr=2026-01-15, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1768455884467, creator=13701087609, updateTime=1768455884467, updator=13701087609, issue=Issue{id=1218551191416525698, tenantId=1146029695717560320, journalId=1189982191388893191, year='2018', volume='53', issue='2', pageStart='163', pageEnd='320', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1768454843620, creator=13701087609, updateTime=1768456934494, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1218559961223843991, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1218551191416525698, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1218559961223843992, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1218551191416525698, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=256, endPage=262, ext={EN=ArticleExt(id=1218555557535993860, articleId=1218555557049454594, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Synthesis and anti-inflammatory activity of novel isobutyl benzophenone derivatives, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=ORIGINAL ARTICLES, runingTitle=null, highlight=null, articleAbstract=

Twenty target compounds were synthesized by the reduction reaction of HUANG Minglong and Friedel-Crafts acylation reaction in this study. The inhibitory effects of the new compounds were tested on NO production in LPS-induced mouse macrophage RAW264.7 cells, a cellular inflammation model. The structure-activity relationships were discussed. The structures of target compounds were confirmed by ESI-MS, 1H NMR and 13C NMR. In vitro activity experiments showed that 18 compounds had certain anti-inflammatory effects at the concentration of 40 μmol·L-1, of which 9a, 8b, 7c and 9c showed strong anti-inflammatory activities, and IC50 of 7c and 9c were comparable to the positive control drug ibuprofen.

, correspAuthors=Yun-lan LI, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2018 Acta Pharmaceutica Sinica. All rights reserved., copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=null, magXml=null, pdfUrl=null, pdf=null, pdfFileSize=null, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=null, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=null, mapNumber=null, authorCompany=null, fund=null, authors=null, authorsList=Lu YANG, Hang SHI, Yun-lan LI, Xi CHEN, Si-qing NIU, Xiao-zhi QIAO, Jia-qi MAI, Qing-shan LI), CN=ArticleExt(id=1218555559675088954, articleId=1218555557049454594, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=新型含异丁基苯甲酮类化合物的合成及抗炎活性的初步研究, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

通过傅克酰基化反应、黄鸣龙还原反应合成了20个目标化合物，并通过LPS诱导的小鼠巨噬细胞RAW264.7炎症模型测定目标化合物对细胞上清液中NO的抑制作用并探讨了构效关系。合成的20个目标化合物全部为新化合物，其结构经ESI-MS、1H NMR和13C NMR确认。体外活性实验表明，有18个目标化合物在浓度为40 μmol·L-1时有一定的抗炎作用，其中以9a、8b、7c和9c表现出较强的抗炎活性，7c和9c的IC50与阳性对照药布洛芬相当。

, correspAuthors=李云兰, authorNote=null, correspAuthorsNote=
* 李云兰, Tel:13111066649, E-mail:
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Regioselective demethylation catalyzed by AlCl3[J]. 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Shanxi University of Chinese Medical, Taiyuan 030619, China), AuthorCompanyExt(id=1218970741937197500, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, companyId=1218970741924614585, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=2.山西中医药大学, 山西 太原 030619)])], figs=[ArticleFig(id=1218970747821806513, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=EN, label=null, caption=null, figureFileSmall=TVDpMR58JYtG4L2Wps+dLQ==, figureFileBig=Aw98Ksh5D00daTppls8qoQ==, tableContent=null), ArticleFig(id=1218970747939247039, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=CN, label=Figure 1, caption=

Molecular design of target compounds

, figureFileSmall=TVDpMR58JYtG4L2Wps+dLQ==, figureFileBig=Aw98Ksh5D00daTppls8qoQ==, tableContent=null), ArticleFig(id=1218970748094436302, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=EN, label=null, caption=null, figureFileSmall=9JLRNlMqP7/b8mUHC5Utng==, figureFileBig=gLJT6jX2g4g4m/5Bfj9TOQ==, tableContent=null), ArticleFig(id=1218970748220265435, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=CN, label=Scheme 1, caption= Synthetic route of compounds <strong>4a</strong>-<strong>9a</strong>

Reagents and conditions: (a) AlCl3, CH2Cl2, rt, 6 h; (b) 80% hydrazine hydrate (4 eq), diethylene glycol, DMSO, NaOH (10%), 165-175 ℃, 10 h; (c) AlCl3, CH2Cl2, 45 ℃ under reflux 24 h.

, figureFileSmall=9JLRNlMqP7/b8mUHC5Utng==, figureFileBig=gLJT6jX2g4g4m/5Bfj9TOQ==, tableContent=null), ArticleFig(id=1218970748329317349, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=EN, label=null, caption=null, figureFileSmall=7o7kyKuIfJGV7mw6IYLy3A==, figureFileBig=p8S/kq5pMUWrIeZNt6rxqw==, tableContent=null), ArticleFig(id=1218970748442563568, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=CN, label=Scheme 2, caption= Synthetic route of compounds <strong>4b</strong>-<strong>11b</strong>

Reagents and conditions: (a) AlCl3, CH2Cl2, rt, 2 h; (b) 80% hydrazine hydrate (4 eq), diethylene glycol, DMSO, NaOH (10%), 165-175 ℃, 10 h; (c) AlCl3, CH2Cl2, 45 ℃ under reflux 24 h.

, figureFileSmall=7o7kyKuIfJGV7mw6IYLy3A==, figureFileBig=p8S/kq5pMUWrIeZNt6rxqw==, tableContent=null), ArticleFig(id=1218970748593557508, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=EN, label=null, caption=null, figureFileSmall=ZPtX4zSMuCcEyIOnOpGanQ==, figureFileBig=JAiDvdxHnoWorTZVkNMvKA==, tableContent=null), ArticleFig(id=1218970748786495506, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=CN, label=Scheme 3, caption= Synthetic route of compounds <strong>4c</strong>-<strong>9c</strong>

Reagents and conditions: (a) AlCl3, CH2Cl2, rt, 2 h; (b) 80% hydrazine hydrate (4 eq), diethylene glycol, DMSO, NaOH (10%), 165-175 ℃, 10 h; (c) AlCl3, CH2Cl2, 45 ℃ under reflux 24 h.

, figureFileSmall=ZPtX4zSMuCcEyIOnOpGanQ==, figureFileBig=JAiDvdxHnoWorTZVkNMvKA==, tableContent=null), ArticleFig(id=1218970748941684767, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=EN, label=null, caption=null, figureFileSmall=cBd2W6yat3yC48xNZeR7Sw==, figureFileBig=AC5BjGwPoznq2zfdWvgjtQ==, tableContent=null), ArticleFig(id=1218970750246113324, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=CN, label=Figure 2, caption=

The docking surface of 7c with COX-2 and hydrogen bonding with key amino acids

, figureFileSmall=cBd2W6yat3yC48xNZeR7Sw==, figureFileBig=AC5BjGwPoznq2zfdWvgjtQ==, tableContent=null), ArticleFig(id=1218970750447439930, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=EN, label=null, caption=null, figureFileSmall=I8L9vDoc/Vyg+Ihd0IwvDQ==, figureFileBig=OnKm7ZWlP/jDtBuyl4ZAKQ==, tableContent=null), ArticleFig(id=1218970750602629192, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=CN, label=Figure 3, caption=

The docking surface of 7c with iNOS and hydrogen bonding with key amino acids

, figureFileSmall=I8L9vDoc/Vyg+Ihd0IwvDQ==, figureFileBig=OnKm7ZWlP/jDtBuyl4ZAKQ==, tableContent=null), ArticleFig(id=1218970750791372887, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Compd. Formula Property log P Yield/% mp/℃ MS (ESI) [M+H]+ m/z
4a C18H27NO5 White solid 3.18 21 145-147 338
5a C18H22O5 Light yellow solid 3.36 42 103-105 319
6a C18H27NO4 White solid 3.57 44 136-138 322
7a C17H24O6 White solid 2.51 34 121-123 325
8a C15H22O4 Colorless oil 4.37 65 - 267
9a C16H25NO4 White solid 2.93 29 78-80 296
4b C17H25NO5 White solid 2.60 12 147-149 324
5b C17H25NO5 White solid 3.05 12 68-70 324
6b C17H20O5 Light yellow solid 2.87 63 87-89 305
7b C17H25NO4 White solid 3.01 11 113-115 308
8b C16H22O6 White solid 0.58 25 199-201 311
9b C14H20O4 Light yellow oil 3.87 6 - 253
10b C15H23NO4 White solid 2.43 11 95-97 282
11b C15H23NO4 Colorless oil 3.13 10 - 282
4c C17H25NO4 White solid 3.12 15 47-49 308
5c C17H20O4 White solid 3.48 24 122-124 289
6c C17H25NO3 Colorless oil 3.59 46 - 292
7c C16H22O5 White solid 1.11 13 79-81 295
8c C15H22O3 Light yellow oil 4.28 8 - 251
9c C15H23NO3 Colorless oil 2.29 45.3 - 266
), ArticleFig(id=1218970750883647583, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=CN, label=Table 1, caption=

The physical and ESI-MS data of target compounds

, figureFileSmall=null, figureFileBig=null, tableContent=
Compd. Formula Property log P Yield/% mp/℃ MS (ESI) [M+H]+ m/z
4a C18H27NO5 White solid 3.18 21 145-147 338
5a C18H22O5 Light yellow solid 3.36 42 103-105 319
6a C18H27NO4 White solid 3.57 44 136-138 322
7a C17H24O6 White solid 2.51 34 121-123 325
8a C15H22O4 Colorless oil 4.37 65 - 267
9a C16H25NO4 White solid 2.93 29 78-80 296
4b C17H25NO5 White solid 2.60 12 147-149 324
5b C17H25NO5 White solid 3.05 12 68-70 324
6b C17H20O5 Light yellow solid 2.87 63 87-89 305
7b C17H25NO4 White solid 3.01 11 113-115 308
8b C16H22O6 White solid 0.58 25 199-201 311
9b C14H20O4 Light yellow oil 3.87 6 - 253
10b C15H23NO4 White solid 2.43 11 95-97 282
11b C15H23NO4 Colorless oil 3.13 10 - 282
4c C17H25NO4 White solid 3.12 15 47-49 308
5c C17H20O4 White solid 3.48 24 122-124 289
6c C17H25NO3 Colorless oil 3.59 46 - 292
7c C16H22O5 White solid 1.11 13 79-81 295
8c C15H22O3 Light yellow oil 4.28 8 - 251
9c C15H23NO3 Colorless oil 2.29 45.3 - 266
), ArticleFig(id=1218970750980116587, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Compd. 1H NMR (400 MHz, CDCl3 or DMSO-d6) δ 13C NMR (100 MHz, CDCl3 or DMSO-d6) δ
4a ①6.54 (s, 1H), 3.81 (s, 3H), 3.79 (s, 3H), 3.68-3.37 (m, 8H), 2.41 (dd, J = 12.8, 6.7 Hz, 1H), 2.04 (dd, J = 12.5, 7.9 Hz, 1H), 1.84 (s, 3H), 1.79-1.66 (m, 1H), 0.82 (t, J = 6.9 Hz, 6H). 156.57, 156.43, 153.00, 149.12, 115.33, 111.61, 93.25, 66.89, 55.77, 55.72, 45.01, 44.29, 32.98, 28.89, 22.84, 22.61, 8.95.
5a ①7.88 (s, 1H), 6.98 (d, J = 3.6 Hz, 1H), 6.63 (dd, J = 3.5, 1.5 Hz, 1H), 5.97 (s, 1H), 4.00 (s, 3H), 3.69 (s, 3H), 2.10 (qd, J = 12.7, 7.2 Hz, 2H), 1.73-1.61 (m, 1H), 1.41 (s, 3H), 0.79 (d, J = 6.6 Hz, 3H), 0.76 (d, J = 6.6 Hz, 3H). 193.93, 180.83, 170.29, 170.12, 149.85, 147.73, 117.69, 112.63, 108.27, 87.26, 62.08, 56.60, 56.51, 30.31, 27.37, 23.73, 22.38, 22.29.
6a ①6.53 (s, 1H), 3.81 (s, 3H), 3.79 (s, 3H), 3.51 (s, 2H), 3.36-3.29 (m, 2H), 2.40 (s, 1H), 2.07 (s, 1H), 1.95-1.89 (m, 2H), 1.88 (d, J = 6.8 Hz, 2H), 1.85 (s, 3H), 1.80-1.67 (m, 1H), 0.82 (s, 3H), 0.80 (s, 3H). 156.10, 155.97, 151.60, 148.93, 114.15, 110.50, 93.05, 55.66, 55.58, 46.19, 46.00, 32.50, 28.26, 25.39, 24.48, 22.47, 8.96.
7a ②6.36 (s, 1H), 3.82 (s, 3H), 3.80 (s, 3H), 2.91 (t, J = 6.5 Hz, 2H), 2.82 (t, J = 6.5 Hz, 2H), 2.27-2.18 (m, 1H), 2.14-2.04 (m, 1H), 1.92 (s, 3H), 1.79 (tt, J = 13.5, 6.7 Hz, 1H), 0.87 (s, 3H), 0.85 (s, 3H). 177.98, 170.01, 156.65, 156.47, 148.94, 114.82, 111.03, 93.43, 55.79, 55.73, 32.90, 28.84, 28.73, 28.66, 22.60, 8.94.
8a ①7.26 (s, 1H), 6.37 (s, 1H), 3.83 (s, 3H), 3.80 (s, 3H), 2.32 (s, 3H), 2.24-2.20 (m, 1H), 2.05 (d, J = 11.8 Hz, 1H), 1.94 (s, 3H), 1.81 (tq, J = 13.5, 6.8 Hz, 1H), 0.87 (s, 3H), 0.86 (s, 3H). 168.95, 156.61, 156.43, 149.04, 114.69, 110.89, 93.23, 55.71, 55.68, 33.04, 28.72, 22.66, 20.63, 9.02.
9a ①6.35 (s, 1H), 3.82 (s, 3H), 3.79 (s, 3H), 3.14 (s, 3H), 3.02 (s, 3H), 2.54 (dd, J = 12.9, 6.7 Hz, 1H), 2.16-2.08 (m, 1H), 1.97 (s, 3H), 1.81 (dp, J = 13.7, 6.8 Hz, 1H), 0.87 (s, 6H). 156.48, 156.34, 154.27, 149.41, 115.50, 111.70, 93.11, 55.76, 55.70, 36.81, 36.37, 32.94, 28.88, 22.80, 22.56, 8.93.
4b ①8.80 (s, 1H), 5.99 (s, 1H), 3.82 (s, 6H), 3.77-3.53 (m, 8H), 2.45 (d, J = 7.3 Hz, 2H), 1.88 (dp, J = 13.7, 6.8 Hz, 1H), 0.89 (s, 3H), 0.87 (s, 3H). 168.22, 161.05, 157.36, 155.23, 110.98, 101.74, 86.65, 67.04, 55.51, 55.41, 31.50, 29.72, 28.30, 22.57.
5b ①6.33 (d, J = 2.3 Hz, 1H), 6.27 (d, J = 2.3 Hz, 1H), 3.77 (s, 6H), 3.77-3.52 (m, 8H), 2.34 (d, J = 7.2 Hz, 2H), 1.80 (dt, J = 13.6, 6.8 Hz, 1H), 0.87 (s, 3H), 0.86 (s, 3H). 159.12, 158.51, 153.46, 150.50, 115.36, 99.10, 96.36, 66.78, 66.64, 55.55, 55.38, 44.89, 44.16, 32.53, 28.77, 22.68.
6b ①11.09 (s, 1H), 7.56 (d, J = 0.9 Hz, 1H), 7.11 (d, J = 3.6 Hz, 1H), 6.52 (dd, J = 3.5, 1.7 Hz, 1H), 6.02 (s, 1H), 3.88 (s, 3H), 3.73 (s, 3H), 2.47 (d, J = 7.3 Hz, 2H), 1.90 (dp, J = 13.7, 6.8 Hz, 1H), 0.90 (s, 3H), 0.88 (s, 3H). 183.43, 162.74, 160.13, 158.88, 152.82, 144.47, 116.73, 110.82, 109.14, 104.51, 85.82, 54.50, 54.43, 30.13, 27.15, 21.53.
7b ①9.64 (s, 1H), 5.99 (s, 1H), 3.83 (s, 3H), 3.82 (s, 3H), 3.63 (s, 2H), 3.42 (s, 2H), 2.45 (d, J = 7.3 Hz, 2H), 2.05-1.97 (m, 1H), 1.97-1.77 (m, 4H), 0.89 (s, 3H), 0.87 (s, 3H). 168.35, 160.87, 157.27, 156.02, 110.30, 103.52, 86.52, 55.37, 31.51, 29.71, 28.27, 22.58, 14.13.
8b ②13.82 (s, 1H), 12.09 (s, 1H), 6.25 (s, 1H), 3.94 (s, 3H), 3.89 (s, 3H), 3.22 (t, J = 6.2 Hz, 2H), 2.52 (d, J = 6.4 Hz, 2H), 2.35 (d, J = 7.3 Hz, 2H), 1.81 (dt, J = 13.6, 6.8 Hz, 1H), 0.82 (s, 3H), 0.81 (s, 3H). 203.81, 174.01, 163.74, 162.76, 161.67, 108.10, 104.58, 87.15, 55.92, 55.79, 30.57, 28.03, 27.51, 22.39.
9b ①6.20 (s, 1H), 3.76 (s, 3H), 3.70 (s, 3H), 2.51 (s, 3H), 2.41 (d, J = 7.4 Hz, 2H), 1.89 (dp, J = 13.8, 6.8 Hz, 1H), 0.93 (s, 3H), 0.92 (s, 3H). 202.64, 157.64, 156.48, 155.83, 118.26, 113.48, 95.25, 62.84, 55.73, 32.55, 32.22, 28.90, 22.64.
10b ①8.96 (s, 1H), 5.99 (s, 1H), 3.82 (s, 3H), 3.82 (s, 3H), 3.02 (s, 6H), 2.45 (d, J = 7.3 Hz, 2H), 1.89 (dp, J = 13.7, 6.8 Hz, 1H), 0.89 (s, 3H), 0.87 (s, 3H). 169.67, 160.82, 157.03, 155.59, 110.57, 102.46, 86.52, 55.42, 55.38, 31.49, 29.71, 28.27, 22.55.
11b ①6.31 (d, J = 2.3 Hz, 1H), 6.29 (d, J = 2.3 Hz, 1H), 3.77 (s, 6H), 3.11 (s, 3H), 3.02 (s, 3H), 2.35 (d, J = 7.2 Hz, 2H), 1.81 (dp, J = 13.6, 6.8 Hz, 1H), 0.87 (s, 3H), 0.86 (s, 3H). 159.10, 158.44, 154.72, 150.85, 115.45, 99.24, 96.20, 55.55, 55.37, 36.77, 36.38, 32.50, 28.78, 22.64.
4c ①6.96 (d, J = 8.4 Hz, 1H), 6.68 (d, J = 8.4 Hz, 1H), 3.81 (s, 3H), 3.73 (m, J = 12.4 Hz, 6H), 3.61 (m, J = 14.2 Hz, 2H), 2.31 (dd, J = 13.1, 7.1 Hz, 2H), 2.04 (s, 3H), 1.79 (dp,
J = 13.5, 6.8 Hz, 1H), 0.90 (s, 3H), 0.88 (s, 3H).		 156.58, 153.04, 148.49, 127.76, 125.98, 119.67, 107.54, 66.82, 55.67, 44.97, 44.27, 39.73, 29.28, 22.60, 9.41.
5c ①7.66 (s, 1H), 7.12 (s, 1H), 7.05 (s, 1H), 6.54 (s, 1H), 5.06 (s, 1H), 3.70 (s, 3H), 2.45 (d, J = 6.7 Hz, 2H), 2.21 (s, 3H), 1.97-1.79 (m, 1H), 0.94 (s, 3H), 0.93 (s, 3H). 182.70, 156.42, 155.66, 152.92, 147.11, 129.60, 123.92, 122.05, 120.51, 117.35, 112.13, 62.54, 39.10, 28.70, 22.53, 8.90.
6c ①6.95 (d, J = 8.4 Hz, 1H), 6.66 (d, J = 8.4 Hz, 1H), 3.80 (s, 3H), 3.60 (t, J = 6.4 Hz, 2H), 3.50 (t, J = 6.6 Hz, 2H), 2.33 (s, 2H), 2.05 (s, 3H), 1.96 (ddt, J = 19.7, 13.3, 6.7 Hz, 4H), 1.82 (m, 1H), 0.89 (s, 3H), 0.88 (s, 3H). 156.54, 152.68, 148.75, 127.58, 126.28, 119.84, 107.32, 55.67, 46.45, 46.36, 39.74, 29.21, 25.93, 25.07, 22.61, 9.51.
7c ②6.97 (d, J = 8.4 Hz, 1H), 6.69 (d, J = 8.4 Hz, 1H), 3.81 (s, 3H), 2.93 (t, J = 6.6 Hz, 2H), 2.83 (t, J = 6.6 Hz, 2H), 2.28 (d, J = 7.1 Hz, 2H), 1.99 (s, 3H), 1.80 (dt, J = 13.4, 6.8 Hz, 1H), 0.88 (s, 3H), 0.87 (s, 3H). 177.90, 170.12, 156.59, 148.32, 127.83, 125.55, 119.17, 107.85, 55.71, 39.55, 29.03, 28.86, 28.64, 22.51, 9.42.
8c ①7.34 (s, 1H), 3.75 (s, 3H), 3.73 (s, 3H), 2.62 (s, 3H), 2.46 (d, J = 7.3 Hz, 2H), 2.25 (s, 3H), 1.91 (dp, J = 13.6, 6.9 Hz, 1H), 0.91 (s, 3H), 0.90 (s, 3H). 200.04, 161.37, 157.51, 130.66, 129.27, 128.61, 125.12, 61.90, 60.45, 38.86, 30.45, 29.27, 22.57, 9.80.
9c ①6.95 (d, J = 8.4 Hz, 1H), 6.66 (d, J = 8.4 Hz, 1H), 3.80 (s, 3H), 3.15 (s, 3H), 3.03 (s, 3H), 2.30 (d, J = 21.5 Hz, 2H), 2.03 (s, 3H), 1.82 (dp, J = 13.5, 6.8 Hz, 1H), 0.90 (s, 3H). 156.54, 154.31, 148.83, 127.60, 126.19, 119.75, 107.37, 55.67, 39.65, 36.82, 36.39, 29.27, 22.58, 9.40.
), ArticleFig(id=1218970751101751419, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=CN, label=Table 2, caption=

1H NMR and 13C NMR data of target compounds. ①CDCl3 as deuterated solvent; ②DMSO-d6 as deuterated solvent

, figureFileSmall=null, figureFileBig=null, tableContent=
Compd. 1H NMR (400 MHz, CDCl3 or DMSO-d6) δ 13C NMR (100 MHz, CDCl3 or DMSO-d6) δ
4a ①6.54 (s, 1H), 3.81 (s, 3H), 3.79 (s, 3H), 3.68-3.37 (m, 8H), 2.41 (dd, J = 12.8, 6.7 Hz, 1H), 2.04 (dd, J = 12.5, 7.9 Hz, 1H), 1.84 (s, 3H), 1.79-1.66 (m, 1H), 0.82 (t, J = 6.9 Hz, 6H). 156.57, 156.43, 153.00, 149.12, 115.33, 111.61, 93.25, 66.89, 55.77, 55.72, 45.01, 44.29, 32.98, 28.89, 22.84, 22.61, 8.95.
5a ①7.88 (s, 1H), 6.98 (d, J = 3.6 Hz, 1H), 6.63 (dd, J = 3.5, 1.5 Hz, 1H), 5.97 (s, 1H), 4.00 (s, 3H), 3.69 (s, 3H), 2.10 (qd, J = 12.7, 7.2 Hz, 2H), 1.73-1.61 (m, 1H), 1.41 (s, 3H), 0.79 (d, J = 6.6 Hz, 3H), 0.76 (d, J = 6.6 Hz, 3H). 193.93, 180.83, 170.29, 170.12, 149.85, 147.73, 117.69, 112.63, 108.27, 87.26, 62.08, 56.60, 56.51, 30.31, 27.37, 23.73, 22.38, 22.29.
6a ①6.53 (s, 1H), 3.81 (s, 3H), 3.79 (s, 3H), 3.51 (s, 2H), 3.36-3.29 (m, 2H), 2.40 (s, 1H), 2.07 (s, 1H), 1.95-1.89 (m, 2H), 1.88 (d, J = 6.8 Hz, 2H), 1.85 (s, 3H), 1.80-1.67 (m, 1H), 0.82 (s, 3H), 0.80 (s, 3H). 156.10, 155.97, 151.60, 148.93, 114.15, 110.50, 93.05, 55.66, 55.58, 46.19, 46.00, 32.50, 28.26, 25.39, 24.48, 22.47, 8.96.
7a ②6.36 (s, 1H), 3.82 (s, 3H), 3.80 (s, 3H), 2.91 (t, J = 6.5 Hz, 2H), 2.82 (t, J = 6.5 Hz, 2H), 2.27-2.18 (m, 1H), 2.14-2.04 (m, 1H), 1.92 (s, 3H), 1.79 (tt, J = 13.5, 6.7 Hz, 1H), 0.87 (s, 3H), 0.85 (s, 3H). 177.98, 170.01, 156.65, 156.47, 148.94, 114.82, 111.03, 93.43, 55.79, 55.73, 32.90, 28.84, 28.73, 28.66, 22.60, 8.94.
8a ①7.26 (s, 1H), 6.37 (s, 1H), 3.83 (s, 3H), 3.80 (s, 3H), 2.32 (s, 3H), 2.24-2.20 (m, 1H), 2.05 (d, J = 11.8 Hz, 1H), 1.94 (s, 3H), 1.81 (tq, J = 13.5, 6.8 Hz, 1H), 0.87 (s, 3H), 0.86 (s, 3H). 168.95, 156.61, 156.43, 149.04, 114.69, 110.89, 93.23, 55.71, 55.68, 33.04, 28.72, 22.66, 20.63, 9.02.
9a ①6.35 (s, 1H), 3.82 (s, 3H), 3.79 (s, 3H), 3.14 (s, 3H), 3.02 (s, 3H), 2.54 (dd, J = 12.9, 6.7 Hz, 1H), 2.16-2.08 (m, 1H), 1.97 (s, 3H), 1.81 (dp, J = 13.7, 6.8 Hz, 1H), 0.87 (s, 6H). 156.48, 156.34, 154.27, 149.41, 115.50, 111.70, 93.11, 55.76, 55.70, 36.81, 36.37, 32.94, 28.88, 22.80, 22.56, 8.93.
4b ①8.80 (s, 1H), 5.99 (s, 1H), 3.82 (s, 6H), 3.77-3.53 (m, 8H), 2.45 (d, J = 7.3 Hz, 2H), 1.88 (dp, J = 13.7, 6.8 Hz, 1H), 0.89 (s, 3H), 0.87 (s, 3H). 168.22, 161.05, 157.36, 155.23, 110.98, 101.74, 86.65, 67.04, 55.51, 55.41, 31.50, 29.72, 28.30, 22.57.
5b ①6.33 (d, J = 2.3 Hz, 1H), 6.27 (d, J = 2.3 Hz, 1H), 3.77 (s, 6H), 3.77-3.52 (m, 8H), 2.34 (d, J = 7.2 Hz, 2H), 1.80 (dt, J = 13.6, 6.8 Hz, 1H), 0.87 (s, 3H), 0.86 (s, 3H). 159.12, 158.51, 153.46, 150.50, 115.36, 99.10, 96.36, 66.78, 66.64, 55.55, 55.38, 44.89, 44.16, 32.53, 28.77, 22.68.
6b ①11.09 (s, 1H), 7.56 (d, J = 0.9 Hz, 1H), 7.11 (d, J = 3.6 Hz, 1H), 6.52 (dd, J = 3.5, 1.7 Hz, 1H), 6.02 (s, 1H), 3.88 (s, 3H), 3.73 (s, 3H), 2.47 (d, J = 7.3 Hz, 2H), 1.90 (dp, J = 13.7, 6.8 Hz, 1H), 0.90 (s, 3H), 0.88 (s, 3H). 183.43, 162.74, 160.13, 158.88, 152.82, 144.47, 116.73, 110.82, 109.14, 104.51, 85.82, 54.50, 54.43, 30.13, 27.15, 21.53.
7b ①9.64 (s, 1H), 5.99 (s, 1H), 3.83 (s, 3H), 3.82 (s, 3H), 3.63 (s, 2H), 3.42 (s, 2H), 2.45 (d, J = 7.3 Hz, 2H), 2.05-1.97 (m, 1H), 1.97-1.77 (m, 4H), 0.89 (s, 3H), 0.87 (s, 3H). 168.35, 160.87, 157.27, 156.02, 110.30, 103.52, 86.52, 55.37, 31.51, 29.71, 28.27, 22.58, 14.13.
8b ②13.82 (s, 1H), 12.09 (s, 1H), 6.25 (s, 1H), 3.94 (s, 3H), 3.89 (s, 3H), 3.22 (t, J = 6.2 Hz, 2H), 2.52 (d, J = 6.4 Hz, 2H), 2.35 (d, J = 7.3 Hz, 2H), 1.81 (dt, J = 13.6, 6.8 Hz, 1H), 0.82 (s, 3H), 0.81 (s, 3H). 203.81, 174.01, 163.74, 162.76, 161.67, 108.10, 104.58, 87.15, 55.92, 55.79, 30.57, 28.03, 27.51, 22.39.
9b ①6.20 (s, 1H), 3.76 (s, 3H), 3.70 (s, 3H), 2.51 (s, 3H), 2.41 (d, J = 7.4 Hz, 2H), 1.89 (dp, J = 13.8, 6.8 Hz, 1H), 0.93 (s, 3H), 0.92 (s, 3H). 202.64, 157.64, 156.48, 155.83, 118.26, 113.48, 95.25, 62.84, 55.73, 32.55, 32.22, 28.90, 22.64.
10b ①8.96 (s, 1H), 5.99 (s, 1H), 3.82 (s, 3H), 3.82 (s, 3H), 3.02 (s, 6H), 2.45 (d, J = 7.3 Hz, 2H), 1.89 (dp, J = 13.7, 6.8 Hz, 1H), 0.89 (s, 3H), 0.87 (s, 3H). 169.67, 160.82, 157.03, 155.59, 110.57, 102.46, 86.52, 55.42, 55.38, 31.49, 29.71, 28.27, 22.55.
11b ①6.31 (d, J = 2.3 Hz, 1H), 6.29 (d, J = 2.3 Hz, 1H), 3.77 (s, 6H), 3.11 (s, 3H), 3.02 (s, 3H), 2.35 (d, J = 7.2 Hz, 2H), 1.81 (dp, J = 13.6, 6.8 Hz, 1H), 0.87 (s, 3H), 0.86 (s, 3H). 159.10, 158.44, 154.72, 150.85, 115.45, 99.24, 96.20, 55.55, 55.37, 36.77, 36.38, 32.50, 28.78, 22.64.
4c ①6.96 (d, J = 8.4 Hz, 1H), 6.68 (d, J = 8.4 Hz, 1H), 3.81 (s, 3H), 3.73 (m, J = 12.4 Hz, 6H), 3.61 (m, J = 14.2 Hz, 2H), 2.31 (dd, J = 13.1, 7.1 Hz, 2H), 2.04 (s, 3H), 1.79 (dp,
J = 13.5, 6.8 Hz, 1H), 0.90 (s, 3H), 0.88 (s, 3H).		 156.58, 153.04, 148.49, 127.76, 125.98, 119.67, 107.54, 66.82, 55.67, 44.97, 44.27, 39.73, 29.28, 22.60, 9.41.
5c ①7.66 (s, 1H), 7.12 (s, 1H), 7.05 (s, 1H), 6.54 (s, 1H), 5.06 (s, 1H), 3.70 (s, 3H), 2.45 (d, J = 6.7 Hz, 2H), 2.21 (s, 3H), 1.97-1.79 (m, 1H), 0.94 (s, 3H), 0.93 (s, 3H). 182.70, 156.42, 155.66, 152.92, 147.11, 129.60, 123.92, 122.05, 120.51, 117.35, 112.13, 62.54, 39.10, 28.70, 22.53, 8.90.
6c ①6.95 (d, J = 8.4 Hz, 1H), 6.66 (d, J = 8.4 Hz, 1H), 3.80 (s, 3H), 3.60 (t, J = 6.4 Hz, 2H), 3.50 (t, J = 6.6 Hz, 2H), 2.33 (s, 2H), 2.05 (s, 3H), 1.96 (ddt, J = 19.7, 13.3, 6.7 Hz, 4H), 1.82 (m, 1H), 0.89 (s, 3H), 0.88 (s, 3H). 156.54, 152.68, 148.75, 127.58, 126.28, 119.84, 107.32, 55.67, 46.45, 46.36, 39.74, 29.21, 25.93, 25.07, 22.61, 9.51.
7c ②6.97 (d, J = 8.4 Hz, 1H), 6.69 (d, J = 8.4 Hz, 1H), 3.81 (s, 3H), 2.93 (t, J = 6.6 Hz, 2H), 2.83 (t, J = 6.6 Hz, 2H), 2.28 (d, J = 7.1 Hz, 2H), 1.99 (s, 3H), 1.80 (dt, J = 13.4, 6.8 Hz, 1H), 0.88 (s, 3H), 0.87 (s, 3H). 177.90, 170.12, 156.59, 148.32, 127.83, 125.55, 119.17, 107.85, 55.71, 39.55, 29.03, 28.86, 28.64, 22.51, 9.42.
8c ①7.34 (s, 1H), 3.75 (s, 3H), 3.73 (s, 3H), 2.62 (s, 3H), 2.46 (d, J = 7.3 Hz, 2H), 2.25 (s, 3H), 1.91 (dp, J = 13.6, 6.9 Hz, 1H), 0.91 (s, 3H), 0.90 (s, 3H). 200.04, 161.37, 157.51, 130.66, 129.27, 128.61, 125.12, 61.90, 60.45, 38.86, 30.45, 29.27, 22.57, 9.80.
9c ①6.95 (d, J = 8.4 Hz, 1H), 6.66 (d, J = 8.4 Hz, 1H), 3.80 (s, 3H), 3.15 (s, 3H), 3.03 (s, 3H), 2.30 (d, J = 21.5 Hz, 2H), 2.03 (s, 3H), 1.82 (dp, J = 13.5, 6.8 Hz, 1H), 0.90 (s, 3H). 156.54, 154.31, 148.83, 127.60, 126.19, 119.75, 107.37, 55.67, 39.65, 36.82, 36.39, 29.27, 22.58, 9.40.
), ArticleFig(id=1218970751214997642, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Compd. Survival rate/%
4a 98.72
5a 91.09
6a 99.14
7a 97.12
8a 100.63
9a 96.82
4b 100.34
5b 98.02
6b 99.39
7b 98.40
Ibuprofen 95.32
LPS 78.44
8b 98.32
9b 99.97
10b 97.21
11b 100.08
4c 97.70
5c 100.16
6c 97.93
7c 98.65
8c 96.03
9c 98.76
LM49 19.92
), ArticleFig(id=1218970751365992603, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=CN, label=Table 3, caption=

The survival rate of target compounds (40 μmol·L-1). Ibuprofen was positive reference compound; LM49 was a lead compound

, figureFileSmall=null, figureFileBig=null, tableContent=
Compd. Survival rate/%
4a 98.72
5a 91.09
6a 99.14
7a 97.12
8a 100.63
9a 96.82
4b 100.34
5b 98.02
6b 99.39
7b 98.40
Ibuprofen 95.32
LPS 78.44
8b 98.32
9b 99.97
10b 97.21
11b 100.08
4c 97.70
5c 100.16
6c 97.93
7c 98.65
8c 96.03
9c 98.76
LM49 19.92
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Compd. Inhibition rate/% (40 μmol·L-1)a IC50/ μmol·L-1 b
4a 7.68 N.D. c
5a – N.D.
6a 10.35 N.D.
7a 4.92 N.D.
8a – N.D.
9a 50.09 N.D.
4b 14.83 N.D.
5b 15.98 N.D.
6b 20.42 N.D.
7b 27.83 N.D.
Ibuprofen 54.08 37.6 ± 6.9
LM49 N.D. 8.6 ± 2.5
8b 50.91 41.8 ± 0.3
9b 14.86 N.D.
10b 20.23 N.D.
11b 43.05 N.D.
4c 39.89 N.D.
5c 39.64 N.D.
6c 30.20 N.D.
7c 72.00 33.2 ± 0.6
8c 43.10 N.D.
9c 53.45 35.8 ± 0.7
), ArticleFig(id=1218970751600873653, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1218555557049454594, language=CN, label=Table 4, caption=

The inhibition rate of target compounds. Ibuprofen was a positive reference compound; LM49 was a lead compound; aAverage value by three independent experimental measurements; bMean ± SD (n= 2); N.D.: Not detection[11]

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Compd. Inhibition rate/% (40 μmol·L-1)a IC50/ μmol·L-1 b
4a 7.68 N.D. c
5a – N.D.
6a 10.35 N.D.
7a 4.92 N.D.
8a – N.D.
9a 50.09 N.D.
4b 14.83 N.D.
5b 15.98 N.D.
6b 20.42 N.D.
7b 27.83 N.D.
Ibuprofen 54.08 37.6 ± 6.9
LM49 N.D. 8.6 ± 2.5
8b 50.91 41.8 ± 0.3
9b 14.86 N.D.
10b 20.23 N.D.
11b 43.05 N.D.
4c 39.89 N.D.
5c 39.64 N.D.
6c 30.20 N.D.
7c 72.00 33.2 ± 0.6
8c 43.10 N.D.
9c 53.45 35.8 ± 0.7
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新型含异丁基苯甲酮类化合物的合成及抗炎活性的初步研究
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杨璐 1 , 史行 1 , 李云兰 1, 2, * , 陈曦 1 , 牛思青 1 , 乔晓枝 1 , 买佳琪 1 , 李青山 2
药学学报 | 研究论文 2018,53(2): 256-262
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药学学报 | 研究论文 2018, 53(2): 256-262
新型含异丁基苯甲酮类化合物的合成及抗炎活性的初步研究
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杨璐1, 史行1, 李云兰1, 2, * , 陈曦1, 牛思青1, 乔晓枝1, 买佳琪1, 李青山2
作者信息
  • 1.山西医科大学药学院, 山西 太原 030001
  • 2.山西中医药大学, 山西 太原 030619

通讯作者:

* 李云兰, Tel:13111066649, E-mail:
Synthesis and anti-inflammatory activity of novel isobutyl benzophenone derivatives
Lu YANG1, Hang SHI1, Yun-lan LI1, 2, * , Xi CHEN1, Si-qing NIU1, Xiao-zhi QIAO1, Jia-qi MAI1, Qing-shan LI2
Affiliations
  • 1. College of Pharmacy, Shanxi Medical University, Taiyuan 030001, China
  • 2. Shanxi University of Chinese Medical, Taiyuan 030619, China
出版时间: 2018-02-12 doi: 10.16438/j.0513-4870.2017-1224
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摘要
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通过傅克酰基化反应、黄鸣龙还原反应合成了20个目标化合物，并通过LPS诱导的小鼠巨噬细胞RAW264.7炎症模型测定目标化合物对细胞上清液中NO的抑制作用并探讨了构效关系。合成的20个目标化合物全部为新化合物，其结构经ESI-MS、1H NMR和13C NMR确认。体外活性实验表明，有18个目标化合物在浓度为40 μmol·L-1时有一定的抗炎作用，其中以9a、8b、7c和9c表现出较强的抗炎活性，7c和9c的IC50与阳性对照药布洛芬相当。

异丁基苯甲酮  /  合成  /  NO  /  抗炎作用

Twenty target compounds were synthesized by the reduction reaction of HUANG Minglong and Friedel-Crafts acylation reaction in this study. The inhibitory effects of the new compounds were tested on NO production in LPS-induced mouse macrophage RAW264.7 cells, a cellular inflammation model. The structure-activity relationships were discussed. The structures of target compounds were confirmed by ESI-MS, 1H NMR and 13C NMR. In vitro activity experiments showed that 18 compounds had certain anti-inflammatory effects at the concentration of 40 μmol·L-1, of which 9a, 8b, 7c and 9c showed strong anti-inflammatory activities, and IC50 of 7c and 9c were comparable to the positive control drug ibuprofen.

isobutylbenzophenone  /  synthesis  /  NO  /  anti-inflammatory effect
杨璐, 史行, 李云兰, 陈曦, 牛思青, 乔晓枝, 买佳琪, 李青山. 新型含异丁基苯甲酮类化合物的合成及抗炎活性的初步研究. 药学学报, 2018 , 53 (2) : 256 -262 . DOI: 10.16438/j.0513-4870.2017-1224
Lu YANG, Hang SHI, Yun-lan LI, Xi CHEN, Si-qing NIU, Xiao-zhi QIAO, Jia-qi MAI, Qing-shan LI. Synthesis and anti-inflammatory activity of novel isobutyl benzophenone derivatives[J]. Acta Pharmaceutica Sinica, 2018 , 53 (2) : 256 -262 . DOI: 10.16438/j.0513-4870.2017-1224
正文
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炎症是生物在漫长的进化过程中逐渐形成的抵御外来病原体入侵的重要保护机制, 然而近几年越来越多的数据显示炎症并不局限于机体受到的外来细菌或病毒等的感染, 而一些非感染损伤如恶性肿瘤和代谢性疾病如肥胖和2型糖尿病中也能够寻找到炎症的踪影[1]。因此, 抗炎治疗已成为感染、创伤、代谢性疾病等的基本策略, 新型抗炎药物的研发成为研究热点[2]。
溴酚类化合物是一类独具特色的化合物, 它具有多样的生物活性, 主要包括酶抑制、抗氧化、抗炎、抗微生物和细胞毒活性等。溴酚类化合物在海洋生物中含量低, 且采集困难, 因此限制了对其生物活性的进一步研究和开发。本课题组前期对溴酚类化合物的研究过程中合成了一系列以二苯甲酮为母核的新型化合物, 并发现其中一些化合物对血管内皮细胞损伤有较高的保护活性, 而对抗炎活性方面研究较少[3, 4]。
本课题运用Sybyl-X 2.0分子对接技术, 根据炎症蛋白COX-2及iNOS在本实验室前期课题的基础之上进行新的结构改造[5], 在A环设计加入了异丁基及羟基、甲氧基, 并用杂环或碳链取代B环[6, 7] (设计思路如图 1)。异丁基在很多活性药物的设计合成中经常被引入, 比如临床上经典抗炎药物布洛芬[8, 9], 异丁基的引入可以增强药物的脂溶性, 促进药物的吸收。因此, 本课题通过引入异丁基和杂环等, 合成了系列含异丁基苯甲酮类化合物, 并对其进行抗炎活性筛选, 以期得到更高活性的新化合物并探讨其构效关系。
结果与讨论
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1 目标化合物的合成
目标化合物4a~9c的合成过程见合成路线1~3, 分别以3种化合物即2, 4, 6-三甲氧基甲苯、2, 4, 6-三甲氧基苯及2, 6-二甲氧基甲苯为原料, 先在无水AlCl3为催化剂的作用下与异丁酰氯发生傅克酰基化反应, 生成化合物2a~2c, 然后在强碱及高温的条件下发生黄鸣龙还原反应将酮羰基还原成亚甲基, 生成化合物3a~3c, 最后再进行傅克酰基化反应生成目标产物, 此步反应由于原料化合物空间位阻较大, 导致酰基化难度加大, 产率较低, 适当升高温度后产率有所上升, 但由于温度上升反应变剧烈, 且催化剂AlCl3有选择性脱甲基作用, 在引入酰基的同时, 酰基邻位的甲氧基会同时脱掉, 生成的游离酚羟基与邻位的羰基形成分子内氢键[10], 具体步骤见实验部分。
目标化合物经ESI-MS、1H NMR和13C NMR确认, 其收率、理化常数及波谱数据见表 1、2。
2 细胞毒性检测
目标化合物4a~9a、4b~11b、4c~9c生存率实验结果见表 3, 从实验结果来看, 各目标化合物与空白对照组相比, 40 μmol·L-1目标化合物均未对RAW264.7细胞的生存率产生影响, 细胞存活率均在85%以上, 而先导化合物LM49在40 μmol·L-1浓度下细胞存活率仅为19.92%。此结果提示, 含异丁基苯甲酮类化合物在40 μmol·L-1浓度下对小鼠巨噬细胞RAW264.7基本没有毒性, 安全性显著提高。
3 抗炎作用初步研究
以已上市的非甾体抗炎药布洛芬和先导化合物LM49为阳性对照药, 采用Griess法测定20个化合物抗炎初步活性, 目标化合物抗炎活性初筛结果见表 4, 结果表明大部分化合物都有一定的抗炎活性, 虽然均弱于先导化合物LM49, 但化合物7c和9c的IC50分别为33.2 ± 0.6 μmol·L-1和35.8 ± 0.7 μmol·L-1, 与阳性对照药布洛芬相当。
4 分子对接
分子对接结果见图 2和3, 结果显示7c对COX-2的对接分数(8.47)优于iNOS (5.00), 提示其抗炎靶点有可能是COX-2;分子对接结果(图 2)显示化合物7c结构中的羧基与COX-2中的His75 (键长2.74 Å )、Arg499 (键长1.91 Å )存在氢键结合, 提高了与受体蛋白的亲和力, 为进一步研究抗炎作用机制提供了思路。
5 小结
本实验合成了20个新型异丁基苯甲酮类化合物, 其结构经ESI-MS、1H NMR和13C NMR确认, 且全部为新化合物。所有目标化合物对LPS诱导的小鼠巨噬细胞炎症因子NO的抑制作用均为首次报道, 初步研究结果显示, 18个目标化合物在40 μmol·L-1浓度下有一定的抗炎作用, 且细胞毒性较小, 安全性高。化合物9a、8b、7c和9c表现出较强的抗炎活性, NO抑制率7c > 9c > 8b > 9a, 7c和9c的IC50分别为33.2 ± 0.6 μmol·L-1和35.8 ± 0.7 μmol·L-1, 虽低于先导化合物LM49, 但与阳性对照药布洛芬相当。结果表明, 含异丁基苯甲酮类化合物有一定的抗炎作用, 且结构中含有酰胺基团时, 其活性明显升高, 酰胺基 > 丁酸基 > 杂环, 但是当苯环上取代基增多时, 位阻增大, 活性下降, 此类化合物的构效关系为进一步寻找高活性抗炎化合物提供了依据。
实验部分
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用X-4数字显示显微熔点仪测定熔点(温度未校正); 核磁共振仪为Bruker Av-400型, TMS为内标; 质谱仪为API-QTRAP 3200液相色谱质谱联用仪测定; 常压柱色谱用200~300目硅胶, 薄层色谱用GF254硅胶, 均为青岛海洋化工厂产品; 所用试剂均为分析纯。
1 化学合成
1.1 2-甲基-1-(2, 4, 6-三甲氧基-3-甲基-苯基)-丙酮(2a)的制备
取2, 4, 6-三甲氧基甲苯5 g于100 mL量瓶中, 加入二氯甲烷20 mL, 再加入无水AlCl3 (1.1 eq), 冰浴10 min, 缓慢滴加异丁酰氯(1.3 eq), 室温反应6 h, TLC检测反应完全, 加入适量冰水及1.0 mol·L-1稀盐酸终止反应[12, 13], 体系分层后用20 mL二氯甲烷萃取3次, 合并有机层, 无水硫酸钠干燥过夜, 减压旋除溶剂, 柱色谱分离(石油醚-乙酸乙酯= 16:1, V:V)即得淡黄色油状液体4.5 g, 收率: 65%。
化合物2b、2c按照此法合成。
1.2 2-异丁基-1, 3, 5-三甲氧基4-甲基苯(3a)的制备
取一缩二乙二醇30 mL和DMSO 15 mL于100 mL圆底烧瓶中, 缓慢加热至115 ℃, 蒸馏0.5 h除水, 完毕后再加入上步制得的化合物2a, 待溶解后缓慢加入过量的80%水合肼, 120 ℃下冷凝回流2 h。完毕后调节油浴温度降至70 ℃, 加入NaOH 4.5 g, 待NaOH完全溶解后升温至130 ℃蒸馏除水, 然后去掉蒸馏装置, 改成回流装置, 加热至 < 165 ℃反应10 h, TLC监测反应进程。待反应结束后, 冷却至室温, 加浓盐酸调节pH至酸性[14, 15]。用石油醚萃取3次, 合并有机层, 无水硫酸钠干燥过夜, 减压旋除溶剂, 柱色谱分离(石油醚-乙酸乙酯= 60:1, V:V)即得黄色油状液体, 收率43%。
化合物3b、3c按照此法合成。
1.3 (2-羟基-3-异丁基-4, 6-二甲氧基-5-甲基苯基)-吗啉-4-甲酮(4a)的制备
取300 mg上步合成的3a于50 mL圆底烧瓶中, 加入二氯甲烷15 mL, 搅拌使其溶解, 再缓慢加入无水AlCl3 (1.3 eq), 冰浴10 min, 然后在冰浴条件下, 缓慢滴加吗啉甲酰氯(1.3 eq), 缓慢升温至45 ℃, 回流反应24 h, TLC监测反应进程, 反应结束后, 加入适量冰水及1.0 mol·L-1稀盐酸终止反应, 体系分层后用20 mL二氯甲烷萃取3次, 合并有机层, 无水硫酸钠干燥过夜, 减压旋除溶剂, 柱色谱分离(石油醚-乙酸乙酯=10:1, V:V)即得白色固体4a[16], 产率约为14%。
化合物5a~9a均按照此方法合成。
1.4 (2-羟基-3-异丁基-4, 6-二甲氧基苯基)-吗啉-4-甲酮(4b)的制备
制备方法与4a类似, 改用2, 4, 6-三甲氧基苯为原料, 二氯甲烷为溶剂, 纯化方法为柱色谱分离(石油醚-乙酸乙酯=8:1, V:V), 得到白色固体4b, 产率约为17%。
化合物6b~10b均按照此方法合成。
1.5 吗啉-4-羧酸-2-异丁基-3, 5-二甲氧基苯基酯(5b)的制备
5b是制备4b过程中柱色谱分离(石油醚-乙酸乙酯=8:1, V:V)得到的副产物, 白色固体, 产率约为9%。
1.6 N, N-二甲基氨基甲酸-2-异丁基-3, 5-二甲氧基苯基酯(11b)的制备
11b是制备10b过程中柱色谱分离(石油醚-乙酸乙酯=10:1, V:V)得到的副产物, 无色油状液体, 产率约为10%。
1.7 (2-羟基-5-异丁基-4-甲氧基-3-甲基-苯基)-吗啉-4-甲酮(4c)的制备
制备方法于4a类似, 改用2, 6-二甲氧基甲苯为原料, 二氯甲烷为溶剂, 纯化方法为柱色谱分离(石油醚-乙酸乙酯=10:1, V:V), 得到白色固体4c, 产率约为15%。
化合物5c~9c均按照此方法合成。
2 细胞毒性的检测
取对数生长期的细胞接种于96孔板中, 5% CO2、37 ℃孵箱中培养24 h, 然后分别加入样品(终浓度为40 μmol·L-1)和脂多糖(LPS) (终质量浓度为1 mg·L-1)处理24 h后吸净细胞上清液后, 在各孔中加入5 g·L-1甲基噻唑基四唑(MTT) 10 μL及无血清培养基100 μL, 继续避光培养4 h后, 轻轻吸弃孔内液体, 每孔加入100 μL二甲基亚砜(DMSO), 振荡使细胞内结晶充分溶解, 于酶标仪490 nm波长处测定各孔的吸光度A值。通过以下公式计算出各组的生存率:生存率(%) = A样品组 / A空白组×100%。
3 抗炎作用初步研究
取对数生长期的细胞接种于96孔板中, 5% CO2、37 ℃孵箱中培养24 h, 换成无血清培养基, 同时加入样品(终浓度为40 μmol·L-1)和LPS (终质量浓度为1 mg·L-1)后, 再培养24 h, 然后吸取细胞上清液50 μL, 用Griess法测定上清液中NO含量, 按“抑制率(%) = (A样品组-A模型组)/(A空白组-A模型组)×100%”计算样品对LPS诱导的小鼠巨噬细胞NO生成的抑制作用。
4 分子对接实验
分子对接所使用的蛋白质晶体结构来源: http://www.rcsb.org/pdb/PDB数据库, 编号为3LN1 (COX-2)、4CX7 (iNOS), 利用Sybyl-X 2.0软件中Applications模块下的Dock-ligands程序进行分子对接, 除特殊说明, 所选参数均为系统默认值。
基金
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  • 山西省自然科学基金资助项目(2014011027-1)
  • 山西省科技计划项目(2013031302)
  • 山西省高校中青年拔尖创新人才计划(2015年)
  • 晋药综合开发利用协同创新项目(2017-JYXT-18)
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2018年第53卷第2期
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doi: 10.16438/j.0513-4870.2017-1224
  • 接收时间：2017-12-08
  • 首发时间：2026-01-15
  • 出版时间：2018-02-12
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  • 收稿日期：2017-12-08
  • 录用日期：2018-01-03
基金
山西省自然科学基金资助项目(2014011027-1)
山西省科技计划项目(2013031302)
山西省高校中青年拔尖创新人才计划(2015年)
晋药综合开发利用协同创新项目(2017-JYXT-18)
作者信息
    1.山西医科大学药学院, 山西 太原 030001
    2.山西中医药大学, 山西 太原 030619

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2种不同金属材料的力学参数
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Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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