Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs
A series of 5-alkylthio (2a-d), 4-arylideneamino (3a-d) and 4-arylideneamino- 5-alkylthio derivatives (4a-f) of 4-amino-3-(2-furyl)-5-mercapto-1,2,4-triazole (1) were synthesized by alkylation of the parent compound with alkyl halides and condensation with aldehydes, respectively. Sulfanyl dimers 5a...
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| Format: | Article |
| Language: | English |
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MDPI AG
2007-08-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/12/8/2003/ |
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| author | Erik De Clercq Myriam Witvrouw Christophe Pannecouque Wenfang Xu Zhong Li Defeng Wang Yuan Cao Xianchao Cheng Xinyong Liu Jingde Wu |
| author_facet | Erik De Clercq Myriam Witvrouw Christophe Pannecouque Wenfang Xu Zhong Li Defeng Wang Yuan Cao Xianchao Cheng Xinyong Liu Jingde Wu |
| author_sort | Erik De Clercq |
| collection | DOAJ |
| description | A series of 5-alkylthio (2a-d), 4-arylideneamino (3a-d) and 4-arylideneamino- 5-alkylthio derivatives (4a-f) of 4-amino-3-(2-furyl)-5-mercapto-1,2,4-triazole (1) were synthesized by alkylation of the parent compound with alkyl halides and condensation with aldehydes, respectively. Sulfanyl dimers 5a-d and 4-iminomethyl dimer 6 were correspondingly prepared by reaction with alkane dibromides and 1,4-diformylbenzene. Mannich base 7 was also synthesized by aminomethylation of the 3-sulfanyltriazole 1 at the N1 position. The newly designed and synthesized substituted s-triazole derivatives were assayed for anti-HIV-1 activity by examination of their inhibition of HIV-1-induced cytopathogenicity in MT-4 cells and by determination of their inhibitory effect on HIV-1 reverse transcriptase. Compound 4e was found to be the most active inhibitor against HIV- 1 replication in cell culture (EC50 = 12 μM) and against HIV-1 reverse transcriptase (IC50 = 43.5 μM), which provided a good lead for further optimization. |
| first_indexed | 2024-12-11T03:01:06Z |
| format | Article |
| id | doaj.art-b9f21403d5374539a880563a9279c310 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T03:01:06Z |
| publishDate | 2007-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b9f21403d5374539a880563a9279c3102022-12-22T01:23:03ZengMDPI AGMolecules1420-30492007-08-011282003201610.3390/12082003Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIsErik De ClercqMyriam WitvrouwChristophe PannecouqueWenfang XuZhong LiDefeng WangYuan CaoXianchao ChengXinyong LiuJingde WuA series of 5-alkylthio (2a-d), 4-arylideneamino (3a-d) and 4-arylideneamino- 5-alkylthio derivatives (4a-f) of 4-amino-3-(2-furyl)-5-mercapto-1,2,4-triazole (1) were synthesized by alkylation of the parent compound with alkyl halides and condensation with aldehydes, respectively. Sulfanyl dimers 5a-d and 4-iminomethyl dimer 6 were correspondingly prepared by reaction with alkane dibromides and 1,4-diformylbenzene. Mannich base 7 was also synthesized by aminomethylation of the 3-sulfanyltriazole 1 at the N1 position. The newly designed and synthesized substituted s-triazole derivatives were assayed for anti-HIV-1 activity by examination of their inhibition of HIV-1-induced cytopathogenicity in MT-4 cells and by determination of their inhibitory effect on HIV-1 reverse transcriptase. Compound 4e was found to be the most active inhibitor against HIV- 1 replication in cell culture (EC50 = 12 μM) and against HIV-1 reverse transcriptase (IC50 = 43.5 μM), which provided a good lead for further optimization.http://www.mdpi.com/1420-3049/12/8/2003/s-TriazoleAlkylationAminomethylationSynthesisHIV-1 NNRTIs |
| spellingShingle | Erik De Clercq Myriam Witvrouw Christophe Pannecouque Wenfang Xu Zhong Li Defeng Wang Yuan Cao Xianchao Cheng Xinyong Liu Jingde Wu Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs Molecules s-Triazole Alkylation Aminomethylation Synthesis HIV-1 NNRTIs |
| title | Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs |
| title_full | Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs |
| title_fullStr | Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs |
| title_full_unstemmed | Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs |
| title_short | Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs |
| title_sort | synthesis of novel derivatives of 4 amino 3 2 furyl 5 mercapto 1 2 4 triazole as potential hiv 1 nnrtis |
| topic | s-Triazole Alkylation Aminomethylation Synthesis HIV-1 NNRTIs |
| url | http://www.mdpi.com/1420-3049/12/8/2003/ |
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