2-phenethylisothiazol-3(2H)-one | 26530-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenethylisothiazol-3(2H)-one
• 英文别名: 2-phenethyl-isothiazol-3-one；2-(2-Phenylethyl)-1,2-thiazol-3-one
• CAS: 26530-16-5
• 化学式: C₁₁H₁₁NOS
• 分子量: 205.28
• InChiKey: HSFILUIYMMOOFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  346.5±35.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenethylisothiazol-3(2H)-one 在 氯 作用下， 以 乙酸乙酯 为溶剂， 生成 2-(Phenaethyl)-4.4.5.5-tetrachlorisothiazolidin-3-on
  参考文献：
  名称：

  Weiler,E.D. et al., Journal of Heterocyclic Chemistry, 1976, vol. 13, p. 1321 - 1323

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3'-disulfanediylbis(N-phenethylpropanamide) 在 磺酰氯 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 2-phenethylisothiazol-3(2H)-one
  参考文献：
  名称：

  Lewis,S.N. et al., Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 571 - 580

  摘要：

  DOI：

文献信息

• S-substituted beta-thioacrylamides and their use as microbicides
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0410726A1

  公开（公告）日：1991-01-30

  S-substituted beta-thioacrylamide compounds have been discovered to be useful as microbicides, particularly fungicides. Compositions comprising said compounds and isothiazolin-3-ones and/or carriers, methods of preparation of the compounds and methods of using the compounds and compositions are also disclosed.

  已发现 S-取代β-硫代丙烯酰胺化合物可用作杀微生物剂，特别是杀真菌剂。此外，还公开了包含上述化合物和异噻唑啉-3-酮和/或载体的组合物、化合物的制备方法以及化合物和组合物的使用方法。
• Benzisothiazolinone Derivatives as Potent Allosteric Monoacylglycerol Lipase Inhibitors That Functionally Mimic Sulfenylation of Regulatory Cysteines
  作者：Riccardo Castelli、Laura Scalvini、Federica Vacondio、Alessio Lodola、Mattia Anselmi、Stefano Vezzosi、Caterina Carmi、Michele Bassi、Francesca Ferlenghi、Silvia Rivara、Ingvar R. Møller、Kasper D. Rand、Jennifer Daglian、Don Wei、Emmanuel Y. Dotsey、Faizy Ahmed、Kwang-Mook Jung、Nephi Stella、Simar Singh、Marco Mor、Daniele Piomelli

  DOI：10.1021/acs.jmedchem.9b01679

  日期：2020.2.13

  We describe a set of benzisothiazolinone (BTZ) derivatives that are potent inhibitors of monoacylglycerol lipase (MGL), the primary degrading enzyme for the endocannabinoid 2-arachidonoyl-sn-glycerol (2-AG). Structure-activity relationship studies evaluated various substitutions on the nitrogen atom and the benzene ring of the BTZ nucleus. Optimized derivatives with nanomolar potency allowed us to investigate the mechanism of MGL inhibition. Site-directed mutagenesis and mass spectrometry experiments showed that BTZs interact in a covalent reversible manner with regulatory cysteines, Cys201 and Cys208, causing a reversible sulfenylation known to modulate MGL activity. Metadynamics simulations revealed that BTZ adducts favor a closed conformation of MGL that occludes substrate recruitment. The BTZ derivative 13 protected neuronal cells from oxidative stimuli and increased 2-AG levels in the mouse brain. The results identify Cys201 and Cys208 as key regulators of MGL function and point to the BTZ scaffold as a useful starting point for the discovery of allosteric MGL inhibitors.
• 3-dialkoxyphosphorylthio-acrylamides and related compounds
  申请人：ROHM AND HAAS COMPANY

  公开号：US03755512A1

  公开（公告）日：1973-08-28
• Weiler,E.D. et al., Journal of Heterocyclic Chemistry, 1977, vol. 14, p. 627 - 630
  作者：Weiler,E.D. et al.

  DOI：——

  日期：——
• WEILER E. D.; PETIGARA R. B.; WOLFERSBERGER M. H.; MILLER G. A., J. HETEROCYCL. CHEM. <JHTC-AD>, 1977, 14, NO 4, 627-630
  作者：WEILER E. D.、 PETIGARA R. B.、 WOLFERSBERGER M. H.、 MILLER G. A.

  DOI：——

  日期：——