5-(5-chloro-thiophen-2-yl)-1-(2',4'-dichloro-phenyl)-4-methyl-1H-pyrazol-3-carboxylic acid ethyl ester | 869891-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(5-chloro-thiophen-2-yl)-1-(2',4'-dichloro-phenyl)-4-methyl-1H-pyrazol-3-carboxylic acid ethyl ester
• 英文别名: 5-(5-chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester；5-(5-chlorothiophen-2-yl)-1-(2',4'-dichloro-phenyl)-4-methyl-1H-pyrazol-3-carboxylic acid ethyl ester；5-(5-chlorothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester；Ethyl 5-(5-chlorothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylate
• CAS: 869891-50-9
• 化学式: C₁₇H₁₃Cl₃N₂O₂S
• 分子量: 415.727
• InChiKey: UQVBWSNFHQDZIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(5-chloro-thiophen-2-yl)-1-(2',4'-dichloro-phenyl)-4-methyl-1H-pyrazol-3-carboxylic acid ethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Hair growth stimulator property of thienyl substituted pyrazole carboxamide derivatives as a cb1 receptor antagonist with in vivo antiobesity effect

  摘要：

  A few thienyl substituted pyrazole derivatives were synthesized to aid in the characterization of the cannabinoid receptor antagonist and also to serve as potentially useful antiobesity agent. Structural requirements for selective CB1 receptor antagonistic activity of 5-thienyl pyrazole derivatives included the structural similarity with potent, specific antagonist rimonabant 1. Compound 3 has been identified as a hair growth stimulator and an antiobesity agent in animal models. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.046
• 作为产物：
  描述：

  以 溶剂黄146 为溶剂， 反应 24.0h， 生成 5-(5-chloro-thiophen-2-yl)-1-(2',4'-dichloro-phenyl)-4-methyl-1H-pyrazol-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Bioisosteric Replacement of the Pyrazole 5-Aryl Moiety of N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A). A Novel Series of Alkynylthiophenes as Potent and Selective Cannabinoid-1 Receptor Antagonists

  摘要：

  Replacing the conventional pyrazole 5-aryl substituent of 1 (SR141716A) with the 2-thienyl rnoiety appended with ail appropriate alkynyl unit, a novel class of 5-(5-alkynyl-2-thienyl)pyrazole derivatives, behaving as highly potent CB1 receptor antagonists with good CB1/2 selectivity, was discovered, many of which, its typified by compound 18, showed significant weight reduction in diet-indUced obese Mouse model, thus pharmacologically validating that the bioisosteric replacement described above is viable. Also encouraging was the finding that a subtle structural modification of the newly developed series could result in a distinct difference in the intrinsic property, as demonstrated by compounds 12 (NA) and its methylated structural isomers 15 (PA) and 18 (IA). Moreover, current structure-activity relationship Studies revealed that around the pyrazole 5-position of 1, a deep and flat crevice surrounded by a sequence of hydrophobic/aromatic residues as indicated by the CB I-receptor homology model might exist in the binding site.

  DOI：

  10.1021/jm800066v

文献信息

• PYRAZOLE COMPOUNDS
  申请人：Shia Kak-Shan

  公开号：US20080090809A1

  公开（公告）日：2008-04-17

  This invention relates to pyrazole compounds of formula (I) shown below: Each variable in formula (I) is defined in the specification. These compounds can be used to treat cannabinoid-receptor mediated disorders.

  这项发明涉及下面所示的式(I)的吡唑化合物：式(I)中的每个变量在说明书中有定义。这些化合物可用于治疗大麻素受体介导的疾病。
• THIOPHENE COMPOUNDS
  申请人：Shia Kak-Shan

  公开号：US20080090810A1

  公开（公告）日：2008-04-17

  This invention relates to thiophene compounds of formula (I) shown below: Each variable in formula (I) is defined in the specification. These compounds can be used to treat cannabinoid-receptor mediated disorders.

  本发明涉及如下所示的公式（I）的噻吩化合物：公式（I）中的每个变量在规范中有定义。这些化合物可用于治疗大麻素受体介导的疾病。
• Pharmaceutical compounds
  申请人：Lazzari Paolo

  公开号：US20050261281A1

  公开（公告）日：2005-11-24

  Pyrazole derivatives of the following formula (I), having affinity for the cannabinoidergic CB1 and/or CB2 receptors: wherein: R is a group selected from: C 1 -C 10 alkyl; aryl, arylalkyl or arylalkenyl, not substituted or having from one to four substituents, equal to or different from each other; A is a group selected from the following: an ether group of formula —(CH 2 )—O—(CH 2 ) v —R″ wherein v is equal to 1 or 2; R″ is as defined in the present application; a ketone group of formula —C(O)-Z′, wherein Z′ is as defined in the present application; a substituent having an hydroxyl function of formula —CH(OH)-Z′, Z′ being as defined in the present application; Description of the industrial invention in the name of: NEUROSCIENZE S.c. a r.l., of Italian nationality, with head office in Cagliari, via Palabanda 9.

  以下式子（I）的吡唑衍生物具有对大麻素受体CB1和/或CB2的亲和力：其中：R是以下组中选择的一组：C1-C10烷基；芳基，芳基烷基或芳基烯基，未取代或具有一个到四个取代基，相互相同或不同；A是以下组中选择的一组：化学式为—（CH2）-O-（CH2）v-R″的醚基，其中v等于1或2；R″如本申请所定义；化学式为—C（O）-Z′的酮基，其中Z′如本申请所定义；具有羟基功能的取代基，化学式为—CH（OH）-Z′，其中Z′如本申请所定义；该工业发明的描述以NEUROSCIENZE S.c. a r.l.的名义进行，该公司是意大利国籍，总部位于卡利亚里，Palabanda 9号。
• EP1602656
  申请人：——

  公开号：——

  公开（公告）日：——
• EP1602656B1
  申请人：——

  公开号：EP1602656B1

  公开（公告）日：2011-06-29