methyl 6-(3-oxoisothiazol-2(3H)-yl)hexanoate | 1134642-93-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 6-(3-oxoisothiazol-2(3H)-yl)hexanoate
• 英文别名: methyl 6-(3-oxo-1,2-thiazol-2-yl)hexanoate
• CAS: 1134642-93-5
• 化学式: C₁₀H₁₅NO₃S
• 分子量: 229.3
• InChiKey: KYUDBJQSLGNBLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙烷-1-硫醇 、 methyl 6-(3-oxoisothiazol-2(3H)-yl)hexanoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以24%的产率得到methyl 6-(3-(propyldisulfanyl)acrylamido)hexanoate
  参考文献：
  名称：

  异噻唑酮; 半胱氨酸蛋白酶组织蛋白酶B和组蛋白乙酰转移酶PCAF的硫醇反应性抑制剂†

  摘要：

  异噻唑酮和5-氯异噻唑酮通过裂解弱的氮硫键形成二硫键，与硫醇发生化学选择性反应。它们根据其取代模式显示出抑制硫醇依赖性半胱氨酸蛋白酶组织蛋白酶B和组蛋白乙酰转移酶p300 / CBP相关因子（PCAF）的选择性。此外，酶动力学和质谱表明5-氯异噻唑酮与组织蛋白酶B共价结合，这证明了它们作为基于活性的蛋白谱分析的探针的潜在用途。

  DOI：

  10.1039/c0ob00464b
• 作为产物：
  描述：

  3,3'-dithiobis[N-(methyl 2-aminohexanoate)propanamide] 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以61%的产率得到methyl 6-(5-chloro-3-oxoisothiazol-2(3H)-yl)hexanoate
  参考文献：
  名称：

  Inhibition of the PCAF histone acetyl transferase and cell proliferation by isothiazolones

  摘要：

  Small molecule HAT inhibitors are useful tools to unravel the role of histone acetyl transferases (HATs) in the cell and have relevance for oncology. We present a systematic investigation of the inhibition of the HAT p300/CBP Associated Factor (PCAF) by isothiazolones with different substitutions. 5-chloroisothiazolones proved to be the most potent inhibitors of PCAF. The growth inhibition of 4 different cell lines was studied and the growth of two cell lines (A2780 and HEK 293) was inhibited at micromolar concentrations by 5-chloroisothiazolones. Furthermore, the 5-chloroisothiazolone preservative Kathon (TM) CG that is used in cosmetics inhibited PCAF and the growth of cell lines A2780 and HEK 293, which indicates that this preservative should be applied with care. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.008

文献信息

• Isothiazolones; thiol-reactive inhibitors of cysteine protease cathepsin B and histone acetyltransferase PCAF
  作者：Rosalina Wisastra、Massimo Ghizzoni、Harm Maarsingh、Adriaan J. Minnaard、Hidde J. Haisma、Frank J. Dekker

  DOI：10.1039/c0ob00464b

  日期：——

  disulfides. They show selectivity for inhibition of the thiol-dependent cysteine protease cathepsin B and the histone acetyltransferase p300/CBP associated factor (PCAF) based on their substitution pattern. Furthermore, enzyme kinetics and mass spectroscopy indicate covalent binding of a 5-chloroisothiazolone to cathepsin B, which demonstrates their potential utility as probes for activity-based protein profiling

  异噻唑酮和5-氯异噻唑酮通过裂解弱的氮硫键形成二硫键，与硫醇发生化学选择性反应。它们根据其取代模式显示出抑制硫醇依赖性半胱氨酸蛋白酶组织蛋白酶B和组蛋白乙酰转移酶p300 / CBP相关因子（PCAF）的选择性。此外，酶动力学和质谱表明5-氯异噻唑酮与组织蛋白酶B共价结合，这证明了它们作为基于活性的蛋白谱分析的探针的潜在用途。
• Inhibition of the PCAF histone acetyl transferase and cell proliferation by isothiazolones
  作者：Frank J. Dekker、Massimo Ghizzoni、Nanette van der Meer、Rosalina Wisastra、Hidde J. Haisma

  DOI：10.1016/j.bmc.2008.12.008

  日期：2009.1

  Small molecule HAT inhibitors are useful tools to unravel the role of histone acetyl transferases (HATs) in the cell and have relevance for oncology. We present a systematic investigation of the inhibition of the HAT p300/CBP Associated Factor (PCAF) by isothiazolones with different substitutions. 5-chloroisothiazolones proved to be the most potent inhibitors of PCAF. The growth inhibition of 4 different cell lines was studied and the growth of two cell lines (A2780 and HEK 293) was inhibited at micromolar concentrations by 5-chloroisothiazolones. Furthermore, the 5-chloroisothiazolone preservative Kathon (TM) CG that is used in cosmetics inhibited PCAF and the growth of cell lines A2780 and HEK 293, which indicates that this preservative should be applied with care. (C) 2008 Elsevier Ltd. All rights reserved.