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Molecules 2007, 12(8), 2003-2016; doi:10.3390/12082003
Article

Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs

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Received: 21 July 2007; in revised form: 17 August 2007 / Accepted: 20 August 2007 / Published: 22 August 2007
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Abstract: 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.
Keywords: s-Triazole; Alkylation; Aminomethylation; Synthesis; HIV-1 NNRTIs s-Triazole; Alkylation; Aminomethylation; Synthesis; HIV-1 NNRTIs
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Wu, J.; Liu, X.; Cheng, X.; Cao, Y.; Wang, D.; Li, Z.; Xu, W.; Pannecouque, C.; Witvrouw, M.; De Clercq, E. Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs. Molecules 2007, 12, 2003-2016.

AMA Style

Wu J, Liu X, Cheng X, Cao Y, Wang D, Li Z, Xu W, Pannecouque C, Witvrouw M, De Clercq E. Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs. Molecules. 2007; 12(8):2003-2016.

Chicago/Turabian Style

Wu, Jingde; Liu, Xinyong; Cheng, Xianchao; Cao, Yuan; Wang, Defeng; Li, Zhong; Xu, Wenfang; Pannecouque, Christophe; Witvrouw, Myriam; De Clercq, Erik. 2007. "Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIs." Molecules 12, no. 8: 2003-2016.


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