16459-44-2Relevant academic research and scientific papers
The optimization and characterization of functionalized sulfonamides derived from sulfaphenazole against Mycobacterium tuberculosis with reduced CYP 2C9 inhibition
Chen, Hui,Wang, Bin,Li, Peng,Yan, Hong,Li, Gang,Huang, Haihong,Lu, Yu
supporting information, (2021/03/26)
In this study, a series of sulfonamide compounds was designed and synthesized through the systematic optimization of the antibacterial agent sulfaphenazole for the treatment of Mycobacterium tuberculosis (M. tuberculosis). Preliminary results indicate that the 4-aminobenzenesulfonamide moiety plays a key role in maintaining antimycobacterial activity. Compounds 10c, 10d, 10f and 10i through the optimization on phenyl ring at the R2 site on the pyrazole displayed promising antimycobacterial activity paired with low cytotoxicity. In particular, compound 10d displayed good activity (MIC = 5.69 μg/mL) with low inhibition of CYP 2C9 (IC50 > 10 μM), consequently low potential risk of drug-drug interaction. These promising results provide new insight into the combination regimen using sulfonamide as one component for the treatment of M. tuberculosis.
VILSMEIER-HAACK REACTION OF 5-AMINO- AND 5-ACYLAMINO-PYRAZOLES
Simay, A.,Takacs, K.,Horvath, K.,Dvortsak, P.
, p. 127 - 140 (2007/10/02)
The Vilsmeier-Haack reaction of 5-aminopyrazole derivatives 1 was investigated in view of contradictory literature reports.Structure 2 of the products was proved both chemically and spectroscopically.The mechanism of the reaction was postulated on the basis of isolated intermediates 7 and 8. 5-Acylaminopyrazoles 9, 10 and 11 were found to give also 2 (and 7) under the Vilsmeier conditions by an acyl splitting reaction, proceeding probably via diacylamino derivatives 12.Compounds 2 provided a simple route to pyrazolopyrimidine derivatives 13 and 14 as well as to azomethine compounds 15-18.
