(2S,4S)-3-acetyl-5,5-dimethyl-2-(2-methoxyphenyl)-4-thiazolidinecarboxylic acid | 125813-83-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4S)-3-acetyl-5,5-dimethyl-2-(2-methoxyphenyl)-4-thiazolidinecarboxylic acid
• 英文别名: (2S,4S)-3-acetyl-2-(2-methoxyphenyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• CAS: 125813-83-4
• 化学式: C₁₅H₁₉NO₄S
• 分子量: 309.386
• InChiKey: GQVXDOIZTZYNLS-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S)-3-acetyl-5,5-dimethyl-2-(2-methoxyphenyl)-4-thiazolidinecarboxylic acid 、 3,4-Dihydro-2-(2-hydroxy-5-methoxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine 在 3,4-Dihydro-2-(2-hydroxy-5-methoxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine 作用下， 以18.1的产率得到[4-methoxy-2-(4-methyl-3-oxo-1,4-benzothiazin-2-yl)phenyl] (2S,4S)-3-acetyl-2-(2-methoxyphenyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate
  参考文献：
  名称：

  Novel benzothiazine derivatives

  摘要：

  本发明涉及一种新的苯并噻嗪衍生物，其化学式为[I]，制备它们的方法以及包含它们作为活性成分的循环系统疾病治疗剂。 其中，R1是氢、低碳基、卤素、硝基、羟基、低烷氧基、低烷酰氧基、氨基、低烷基氨基和低烷氧羰基氧基等中的一个或多个基团；R2是氢、低碳基或（C3-C6）环烷基；R3是氢、低碳基、羟基、低烷氧基、卤素、硝基、低烷二氧基、低烷酰氧基、低烷酰基、氨基、低烷基氨基、低烷酰氨基和低烷氧羰基氧基中的一个或多个基团，或者是##STR2##；R4是氢或低碳基。

  公开号：

  US04786635A1
• 作为产物：
  描述：

  D-青霉胺 以 乙醇 、 水 为溶剂， 反应 11.0h， 生成 (2S,4S)-3-acetyl-5,5-dimethyl-2-(2-methoxyphenyl)-4-thiazolidinecarboxylic acid
  参考文献：
  名称：

  Synthesis and calcium ion antagonistic activity of 2-[2-[(aminoalkyl)oxy]-5-methoxyphenyl]-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzothiazines

  摘要：

  As an extension of the previous investigation (J. Med. Chem. 1988, 31, 919), we synthesized a series of 2-[2-[(aminoalkyl)oxy]-5-methoxyphenyl]-3,4-dihydro-4-methyl-3-oxo-2H- 1,4-benzothiazines (3) and evaluated their Ca2+ antagonistic activities. Ca2+ antagonistic activity was measured with isolated depolarized guinea pig taenia cecum. On the basis of their potent Ca2+ antagonistic activity, six benzothiazines were selected and further evaluated for their vasocardioselectivity. Among these six compounds, the key compound 15 [3,4-dihydro-2-[5-methoxy-2-[3-[N-methyl-N-[2-[3,4- (methylenedioxy)phenoxy]ethyl]amino]propoxy]phenyl]-4-methyl-3-oxo- 2H-1,4-benzothiazine hydrogen fumarate] was recognized as having the lowest cardioselectivity. Following optical resolution, the absolute configuration of the compound's optically active enantiomer was determined by means of X-ray crystallography of a synthetic precursor (+)-4a. The Ca2+ antagonistic activity of 15 was found to reside primarily in (+)-15 (which was about 7 times more potent than (-)-15). The in vitro study showed that (+)-15 had a low cardioselectivity compared to verapamil and diltiazem. This result suggests that (+)-15 would exhibit less adverse effects due to cardiac inhibition than diltiazem and verapamil in therapeutic use.

  DOI：

  10.1021/jm00169a011

文献信息

• NOVEL BENZOTHIAZINE DERIVATIVES
  申请人：SANTEN PHARMACEUTICAL CO., LTD.

  公开号：EP0237573A1

  公开（公告）日：1987-09-23

  Novel benzothiazine derivatives represented by the following general formula (I), process for their preparation, and agents for treating diseases of circulatory organs containing these compounds as effective ingredients: wherein R' represents one or more groups selected from among a hydrogen atom, a lower alkyl group, a halogen atom, a nitro group, a hydroxy group, a lower alkoxy group, a lower alkanoyloxy group, an amino group, a lower alkylamino group and a lower alkoxycarbonyloxy group, R2 represents a hydrogen atom, a lower alkyl group or a (C3 - C6) cycloalkyl group, R3 represents one or more of a hydrogen atom, a lower alkyl group, a hydroxy group, a lower alkoxy group, a halogen atom, a nitro group, a lower alkylenedioxy group, a lower alkanoyloxy group, a lower alkanoyl group, an amino group, a lower alkylamino group, a lower alkanoylamino group and a lower alkoxycarbonyloxy group, or (CH2)n, R4 represents a hydrogen atom or a lower alkyl group, A and B which may be the same or different and each represents a lower alkylene group containing 1 to 6 carbon atoms, and n represents 3 or4.

  由以下通式(I)表示的新型苯并噻嗪衍生物、其制备方法以及含有这些化合物作为有效成分的治疗循环器官疾病的制剂：其中 R'代表一个或多个选自氢原子、低级烷基、卤素原子、硝基、羟基、低级烷氧基、低级烷酰氧基、氨基、低级烷基氨基和低级烷氧基羰基的基团；R2 代表氢原子、低级烷基或 (C3 - C6) 环烷基；R3 代表氢原子、低级烷基、羟基R4 代表氢原子或低级烷基，A 和 B 可以相同或不同，各自代表含有 1 至 6 个碳原子的低级亚烷基，n 代表 3 或 4。
• J. Med. Chem. 1990, 33, 1898-1905
  作者：

  DOI：——

  日期：——
• IWAO, JUN-ICHI;ISO, TADASHI;OYA, MASAYUKI
  作者：IWAO, JUN-ICHI、ISO, TADASHI、OYA, MASAYUKI

  DOI：——

  日期：——
• FUJITA, MASANOBU;ITO, SUSUMU;OTA, ATSUTOSHI;KATO, NOBUHARU;YAMAMOTO, KOJI+, J. MED. CHEM., 33,(1990) N, C. 1898-1905
  作者：FUJITA, MASANOBU、ITO, SUSUMU、OTA, ATSUTOSHI、KATO, NOBUHARU、YAMAMOTO, KOJI+

  DOI：——

  日期：——
• US4786635A
  申请人：——

  公开号：US4786635A

  公开（公告）日：1988-11-22