4-chloro-N-(3-((2-hydroxy-3-oxocyclopent-1-en-1-yl)methyl)phenethyl)benzenesulfonamide | 1416806-40-0

• 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-chloro-N-(3-((2-hydroxy-3-oxocyclopent-1-en-1-yl)methyl)phenethyl)benzenesulfonamide
• 英文别名: 4-chloro-N-[2-[3-[(2-hydroxy-3-oxocyclopenten-1-yl)methyl]phenyl]ethyl]benzenesulfonamide
• CAS: 1416806-40-0
• 化学式: C₂₀H₂₀ClNO₄S
• 分子量: 405.902
• InChiKey: SQXMMOCBEUPMFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Diethyl 4-[[3-[2-[(4-chlorophenyl)sulfonyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]methoxy]-1-[[3-[2-[(4-chlorophenyl)sulfonyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]methyl]-5-oxocyclopent-3-ene-1,3-dicarboxylate 在 盐酸 、 水 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以0.051 g的产率得到4-chloro-N-(3-((2-hydroxy-3-oxocyclopent-1-en-1-yl)methyl)phenethyl)benzenesulfonamide
  参考文献：
  名称：

  Evaluation of the cyclopentane-1,2-dione as a potential bio-isostere of the carboxylic acid functional group

  摘要：

  Cycloalkylpolyones hold promise in drug design as carboxylic acid bio-isosteres. To investigate cyclopentane-1,2-diones as potential surrogates of the carboxylic acid functional group, the acidity, tautomerism, and geometry of hydrogen bonding of representative compounds were evaluated. Prototypic derivatives of the known thromboxane Ay prostanoid (TP) receptor antagonist, 3-(3-(2-((4-chlorophenyl)-sulfon-amido)-ethyl)phenyl)propanoic acid, in which the carboxylic acid moiety is replaced by the cyclopentane-1,2-dione unit, were synthesized and evaluated as TP receptor antagonists. Cyclopentane-1,2-dione derivative 9 was found to be a potent TP receptor antagonist with an IC50 value comparable to that of the parent carboxylic acid. These results indicate that the cyclopentane-1,2-dione may be a potentially useful carbox ylic acid bio-isostere. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.047

文献信息

• Cycloalkyl-dione Derivatives And Methods Of Their Use
  申请人：Atasoylu Onur

  公开号：US20120329877A1

  公开（公告）日：2012-12-27

  The present invention is directed to compounds of formula I: wherein A is n is 0, 1, or 2; m is 0 or 1; R 1 is H or C 1-6 alkyl and R 2 is H, C 1-6 alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and X is O or N; as well as tautomers and pharmaceutically acceptable salt forms thereof. Uses of these compounds are also described.

  本发明涉及以下式I的化合物：其中A为0、1或2；m为0或1；R1为H或C1-6烷基，R2为H、C1-6烷基、取代或未取代芳基，或取代或未取代杂环芳基；X为O或N；以及它们的互变异构体和药学上可接受的盐形式。还描述了这些化合物的用途。
• US8530520B2
  申请人：——

  公开号：US8530520B2

  公开（公告）日：2013-09-10