2'-chloro-5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxyanilide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2'-chloro-5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxyanilide
• 英文别名: N-(2-chlorophenyl)-5-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]thiophene-2-carboxamide
• 化学式: C₁₆H₁₁ClF₃N₃OS
• 分子量: 385.797
• InChiKey: IWYBZGILVOYCDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-甲基-5-(2-噻吩基)-3-三氟甲基-1H-吡唑 在 吡啶 、 sodium hydroxide 、 正丁基锂 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 7.25h， 生成 2'-chloro-5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxyanilide
  参考文献：
  名称：

  Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 1: Synthesis and inhibitory activity of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides

  摘要：

  We synthesized and evaluated a series of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides to identify potent inhibitors of calcium-release-activated calcium (CRAC) channels with greater selectivity than voltage-operated calcium (VOC) channels. These efforts resulted in identification of compounds 22 and 24. The former exhibits highly potent and selective CRAC channel inhibitory activity, and the latter inhibited phytohemagglutinin-induced interleukin-2 production by Jurkat T lymphocytes and concanavalin A-induced hepatitis in mice. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.024

文献信息

• Pharmaceutical compound comprising a pyrazole derivative and methods of using the same for the treatment of calcium release-activated calcium channel associated diseases
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US06348480B1

  公开（公告）日：2002-02-19

  The present invention is directed to drugs, in particular, pyrazole derivatives represented by the following general formula (I) which have a calcium release-activated calcium channel inhibitory effect and medicinal compositions, in particular, calcium release-activated calcium channel inhibitors containing the above compounds as the active ingredient, wherein each substituent is defined in the specification. The present invention also relates to a pharmaceutical composition containiing an effective amount of the compound of formula (I) and a pharmaceutically effective carrier. The present invention further relates to methods of treatment of diseases associated with calcium release-activated calcium channels, diseases associated with IL-2 production, and methods of treatment of allergic, inflammatory or auto-immune diseases.

  本发明涉及药物，特别是由以下一般式（I）表示的吡唑衍生物，其具有钙释放激活的钙通道抑制作用和药用组合物，特别是含有上述化合物作为活性成分的钙释放激活的钙通道抑制剂，其中每个取代基在规范中定义。本发明还涉及含有一定量的式（I）化合物和药效载体的药用组合物。本发明还涉及与钙释放激活的钙通道相关的疾病、与IL-2产生相关的疾病以及过敏、炎症或自身免疫疾病的治疗方法。
• Pyrazole derivative
  申请人：——

  公开号：US20010011090A1

  公开（公告）日：2001-08-02

  Drugs, in particular, pyrazole derivatives represented by the following general formula (I) which have a calcium release-dependent calcium channel inhibitory effect and medicinal compositions, in particular, calcium release-dependent calcium channel inhibitors containing the above compounds as the active ingredient, 1 (in the formula, each symbol has the following meaning: B: phenylene, a nitrogen-containing, divalent, saturated ring group, or a monocyclic, divalent heteroaromatic ring group which may be substituted with Alk, X: —NR 1 —CR 2 R 3 —, —CR 2 R 3 —NR 1 —, —NR 1 SO 2 —, —SO 2 —NR 1 — or —CR 4 ═CR 5 —, and A: benzene ring which may have one or more substituents; mono-, di- or tricyclic fused heteroaryl which may have one or more substituents; cycloalkyl which may have one or more substituents; a nitrogen-containing, saturated ring group which may have one or more substituents; lower alkenyl which may have one or more substituents; lower alkynyl which may have one or more substituents; or Alk which may have one or more substituents).

  药物，特别是由以下一般公式（I）代表的吡唑衍生物，具有依赖钙释放的钙通道抑制作用和药用组合物，特别是含有上述化合物作为活性成分的依赖钙释放的钙通道抑制剂，1（在公式中，每个符号具有以下含义：B：苯基，含氮，二价，饱和环基，或带有Alk取代基的单环，二价杂芳环基；X：—NR1—CR2R3—，—CR2R3—NR1—，—NR1SO2—，—SO2—NR1—或—CR4═CR5—，和A：苯环，可能具有一个或多个取代基；单环、双环或三环融合的杂芳基，可能具有一个或多个取代基；可能具有一个或多个取代基的环烷基；可能具有一个或多个取代基的含氮饱和环基；可能具有一个或多个取代基的低烯基；可能具有一个或多个取代基的低炔基；或可能具有一个或多个取代基的Alk）。
• Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 1: Synthesis and inhibitory activity of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides
  作者：Yasuhiro Yonetoku、Hirokazu Kubota、Yoshinori Okamoto、Akira Toyoshima、Masashi Funatsu、Jun Ishikawa、Makoto Takeuchi、Mitsuaki Ohta、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2006.03.024

  日期：2006.7.15

  We synthesized and evaluated a series of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides to identify potent inhibitors of calcium-release-activated calcium (CRAC) channels with greater selectivity than voltage-operated calcium (VOC) channels. These efforts resulted in identification of compounds 22 and 24. The former exhibits highly potent and selective CRAC channel inhibitory activity, and the latter inhibited phytohemagglutinin-induced interleukin-2 production by Jurkat T lymphocytes and concanavalin A-induced hepatitis in mice. (c) 2006 Elsevier Ltd. All rights reserved.