7-(2-aminoethyl)-5-hydroxy-1,4-benzothiazine-3-carboxylic acid | 171776-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 7-(2-aminoethyl)-5-hydroxy-1,4-benzothiazine-3-carboxylic acid
• 英文别名: 7-(2-aminoethyl)-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid
• CAS: 171776-48-0
• 化学式: C₁₁H₁₂N₂O₃S
• 分子量: 252.294
• InChiKey: WQYOTANUJHVJQB-UHFFFAOYSA-N

物化性质

• 沸点：
  551.0±60.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(2-aminoethyl)-5-hydroxy-1,4-benzothiazine-3-carboxylic acid 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 反应 0.17h， 生成 7-(2-aminoethyl)-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid
  参考文献：
  名称：

  半胱氨酸存在下多巴胺的氧化：新有毒产品的表征。

  摘要：

  先前的研究表明，在pH 7.4的L-半胱氨酸（CySH）存在下，多巴胺（DA）的氧化产生了神经递质的半胱氨酰共轭物的复杂混合物，该混合物很容易被进一步氧化为许多二氢苯并噻嗪（DHBT）以及未知的黄色产品。在这项调查中，已经确定了其中三种产品。5-S-半胱氨酰多巴胺（5-S-CyS-DA）和7的氧化反应生成7-（2氨基乙基）-5-羟基-1,4-苯并噻嗪-3-羧酸（BT-1） -（2-氨基乙基）-3,4-二氢-5-羟基-2H-1,4-苯并噻嗪-3-羧酸（DHBT-1）。区域异构体6-（2-氨基乙基）-1,8,9,10-四氢苯并[1,2-b：4,3-b']双[1,4]噻嗪-9-羧酸（12）和6- （2-氨基乙基）-1,2,3,10-四氢苯并[1,2-b：4,3-b']双[1,4]噻嗪-2-羧酸（13）是通过2的氧化而形成的，5-bi-S-CyS-DA），6-S-半胱氨酰基-7-（2-氨基乙基）-

  DOI：

  10.1021/tx960145c
• 作为产物：
  描述：

  5-S-半胱氨酰多巴胺 以 水 为溶剂， 生成 7-(2-aminoethyl)-5-hydroxy-1,4-benzothiazine-3-carboxylic acid 、
  参考文献：
  名称：

  Reactions of Cysteine and Cysteinyl Derivatives with Dopamine-o-quinone and Further Insights into the Oxidation Chemistry of 5-S-Cysteinyldopamine: Potential Relevance to Idiopathic Parkinson′s Disease

  摘要：

  Recent studies suggest that elevated rates of autoxidation of dopamine (DA) in the cytoplasm of neuromelanin-pigmented dopaminergic cell bodies in the substantia nigra (SN) and/or reactions of its proximate oxidation product, DA-o-quinone, with glutathione (GSH) or L-cysteine (CySH) might yield endotoxins that play roles in the pathogenesis of idiopathic Parkinson's Disease (PD). In this study the reactions between DA-o-quinone and CySH and some cysteine derivatives have been studied. The reactions between DA-o-quinone and CySH or cysteine methyl ester are rapid and give the corresponding 5-S-cysteinyl conjugates of DA as the predominant products. By contrast, the reaction between the sterically hindered D-penicillamine methyl ester (PME) and DA-o-quinone is much slower to give, initially, a mixture of the 2-S-, 5-S-, and 6-S-PME conjugates of DA. These conjugates are then further oxidized by unreacted DA-o-quinone to give a complex mixture of products which include 7-(2-aminoethyl)-5-hydroxy-2,2-dimethyl-1,4-benzothiazine-3-carboxylic acid methyl ester (13). Large increases in the 5-S-cysteinyldopamine (5-S-CyS-DA)/DA concentration ratio have been measured in the Parkinsonian SN and have been interpreted to reflect elevated rates of DA autoxidation in this structure that degenerates in PD. However, the present study reveals that at physiological pH 5-S-CyS-DA is not only more easily oxidized than DA but a bicyclic o-quinone imine (5) intermediate is formed that can chemically oxidize the former conjugate in a reaction that leads to 7-(2-aminoethyl)-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (6). Compound 6 is lethal when administered into the brains of mice. However, this putative dihydrobenzothiazine endotoxin is even more easily oxidized than 5-S-CyS-DA in a rather complex reaction that ultimately forms 7-(2-aminoethyl)-5-hydroxy-1,4-benzothiazine-3-carboxylic acid (15). Although this benzothiazine could not be isolated it was identified by comparison of its electrochemical and spectroscopic properties in solution with those of 13. The results of this study suggest that benzothiazine 15 might serve as a better analytical marker molecule than 5-S-CyS-DA for either elevated rates of DA autoxidation and/or for roles of GSH and CySH in the neurodegenerative mechanisms in the SN that contribute to PD. (C) 1995 Academic Press, Inc.

  DOI：

  10.1006/bioo.1995.1016