2-(3-methoxyphenyl)benzo[d]isothiazol-3(2H)-one | 35159-88-7

• 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-(3-methoxyphenyl)benzo[d]isothiazol-3(2H)-one
• 英文别名: 2-(3-methoxyphenyl)-2-hydrobenzo[d]isothiazol-3-one；2-(3-Methoxyphenyl)-1,2-benzothiazol-3-one
• CAS: 35159-88-7
• 化学式: C₁₄H₁₁NO₂S
• 分子量: 257.313
• InChiKey: OTXSJKFJDSAKGO-UHFFFAOYSA-N

物化性质

• 沸点：
  440.7±47.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(m-methoxyphenyl)-2-sulfanyl-benzamide 在 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以77%的产率得到2-(3-methoxyphenyl)benzo[d]isothiazol-3(2H)-one
  参考文献：
  名称：

  通过脱氢 NS 键形成电化学合成苯并异噻唑-3(2H)-酮

  摘要：

  在此，我们报告了一种从 2-巯基苯甲酰胺合成苯并异噻唑-3(2H)-酮的电化学方法。电化学反应通过分子内 N H/S H 偶联环化反应进行，生成 H 2作为无害副产物。此外，该方法反应时间短，条件温和，底物范围广，无需使用金属催化剂和外源性氧化剂。2009 Elsevier Ltd. 版权所有。

  DOI：

  10.1016/j.tetlet.2021.153323

文献信息

• [EN] METHODS AND COMPOUNDS TO TREAT SARS INFECTIONS<br/>[FR] PROCÉDÉS ET COMPOSÉS POUR TRAITER LES INFECTIONS À SARS-COV-2
  申请人：UNIV CALIFORNIA

  公开号：WO2022081984A1

  公开（公告）日：2022-04-21

  This disclosure features chemical entities (e.g., a compound (e.g., a compound of Formula (I), (II), (III), or (IV)), or a pharmaceutically acceptable salt, and/or hydrate, and/or cocrystal, and/or drug combination of the compound) that inhibit the main protease (MPro) of a coronavirus (e.g., SARS-CoV-2). Said chemical entities are useful, e.g., for treating a coronavirus infection (e.g., SARS-CoV-2 infection (e.g., COVID-19)) in a subject (e.g., a human). This disclosure also features compositions containing the same as well as methods of using and making the same.

  本文披露了一些化合物（例如，化合物（例如，公式（I），（II），（III）或（IV）的化合物），或药物的可接受盐，和/或水合物，和/或共晶体，和/或化合物的药物组合），它们能够抑制冠状病毒（例如，SARS-CoV-2）的主要蛋白酶（MPro）。这些化合物可用于治疗受体（例如，人类）的冠状病毒感染（例如，SARS-CoV-2感染（例如，COVID-19））。本文还涉及含有相同化合物的组合物，以及使用和制备这些化合物的方法。
• Potent, Selective, and Orally Available Benzoisothiazolone Phosphomannose Isomerase Inhibitors as Probes for Congenital Disorder of Glycosylation Ia
  作者：Russell Dahl、Yalda Bravo、Vandana Sharma、Mie Ichikawa、Raveendra-Panickar Dhanya、Michael Hedrick、Brock Brown、Justin Rascon、Michael Vicchiarelli、Arianna Mangravita-Novo、Li Yang、Derek Stonich、Ying Su、Layton H. Smith、Eduard Sergienko、Hudson H. Freeze、Nicholas D. P. Cosford

  DOI：10.1021/jm101401a

  日期：2011.5.26

  We report the discovery and validation of a series of benzoisothiazolones as potent inhibitors of phosphomannose isomerase (PM), an enzyme that converts mannose-6-phosphate (Man-6-P) into fructose-6-phosphate (Fru-6-P) and, more importantly, competes with phosphomannomutase 2 (PMM2) for Man-6-P, diverting this substrate from critical protein glycosylation events. In congenital disorder of glycosylation type Ia, PMM2 activity is compromised.; thus, PMI inhibition is a potential strategy for the development of therapeutics. High-throughput screening (HTS) and subsequent chemical optimization led to the identification of a novel class of benzoisothiazolones as potent PMI inhibitors having little or no PMM2 inhibition. Two complementary synthetic routes were developed, enabling the critical structural requirements for activity to be determined, and the compounds were subsequently profiled in biochemical and cellular assays to assess efficacy. The most promising compounds were also profiled for bioavailability parameters, including metabolic stability, plasma stability, and permeability. The pharmacokinetic profile of a representative of this series (compound 19; ML089) was also assessed, demonstrating the potential of this series for in vivo efficacy when dosed orally in disease models.
• Anti-fouling compositions or fouling control of harmful aquatic oranisms
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0644243B1

  公开（公告）日：1999-01-27
• BENZOISOTHIAZOLONES AS INHIBITORS OF PHOSPHOMANNOSE ISOMERASE
  申请人：Cosford Nicholas D. P.

  公开号：US20110257233A1

  公开（公告）日：2011-10-20

  The disclosure provides new compounds and compositions thereof, and methods for treating or ameliorating a disorder relating to CDG-Ia. In particular, the disclosure provides benzoisothiazolone inhibitors of PMI, which have been synthesized and their ability to drive glycosylation has been demonstrated. The disclosure provides two synthetic routes for these compounds, including a new copper-catalyzed N-arylation reaction amenable to parallel derivitization. The disclosed compounds represent potent inhibitors of PMI, and their dose-dependent efficacy in cell-based models of glycosylation have been demonstrated. In addition, the disclosed compounds are selective over PMM and therefore, are useful in treating or ameliorating a disorder relating to CDG-Ia.
• [EN] BENZOISOTHIAZOLONES AS INHIBITORS OF PHOSPHOMANNOSE ISOMERASE<br/>[FR] BENZOISOTHIAZOLONES EN TANT QU'INHIBITEURS DE PHOSPHOMANNOSE ISOMÉRASE (PMI)
  申请人：SANFORD BURNHAM MED RES INST

  公开号：WO2011116355A2

  公开（公告）日：2011-09-22

  The disclosure provides new compounds and compositions thereof, and methods for treating or ameliorating a disorder relating to CDG-Ia. In particular, the disclosure provides benzoisothiazolone inhibitors of PMI, which have been synthesized and their ability to drive glycosylation has been demonstrated. The disclosure provides two synthetic routes for these compounds, including a new copper-catalyzed N-arylation reaction amenable to parallel derivitization. The disclosed compounds represent potent inhibitors of PMI, and their dose- dependent efficacy in cell-based models of glycosylation have been demonstrated. In addition, the disclosed compounds are selective over PMM and therefore, are useful in treating or ameliorating a disorder relating to CDG-Ia.