4-(3-Isothiazolon-2-yl)buttersaeuremethylester | 27337-41-3

• 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: 4-(3-Isothiazolon-2-yl)buttersaeuremethylester
• 英文别名: methyl 4-(3-oxoisothiazol-2(3H)-yl)butanoate；4-(3-oxo-3H-isothiazol-2-yl)-butyric acid methyl ester；methyl 4-(3-oxo-1,2-thiazol-2-yl)butanoate
• CAS: 27337-41-3
• 化学式: C₈H₁₁NO₃S
• 分子量: 201.246
• InChiKey: DKQYKQNEEYKIDM-UHFFFAOYSA-N

物化性质

• 沸点：
  315.2±44.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4-(3-Isothiazolon-2-yl)buttersaeuremethylester 、 、 磺酰氯 在 乙酸乙酯 作用下， 反应 1.0h， 以During this time a white precipitate formed (5-chloro-2-(3-methoxycarbonylpropyl)-3-isothiazolone (200 mg)) which的产率得到methyl 4-(5-chloro-3-oxoisothiazol-2(3H)-yl)butanoate
  参考文献：
  名称：

  Immunoassay for isothiazolones

  摘要：

  基于单克隆抗体的异噻唑啉免疫测定，该抗体与异噻唑啉特别是5-氯-2-甲基-3-异噻唑啉反应，产生这种抗体的杂交瘤，特别是ATCC HB 11435，制备异噻唑啉和大分子载体的免疫原结合物的方法，制备与异噻唑啉反应的单克隆抗体的方法，以及包含单克隆或多克隆抗体的组合物，这些抗体与异噻唑啉反应。

  公开号：

  US05554542A1
• 作为产物：
  描述：

  3,3'-dithiobis[N-(methyl 2-aminobutanoate)propanamide] 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以67%的产率得到methyl 4-(5-chloro-3-oxoisothiazol-2(3H)-yl)butanoate
  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

• Isothiazole chemistry—X
  作者：A.W.K. Chan、W.D. Crow、I. Gosney

  DOI：10.1016/s0040-4020(01)92824-8

  日期：1970.1

  3-Hydroxyisothiazole exists as the lactim in nonpolar solvents, the lactam form predominating in aqueous solution. Acylation, although extremely rapid in nonpolar solvents, depends on the relative rates of reaction of the two tautomers rather than on their relative proportions. The size of the acyl group, and the steric requirements of the catalyst, are shown to be the critical factors in determining

  3-羟基异噻唑作为内酰胺存在于非极性溶剂中，内酰胺形式在水溶液中占主导地位。尽管在非极性溶剂中酰化反应非常迅速，但酰化反应取决于两种互变异构体的相对反应速率，而不是取决于它们的相对比例。酰基的大小和催化剂的空间要求被证明是确定酰化位点的关键因素。3-羟基异噻唑的烷基化导致产物的混合物，其中3-烷氧基异噻唑占主导。没有观察到烷基的迁移。
• US5554542A
  申请人：——

  公开号：US5554542A

  公开（公告）日：1996-09-10
• 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.
• Immunoassay for isothiazolones
  申请人：Rohm and Haas Company

  公开号：US05554542A1

  公开（公告）日：1996-09-10

  Immunoassay for isothiazolones based on monoclonal antibodies that react with isothiazolones, particularly, 5-chloro-2-methyl-3-isothiazolone, hybridomas that produce such antibodies, especially ATCC HB 11435, a method of preparing an immunogenic conjugate of isothiazolones and a macromolecule carrier, a method of producing monoclonal antibodies reactive with isothiazolones, and compositions comprising monoclonal or polyclonal antibodies reactive with isothiazolones.

  基于单克隆抗体的异噻唑啉免疫测定，该抗体与异噻唑啉特别是5-氯-2-甲基-3-异噻唑啉反应，产生这种抗体的杂交瘤，特别是ATCC HB 11435，制备异噻唑啉和大分子载体的免疫原结合物的方法，制备与异噻唑啉反应的单克隆抗体的方法，以及包含单克隆或多克隆抗体的组合物，这些抗体与异噻唑啉反应。