2-tert-butyl-5-chloroisothiazol-3(2H)-one-1-oxide | 850322-81-5

• 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: 2-tert-butyl-5-chloroisothiazol-3(2H)-one-1-oxide
• 英文别名: 2-Tert-butyl-5-chloroisothiazol-3(2H)-one 1-oxide；2-tert-butyl-5-chloro-1-oxo-1,2-thiazol-3-one
• CAS: 850322-81-5
• 化学式: C₇H₁₀ClNO₂S
• 分子量: 207.681
• InChiKey: XPUSAGLDGBTNOA-UHFFFAOYSA-N

物化性质

• 沸点：
  295.2±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-tert-butyl-5-chloroisothiazol-3(2H)-one-1-oxide 、 十二硫醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以57%的产率得到2-tert-butyl-5-(dodecylthio)isothiazol-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：

  2-叔丁基-5-氯异噻唑-3(2H)-酮 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到2-tert-butyl-5-chloroisothiazol-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

文献信息

• Design and synthesis of nonpeptidic, small molecule inhibitors for the Mycobacterium tuberculosis protein tyrosine phosphatase PtpB
  作者：Katherine A. Rawls、Christoph Grundner、Jonathan A. Ellman

  DOI：10.1039/c0ob00182a

  日期：——

  The design and synthesis of new inhibitor analogues for the Mycobacterium tuberculosis (Mtb) phosphatase PtpB is described. Analogues were synthesized by incorporation of two common and effective phosphate mimetics, the isothiazolidinone (IZD) and the difluoromethylphosphonic acid (DFMP). The basic scaffold of the inhibitor was identified from structure–activity relationships established for a previously published isoxazole inhibitor, while the phosphate mimetics were chosen based on their proven cell permeability and activity when incorporated into previously reported inhibitors for the phosphatase PTP1B. The inhibitory activity of each compound was evaluated, and each was found to have low or submicromolar affinity for PtpB.

  描述了结核分枝杆菌 (Mtb) 磷酸酶 PtpB 的新型抑制剂类似物的设计和合成。通过掺入两种常见且有效的磷酸盐模拟物异噻唑烷酮 (IZD) 和二氟甲基膦酸 (DFMP) 来合成类似物。该抑制剂的基本支架是根据先前发表的异恶唑抑制剂建立的结构-活性关系确定的，而磷酸盐模拟物是根据其已证实的细胞渗透性和当纳入先前报道的磷酸酶 PTP1B 抑制剂时的活性来选择的。评估了每种化合物的抑制活性，发现每种化合物对 PtpB 具有低或亚微摩尔的亲和力。
• 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.