4-[(1,1,3-Trioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]benzoic acid | 694473-93-3

• 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: 4-[(1,1,3-Trioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]benzoic acid
• 英文别名: 4-((1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)methyl)benzoic acid；4-[(1,1-dioxide-3-oxo-2H-benzo[d]isothiazol-2-yl)methyl]benzoic acid；4-[(1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl]benzoic acid；4-[(1,1,3-trioxo-1,2-benzothiazol-2-yl)methyl]benzoic acid
• CAS: 694473-93-3
• 化学式: C₁₅H₁₁NO₅S
• mdl: MFCD04213399
• 分子量: 317.322
• InChiKey: SZXYUCMJXHGNGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(1,1,3-Trioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]benzoic acid 在 氯化亚砜 作用下， 反应 3.0h， 以99%的产率得到4-[(1,1,3-Trioxo-2,3-dihydro-1λ6,2-benzothiazol-2-yl)methyl]benzoyl chloride
  参考文献：
  名称：

  Saccharin Derivatives as Inhibitors of Interferon-Mediated Inflammation

  摘要：

  A series of novel, saccharin-based antagonists have been identified for the interferon signaling pathway. Through in vitro high-throughput screening with the Colorado Center for Drug Discovery (C2D2) Pilot Library, we identified hit compound 1, which was the basis for extensive structure-activity relationship studies. Our efforts produced a lead anti-inflammatory compound, tert-butyl N-(furan-2-ylmethyl)-N-{4-[(1,1,3-trioxo-2,3-dihydro-1λ(6),2-benzothiazol-2-yl)methyl]benzoyl}carbamate CU-CPD103 (103), as a potent inhibitor using an established nitric oxide (NO) signaling assay. With further studies of its inhibitory mechanisms, we demonstrated that 103 carries out this inhibition through the JAK/STAT1 pathway, providing a drug-like small molecule inflammation suppressant for possible therapeutic uses.

  DOI：

  10.1021/jm500409k
• 作为产物：
  描述：

  4-溴甲基苯甲酸叔丁酯 在 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 20.33h， 生成 4-[(1,1,3-Trioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]benzoic acid
  参考文献：
  名称：

  Saccharin Derivatives as Inhibitors of Interferon-Mediated Inflammation

  摘要：

  A series of novel, saccharin-based antagonists have been identified for the interferon signaling pathway. Through in vitro high-throughput screening with the Colorado Center for Drug Discovery (C2D2) Pilot Library, we identified hit compound 1, which was the basis for extensive structure-activity relationship studies. Our efforts produced a lead anti-inflammatory compound, tert-butyl N-(furan-2-ylmethyl)-N-{4-[(1,1,3-trioxo-2,3-dihydro-1λ(6),2-benzothiazol-2-yl)methyl]benzoyl}carbamate CU-CPD103 (103), as a potent inhibitor using an established nitric oxide (NO) signaling assay. With further studies of its inhibitory mechanisms, we demonstrated that 103 carries out this inhibition through the JAK/STAT1 pathway, providing a drug-like small molecule inflammation suppressant for possible therapeutic uses.

  DOI：

  10.1021/jm500409k

文献信息

• DERIVATIVES OF BENZO[D] ISOTHIAZOLES AS HISTONE DEACETYLASE INHIBITORS
  申请人：Universidad De Granada

  公开号：EP2045246A1

  公开（公告）日：2009-04-08

  The invention relates to derivatives of benzo[d]isothiazoles as histone deacetylase inhibitors, selected from among compounds of general formula (Ia) and (Ib) or one of the salts thereof, particularly one of the pharmaceutically acceptable salts thereof, or one of the corresponding solvates thereof. These compounds are histone deacetylase enzyme inhibitors and are suitable as pharmacologically active agents in a medicament for the treatment and/or prophylaxis of disorders or diseases associated to histone deacetylases. The invention also describes a process for obtaining the mentioned compounds and the pharmaceutical compositions containing them

  本发明涉及作为组蛋白去乙酰化酶抑制剂的苯并[d]异噻唑衍生物，它们选自通式(Ia)和(Ib)化合物或其盐类之一，特别是其药学上可接受的盐类之一，或其相应的溶解物之一。这些化合物是组蛋白去乙酰化酶抑制剂，可作为药理活性剂用于治疗和/或预防与组蛋白去乙酰化酶有关的紊乱或疾病。本发明还描述了获得上述化合物和含有这些化合物的药物组合物的过程
• Design, synthesis and biological evaluation of saccharin-based N -hydroxybenzamides as histone deacetylases (HDACs) inhibitors
  作者：Huansheng Fu、Leiqiang Han、Xuben Hou、Yanyan Dun、Lei Wang、Xiaowei Gong、Hao Fang

  DOI：10.1016/j.bmc.2015.07.008

  日期：2015.9

  We report the development of a novel series of saccharin-based N-hydroxybenzamides as histone deacetylases inhibitors. Among them, 6j exhibited potent HDACs inhibitory activity against Hela nuclear extract. Further biological evaluation found 6i showed similar antiproliferative activities in vitro compared with the approved SAHA. (C) 2015 Elsevier Ltd. All rights reserved.
• EP2045246
  申请人：——

  公开号：——

  公开（公告）日：——
• DERIVATIVES OF BENZO[D]ISOTHIAZOLES AS HISTONES DEACETYLASE INHIBITORS
  申请人：Gomez Vidal Jose Antonio

  公开号：US20090312377A1

  公开（公告）日：2009-12-17

  The invention relates to derivatives of benzo[d]isothiazoles as histone deacetylase inhibitors, selected from among compounds of general formula (Ia) and (Ib) or one of the salts thereof, particularly one of the pharmaceutically acceptable salts thereof, or one of the corresponding solvates thereof. These compounds are histone deacetylase enzyme inhibitors and are suitable as pharmacologically active agents in a medicament for the treatment and/or prophylaxis of disorders or diseases associated to histone deacetylases. The invention also describes a process for obtaining the mentioned compounds and the pharmaceutical compositions containing them
• [EN] DERIVATIVES OF BENZO[D]ISOTHIAZOLES AS HISTONE DEACETYLASE INHIBITORS<br/>[ES] DERIVADOS DE BENZO[D]ISOTIAZOLES COMO INHIBIDORES DE LAS HISTONE DESACETILASAS<br/>[FR] DÉRIVÉS DE BENZO[D]ISOTHIAZOLES UTILISÉS COMME INHIBITEURS DES HISTONE-DÉSACÉTYLASES
  申请人：UNIV GRANADA

  公开号：WO2008003800A1

  公开（公告）日：2008-01-10

  [EN] The invention relates to derivatives of benzo[d]isothiazoles as histone deacetylase inhibitors, selected from among compounds having general formula (la) and (lb), one of the salts thereof, particularly one of the pharmaceutically-acceptable salts, or one of the corresponding solvates. Said compounds inhibit histone deacetylase enzymes and are suitable for use as pharmacologically-active agents in a medicament for the treatment and/or prophylaxis of disorders and diseases associated with histone deacetylases. The invention also relates to a method for obtaining the aforementioned compounds and to pharmaceutical compositions containing same.
  [FR] L'invention concerne des dérivés de benzo[d]isothiazoles utilisés comme inhibiteurs des histone-désacétylases, sélectionnés parmi les composés représentés par les formules générales (Ia) et (Ib) ou un de leurs sels, en particulier un de leurs sels de qualité pharmaceutique ou un de leurs solvates correspondants. Ces composés sont des inhibiteurs des enzymes histone-désacétylases et peuvent être utilisés comme agents actifs sur le plan pharmacologique dans un médicament destiné au traitement et/ou à la prévention de troubles ou de maladies associés aux histone-désacétylases. L'invention concerne également un procédé permettant d'obtenir lesdits composés et les compositions pharmaceutiques contenant ces composés.
  [ES] Derivados de benzo[d]isotiazoles como inhibidores de las histonas desacetilasas, seleccionados de entre los compuestos de fórmula general (Ia) y (Ib) o una de sus sales, en particular una de sus sales farmacéuticamente aceptables, o uno de sus solvatos correspondientes. Estos compuestos son inhibidores de las enzimas histonas desacetilasas y son adecuados como agentes farmacológicamente activos en un medicamento para el tratamiento y/o profilaxis de trastornos o enfermedades asociados a las histonas desacetilasas. La invención describe asimismo un procedimiento de obtención de los citados compuestos y las composiciones farmacéuticas que los contienen.