methyl 3-[4-chloro-5-(dodecylthio)-1-oxido-3-oxoisothiazol-2(3H)-yl]propanoate | 1203704-50-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl 3-[4-chloro-5-(dodecylthio)-1-oxido-3-oxoisothiazol-2(3H)-yl]propanoate
• 英文别名: methyl 3-(4-chloro-5-dodecylsulfanyl-1,3-dioxo-1,2-thiazol-2-yl)propanoate
• CAS: 1203704-50-0
• 化学式: C₁₉H₃₂ClNO₄S₂
• 分子量: 438.052
• InChiKey: SCZPCNQHBPMVMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 3-[5-(dodecylthio)-1-oxido-3-oxoisothiazol-2(3H)-yl]propanoate 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到methyl 3-[4-chloro-5-(dodecylthio)-1-oxido-3-oxoisothiazol-2(3H)-yl]propanoate
  参考文献：
  名称：

  Reactivity of isothiazolones and isothiazolone-1-oxides in the inhibition of the PCAF histone acetyltransferase

  摘要：

  Development of small molecule inhibitors of the histone acetyltransferase p300/CBP associated factor (PCAF) is relevant for oncology. The inhibition of the enzyme PCAF and proliferation of the cancer cell line HEP G2 by a series of 5-chloroisothiazolones was compared to a series of 5-chloroisothiazolone-1-oxides. The PCAF inhibitory potency of 5-chloroisothiazolones and 5-chloroisothiazolone-1-oxides is influenced by substitution in the 4-position. A study on the reactivity of the HAT inhibitors towards thiols and thiolates indicates that 5-chloroisothiazolones reacted quickly with propane-1-thiolate to provide many products, whereas 5-chloroisothiazolone-1-oxides provide only one defined product. Growth inhibition studies indicate that 5-chloroisothiazolones inhibit proliferation of HEP G2 cells at concentrations between 8.6 and 24 mu M, whereas 5-chloroisothiazolone-1-oxides required higher concentrations or showed no inhibition. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.07.025

文献信息

• Reactivity of isothiazolones and isothiazolone-1-oxides in the inhibition of the PCAF histone acetyltransferase
  作者：Massimo Ghizzoni、Hidde J. Haisma、Frank J. Dekker

  DOI：10.1016/j.ejmech.2009.07.025

  日期：2009.12

  Development of small molecule inhibitors of the histone acetyltransferase p300/CBP associated factor (PCAF) is relevant for oncology. The inhibition of the enzyme PCAF and proliferation of the cancer cell line HEP G2 by a series of 5-chloroisothiazolones was compared to a series of 5-chloroisothiazolone-1-oxides. The PCAF inhibitory potency of 5-chloroisothiazolones and 5-chloroisothiazolone-1-oxides is influenced by substitution in the 4-position. A study on the reactivity of the HAT inhibitors towards thiols and thiolates indicates that 5-chloroisothiazolones reacted quickly with propane-1-thiolate to provide many products, whereas 5-chloroisothiazolone-1-oxides provide only one defined product. Growth inhibition studies indicate that 5-chloroisothiazolones inhibit proliferation of HEP G2 cells at concentrations between 8.6 and 24 mu M, whereas 5-chloroisothiazolone-1-oxides required higher concentrations or showed no inhibition. (C) 2009 Elsevier Masson SAS. All rights reserved.