alpha-环己基噻吩-3-乙酸 | 16199-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: alpha-环己基噻吩-3-乙酸
• 英文名称: (+/-)-2-cyclohexyl-2-(3-thienyl)ethanoic acid
• 英文别名: 2-cyclohexyl-2-(3-thienyl)ethanoic acid；2-cyclohexyl-2-(3-thienyl)acetic acid；cyclohexyl-thiophen-3-yl-acetic acid；α-cyclohexylthiophen-3-acetic acid；(thienyl-3)-cyclohexyl-acetic acid；alpha-Cyclohexylthiophen-3-acetic acid；2-cyclohexyl-2-thiophen-3-ylacetic acid
• CAS: 16199-74-9
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: OEEPFYFKBOUIEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  369.6±17.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 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：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  alpha-环己基噻吩-3-乙酸 在 硝酸 作用下， 以 氯仿 、 乙腈 为溶剂， 生成 (5-Nitro-thienyl-3)-cyclohexyl-acetic acid
  参考文献：
  名称：

  Substituted thienyl-acetic acid esters

  摘要：

  公式为：##STR1##中的噻吩乙酸酯，其中R.sub.1和R.sub.2各自独立地为H、CH.sub.3、C.sub.2 H.sub.5、C.sub.3 H.sub.7、OCH.sub.3、SCH.sub.3、Cl、Br或NO.sub.2，R.sub.3为苯基或环己基，R.sub.4为H，或者R.sub.3和R.sub.4一起为环己基亚甲基，n为2或3，A为单烷基胺或双烷基胺，每个烷基基团含有1至4个碳原子，或者来自含有5至7个链成员的环烷胺的氨基，该环烷胺可能包含额外的杂原子，前提是如果R.sub.3为苯基或环己基且R.sub.4为H，则R.sub.1和R.sub.2中的每一个都不是H，其外消旋体、光学异构体及其与烷基卤化物得到的药用可接受酸盐和季铵盐具有显著的周围血管扩张剂、血小板聚集抑制剂、解痉剂、冠脉和脑血管扩张剂以及类似阿片类的活性。

  公开号：

  US04005095A1
• 作为产物：
  描述：

  3-噻吩乙酸 在 盐酸 、 氢氧化钾 、 lithium diisopropyl amide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.92h， 生成 alpha-环己基噻吩-3-乙酸
  参考文献：
  名称：

  外消旋西替地尔的有效新合成和利用温和条件制备 α-酮羧酸的新途径

  摘要：

  我们描述了规定的外消旋药物西替地尔 [(±)-2-cyclohexyl-2-(3-thienyl)ethanoic acid 2-(hexahydro-1 H-azepin-1-yl)ethylester] 的新有效合成。此外，我们在此报告了一种高产大规模的酸前体 7 途径，随后能够大规模合成西替地尔的手性形式，并进行详细的药理学研究。此外，我们描述了一种从容易获得或容易获得的醛开始制备 α-酮羧酸的新途径：所使用的温和条件使其适用于具有生物学意义的分子。

  DOI：

  10.1055/s-2007-977414

文献信息

• 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.
• De Cointet; Grossi; Pigerol, European Journal of Medicinal Chemistry, 1980, vol. 15, # 3, p. 223 - 227
  作者：De Cointet、Grossi、Pigerol、et al.

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• Discovery of new C3aR ligands. Part 2: Amino-piperidine derivatives
  作者：Frédéric Denonne、Sophie Binet、Maggi Burton、Philippe Collart、Sabine Defays、Alan Dipesa、Maria Eckert、Alexander Giannaras、Seema Kumar、Beth Levine、Jean-Marie Nicolas、Patrick Pasau、Cécile Pégurier、Dorin Preda、Nathalie Van houtvin、Andrew Volosov、Dong Zou

  DOI：10.1016/j.bmcl.2007.04.023

  日期：2007.6

  The synthesis and structure-activity relationships against the C3a receptor of a series of substituted aminopiperidine derivatives are reported. DMPK properties and functional activities of selected compounds are described. The compounds obtained are the first non-arginine ligands of C3aR. (c) 2007 Elsevier Ltd. All rights reserved.
• Roxburgh, Craig J.; Ganellin, C. Robin; Shiner, Mark A. R., Journal of Pharmacy and Pharmacology, 1996, vol. 48, # 8, p. 851 - 857
  作者：Roxburgh, Craig J.、Ganellin, C. Robin、Shiner, Mark A. R.、Benton, David C. H.、Dunn, Philip M.、Ayalew, Yeshi、Jenkinson, Donald H.

  DOI：——

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• COINTET P. DE; GROSSI P.-J.; PIGEROL C.; BROLL M.; EYMARD P., EUR. J. MED. CHEM.-CHIM. THER., 1980, 15, NO 3, 223-227
  作者：COINTET P. DE、 GROSSI P.-J.、 PIGEROL C.、 BROLL M.、 EYMARD P.

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  日期：——