2-phenyl-1,2-benzisothiazol-3(2H)-one 1-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-phenyl-1,2-benzisothiazol-3(2H)-one 1-oxide
• 英文别名: 2-phenylbenzo[d]isothiazol-3(2H)-one 1-oxide；1-Oxo-2-phenyl-1,2-benzothiazol-3-one
• 化学式: C₁₃H₉NO₂S
• 分子量: 243.286
• InChiKey: QOMHFTHJJLXALW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯基-1,2-苯并噻唑-3-酮 在 air 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以99%的产率得到2-phenyl-1,2-benzisothiazol-3(2H)-one 1-oxide
  参考文献：
  名称：

  Potassium bromide catalyzed N S bond formation via oxidative dehydrogenation

  摘要：

  N-Substituted benzo[d]isothiazol-3(2H)-ones are a family of compounds with extremely important application. Recently, we have developed a new green pathway to synthesize these compounds via potassium bromide-catalyzed intramolecular oxidative dehydrogenative cyclization. This reaction has high functional group tolerance and affords excellent yield even in gram scale. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.03.065

文献信息

• Photochemical Ring-expansion Reaction of 1,2-Benzisothiazolinones
  作者：Nobumasa Kamigata、Satoshi Hashimoto、Michio Kobayashi、Hiroshi Nakanishi

  DOI：10.1246/bcsj.58.3131

  日期：1985.11

  The photochemical reaction of a series of 2-aryl-1,2-benzisothiazol-3(2H)-ones (1) under deaerated conditions was found to give dibenzo[b,f][1,4]thiazepin-11(10H)-ones (2). A mechanism through a biradical species is proposed for the photoreaction. When the photolysis of 1 was carried out in the presence of oxygen, 2-aryl-1,2-benzisothiazol-3(2H)-one 1-oxides (11) were formed together with compounds

  发现一系列 2-芳基-1,2-苯并异噻唑-3(2H)-酮 (1) 在脱气条件下的光化学反应得到二苯并[b,f][1,4]thiazepin-11(10H) -一个（2）。提出了通过双自由基物种的机制用于光反应。当 1 在氧气存在下进行光解时，2-芳基-1,2-苯并异噻唑-3(2H)-one 1-氧化物 (11) 与化合物 2 一起形成。
• Reactions of an organoruthenium anticancer complex with 2-mercaptobenzanilide—a model for the active-site cysteine of protein tyrosine phosphatase 1B
  作者：Yumiao Han、Qun Luo、Xiang Hao、Xianchan Li、Fuyi Wang、Wenbing Hu、Kui Wu、Shuang Lü、Peter J. Sadler

  DOI：10.1039/c1dt11189b

  日期：——

  The organometallic anticancer complex [(η6-p-cymene)Ru(en)Cl]PF6 (1, en = ethylenediamine) readily reacts with thiols and forms stable sulfenate/sulfinate adducts which may be important for its biological activity. Protein tyrosine phosphatase 1B (PTP1B), a therapeutic target, contains a catalytic cysteinyl thiol and is involved in the regulation of insulin signaling and the balance of protein tyrosine kinase activity. On oxidation, the catalytic Cys215 can form an unusual sulfenyl-amide intermediate which can subsequently be reduced by glutathione. Here we study reactions of 1 with 2-mercaptobenzanilide, 2, a recognized model for the active site of PTP1B. We have characterized crystallographically compound 2 and its oxidized sulfenyl-amide derivative 2-phenyl-1,2-benzisothiazol-3(2H)-one (4), which shows a close structural similarity to the sulfenyl-amide in oxidized PTP1B. At pH 7.4 and 5.3, 1 reacted with 2, affording a mono-ruthenium thiolato complex [(η6-cym)Ru(en)(S-RS)]+ (7+, R = (C6H4)CONH(C6H5)) and a triply-S-bridged thiolato complex [((η6-cym)Ru)2(μ-S-RS)3]+ (8+), respectively. Coordination of Ru to the S atom in 7 allows formation of a strong H-bond (2.02 Å) between the en-NH and the carbonyl oxygen. To assess the possible effect of ruthenium coordination on the redox regulation of PTP1B, reactions of these thiolato products with H2O2 and/or GSH were then investigated, demonstrating that coordination to Ru largely retards both the oxidation (deactivation) of the thiol in compound 2 by H2O2 and the subsequent reduction (reactivation) of the sulfenyl-amide by GSH, implying that the inhibition of complex 1 on PTP1B (IC50 of 19 μM) may be attributed to coordination to its catalytic cysteine.

  有机金属抗癌复合物[(η^6-p-石榴烯)Ru(en)Cl]PF6 (1, en = 乙二胺)能够迅速与硫醇反应，形成稳定的亚硫酸盐/亚硫酸酯加合物，这可能对其生物活性具有重要作用。蛋白酪氨酸磷酸酶1B (PTP1B)是一种治疗靶点，含有一个催化性半胱氨酸硫醇，参与胰岛素信号传导和蛋白酪氨酸激酶活性平衡的调节。在氧化过程中，催化性Cys215可以形成一种不寻常的亚硫酰胺中间体，随后可以通过谷胱甘肽还原。在这里，我们研究了1与2-巯基苯乙酰胺（2）之间的反应，2被视为PTP1B活性位点的典型模型。我们通过晶体学对化合物2及其氧化的亚硫酰胺衍生物2-苯基-1,2-苯并异噻唑-3(2H)-酮（4）进行了表征，发现其在结构上与氧化的PTP1B中的亚硫酰胺非常相似。在pH 7.4和5.3条件下，1与2反应，分别生成单铑硫醇化合物[(η^6-石榴烯)Ru(en)(S-RS)]+ (7+, R = (C6H4)CONH(C6H5))和三硫桥联硫醇化合物[((η^6-石榴烯)Ru)2(μ-S-RS)3]+ (8+)。在复合物7中，Ru与S原子的配位使得en-NH与羰基氧之间形成强氢键（2.02 Å）。为了评估铑配位对PTP1B的氧化还原调控的可能影响，随后研究了这些硫醇化合物与H2O2和/或谷胱甘肽的反应，结果表明，配位于Ru显著延缓了H2O2对化合物2中硫醇的氧化（失活）以及谷胱甘肽对亚硫酰胺的后续还原（再活化），这暗示了复合物1对PTP1B的抑制（IC50为19 μM）可能归因于其与催化性半胱氨酸的配位。
• KAMIGATA, NOBUMASA;HASHIMOTO, SATOSHI;KOBAYASHI, MICHIO;NAKANISHI, HIROSH+, BULL. CHEM. SOC. JAP., 1985, 58, N 11, 3131-3136
  作者：KAMIGATA, NOBUMASA、HASHIMOTO, SATOSHI、KOBAYASHI, MICHIO、NAKANISHI, HIROSH+

  DOI：——

  日期：——
• KLYUEV V. N.; KORZHENEVSKIJ A. B.; BEREZIN B. D., IZV. VUZ. XIMIYA I XIM. TEXNOL., 1978, 21, HO 1, 31-33
  作者：KLYUEV V. N.、 KORZHENEVSKIJ A. B.、 BEREZIN B. D.

  DOI：——

  日期：——
• Potassium bromide catalyzed N S bond formation via oxidative dehydrogenation
  作者：Tian-Qun Yu、Yong-Sheng Hou、Yi Jiang、Wen-Xuan Xu、Tao Shi、Xia Wu、Jin-Chao Zhang、Dian He、Zhen Wang

  DOI：10.1016/j.tetlet.2017.03.065

  日期：2017.5

  N-Substituted benzo[d]isothiazol-3(2H)-ones are a family of compounds with extremely important application. Recently, we have developed a new green pathway to synthesize these compounds via potassium bromide-catalyzed intramolecular oxidative dehydrogenative cyclization. This reaction has high functional group tolerance and affords excellent yield even in gram scale. (C) 2017 Elsevier Ltd. All rights reserved.