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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=null), CN=ArticleExt(id=1210517380049015284, articleId=1210517372818034771, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=老药改造: 根治性的抗疟药他非诺奎, columnId=1190335351748137800, journalTitle=药学学报, columnName=新药发现与研究实例简析, runingTitle=null, highlight=null, articleAbstract=null, correspAuthors=null, authorNote=null, correspAuthorsNote=null, copyrightStatement=版权所有©《药学学报》编辑部2022, copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=hkyQ5lPO2g5HLYQPxZ2L7g==, magXml=5jH73HASuXzYoFcFuk+fcA==, pdfUrl=null, pdf=TeXjSCPyWCUYWSoN9AIC7w==, pdfFileSize=792187, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=null, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=SkBBNhb3XAJrwxIGg6hGvQ==, mapNumber=null, authorCompany=null, fund=null, authors=null, authorsList=郭宗儒)}, authors=[Author(id=1210517380518777363, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517372818034771, orderNo=0, firstName=null, middleName=null, lastName=null, nameCn=null, orcid=null, stid=null, country=null, authorPic=null, dead=0, email=null, emailSecond=null, emailThird=null, correspondingAuthor=0, authorType=1, ext={CN=AuthorExt(id=1210517380652995104, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517372818034771, authorId=1210517380518777363, language=CN, stringName=郭宗儒, firstName=宗儒, middleName=null, lastName=郭, prefix=null, suffix=null, authorComment=null, nameInitials=null, affiliation=null, department=null, xref=null, address=中国医学科学院、北京协和医学院药物研究所, 北京 100050, bio=null, bioImg=null, bioContent=null, aboutCorrespAuthor=null)}, companyList=[AuthorCompany(id=1210517380359393801, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517372818034771, xref=null, ext=[AuthorCompanyExt(id=1210517380367782410, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517372818034771, companyId=1210517380359393801, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=中国医学科学院、北京协和医学院药物研究所, 北京 100050)])])], keywords=null, refs=null, funds=null, companyList=[AuthorCompany(id=1210517380359393801, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517372818034771, xref=null, ext=[AuthorCompanyExt(id=1210517380367782410, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517372818034771, companyId=1210517380359393801, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=中国医学科学院、北京协和医学院药物研究所, 北京 100050)])], figs=[ArticleFig(id=1210517380787212842, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517372818034771, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
 |
| Compd. | R | | Compd. | R | | Compd. | R |
| 7 |  | | 12 |  | | 18 | NH2 |
| 8 |  | 13 |  | 19 |  |
| 9 |  | 14 |  | 20 |  |
| 10 |  | 16 |  | 21 | OH |
| 11 |  | 17 |  | |
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Typical compounds with varied 4-substituents or 8-diamino side chain
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| |
| Compd. | R | | Compd. | R | | Compd. | R |
| 7 | | | 12 | | | 18 | NH2 |
| 8 | | 13 | | 19 | |
| 9 | | 14 | | 20 | |
| 10 | | 16 | | 21 | OH |
| 11 | | 17 | | |
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| Compd. | P. cynomolgi (rhesus monkey) | | P. berghei (mice), ΔMST, days at mg·kg-1 |
| Daily dose/mg·kg-1 (×7) | Activity | | 20 | 40 | 80 | 160 | 320 | 640 |
| 22 | 1.00 | Inactive | | 0.1 | 0.1 | 1.3 | 3.5 | 6.7 | 8.1 |
| 23 | 0.25 | Inactive | NT | NT | NT | 3.9 | 5.5 | 5/5 T*** |
| 0.50 | 1/4 C* | NT | NT | NT | NT | NT | NT |
| 1.00 | 2/4 C | NT | NT | NT | NT | NT | NT |
| 24 | 0.50 | Inactive | 5.8 | 7.0 | 10.4 | 3/5 C** | 5/5 C | 5/5 C |
| 1.00 | 1/1 C | NT | NT | NT | NT | NT | NT |
| 3 | 0.25 | Inactive | NT | 5.0 | 9.4 | 2T | 5T | 5T |
| 0.50 | 10/12 C | NT | NT | NT | NT | NT | NT |
| 1.00 | 4/4 C | NT | NT | NT | NT | NT | NT |
| 6 | 0.25 | 8/12 C | NT | NT | NT | NT | NT | NT |
| 0.50 | 13/13 C | NT | NT | 5.5 | 8.0 | 10.1 | 3C, 1T |
| 1.00 | 1/1 C | NT | NT | NT | | | |
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Antimalarial activity of typical compounds. *Means one monkey was cured in four animals. **Means three mice were cured. ***Means toxicity for all five mice. ΔMST = Numbers with decimal point; NT = Not test
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| Compd. | P. cynomolgi (rhesus monkey) | | P. berghei (mice), ΔMST, days at mg·kg-1 |
| Daily dose/mg·kg-1 (×7) | Activity | | 20 | 40 | 80 | 160 | 320 | 640 |
| 22 | 1.00 | Inactive | | 0.1 | 0.1 | 1.3 | 3.5 | 6.7 | 8.1 |
| 23 | 0.25 | Inactive | NT | NT | NT | 3.9 | 5.5 | 5/5 T*** |
| 0.50 | 1/4 C* | NT | NT | NT | NT | NT | NT |
| 1.00 | 2/4 C | NT | NT | NT | NT | NT | NT |
| 24 | 0.50 | Inactive | 5.8 | 7.0 | 10.4 | 3/5 C** | 5/5 C | 5/5 C |
| 1.00 | 1/1 C | NT | NT | NT | NT | NT | NT |
| 3 | 0.25 | Inactive | NT | 5.0 | 9.4 | 2T | 5T | 5T |
| 0.50 | 10/12 C | NT | NT | NT | NT | NT | NT |
| 1.00 | 4/4 C | NT | NT | NT | NT | NT | NT |
| 6 | 0.25 | 8/12 C | NT | NT | NT | NT | NT | NT |
| 0.50 | 13/13 C | NT | NT | 5.5 | 8.0 | 10.1 | 3C, 1T |
| 1.00 | 1/1 C | NT | NT | NT | | | |
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 |
| Compd. | R1 | R2 | R3 | P. berghei (mice), ΔMST, mg·kg-1, sc |
| 5 | 10 | 20 | 40 | 80 | 160 | 320 | 640 |
| 25 | H | CH3 | CH(CH3)(CH2)3NH2 | NT | NT | 5.7 | 7.1 | 8.9 | 9.9
1T | 11.9
4T | 5T |
| 26 | H | CH3 | (CH2)3CH(CH3)NH2 | NT | NT | 11.4
3T | 5T | NT | 5T | NT | 5T |
| 27 | H | CH3 | CH(CH2CH3)(CH2)3NH2 | NT | NT | - | 0.1 | NT | 5T | NT | 5T |
| 28 | H | CH3 | (CH2)4CH(CH3) NH2 | NT | NT | 7.5
1T | 8.7
1T | NT | 5T | NT | 5T |
| 29 | H | CH3 | CH(CH3)(CH2)4NH2 | NT | NT | 3C | 1C
1T | NT | 5T | NT | 5T |
| 30 | CH3 | CH3 | CH(CH3)(CH2)3NH2 | NT | NT | 4.9 | 6.3
3T | NT | 5T | NT | 5T |
| 31 | H | H | (CH2)3CH(CH3)NH2 | NT | NT | 1.3 | 3.1 | 5.1 | 7.3 | 9.9
3T | 5T |
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Antimalarial activity of 5, 6-dimethoxy-8-quinolinediamines. NT = Not test
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| |
| Compd. | R1 | R2 | R3 | P. berghei (mice), ΔMST, mg·kg-1, sc |
| 5 | 10 | 20 | 40 | 80 | 160 | 320 | 640 |
| 25 | H | CH3 | CH(CH3)(CH2)3NH2 | NT | NT | 5.7 | 7.1 | 8.9 | 9.9
1T | 11.9
4T | 5T |
| 26 | H | CH3 | (CH2)3CH(CH3)NH2 | NT | NT | 11.4
3T | 5T | NT | 5T | NT | 5T |
| 27 | H | CH3 | CH(CH2CH3)(CH2)3NH2 | NT | NT | - | 0.1 | NT | 5T | NT | 5T |
| 28 | H | CH3 | (CH2)4CH(CH3) NH2 | NT | NT | 7.5
1T | 8.7
1T | NT | 5T | NT | 5T |
| 29 | H | CH3 | CH(CH3)(CH2)4NH2 | NT | NT | 3C | 1C
1T | NT | 5T | NT | 5T |
| 30 | CH3 | CH3 | CH(CH3)(CH2)3NH2 | NT | NT | 4.9 | 6.3
3T | NT | 5T | NT | 5T |
| 31 | H | H | (CH2)3CH(CH3)NH2 | NT | NT | 1.3 | 3.1 | 5.1 | 7.3 | 9.9
3T | 5T |
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 |
| Compd. | n | R | P. berghei (mice), ΔMST, mg·kg-1, sc |
| 5 | 10 | 20 | 40 | 80 | 160 | 320 | 640 |
| 32 | 1 | CH3 | - | - | - | 0.1 | - | 0.1 | - | 0.3 |
| 33 | 2 | CH3 | 6.7 | 8.3 | 11.1 | 5T | | 5T | - | 5T |
| 34 | 1 | C2H5 | - | - | - | 0.5 | - | 0.5 | - | 0.9 |
| 35 | 2 | C2H5 | 7.8 | 7.6 | 7.2 | 7.6 | | 5T | - | 5T |
| 3 | | | - | - | - | 5.0 | 9.4 | 2T | 5T | 5T |
| 6 | | | - | - | 3.1 | 4.9 | 5.5 | 9.1 | 10.1 | 3C
1T |
), ArticleFig(id=1210517382674649701, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517372818034771, language=CN, label=Table 4, caption=
Antimalarial activity of 5, 6-alkenedioxy-8-quinolinediamines
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| |
| Compd. | n | R | P. berghei (mice), ΔMST, mg·kg-1, sc |
| 5 | 10 | 20 | 40 | 80 | 160 | 320 | 640 |
| 32 | 1 | CH3 | - | - | - | 0.1 | - | 0.1 | - | 0.3 |
| 33 | 2 | CH3 | 6.7 | 8.3 | 11.1 | 5T | | 5T | - | 5T |
| 34 | 1 | C2H5 | - | - | - | 0.5 | - | 0.5 | - | 0.9 |
| 35 | 2 | C2H5 | 7.8 | 7.6 | 7.2 | 7.6 | | 5T | - | 5T |
| 3 | | | - | - | - | 5.0 | 9.4 | 2T | 5T | 5T |
| 6 | | | - | - | 3.1 | 4.9 | 5.5 | 9.1 | 10.1 | 3C
1T |
), ArticleFig(id=1210517382834033260, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517372818034771, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
| Compd. | P. cynomolgi (rhesus): mg·kg-1 per day (×7), po |
| 0.75 | 0.5 | 0.35 | 0.125 | 0.0625 |
| 25 | NT | 1/1C | 3/4C | 11/13C | 0/5 |
| 26 | NT | 1/1C | 5/6C | NT | NT |
| 27 | 4/5C | NT | 4/4C | 6/10C | 0/2C |
| 28 | 3/3C | NT | 2/2C | NT | NT |
| 29 | 3/5C | NT | 1/4C | NT | NT |
| 30 | 4/5C | NT | 2/4C | NT | NT |
| 31 | 0/2C | NT | 0/2C | NT | NT |
| 32 | 0/3C | NT | 0/3C | NT | NT |
| 33 | 0/2C | NT | 0/3C | NT | NT |
| 34 | 0/5C | NT | 0/3C | NT | NT |
| 3 | 4/4C | 10/12C | 0/2C | NT | NT |
| 6 | 1/1C | 13/14C | 8/14C | NT | NT |
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Radical curative antimalarial data of compounds 25-35. NT = Not test
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| Compd. | P. cynomolgi (rhesus): mg·kg-1 per day (×7), po |
| 0.75 | 0.5 | 0.35 | 0.125 | 0.0625 |
| 25 | NT | 1/1C | 3/4C | 11/13C | 0/5 |
| 26 | NT | 1/1C | 5/6C | NT | NT |
| 27 | 4/5C | NT | 4/4C | 6/10C | 0/2C |
| 28 | 3/3C | NT | 2/2C | NT | NT |
| 29 | 3/5C | NT | 1/4C | NT | NT |
| 30 | 4/5C | NT | 2/4C | NT | NT |
| 31 | 0/2C | NT | 0/2C | NT | NT |
| 32 | 0/3C | NT | 0/3C | NT | NT |
| 33 | 0/2C | NT | 0/3C | NT | NT |
| 34 | 0/5C | NT | 0/3C | NT | NT |
| 3 | 4/4C | 10/12C | 0/2C | NT | NT |
| 6 | 1/1C | 13/14C | 8/14C | NT | NT |
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 |
| Compd. | R | Mouse test infected by P. berghei, five mice, mg·kg-1 (×l) |
| 5 | 10 | 20 | 40 | 80 | 160 | 320 | 640 |
| 36 | 3-CF3 | 6.5 | 2C | 5C | 5C | 5C | 5C | 5C | 1C, 2T |
| 37 | 2, 4-Cl2 | 4.0 | 1C | 5C | 5C | 5C | 5C | 4C, 1T | 3C, 1T |
| 38 | 3, 4-Cl2 | 4C | 5C | 5C | 5C | 5C | 5C | 5C | 5C |
| 39 | 4-OCH3 | 5.5 | 5.9 | 1C | 5C | 5C | 5C | 5C | 2C, 3T |
| 40 | 4-F | 7.0 | 3C | 4C | 5C | 5C | 5C | 4C, 1T | 3C, 2T |
| 3 | NT | NT | NT | 2.2 | 4.2 | 6.4 | 7.0 | 5T | 5T |
| 6 | NT | NT | NT | 4.0 | 5.0 | 9.4 | 10.8, 2T | 5T | 5T |
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Suppressive antimalarial activity of compounds 36-40 on infected mice. NT = Not test
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| |
| Compd. | R | Mouse test infected by P. berghei, five mice, mg·kg-1 (×l) |
| 5 | 10 | 20 | 40 | 80 | 160 | 320 | 640 |
| 36 | 3-CF3 | 6.5 | 2C | 5C | 5C | 5C | 5C | 5C | 1C, 2T |
| 37 | 2, 4-Cl2 | 4.0 | 1C | 5C | 5C | 5C | 5C | 4C, 1T | 3C, 1T |
| 38 | 3, 4-Cl2 | 4C | 5C | 5C | 5C | 5C | 5C | 5C | 5C |
| 39 | 4-OCH3 | 5.5 | 5.9 | 1C | 5C | 5C | 5C | 5C | 2C, 3T |
| 40 | 4-F | 7.0 | 3C | 4C | 5C | 5C | 5C | 4C, 1T | 3C, 2T |
| 3 | NT | NT | NT | 2.2 | 4.2 | 6.4 | 7.0 | 5T | 5T |
| 6 | NT | NT | NT | 4.0 | 5.0 | 9.4 | 10.8, 2T | 5T | 5T |
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 |
| Compd. | R | Test of infected monkeys, dose in mg·kg-1 (×7) | Molar primaquine index* |
| 0.1 | 0.316 | 1.0 |
| 36 | 3-CF3 | 0/2 C | 2/2 C | 2/2 C | 4.8 |
| 37 | 2, 4-Cl2 | 0/3 C | 1/2 C | 3/3 C | 1.4 |
| 38 | 3, 4-Cl2 | 0/3 C | 1/2 C | 3/3 C | 1.3 |
| 39 | 4-OCH3 | 0/2 C | 2/2 C | 3/3 C | 4.3 |
| 40 | 4-F | 0/3 C | 2/2 C | 3/3C | 4.2 |
| 3 | - | Not test | 0/2 C | 1/2 C | 1.0 |
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Radical curative activity of 4-methyl-5-(aryloxy)primaquine analogues on infected monkey. *Ratio of moles of primaquine to achieve 100% cures divided by moles of test compound to achieve 100% cures
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| |
| Compd. | R | Test of infected monkeys, dose in mg·kg-1 (×7) | Molar primaquine index* |
| 0.1 | 0.316 | 1.0 |
| 36 | 3-CF3 | 0/2 C | 2/2 C | 2/2 C | 4.8 |
| 37 | 2, 4-Cl2 | 0/3 C | 1/2 C | 3/3 C | 1.4 |
| 38 | 3, 4-Cl2 | 0/3 C | 1/2 C | 3/3 C | 1.3 |
| 39 | 4-OCH3 | 0/2 C | 2/2 C | 3/3 C | 4.3 |
| 40 | 4-F | 0/3 C | 2/2 C | 3/3C | 4.2 |
| 3 | - | Not test | 0/2 C | 1/2 C | 1.0 |
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| Compd. | ΔMST, cure, toxic or inactive at mg·kg-1, sc* |
| 5 | 10 | 20 | 40 | 80 | 160 | 320 | 640 |
| 3 | NT | NT | NT | I | I | 9.0 | 2T | 5T |
| 36 | I | I | 1C | 4C | 5C | 5C | 5C | 4C/1T |
| 41 | I | I | 3C | 5C | 5C | 5C | 5C | 4C/1T |
| 45 | I | I | 10.5 | 2C | 5C | 4C | 5T | 5T |
| 46 | I | 8.1 | 1C | 2C | 2C/1T | 1C/4T | 3T | NT |
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Suppressive antimalarial activity of typical compounds for P. berghei infected rane mice. *Abbreviations used are I = Inactive, C = Cure, T = Toxic, NT = Not test
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| Compd. | ΔMST, cure, toxic or inactive at mg·kg-1, sc* |
| 5 | 10 | 20 | 40 | 80 | 160 | 320 | 640 |
| 3 | NT | NT | NT | I | I | 9.0 | 2T | 5T |
| 36 | I | I | 1C | 4C | 5C | 5C | 5C | 4C/1T |
| 41 | I | I | 3C | 5C | 5C | 5C | 5C | 4C/1T |
| 45 | I | I | 10.5 | 2C | 5C | 4C | 5T | 5T |
| 46 | I | 8.1 | 1C | 2C | 2C/1T | 1C/4T | 3T | NT |
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| Compd. | mg·kg-1 per day (×7), po | Molar primaquine index |
| 0.031 6 | 0.1 | 0.316 | 1.0 | 1.3 |
| 3 | NT | 0/2 C | 0/2 C | 1/2 C | 6/6 C | 1.0 |
| 36 | 0/2 C | 0/2 C | 2/2 C | 2/2 C | NT | 6.8 |
| 41 | 0/2 C | 2/4 C | 4/4 C | 2/2 C | NT | 12.8 |
| 45 | 0/3 C | 1/4 C | 3/3 C | 2/2 C | NT | NT |
| 46 | NT | NT | NT | NT | NT | NT |
), ArticleFig(id=1210517383983272627, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517372818034771, language=CN, label=Table 9, caption=
Radical curative antimalarial activity of typical compounds for P. cynomolgi infected rhesus monkeys. NT = Not test
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| Compd. | mg·kg-1 per day (×7), po | Molar primaquine index |
| 0.031 6 | 0.1 | 0.316 | 1.0 | 1.3 |
| 3 | NT | 0/2 C | 0/2 C | 1/2 C | 6/6 C | 1.0 |
| 36 | 0/2 C | 0/2 C | 2/2 C | 2/2 C | NT | 6.8 |
| 41 | 0/2 C | 2/4 C | 4/4 C | 2/2 C | NT | 12.8 |
| 45 | 0/3 C | 1/4 C | 3/3 C | 2/2 C | NT | NT |
| 46 | NT | NT | NT | NT | NT | NT |
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