4-(pyrrolidin-1-ylsulfonyl)benzoyl chloride | 23965-96-0

• 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: 4-(pyrrolidin-1-ylsulfonyl)benzoyl chloride
• 英文别名: 4-pyrrolidin-1-ylsulfonylbenzoyl chloride
• CAS: 23965-96-0
• 化学式: C₁₁H₁₂ClNO₃S
• 分子量: 273.74
• InChiKey: YFGJTXSHQFLFGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(pyrrolidin-1-ylsulfonyl)benzoyl chloride 、 5-hydroxy-2-(((4-methylpyrimidin-2-yl)thio)methyl)-4H-pyran-4-one 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 生成 6-(((4-methylpyrimidin-2-yl)thio)methyl)-4-oxo-4H-pyran-3-yl 4-(pyrrolidin-1-ylsulfonyl)benzoate
  参考文献：
  名称：

  Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor

  摘要：

  The recently discovered apelin/APJ system has emerged as a critical mediator of cardiovascular homeostasis and is associated with the pathogenesis of cardiovascular disease. A role for apelin/APJ in energy metabolism and gastrointestinal function has also recently emerged. We disclose the discovery and characterization of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221), a potent APJ functional antagonist in cell-based assays that is >37-fold selective over the closely related angiotensin II type 1 (AT1) receptor. ML221 was derived from an HTS of the similar to 330,600 compound MLSMR collection. This antagonist showed no significant binding activity against 29 other GPCRs, except to the kappa-opioid and benzodiazepinone receptors (<50/<70%I at 10 mu M). The synthetic methodology, development of structure-activity relationship (SAR), and initial in vitro pharmacologic characterization are also presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.105
• 作为产物：
  描述：

  4-(吡咯烷-1-基磺酰基)苯甲酸 在 氯化亚砜 作用下， 以88%的产率得到4-(pyrrolidin-1-ylsulfonyl)benzoyl chloride
  参考文献：
  名称：

  [EN] CRTH2 MODULATORS
  [FR] MODULATEURS DE CRTH2

  摘要：

  CRTH2的调节剂，特别是CRTH2的拮抗剂，可用于治疗包括哮喘和呼吸道疾病在内的各种疾病。这些化合物属于由式I描述的一类。

  公开号：

  WO2010039982A1

文献信息

• CRTH2 MODULATORS
  申请人：JIA James

  公开号：US20110311483A1

  公开（公告）日：2011-12-22

  Compounds of Formulae I-1 to I-9 are disclosed, which are modulators of CRTH2, particularly antagonists of CRTH2, that are useful for treating various disorders, including asthma and respiratory disorders.

  公开了化学式I-1到I-9的化合物，这些化合物是CRTH2的调节剂，特别是CRTH2的拮抗剂，适用于治疗包括哮喘和呼吸系统疾病在内的各种疾病。
• New method for the synthesis of pyrrolo[2,3- b ]dihydroquinolines
  作者：Anatolii R. Syniugin、Maksym O. Chekanov、Pavel V. Savitskiy、Alexander E. Pashenko、Tatyana S. Zhuk、Sergiy M. Yarmoluk、Andrey A. Fokin

  DOI：10.1016/j.tetlet.2015.12.011

  日期：2016.1

  Intramolecular cyclization of [2-(2-chloroquinolin-3-yl)ethyl]amines, formed in situ from the reaction of N-phthaloyl-protected [2-(2-chloroquinolin-3-yl)ethyl]amines and hydrazine hydrate gave pyrrolo [2,3-b]dihydroquinolines in high yields. (C) 2015 Elsevier Ltd. All rights reserved.
• [EN] CRTH2 MODULATORS<br/>[FR] MODULATEURS DE CRTH2
  申请人：IRONWOOD PHARMACEUTICALS INC

  公开号：WO2010039982A1

  公开（公告）日：2010-04-08

  Modulators of CRTH2, particularly antagonists of CRTH2, that are useful for treating various disorders, including asthma and respiratory disorders are disclosed. The compounds fall within a genus described by formula I.

  CRTH2的调节剂，特别是CRTH2的拮抗剂，可用于治疗包括哮喘和呼吸道疾病在内的各种疾病。这些化合物属于由式I描述的一类。
• Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor
  作者：Patrick R. Maloney、Pasha Khan、Michael Hedrick、Palak Gosalia、Monika Milewski、Linda Li、Gregory P. Roth、Eduard Sergienko、Eigo Suyama、Eliot Sugarman、Kevin Nguyen、Alka Mehta、Stefan Vasile、Ying Su、Derek Stonich、Hung Nguyen、Fu-Yue Zeng、Arianna Mangravita Novo、Michael Vicchiarelli、Jena Diwan、Thomas D.Y. Chung、Layton H. Smith、Anthony B. Pinkerton

  DOI：10.1016/j.bmcl.2012.08.105

  日期：2012.11

  The recently discovered apelin/APJ system has emerged as a critical mediator of cardiovascular homeostasis and is associated with the pathogenesis of cardiovascular disease. A role for apelin/APJ in energy metabolism and gastrointestinal function has also recently emerged. We disclose the discovery and characterization of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221), a potent APJ functional antagonist in cell-based assays that is >37-fold selective over the closely related angiotensin II type 1 (AT1) receptor. ML221 was derived from an HTS of the similar to 330,600 compound MLSMR collection. This antagonist showed no significant binding activity against 29 other GPCRs, except to the kappa-opioid and benzodiazepinone receptors (<50/<70%I at 10 mu M). The synthetic methodology, development of structure-activity relationship (SAR), and initial in vitro pharmacologic characterization are also presented. (C) 2012 Elsevier Ltd. All rights reserved.