4,5-Dichloro-2-ethylisothiazol-3(2H)-one

• 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: 4,5-Dichloro-2-ethylisothiazol-3(2H)-one
• 英文别名: 4,5-dichloro-2-ethyl-1,2-thiazol-3-one
• 化学式: C₅H₅Cl₂NOS
• 分子量: 198.07
• InChiKey: CULLRSWFYPMIDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,5-Dichloro-2-ethylisothiazol-3(2H)-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到4,5-dichloro-2-ethylisothiazol-3(2H)-one-1-oxide
  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
• 作为产物：
  描述：

  5-Chlor-2-ethyl-4-isothiazolin-3-on 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到4,5-Dichloro-2-ethylisothiazol-3(2H)-one
  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

• Isothiazoles. Part 14: New 3-aminosubstituted isothiazole dioxides and their mono- and dihalogeno derivatives
  作者：Francesca Clerici、Alessandro Contini、Maria Luisa Gelmi、Donato Pocar

  DOI：10.1016/j.tet.2003.09.064

  日期：2003.11

  3-Alkylamino- and 3-arylamino isothiazole dioxides unsubstituted at C-4 and C-5 were synthesized starting from dithiopropionic amides. Taking advantage of the direct chlorination during the cyclization process or realizing an addition–elimination process with bromine on the final 3-aminoisothiazole dioxide derivatives, the corresponding 5-chloro-, 4,5-dichloro- or the 4-bromoisothiazole dioxides could

  由二硫代丙酰胺开始合成在C-4和C-5未取代的3-烷基氨基-和3-芳基氨基异噻唑二氧化物。利用环化过程中的直接氯化或在最终的3-氨基异噻唑二氧化物衍生物上用溴进行加成-消除过程，相应的5-氯-，4,5-二氯-或4-溴异噻唑也可能是提供。
• 2-Alkyl-3-haloisothiazolium salts and their derivatives
  申请人：Givaudan Corporation

  公开号：US04281136A1

  公开（公告）日：1981-07-28

  This disclosure relates to a novel class of 2-alkyl-3-haloisothiazolium salts. These salts have been found to be useful in controlling the growth of bacteria and fungi. They have also been found to be useful intermediates in the preparation of novel and known antibacterial and antifungal compounds.

  本公开涉及一种新型的2-烷基-3-卤代异噻唑盐类。这些盐类被发现对细菌和真菌的生长具有控制作用。同时，它们也被发现是制备新型和已知抗菌和抗真菌化合物的有用中间体。
• 2-alkyl-3-haloisothiazol-3-thione
  申请人：Givaudan Corporation

  公开号：US04841063A1

  公开（公告）日：1989-06-20

  This disclosure relates to a novel class of 2-alkyl-3-haloisothiazolium salts. These salts have been found to be useful in controlling the growth of bacteria and fungi. They have also been found to be useful intermediates in the preparation of novel and known antibacterial and antifungal compounds.

  本公开涉及一种新型的2-烷基-3-卤代异噻唑盐类。发现这些盐类对细菌和真菌的生长具有控制作用。同时，它们还被发现是制备新型和已知抗菌和抗真菌化合物的有用中间体。
• 3-Dicyanomethylene-4-isothiazolines
  申请人：Givaudan Corporation

  公开号：US04328347A1

  公开（公告）日：1982-05-04

  This disclosure relates to a novel class of 2-alkyl-3-haloisothiazolium salts. These salts have been found to be useful in controlling the growth of bacteria and fungi. They have also been found to be useful intermediates in the preparation of novel and known antibacterial and antifungal compounds.

  本公开涉及一种新型的2-烷基-3-卤代异噻唑盐类。发现这些盐类对于控制细菌和真菌的生长非常有用。同时，它们也被发现是制备新型和已知的抗菌和抗真菌化合物的有用中间体。
• NOVEL CLATHRATE COMPOUND, PROCESS FOR PRODUCING THE SAME, AND ANTIFOULING AGENT
  申请人：NIPPON SODA CO., LTD.

  公开号：EP0709358A1

  公开（公告）日：1996-05-01

  A clathrate compound comprising a tetrakisphenol represented by general formula (I) as the host compound and 4,5-dichloro-2-alkyl-3(2H)-isothiazolone as the guest compound, wherein X represents -(CH₂)n-; n represents 0, 1, 2 or 3; and R¹ to R⁸ represent each hydrogen, lower alkyl, halogen, lower alkoxy or optionally substituted phenyl.

  一种由通式(I)代表的四联酚作为主化合物和 4,5-二氯-2-烷基-3(2H)-异噻唑 酮作为客体化合物组成的凝胶化合物，其中 X 代表-(CH₂)n-；n 代表 0、1、2 或 3；R¹ 至 R⁸ 分别代表氢、低级烷基、卤素、低级烷氧基或任选取代的苯基。