245745-65-7Relevant academic research and scientific papers
Microwave-assisted and continuous flow multistep synthesis of 4-(pyrazol-1-yl)carboxanilides
Obermayer, David,Glasnov, Toma N.,Kappe, C. Oliver
, p. 6657 - 6669 (2011/10/18)
A series of 4-(pyrazol-1-yl)carboxanilides active as inhibitors of canonical transient receptor potential channels were synthesized in an efficient three-step protocol using controlled microwave heating. The general synthetic strategy involves condensation of 4-nitrophenylhydrazine with appropriate 1,3-dicarbonyl building blocks, followed by reduction of the nitro group to the amine, which is then amidated with carboxylic acids. Compared to the conventional protocol a dramatic reduction in overall processing time from ～2 days to a few minutes was achieved, accompanied by significantly improved product yields. In addition, the first two steps in the synthetic pathway were also performed under continuous flow conditions providing similar isolated product yields. As an alternative to the three-step protocol, a novel two-step route to the desired 4-(pyrazol-1-yl)carboxanilides was devised involving condensation of 4-bromophenylhydrazine with appropriate 1,3-dicarbonyl building blocks, followed by Pd-catalyzed Buchwald-Hartwig amidation with carboxylic acid amides.
Novel potent and selective Ca2+ release-activated Ca2+ (CRAC) channel inhibitors. Part 3: Synthesis and CRAC channel inhibitory activity of 4′-[(trifluoromethyl)pyrazol-1-yl]carboxanilides
Yonetoku, Yasuhiro,Kubota, Hirokazu,Miyazaki, Yoji,Okamoto, Yoshinori,Funatsu, Masashi,Yoshimura-Ishikawa, Noriko,Ishikawa, Jun,Yoshino, Taiji,Takeuchi, Makoto,Ohta, Mitsuaki
experimental part, p. 9457 - 9466 (2009/04/07)
From a series of 4'-[(trifluoromethyl)pyrazol-1-yl]carboxanilides derived from 4-methyl-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-1,2,3-thiadiazole-5-carboxanilide, one inhibited thapsigargin-induced Ca2+ influx in Jurkat T cells (IC50 = 77 nM) and exhibited high selectivity for the CRAC channel over the VOC channel (index: >130). Another acted as an inhibitor for both T lymphocyte activation-induced diseases and ovalbumin-induced airway eosinophilia in rats (ED50 = 1.3 mg/kg) p.o.
AZOLE INHIBITORS OF CYTOKINE PRODUCTION
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, (2008/06/13)
Compounds having the formula are useful for treating diseases that are prevented by or ameliorated with Interleukin-2, Interleukin-4, or Interleukin-5 production inhibitors.
3,5-Bis(trifluoromethyl)pyrazoles: A novel class of NFAT transcription factor regulator
Djuric,Wiedeman,Zhou,Ballaron,Bauch,Chen,Chiou,Fey,Gauvin,Gubbins,Hsieh,Bamaung,Marsh,Mollison,Pong,Shaughnessy,Sheets,Smith,Trevillyan,Warrior,Wegner,Carter,Basha,Liu,Luly,Madar,Sciotti,Tu,Wagenaar
, p. 2975 - 2981 (2007/10/03)
A series of bis(trifiuoromethyl)pyrazoles (BTPs) has been found to be a novel inhibitor of cytokine production. Identified initially as inhibitors of IL-2 synthesis, the BTPs have been optimized in this regard and even inhibit IL-2 production with a 10-fold enhancement over cyclosporine in an ex vivo assay. Additionally, the BTPs show inhibition of IL-4, IL-5, IL-8, and eotaxin production. Unlike the IL-2 inhibitors, cyclosporine and FK506, the BTPs do not directly inhibit the dephosphorylation of NFAT by calcineurin.
