1225464-96-9Relevant academic research and scientific papers
Synthesis and Anti-HIV Activity of Aryl-2-[(4-cyanophenyl)amino]-4-pyrimidinone hydrazones as Potent Non-nucleoside Reverse Transcriptase Inhibitors
Ma, Xiao-Dong,Yang, Shi-Qiong,Gu, Shuang-Xi,He, Qiu-Qin,Chen, Fen-Er,DeClercq, Erik,Balzarini, Jan,Pannecouque, Christophe
, p. 2225 - 2232 (2012/04/11)
A series of novel diarylpyrimidines (DAPYs) with a ketone hydrazone substituent on the methylene linker between the pyrimidine nucleus and the aryl moiety at the C-4 position were synthesized, and their antiviral activity against human immunodeficiency virus (HIV)-1 in MT-4 cells was evaluated. Most compounds of this class exhibited excellent activity against wild-type HIV-1, with EC50 values in the range of 1.7-13.2nM. Of these compounds, 2-bromophenyl-2-[(4-cyanophenyl)amino]-4-pyrimidinone hydrazone (9k) displayed the most potent anti-HIV-1 activity (EC50=1.7±0.6nM), with excellent selectivity for infected over uninfected cells (SI=5762). In addition, the 4-methyl phenyl analogue 9d (EC50=2.4±0.2nM, SI=18461) showed broad spectrum HIV inhibitory activity, with EC50 values of 2.4±0.2nM against wild-type HIV-1, 5.3±0.4μM against HIV-1 double-mutated strain RES056 (K103N+Y181C), and 5.5μM against HIV-2 ROD strain. Furthermore, structure-activity relationship (SAR) data and molecular modeling results for these compounds are also discussed. Antiviral agents: A series of new diarylpyrimidine (DAPY) derivatives with a ketone hydrazine substituent on the CH2 linker between the pyrimidine nucleus and the phenyl ring were synthesized, and their anti-HIV activity in MT-4 cells was evaluated. Most compounds of this class exhibited excellent activity against wild-type HIV-1, with EC50 values in the range of 1.7-13.2nM.
Synthesis and biological evaluation of 4-(hydroxyimino)arylmethyl diarylpyrimidine analogues as potential non-nucleoside reverse transcriptase inhibitors against HIV
Feng, Xiao-Qing,Zeng, Zhao-Sen,Liang, Yong-Hong,Chen, Fen-Er,Pannecouque, Christophe,Balzarini, Jan,Clercq, Erik De
experimental part, p. 2370 - 2374 (2010/06/16)
A series of novel diarylpyrimidine analogues featuring a hydroxyiminomethyl group between the pyrimidine scaffold and the aryl wing I have been synthesized and tested in MT-4 cells culture as non-nucleoside reverse transcriptase inhibitors against human immunodeficiency virus (HIV). Most of these new congeners exhibited moderate to excellent activity against wild-type virus with an EC50 value ranging from 0.569 μM to 0.005 μM. 4-(4-((Hydroxyimino) (3-methoxyphenyl)methyl)pyrimidin-2-ylamino)benzonitrile (12n) was identified as the most active compound of this new series (EC50 = 0.025 μM, SI >1223) associated with moderate activity against HIV-1 double mutant strains (K103N + Y181C) (EC50 = 8.72 μM) in addition to its anti-HIV-2 activity with an EC50 value of 8.31 μM. Preliminary structure-activity relationship (SAR) among the newly synthesized DAPYs was also investigated.
