4-(5-chloro-3-trifluoromethyl-1H-pyrazol-1-yl)anline | 245748-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-chloro-3-trifluoromethyl-1H-pyrazol-1-yl)anline
• 英文别名: 1-(4'-Aminophenyl)-5-chloro-3-trifluoromethylpyrazole；4-[5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]aniline；4-[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]aniline
• CAS: 245748-40-7
• 化学式: C₁₀H₇ClF₃N₃
• 分子量: 261.634
• InChiKey: RROQKYJSGZRYBP-UHFFFAOYSA-N

物化性质

• 沸点：
  335.6±42.0 °C(predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-甲基-1,2,3-噻二唑-5-羧酸 、 4-(5-chloro-3-trifluoromethyl-1H-pyrazol-1-yl)anline 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到4'-(5-chloro-3-trifluoromethyl-1H-pyrazol-1-yl)-4-methyl-1,2,3-thiadiazole-5-carboxanilide
  参考文献：
  名称：

  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

  摘要：

  From a series of 4 '-[(trifluoromethyl)pyrazol-1-yl]carboxanilides derived from 4-methyl-4 '-[3,5-bis(tri- fluoromethyl)-1H-pyrazol-1-yl]-1,2,3-thiadiazole-5-carboxanilide, one inhibited thapsigargin-induced Ca(2+) influx in Jurkat T cells (IC(50) = 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 (ED(50) = 1.3 mg/kg) p.o. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.047
• 作为产物：
  描述：

  1-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-ol 在 苯膦酰二氯 、 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 生成 4-(5-chloro-3-trifluoromethyl-1H-pyrazol-1-yl)anline
  参考文献：
  名称：

  3,5-Bis(trifluoromethyl)pyrazoles:  A Novel Class of NFAT Transcription Factor Regulator

  摘要：

  A series of bis(trifluoromethyl)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, cycloseorine and FK506, the BTPs do not directly inhibit the dephosphorylation of NFAT by calcineurin.

  DOI：

  10.1021/jm990615a

文献信息

• AZOLE INHIBITORS OF CYTOKINE PRODUCTION
  申请人：——

  公开号：US20010044445A1

  公开（公告）日：2001-11-22

  Compounds having the formula 1 are useful for treating diseases that are prevented by or ameliorated with Interleukin-2, Interleukin-4, or Interleukin-5 production inhibitors.

  具有以下化学式的化合物对于治疗由白细胞介素-2、白细胞介素-4或白细胞介素-5产生抑制剂预防或改善的疾病是有用的。
• Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：US06506747B1

  公开（公告）日：2003-01-14

  1-(4-aminophenyl)pyrazoles optionally substituted on the 3- and 5-positions of the pyrazole ring and on the amino group at the 4-position of the phenyl ring are disclosed and described, which pyrazoles inhibit IL-2 production in T-lymphocytes.

  所述的1-(4-氨基苯基)吡唑可以选择地在吡唑环的3-和5-位置以及苯环的4-位置上取代氨基团，并且这些吡唑抑制T淋巴细胞中的IL-2产生。
• US6506747B1
  申请人：——

  公开号：US6506747B1

  公开（公告）日：2003-01-14