(+/-)-2-cyclohexyl-2-hydroxy-2-(3-thienyl)ethanoic acid | 3193-02-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (+/-)-2-cyclohexyl-2-hydroxy-2-(3-thienyl)ethanoic acid
• 英文别名: (+/-)-2-(3-thienyl)-2-cyclohexyl-2-hydroxy acetic acid；2-cyclohexyl-2-hydroxy-2-(3-thienyl)ethanoic acid；cyclohexyl-hydroxy-thiophen-3-yl-acetic acid；3-Thienylcyclohexyl-glycolic acid；2-cyclohexyl-2-hydroxy-2-thiophen-3-ylacetic acid
• CAS: 3193-02-0
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: FETMUBULKNUROR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-2-cyclohexyl-2-hydroxy-2-(3-thienyl)ethanoic acid 在 盐酸 、 tin(ll) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 5.5h， 以58%的产率得到alpha-环己基噻吩-3-乙酸
  参考文献：
  名称：

  Roxburgh, Craig J.; Ganellin, C. Robin; Shiner, Mark A. R., Journal of Pharmacy and Pharmacology, 1996, vol. 48, # 8, p. 851 - 857

  摘要：

  DOI：
• 作为产物：
  描述：

  2-cyclohexyl-2-hydroxyacetonitrile 在 chromium(VI) oxide 、 盐酸 、 硫酸 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 反应 21.0h， 生成 (+/-)-2-cyclohexyl-2-hydroxy-2-(3-thienyl)ethanoic acid
  参考文献：
  名称：

  Roxburgh, Craig J.; Ganellin, C. Robin; Shiner, Mark A. R., Journal of Pharmacy and Pharmacology, 1996, vol. 48, # 8, p. 851 - 857

  摘要：

  DOI：

文献信息

• [EN] COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY<br/>[FR] COMPOSÉS AYANT UNE ACTIVITÉ ANTAGONISTE DES RÉCEPTEURS MUSCARINIQUES ET UNE ACTIVITÉ AGONISTE DES RÉCEPTEURS ADRÉNERGIQUE BÊTA-2
  申请人：CHIESI FARMA SPA

  公开号：WO2012168349A1

  公开（公告）日：2012-12-13

  The present invention relates to compounds of general formula (I), acting both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists, to processes for their preparation, to compositions comprising them, to therapeutic uses and combinations with other pharmaceutical active ingredients.

  这项发明涉及一般式(I)的化合物，它们既作为肌肉收缩受体拮抗剂，又作为β2肾上腺素受体激动剂，涉及它们的制备方法，包含它们的组合物，治疗用途以及与其他药用活性成分的组合。
• Synthesis and Structure−Activity Relationships of Cetiedil Analogues as Blockers of the Ca²⁺-Activated K⁺ Permeability of Erythrocytes
  作者：Craig J. Roxburgh、C. Robin Ganellin、Salah Athmani、Alessandra Bisi、Wilma Quaglia、David C. H. Benton、Mark A. R. Shiner、Misbah Malik-Hall、Dennis G. Haylett、Donald H. Jenkinson

  DOI：10.1021/jm001113w

  日期：2001.9.1

  Cetiedil, [2-cyclohexyl-2-(3-thienyl)ethanoic acid 2-(hexahydro-1H-azepin-1-yl)ethyl ester], which blocks the intermediate calcium-activated potassium ion permeability (IKCa) in red blood cells, was used as a lead for investigating structure-activity relationships with the aim of determining the pharmacophore and of synthesizing agents of greater potency. A series of compounds having structures related to cetiedil was made and tested on rabbit erythrocytes. Channel blocking activity within the series was found to correlate well with octanol-water partition coefficients but not with the specific chemical structure of the acid moiety. However, whereas log P for the compounds spans a range of values over 4 orders of magnitude, potency only increases by 2 orders. This suggests that hydrophobic interactions with an active site on the channel are probably not the main determinants of activity. It seems more likely that increased lipophilicity enhances access to the channel, probably from within the cell membrane. In keeping with this interpretation, cetiedil methoiodide was found to be inactive, Triphenylethanoic was found to be a more effective acid grouping than 2-cyclohexyl-2-(3-thienyl)ethanoic, and its 2-(hexahydro-1H-azepin-l-yl)ethyl ester (11) was approximately 3 times more potent than cetiedil. The 9-benzylfluoren-9-yl carboxylic acid ester (21) was found to be approximately 9 times more active than cetiedil, and replacing -CO2- in 21 by an ethynyl (-C dropC-) linkage (compound 26, UCL 1608) increased potency by some 15-fold over that of cetiedil.
• Tambute, Andre; Collet, Andre, Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 77 - 82
  作者：Tambute, Andre、Collet, Andre

  DOI：——

  日期：——
• Robba,M.; Le Guen,Y., Chimica Therapeutica, 1966, vol. 1, p. 238 - 245
  作者：Robba,M.、Le Guen,Y.

  DOI：——

  日期：——
• TAMBUTE, A.;COLLET, A., BULL. SOC. CHIM. FR., 1984, N 1-2, 77-82
  作者：TAMBUTE, A.、COLLET, A.

  DOI：——

  日期：——