3,4-dihydro-2H-benzo[b][1,4]thiazine-6,7-dione | 157950-94-2

• 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: 3,4-dihydro-2H-benzo[b][1,4]thiazine-6,7-dione
• 英文别名: dihydro-1,4-benzothiazine-6,7-quinone；dihydro-1,4-benzothiazine-6,7-dione；2H-1,4-Benzothiazine-6,7-dione, 3,4-dihydro-；3,4-dihydro-2H-1,4-benzothiazine-6,7-dione
• CAS: 157950-94-2
• 化学式: C₈H₇NO₂S
• 分子量: 181.215
• InChiKey: YKQBOVAOIFUWMI-UHFFFAOYSA-N

物化性质

• 沸点：
  299.2±40.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3,4-dihydro-2H-benzo[b][1,4]thiazine-6,7-dione 在 锌 作用下， 反应 0.67h， 生成
  参考文献：
  名称：

  Biomimetic oxidation of the antimelanoma agent 4-S-cysteaminylphenol and related catechol thioethers: Isolation and reaction behaviour of novel dihydrobenzothiazinequinones

  摘要：

  Enzymatic and chemical oxidation of 4-S-cysteaminylpheno1 (1) and 4-S-cysteaminylcatechol (2) leads to the formation of the hitherto unknown dihydrobenzothiazine-6,7-quinone 4 via intramolecular cyclisation of the o-quinone 6. Oxidation of 4-S-cysteinylcatechol (3) gives the corresponding dihydrobenzothiazinequinone 9, which undergoes rearrangement with partial decarboxylation to give 6,7-dihydroxybenzothiazine derivatives, isolated as 8 and 5 after reduction and acetylation of the mixture. Oxidation of 2 and 3 with periodate or iodate gives mainly the iodinated quinones 7 and 13, respectively.

  DOI：

  10.1016/s0040-4020(01)85349-7
• 作为产物：
  描述：

  4-羟基苯硫酚 在 盐酸 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 3,4-dihydro-2H-benzo[b][1,4]thiazine-6,7-dione
  参考文献：
  名称：

  Biomimetic oxidation of the antimelanoma agent 4-S-cysteaminylphenol and related catechol thioethers: Isolation and reaction behaviour of novel dihydrobenzothiazinequinones

  摘要：

  Enzymatic and chemical oxidation of 4-S-cysteaminylpheno1 (1) and 4-S-cysteaminylcatechol (2) leads to the formation of the hitherto unknown dihydrobenzothiazine-6,7-quinone 4 via intramolecular cyclisation of the o-quinone 6. Oxidation of 4-S-cysteinylcatechol (3) gives the corresponding dihydrobenzothiazinequinone 9, which undergoes rearrangement with partial decarboxylation to give 6,7-dihydroxybenzothiazine derivatives, isolated as 8 and 5 after reduction and acetylation of the mixture. Oxidation of 2 and 3 with periodate or iodate gives mainly the iodinated quinones 7 and 13, respectively.

  DOI：

  10.1016/s0040-4020(01)85349-7

文献信息

• Dihydro-1,4-benzothiazine-6,7-dione, the ultimate toxic metabolite of 4-S-Cysteaminylphenol and 4-S-Cysteaminylcatechol
  作者：Katsutoshi Hasegawa、Shosuke Ito、Shigeki Inoue、Kazumasa Wakamatsu、Hiroyuki Ozeki、Isao Ishiguro

  DOI：10.1016/s0006-2952(97)00075-0

  日期：1997.5

  4-S-Cysteaminylphenol (4-S-CAP) and the corresponding catechol 4-S-cysteaminylcatechol (4-S-CAC) have been evaluated for melanocytotoxicity. It was shown recently that tyrosinase oxidation of these substrates produces a violet pigment, dihydro-1,4-benzothiazine-6,1-dione (BQ). In this study we examined whether BQ is the ultimate toxic metabolite produced in melanoma cells from 4-S-CAP/4-S-CAC. Biochemical experiments showed that (1) BQ was formed by autoxidation of 4-S-CAC as well as by tyrosinase oxidation of 4-S-CAP/4-S-CAC, (2) BQ reacted rapidly with thiols such as reduced glutathione (GSH), and (3) BQ inhibited the activity of alcohol dehydrogenase, an SH enzyme. In vitro experiments showed that (1) the cytotoxicity of 4-S-CAC was mostly prevented by catalase and superoxide dismutase, (2) Ba was highly cytotoxic to B16 melanoma cells (IC50 being 3.9 mu M as compared with 507 mu M for 4-S-CAP), (3) BQ was metabolized rapidly to a GSH adduct in melanoma cells, and (4) the same GSH adduct was also formed upon incubation of melanoma cells with 4-S-CAP, the reaction being tyrosinase dependent. In vivo experiments showed that intratumoral administration of BQ (0.5 mu mol) inhibited the subcutaneous growth of B16 melanoma nearly as effectively as 4-S-CAP/4-S-CAC (20 mu mol). These results indicate that BQ is the ultimate toxic metabolite produced by tyrosinase oxidation of 4-S-CAP/4-S-CAC. BQ deprives melanoma cells of GSH and may inactivate SH enzymes essential for DNA synthesis and cell proliferation by covalent binding through their cysteine residues, thereby exerting melanocytotoxicity. Cytotoxicity of 4-S-CAC depends mostly on autoxidation producing BQ and active oxygens. (C) 1997 Elsevier Science Inc.
• Habibi, Davood; Aarezi, Fatemeh, Asian Journal of Chemistry, 2010, vol. 22, # 9, p. 7039 - 7042
  作者：Habibi, Davood、Aarezi, Fatemeh

  DOI：——

  日期：——
• Biomimetic oxidation of the antimelanoma agent 4-S-cysteaminylphenol and related catechol thioethers: Isolation and reaction behaviour of novel dihydrobenzothiazinequinones
  作者：Donatella Mascagna、Claudio Costantini、Marco d'Ischia、Giuseppe Prota

  DOI：10.1016/s0040-4020(01)85349-7

  日期：1994.1

  Enzymatic and chemical oxidation of 4-S-cysteaminylpheno1 (1) and 4-S-cysteaminylcatechol (2) leads to the formation of the hitherto unknown dihydrobenzothiazine-6,7-quinone 4 via intramolecular cyclisation of the o-quinone 6. Oxidation of 4-S-cysteinylcatechol (3) gives the corresponding dihydrobenzothiazinequinone 9, which undergoes rearrangement with partial decarboxylation to give 6,7-dihydroxybenzothiazine derivatives, isolated as 8 and 5 after reduction and acetylation of the mixture. Oxidation of 2 and 3 with periodate or iodate gives mainly the iodinated quinones 7 and 13, respectively.