methyl 3-(5-chloro-3-oxoisothiazol-2(3H)-yl)propanoate | 209002-70-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: methyl 3-(5-chloro-3-oxoisothiazol-2(3H)-yl)propanoate
• 英文别名: methyl 3-(5-chloro-3-oxo-1,2-thiazol-2-yl)propanoate
• CAS: 209002-70-0
• 化学式: C₇H₈ClNO₃S
• 分子量: 221.664
• InChiKey: IUQRHPPJEZXEGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  methyl 3-(5-chloro-3-oxoisothiazol-2(3H)-yl)propanoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以50%的产率得到methyl 3-(5-chloro-1-oxido-3-oxoisothiazol-2(3H)-yl)propanoate
  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
• 作为产物：
  描述：

  3,3'-dithiobis[N-(methyl 2-aminopropionate)propanamide] 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以49%的产率得到methyl 3-(5-chloro-3-oxoisothiazol-2(3H)-yl)propanoate
  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

• 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.
• 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.