9-Benzyl-6-(dimethylamino)-9H-purines with antirhinovirus activity
A series of 9-benzyl-6-(dimethylamino)-9H-purines and 9-benzyl-2-chloro-6-(dimethylamino)-9H-purines were synthesized and tested in cell culture for activity against rhinovirus type 1B. The 9-benzylpurines that were unsubstituted in the 2-position had weak activity. However, introduction of a 2-chlo...
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| Veröffentlicht in: | Journal of medicinal chemistry 1988-10, Vol.31 (10), p.2001-2004 |
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| container_end_page | 2004 |
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| container_issue | 10 |
| container_start_page | 2001 |
| container_title | Journal of medicinal chemistry |
| container_volume | 31 |
| creator | Kelley, James L Linn, James A Krochmal, Mark P Selway, J. W. T |
| description | A series of 9-benzyl-6-(dimethylamino)-9H-purines and 9-benzyl-2-chloro-6-(dimethylamino)-9H-purines were synthesized and tested in cell culture for activity against rhinovirus type 1B. The 9-benzylpurines that were unsubstituted in the 2-position had weak activity. However, introduction of a 2-chloro substituent resulted in a substantial increase in antiviral activity. One of the most active compounds, 2-chloro-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purine (29), had an IC50 value of 0.08 microM against serotype 1B. Four compounds were tested against 18 other rhinovirus serotypes, but the majority tested were less sensitive than type 1B. The range of serotype sensitivity for 29 varied from 0.08 to 14 microM. These 9-benzyl-2-chloro-9H-purines represent a new class of antiviral agents with in vitro activity against rhinoviruses. |
| doi_str_mv | 10.1021/jm00118a025 |
| format | Article |
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W. T</creatorcontrib><title>9-Benzyl-6-(dimethylamino)-9H-purines with antirhinovirus activity</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of 9-benzyl-6-(dimethylamino)-9H-purines and 9-benzyl-2-chloro-6-(dimethylamino)-9H-purines were synthesized and tested in cell culture for activity against rhinovirus type 1B. The 9-benzylpurines that were unsubstituted in the 2-position had weak activity. However, introduction of a 2-chloro substituent resulted in a substantial increase in antiviral activity. One of the most active compounds, 2-chloro-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purine (29), had an IC50 value of 0.08 microM against serotype 1B. Four compounds were tested against 18 other rhinovirus serotypes, but the majority tested were less sensitive than type 1B. The range of serotype sensitivity for 29 varied from 0.08 to 14 microM. 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W. T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>9-Benzyl-6-(dimethylamino)-9H-purines with antirhinovirus activity</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1988-10-01</date><risdate>1988</risdate><volume>31</volume><issue>10</issue><spage>2001</spage><epage>2004</epage><pages>2001-2004</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>A series of 9-benzyl-6-(dimethylamino)-9H-purines and 9-benzyl-2-chloro-6-(dimethylamino)-9H-purines were synthesized and tested in cell culture for activity against rhinovirus type 1B. The 9-benzylpurines that were unsubstituted in the 2-position had weak activity. However, introduction of a 2-chloro substituent resulted in a substantial increase in antiviral activity. One of the most active compounds, 2-chloro-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purine (29), had an IC50 value of 0.08 microM against serotype 1B. 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| subjects | Anticonvulsants - pharmacology Antiviral Agents - pharmacology Chemistry Cytopathogenic Effect, Viral Exact sciences and technology HeLa Cells - drug effects Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Humans Organic chemistry Preparations and properties Purines - pharmacology rhinovirus Rhinovirus - drug effects Structure-Activity Relationship |
| title | 9-Benzyl-6-(dimethylamino)-9H-purines with antirhinovirus activity |
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