4-羟基-2-甲基-2H-1,2-苯并噻嗪-3-甲酰胺 1,1-二氧化物; 吡罗昔康杂质 C | 24683-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 中文名称: 4-羟基-2-甲基-2H-1,2-苯并噻嗪-3-甲酰胺 1,1-二氧化物; 吡罗昔康杂质 C
• 中文别名: 4-羟基-2-甲基-2H-1,2-苯并噻嗪-3-甲酰胺1,1-二氧化物;吡罗昔康杂质C；吡罗昔康杂质C
• 英文名称: 4-hydroxy-2-methyl-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide
• 英文别名: 2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid amide；4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide；4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide；4-hydroxy-2-methyl-1,1-dioxo-1λ6,2-benzothiazine-3-carboxamide
• CAS: 24683-25-8
• 化学式: C₁₀H₁₀N₂O₄S
• 分子量: 254.266
• InChiKey: BBOFTHBIXOWDMA-UHFFFAOYSA-N

物化性质

• 沸点：
  517.9±60.0 °C(Predicted)
• 密度：
  1.603±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-羟基-2-甲基-2H-1,2-苯并噻嗪-3-甲酰胺 1,1-二氧化物; 吡罗昔康杂质 C 在 sodium hydroxide 作用下， 生成 5-methyl-6,6-dioxo-5,6-dihydro-6λ⁶-benzo[5,6][1,2]thiazino[3,4-e][1,3]oxazine-2,4-dione
  参考文献：
  名称：

  3-Acyl-4-hydroxy-2H-1,2-benzothiazine 1,1-dioxides. I. Alkylation, amination, and ethoxycarbonylation

  摘要：

  DOI：

  10.1021/jo00924a023
• 作为产物：
  描述：

  2,3-二氢-3-氧代-1,2-苯并异噻唑-2-乙酸乙酯-1,1-二氧化物 在 ammonium hydroxide 、 sodium methylate 、 sodium ethanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-羟基-2-甲基-2H-1,2-苯并噻嗪-3-甲酰胺 1,1-二氧化物; 吡罗昔康杂质 C
  参考文献：
  名称：

  3-Acyl-4-hydroxy-2H-1,2-benzothiazine 1,1-dioxides. I. Alkylation, amination, and ethoxycarbonylation

  摘要：

  DOI：

  10.1021/jo00924a023

文献信息

• 4-Hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides and salts
  申请人：Boehringer Ingelheim GmbH

  公开号：US04233299A1

  公开（公告）日：1980-11-11

  Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, methyl or ethyl; R.sub.2 is methyl, ethyl or n-propyl; and Y is hydrogen, methyl, methoxy, fluorine or chlorine; and non-toxic, pharmacologically acceptable salts thereof formed with an inorganic or organic base. The compounds as well as their salts are useful as antiphlogistics.

  式##STR1##中的化合物，其中R.sub.1为氢、甲基或乙基；R.sub.2为甲基、乙基或正丙基；Y为氢、甲基、甲氧基、氟或氯；以及与无机或有机碱形成的非毒性、药理学上可接受的盐。这些化合物及其盐可用作抗炎药。
• 4-Hydroxy-N-(5((substituted hetero) methyl)-3-isoxazolyl-2H-1,2-benzothiazine-3-carboxamide,1,1-dioxide and 4-hydroxy-2-alkyl-N-(5-((substituted hetero) methyl)-3-isoxazolyl)2H-1,2-benzothiazine-3-carboxamide,1,1-dioxide
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0123418A1

  公开（公告）日：1984-10-31

  4-Hydroxy-N-[5-[(substituted hetero) methyl]-3-isoxazolyl]-2H-1,2-benzothiazine-3-carboxamide 1,1- dioxides as agents for treating pain in mammals resulting from inflammation are disclosed. Also disclosed are processes for their production and pharmaceutical compositions comprising the new compositions.

  本发明公开了 4-羟基-N-[5-[（取代的杂）甲基]-3-异恶唑基]-2H-1,2-苯并噻嗪-3-甲酰胺 1,1- 二氧羰基化合物，作为治疗哺乳动物因炎症引起的疼痛的药物。 还公开了其生产工艺和包含新组合物的药物组合物。
• Ru ^II (η ⁶ ‐ <i>p</i> ‐cymene) Complexes of Bioactive 1,2‐Benzothiazines: Protein Binding vs. Antitumor Activity
  作者：Adnan Ashraf、Mario Kubanik、Farhana Aman、Hannah Holtkamp、Tilo Söhnel、Stephen M. F. Jamieson、Muhammad Hanif、Waseeq Ahmad Siddiqui、Christian G. Hartinger

  DOI：10.1002/ejic.201501361

  日期：2016.3

  Abstract1,2‐Benzothiazine‐3‐carboxamide 1,1‐dioxide derivatives such as meloxicam are known to display numerous pharmacological activities. We prepared a series of 4‐hydroxy‐2‐alkyl‐2H‐benzo[e][1,2]thiazine‐3‐carboxamide 1,1‐dioxide ligands 1a–f and their Ru(η6‐p‐cymene) complexes 2a–f, inspired by synergistic effects observed with other bioactive ligands coordinated to metal centres. The molecular structures of 1a, 2a, and 2b were determined by X‐ray diffraction analyses. The stability of the metal complexes was characterized in DMSO and DMSO/H2O on the basis of 1H NMR spectroscopy and their protein binding capabilities were studied using mass spectrometry. In vitro cytotoxicities of the Ru complexes were determined against human colorectal carcinoma (HCT116), non‐small cell lung carcinoma (NCI‐H460) and cervical carcinoma (SiHa) cell lines. The low levels of biological activity observed for these Ru complexes were put into context by considering their chemical reactivity with proteins. The binding of proteins resulted in cleavage of the benzothiazine backbone when the complex was present in concentrations equimolar with respect to protein.
• JPS58201772A
  申请人：——

  公开号：JPS58201772A

  公开（公告）日：1983-11-24
• US4011332A
  申请人：——

  公开号：US4011332A

  公开（公告）日：1977-03-08