10-benzothiazol-2-yl-8-carboxy-5-hydroxy-3-oxo-3,4,7,8,9,10-hexahydro-2H-[1,4]thiazino[5,6-h]isoquinoline | 1274944-10-3

• 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: 10-benzothiazol-2-yl-8-carboxy-5-hydroxy-3-oxo-3,4,7,8,9,10-hexahydro-2H-[1,4]thiazino[5,6-h]isoquinoline
• 英文别名: 10-(1,3-benzothiazol-2-yl)-5-hydroxy-3-oxo-7,8,9,10-tetrahydro-4H-pyrido[4,3-h][1,4]benzothiazine-8-carboxylic acid
• CAS: 1274944-10-3
• 化学式: C₁₉H₁₅N₃O₄S₂
• 分子量: 413.478
• InChiKey: YJGUGGJZNHQYHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯并噻唑-2-甲醛 、 7-(2-amino-2-carboxyethyl)-5-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzothiazine 以 乙腈 为溶剂， 反应 7.0h， 以4%的产率得到10-benzothiazol-2-yl-8-carboxy-5-hydroxy-3-oxo-3,4,7,8,9,10-hexahydro-2H-[1,4]thiazino[5,6-h]isoquinoline
  参考文献：
  名称：

  Uncovering the Structure of Human Red Hair Pheomelanin: Benzothiazolylthiazinodihydroisoquinolines As Key Building Blocks

  摘要：

  Biomimetic oxidation of the pheomelanin precursor-5-S-cysteinyldopa in the presence of Zn2+; ions led to the, isolation of two isomeric products, one of which could be identified as the benzothiazolythiazinodihydroisoquinoline 5, while the other proved too unstable for a complete characterization. Both these products were converted into more stable oxidized forms, which after ethylchloroformate derivatization, were characterized as the ethyl ester/ethoxycarbonyl isoquino. lines 8 and 9. Compound. 5 exhibited,absorption characteristics,similar to those of red hair pheomelanin, including a main band around 400 tun in acids Similarly to red hair pheomelanin and synthetic pigments, 5 afforded on chemical degradation a thiazolylpridinecarboxylic add fragment Model chemical studies allowed the proposal of a formation mechanisin for the benzothiazole and dihydroisoquinoline systems in compound 5:

  DOI：

  10.1021/np100740n

文献信息

• Uncovering the Structure of Human Red Hair Pheomelanin: Benzothiazolylthiazinodihydroisoquinolines As Key Building Blocks
  作者：Giorgia Greco、Lucia Panzella、Luisella Verotta、Marco d’Ischia、Alessandra Napolitano

  DOI：10.1021/np100740n

  日期：2011.4.25

  Biomimetic oxidation of the pheomelanin precursor-5-S-cysteinyldopa in the presence of Zn2+; ions led to the, isolation of two isomeric products, one of which could be identified as the benzothiazolythiazinodihydroisoquinoline 5, while the other proved too unstable for a complete characterization. Both these products were converted into more stable oxidized forms, which after ethylchloroformate derivatization, were characterized as the ethyl ester/ethoxycarbonyl isoquino. lines 8 and 9. Compound. 5 exhibited,absorption characteristics,similar to those of red hair pheomelanin, including a main band around 400 tun in acids Similarly to red hair pheomelanin and synthetic pigments, 5 afforded on chemical degradation a thiazolylpridinecarboxylic add fragment Model chemical studies allowed the proposal of a formation mechanisin for the benzothiazole and dihydroisoquinoline systems in compound 5: