3-(4-tert-butyl-phenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester | 861967-94-4

• 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: 3-(4-tert-butyl-phenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 3-(4-tert-butylphenyl)-4-cyano-5-(methylthio)thiophene-2-carboxylate；ethyl 3-(4-tert-butylphenyl)-4-cyano-5-methylsulfanylthiophene-2-carboxylate
• CAS: 861967-94-4
• 化学式: C₁₉H₂₁NO₂S₂
• 分子量: 359.513
• InChiKey: ITBKXYIQENUVSN-UHFFFAOYSA-N

物化性质

• 沸点：
  491.0±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-tert-butyl-phenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以30%的产率得到3-(4-tert-Butyl-phenyl)-4-cyano-thiophene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  A novel class of AMPA receptor allosteric modulators. Part 1: Design, synthesis, and SAR of 3-aryl-4-cyano-5-substituted-heteroaryl-2-carboxylic acid derivatives

  摘要：

  The synthesis and initial SAR studies of novel, highly potent positive allosteric modulators of AMPA receptors based on 3-(4-tert-butylphenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid (6a) are described. SAR studies at the thioether moiety indicated that substitution at this position was mandatory and better potency was achieved with small groups. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.035
• 作为产物：
  描述：

  2-(4-tert-butylbenzoyl)-3,3-bis-methylsulfanyl-acrylonitrile 、 巯基乙酸乙酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 3-(4-tert-butyl-phenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  A novel class of AMPA receptor allosteric modulators. Part 1: Design, synthesis, and SAR of 3-aryl-4-cyano-5-substituted-heteroaryl-2-carboxylic acid derivatives

  摘要：

  The synthesis and initial SAR studies of novel, highly potent positive allosteric modulators of AMPA receptors based on 3-(4-tert-butylphenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid (6a) are described. SAR studies at the thioether moiety indicated that substitution at this position was mandatory and better potency was achieved with small groups. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.035

文献信息

• [EN] THIOPHENE AND FURAN COMPOUNDS<br/>[FR] COMPOSES DE THIOPHENE ET DE FURANE
  申请人：LILLY CO ELI

  公开号：WO2005070916A1

  公开（公告）日：2005-08-04

  The present invention relates to thiophene and furan compounds and their pharmaceutically acceptable salts, and further relates to their use in treating schizophrenia, cognitive deficits associated with schizophrenia, Alzheimer's disease, dementia of the Alzheimer's type, mild cognitive impairment, or depression.

  本发明涉及噻吩和呋喃化合物及其药用可接受的盐，以及它们在治疗精神分裂症、与精神分裂症相关的认知缺陷、阿尔茨海默病、阿尔茨海默型痴呆、轻度认知障碍或抑郁症方面的用途。
• Thiophene and furan compounds
  申请人：Castano Mansanet Maria Ana

  公开号：US20070105852A1

  公开（公告）日：2007-05-10

  The present invention relates to thiophene and furan compounds and their pharmaceutically acceptable salts, and further relates to their use in treating schizophrenia, cognitive deficits associated with schizophrenia, Alzheimer's disease, dementia of the Alzheimer's type, mild cognitive impairment, or depression.

  本发明涉及噻吩和呋喃化合物及其药学上可接受的盐，并进一步涉及它们在治疗精神分裂症、与精神分裂症相关的认知缺陷、阿尔茨海默病、阿尔茨海默型痴呆、轻度认知障碍或抑郁症中的应用。
• THIOPHENE AND FURAN COMPOUNDS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1706395A1

  公开（公告）日：2006-10-04
• US7642361B2
  申请人：——

  公开号：US7642361B2

  公开（公告）日：2010-01-05
• A novel class of AMPA receptor allosteric modulators. Part 1: Design, synthesis, and SAR of 3-aryl-4-cyano-5-substituted-heteroaryl-2-carboxylic acid derivatives
  作者：Maria-Carmen Fernandez、Ana Castaño、Esteban Dominguez、Ana Escribano、Delu Jiang、Alma Jimenez、Eric Hong、William J. Hornback、Eric S. Nisenbaum、Nancy Rankl、Eric Tromiczak、Grant Vaught、Hamideh Zarrinmayeh、Dennis M. Zimmerman

  DOI：10.1016/j.bmcl.2006.07.035

  日期：2006.10

  The synthesis and initial SAR studies of novel, highly potent positive allosteric modulators of AMPA receptors based on 3-(4-tert-butylphenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid (6a) are described. SAR studies at the thioether moiety indicated that substitution at this position was mandatory and better potency was achieved with small groups. (c) 2006 Elsevier Ltd. All rights reserved.