methyl 7-chloro-4-hydroxy-1,1-dioxo-1,2-dihydro-1H,1H -1λ⁶,2-benzothiazine-3-carboxylate | 183859-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl 7-chloro-4-hydroxy-1,1-dioxo-1,2-dihydro-1H,1H -1λ⁶,2-benzothiazine-3-carboxylate
• 英文别名: 7-Chloro-4-hydroxy-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester；methyl 7-chloro-4-hydroxy-1,1-dioxo-2H-1lambda6,2-benzothiazine-3-carboxylate；methyl 7-chloro-4-hydroxy-1,1-dioxo-2H-1λ6,2-benzothiazine-3-carboxylate
• CAS: 183859-72-5
• 化学式: C₁₀H₈ClNO₅S
• 分子量: 289.696
• InChiKey: WIKFZUGTEPIRND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 7-chloro-4-hydroxy-1,1-dioxo-1,2-dihydro-1H,1H -1λ⁶,2-benzothiazine-3-carboxylate 在 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Benzo[1,3]dioxol-5-ylmethyl-7-chloro-1,1-dioxo-4-trifluoromethanesulfonyloxy-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Endothelin receptor antagonists: synthesis and structure–activity relationships of substituted benzothiazine-1,1-dioxides

  摘要：

  The development of benzothiazine-1,1-dioxide derivatives as a new structural class of potent endothelin receptor antagonists is described. Structure-activity relationships (SAR) revealed that PD164800 (1) is a potent antagonist of the ETA receptor subtype. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00080-7
• 作为产物：
  描述：

  sodium 6-chloro-1,2-benzisothiazol-3(2H)-one 1,1-dioxide 在 sodium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.03h， 生成 methyl 7-chloro-4-hydroxy-1,1-dioxo-1,2-dihydro-1H,1H -1λ⁶,2-benzothiazine-3-carboxylate
  参考文献：
  名称：

  Kwon, Soon-Kyoung; Park, Myung-Sook, Arzneimittel-Forschung/Drug Research, 1996, vol. 46, # 10, p. 966 - 971

  摘要：

  DOI：

文献信息

• Synthesis of Potential Biologically Active 1,2-Benzothiazin-3-yl-quinazolin-4(3H)-ones
  作者：Muhammad Zia-ur-Rehman、Jamil Anwar Choudary、Saeed Ahmad、Hamid Latif Siddiqui

  DOI：10.1248/cpb.54.1175

  日期：——

  A series of potential biologically active 2-(4-hydroxy-1,1-dioxido-2H-1,2-benzothiazin-3-yl)quinazolin-4(3H)-ones was synthesized in a straight forward manner by condensation of respective 4-hydroxy-1,2-benzothiazine-1,1-dioxides with anthranilamide followed by simple and high throughput cyclization of N-[2-(aminocarbonyl)phenyl]-4-hydroxy-1,2-benzothiazine-3-carboxamide-1,1-dioxides. All the synthesized compounds were subjected to preliminary evaluation for their biological activity against Gram positive and Gram negative bacteria. Some of the assayed compounds showed marked activity against Bacillus subtilis.

  2-苯并噻嗪-3-基）喹唑啉-4(3H)-酮的简单高通量环化反应。对所有合成化合物进行了初步评估，以确定其对革兰氏阳性和革兰氏阴性细菌的生物活性。其中一些化合物对枯草杆菌具有明显的活性。
• N‐Heterocyclic Carbene Organocatalyzed [3+3] Annulation for the Enantioselective Synthesis of Benzopyranothiazinones
  作者：Karina Mroczyńska、Zbigniew Rafiński

  DOI：10.1002/adsc.202301082

  日期：2024.3.19

  The design, inspired by the core-structure of oxicam has allowed the enantioselective synthesis of benzopyranothiazinone motifs employing N-heterocyclic carbene (NHC) catalysis. The NHC-mediated transformation involves the reaction of α,β-unsaturated aldehydes with suitable substituted benzothiazinone derivatives. This process encompasses the initial formation of α,β-unsaturated acylazoliums from ynals

  该设计受奥昔康核心结构的启发，允许采用 N-杂环卡宾 (NHC) 催化对映选择性合成苯并吡喃噻嗪酮基序。 NHC 介导的转化涉及 α,β-不饱和醛与合适的取代苯并噻嗪酮衍生物的反应。该过程包括从炔醛初始形成 α,β-不饱和酰唑鎓，同时从苯并噻嗪酮生成烯醇化物。这些反应的最终结果是有效的环化，产生具有合理产率和高立体选择性的所需产物。这项研究强调了 NHC 催化在简化复杂杂环结构合成中的潜力。
• Effect of Structural Modification of Enol−Carboxamide-Type Nonsteroidal Antiinflammatory Drugs on COX-2/COX-1 Selectivity
  作者：Edward S. Lazer、Clara K. Miao、Charles L. Cywin、Ronald Sorcek、Hin-Chor Wong、Zhaoxing Meng、Ian Potocki、MaryAnn Hoermann、Roger J. Snow、Matt A. Tschantz、Terence A. Kelly、Daniel W. McNeil、Simon J. Coutts、Laurie Churchill、Anne G. Graham、Eva David、Peter M. Grob、Wolfhard Engel、Hans Meier、Günter Trummlitz

  DOI：10.1021/jm9607010

  日期：1997.3.1

  Meloxicam (5), an NSAID in the enol-carboxamide class, was developed on the basis of its antiinflammatory activity and relative safety in animal models. In subsequent screening in microsomal assays using human COX-1 and COX-2, we discovered that it possessed a selectivity profile for COX-2 superior to piroxicam and other marketed NSAIDs. We therefore embarked on a study of enol-carboxamide type compounds to determine if COX-2 selectivity and potency could be dramatically improved by structural modification. Substitution at the 6- and 7-positions of the 4-oxo-1,2-benzothiazine-3-carboxamide, alteration of the N-methyl substituent, and amide modification were all examined. In addition we explored several related systems including the isomeric 3-oxo-1,2-benzothiazine-4-carboxamides, thienothiazines, indolothiazines, benzothienothiazines, naphthothiazines, and 1,3- and 1,4-dioxoisoquinolines. While a few examples were found with greater potency in the COX-2 assay, no compound tested had a better COX-2/COX-1 selectivity profile than that of 5.