65855-03-0Relevant academic research and scientific papers
Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: Design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties
Singh, Udaya Pratap,Bhat, Hans Raj,Verma, Amita,Kumawat, Mukesh Kumar,Kaur, Rajinder,Gupta,Singh, Ramendra K.
, p. 17335 - 17348 (2013/09/24)
A novel series of phenyl hydrazone bearing pyrazole and pyrimidine hybrid compounds has been designed using the molinspiration toolkit based on Lipinski's rule of five and developed via sequential reactions starting from the diazotization of different anilines and further active methylation with acetyl acetone, ethyl acetoacetate and ethyl cyanoacetate to generate hydrazono derivatives. The target hybrid compounds were synthesized on cyclisation of the resulting hydrazono derivatives with hydrazine, phenyl hydrazine and urea. These molecules have been subsequently tested for anti-HIV activity using TZM-bl cell lines. The MTT assay was also carried out for the cytotoxicity determination of the active compounds. Further, to exemplify the key structural features of the molecules, a molecular docking analysis of the most active compounds was performed at the NNIBP of the HIV-RT protein. The antibacterial activity of the target compounds was also determined against a panel of four Gram-positive and four Gram-negative human pathogens. All molecules showed a potent anti-HIV activity along with a prominent inhibition of bacterial organisms.
Synthesis and antimicrobial evaluation of novel pyrazolones and pyrazolone nucleosides
Hassan, Abdalla E. A.,Moustafa, Ahmed H.,Tolbah, Mervat M.,Zohdy, Hussein F.,Haikal, Abdelfattah Z.
, p. 783 - 800 (2013/01/16)
The synthesis of a novel series of 4-Arylhydrazono-5-methyl-1,2- dihydropyrazol-3-ones 4a-h, and their N 2-Alkyl and acyclo, glucopyranosyl, and ribofuranosyl derivatives is described. K2CO 3 catalyzed alkylation of 4a-h with allyl bromide, propargyl bromide, 4-bromobutyl acetate, 2-Acetoxyethoxymethyl bromide, and 2,3,4,6-tetra-O- Acetyl-D-glucopyranosyl bromide proceeded selectively at the N 2-position of the pyrazolinone ring. Glycosylation of 4a with 1,2,3,5-tetra-O-Acetyl-D-ribofuranose under Vorbruggen glycosylation conditions gave the corresponding N 2-4-Arylhydrazonopyrazolone ribofuranoside 9a in good yield. Conventional deprotection of the acetyl protected nucleosides furnished the corresponding 4-Arylhydrazonopyrazolone nucleosides in good yields. Selected numbers of the newly synthesized compounds were screened for antimicrobial activity. Compounds 4b, 12a, and 14d showed moderate activities against Aspergillus flavus, Penicillium sp., and Escherichia coli.
