Hua Chen

Design, microwave-assisted synthesis and HIV-RT inhibitory activity of 2-(2,6-dihalophenyl)-3-(4,6-dimethyl-5-(un)substituted-pyrimidin-2-yl)thiazolidin-4-ones

A series of novel thiazolidin-4-ones bearing a hydrophobic substituent at 5-position on the 4,6-dimethyl-pyrimidine ring at N-3 (5c-i and 6c-i) were designed on the prediction of QSAR studies, synthesized in good yields of 60.1-85.3% by microwave-assisted one-pot protocol with the combination of using dicyclohexylcarbonimide (DCC) as the promotor, and evaluated as HIV-1 reverse transcriptases inhibitors. The results of in vitro HIV-1 RT kit assay showed that some of the new compounds, such as 5c, 6c, 5d, 6d, 5g, 5h and 6i, could effectively inhibit RT activity. Among them, compounds 5c and 6c where ethyl group existed at 5-position on N-3 pyrimidine ring were the best ones with the IC(50) value of 0.26 microM and 0.23 microM, respectively. Structure-activity relationship analysis of these analogues suggested that the overall hydrophobicity and steric factor were important to the anti-HIV RT activity. The mechanism of the intramolecular cycloamidation promoted by DCC was also investigated with the key uncyclized intermediate 13.

Direct and Convenient Method of Regioselective Benzylation of Methyl α‐D‐Glucopyranoside

Abstract A facile and convenient method for the direct preparation of methyl 2,3,6‐tri‐O‐benzyl‐α‐D‐glucopyranoside (2) by the regioselective benzylation of methyl α‐D‐glucopyranoside (1) with benzyl bromide in the presence of mild bases K2CO3 and KOH (1∶1) without solvents is reported.

Convenient, Microwave-Assisted, One-Pot Synthesis of Photochromic Fulgimides Bearing Reactive Groups

A convenient, microwave-assisted, one-pot synthesis of the fulgimides (3) bearing reactive groups on N-substituents from the corresponding fulgides (1a–d) and amines (2a–e) is described. The synthesis provided the functionalized fulgimides (3) in yields of 50–84% under microwave irradiation within 25 min in the presence of 4-dimethylaminopyridine (DMAP) and dicyclohexylcarbodiimide (DCC).

Microwave-assisted synthesis of dinucleoside analogues containing a thiazolidin-4-one linkage via one-pot tandem Staudinger/aza-Wittig/cyclization

Dinucleosides containing a thiazolidin-4-one linkage were prepared by one-pot tandem Staudinger/aza-Wittig/intermolecular cyclization under microwave irradiation and their structures were confirmed. Preliminary examination of HIV-RT inhibition showed that the dinucleosides containing (R)-thiazolidin-4-one linkage are significantly more active than those containing (S)-thiazolidin-4-one linkage.