(E)-3-(benzylthio)crotonic acid | 67959-54-0

• 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: (E)-3-(benzylthio)crotonic acid
• 英文别名: (E)-3-methyl-3-(benzylsulfanyl)propenoic acid；3-benzylsulfanyl-cis-crotonic acid；3-Benzylmercapto-cis-crotonsaeure；(E)-3-benzylsulfanylbut-2-enoic acid
• CAS: 67959-54-0
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: ISDFRMQXMDCKOH-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(benzylthio)crotonic acid 生成 苄硫醇
  参考文献：
  名称：

  Autenrieth, Chemische Berichte, 1896, vol. 29, p. 1669

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 (E)-3-(benzylthio)crotonic acid
  参考文献：
  名称：

  Posner, Chemische Berichte, 1901, vol. 34, p. 2658

  摘要：

  DOI：

文献信息

• Scheibler; Voss, Chemische Berichte, 1920, vol. 53, p. 384
  作者：Scheibler、Voss

  DOI：——

  日期：——
• Synthesis of isothiazol-3-one derivatives as inhibitors of histone acetyltransferases (HATs)
  作者：Stephen Gorsuch、Vassilios Bavetsias、Martin G. Rowlands、G. Wynne Aherne、Paul Workman、Michael Jarman、Edward McDonald

  DOI：10.1016/j.bmc.2008.11.079

  日期：2009.1

  High-throughput screening led to the identification of isothiazolones 1 and 2 as inhibitors of histone acetyltransferase (HAT) with IC50s of 3 mu M and 5 mu M, respectively. Analogues of these hit compounds with variations of the N-phenyl group, and with variety of substituents at C-4, C-5 of the thiazolone ring, were prepared and assayed for inhibition of the HAT enzyme PCAF. Potency is modestly favoured when the N-aryl group is electron deficient (4-pyridyl derivative 10 has IC50 = 1.5 mu M); alkyl substitution at C-4 has little effect, whilst similar substitution at C-5 causes a significant drop in potency. The ring-fused compound 38 has activity (IC50 = 6.1 mu M) to encourage further exploration of this bicyclic structure. The foregoing SAR is consistent with an inhibitory mechanism involving cleavage of the S-N bond of the isothiazolone ring by a catalytically important thiol residue. (C) 2008 Elsevier Ltd. All rights reserved.
• CHAN T. H.; PRASAD C. V. C., J. ORG. CHEM., 51,(1986) N 15, 3012-3016
  作者：CHAN T. H.、 PRASAD C. V. C.

  DOI：——

  日期：——
• Autenrieth, Chemische Berichte, 1896, vol. 29, p. 1669
  作者：Autenrieth

  DOI：——

  日期：——
• Posner, Chemische Berichte, 1901, vol. 34, p. 2658
  作者：Posner

  DOI：——

  日期：——