Journal ArticleDOI
Novel heterocyclic nitrofurfural hydrazones. In vivo antitrypanosomal activity
Novinsion T,Bhooshan B,Takayuki Okabe,G. R. Revankar,Roland K. Robins,Keitaro Senga,H. R. Wilson +6 more
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TLDR
An interesting structure-activity relationship was uncovered, revealing that 5-methyl-7-(5-nitrofurfurylidenehydrazino)pyrazolo[1,5-alpha]pyrimidine (2d) greatly increased the mean survival time (IMST) of mice with terminal infections.Abstract:
Hydrazine derivatives of several pyrazolo[1,5-alpha]pyrimidines (A), pyrazolo[1,5-alpha]-1,3,5-triazines (B), s-triazolo[1,5-alpha]pyrimidines (C), and imidazo[1,2-alpha]pyrimidines (D) were synthesized and condensed with 5-nitrofurfural in order to obtain the corresponding nitrofurfural hydrazones of each heterocycle (1d-14d). Each compound was screened for in vitro activity against Trypanosoma cruzi. The compounds were then tested in vivo against experimental infections of T. cruzi in laboratory (C3H/He strain) mice. An interesting structure-activity relationship was uncovered, revealing that 5-methyl-7-(5-nitrofurfurylidenehydrazino)pyrazolo[1,5-alpha]pyrimidine (2d) greatly increased the mean survival time (IMST) of mice with terminal infections. Subtle alterations in the structure of 2d, such as the substitution of a 5-hydrogen for the 5-methyl group (1d) or the substitution of the 3-hydrogen by the water-soluble 3-sulfonic acid (3d) or 3-sodium sulfonate (4d), resulted in a drastic loss of in vivo and in vitro activity.read more
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Patent
1,2,3-Trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
Robert M. Jones,Graeme Semple,Fioravanti Beatriz,Guilherme Pereira,Imelda Calderon,Uy Jane,Duvvuri Kameshwari,Choi Jin Sun Karoline,Yifeng Xiong,Dave Vibha,Azimioara Mihai D +10 more
TL;DR: In this article, aryl and heteroaryl derivatives of Fomula (Ia) have been used in the prophylaxis or treatment of metabolic disorders and complications thereof, such as diabetes and obesity.
Patent
Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto
Robert M. Jones,Graeme Semple,Yifeng Xiong,Young-Jun Shin,Albert S. Ren,Imelda Calderon,Fioravanti Beatriz,Choi Jin Sun Karoline,Carleton R. Sage +8 more
TL;DR: In this paper, the authors proposed a modification of Formula (I) that is useful in the prophylaxis or treatment of metabolic disorders and complications thereof, such as, diabetes and obesity.
Journal ArticleDOI
An insight on synthetic and medicinal aspects of pyrazolo[1,5-a]pyrimidine scaffold
Srinivasulu Cherukupalli,Rajshekhar Karpoormath,Balakumar Chandrasekaran,Girish A. Hampannavar,Neeta Thapliyal,Venkata Narayana Palakollu +5 more
TL;DR: Current review is the first attempt made towards the compilation of significant advances made on pyrazolo[1,5-a]pyrimidines reported since 1980s and extensively reveals significant biological properties along with SAR studies.
Book ChapterDOI
Chemistry of Pyrazolopyrimidines
TL;DR: In this paper, the chemistry and biological properties of pyrazolopyrimidines and pyrazolo[3,4-d]pyrimidine were discussed. But the authors focused on theoretical methods, spectra, and tautomerism.
Journal ArticleDOI
Purine analog inhibitors of xanthine oxidase: structure activity relationships and proposed binding of the molybdenum cofactor
Roland K. Robins,G. R. Revankar,Darrell E. O'Brien,Robert H. Springer,Thomas Novinson Anthony Albert,Keitaro Senga,Jon P. Miller,David G. Streeter +7 more
TL;DR: In this article, a number of new hypoxanthine analogs have been prepared as substrate inhibitors of xanthine oxidase, and the structure-activity relationships of these new phenyl substitutions are discussed and compared with the 3-m-tolyl- and 3-phenyl-7-hydroxypyrazolo[1,5-a]pyrimidin-5-ones.