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Full Open Access Publishing Policy Imposed in 2007: Molecules Publishes Many More Papers This Year – More than 2000 Pages Published up to Issue 8
Molecules 2007, 12(8), 2003-2016; doi:10.3390/12082003

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

1, 1,* , 1, 1, 1, 1, 1, 2, 2 and 2
1 Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No.44, Wenhuaxi Road, Jinan, 250012, P.R. China 2 Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000 Leuven, Belgium
* Author to whom correspondence should be addressed.
Received: 21 July 2007 / Revised: 17 August 2007 / Accepted: 20 August 2007 / Published: 22 August 2007
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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 (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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