methyl 7-chloro-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide | 183859-75-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: methyl 7-chloro-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide
• 英文别名: methyl 7-chloro-4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1H,1H -1λ⁶,2-benzothiazine-3-carboxylate；Methyl 7-chloro-4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylate；methyl 7-chloro-4-hydroxy-2-methyl-1,1-dioxo-1λ6,2-benzothiazine-3-carboxylate
• CAS: 183859-75-8
• 化学式: C₁₁H₁₀ClNO₅S
• 分子量: 303.723
• InChiKey: MPQNKMJYFWTMOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 7-chloro-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide 在 potassium tert-butylate 作用下， 以 xylene 、 叔丁醇 为溶剂， 反应 15.0h， 生成 2-(7-Chloro-4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazin-3-yl)-3H-quinazolin-4-one
  参考文献：
  名称：

  Synthesis of Potential Biologically Active 1,2-Benzothiazin-3-yl-quinazolin-4(3H)-ones

  摘要：

  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。

  DOI：

  10.1248/cpb.54.1175
• 作为产物：
  描述：

  5-氯-2-甲基苯磺酰氯 在 氢氧化钾 、 sodium hydroxide 、 potassium permanganate 、 氨 、 sodium 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.03h， 生成 methyl 7-chloro-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide
  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

• 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.