5-Oxo-azepane-1,4-dicarboxylic acid 4-ethyl ester 1-methyl ester | 71233-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: 5-Oxo-azepane-1,4-dicarboxylic acid 4-ethyl ester 1-methyl ester
• 英文别名: Ethyl 1-methoxycarbonyl-4-oxoperhydroazepine-5-carboxylate；4-O-ethyl 1-O-methyl 5-oxoazepane-1,4-dicarboxylate
• CAS: 71233-14-2
• 化学式: C₁₁H₁₇NO₅
• 分子量: 243.26
• InChiKey: AYDBSJDUFLJBJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Oxo-azepane-1,4-dicarboxylic acid 4-ethyl ester 1-methyl ester 在 ammonium hydroxide 作用下， 反应 72.0h， 以36%的产率得到1-(methoxycarbonyl)-4-oxoperhydroazepine-5-carboxamide
  参考文献：
  名称：

  4,5,6,7-Tetrahydroisothiazolo[5,4-c]pyridin-3-ol and related analogs of THIP. Synthesis and biological activity

  摘要：

  The thio analogues of the GABA (gamma-aminobutyric acid) agonist THIP (4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol), the GABA uptake inhibitor THPO (4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridin-3-ol), and the glycine antagonist THAZ (5,6,7,8-tetrahydro-4H-isoxazolo[4,5-d]azepin-3-ol) have been synthesized and tested biologically on single neurons in the cat spinal cord and in vitro by using synaptic membrane preparations obtained from rat brains. In contrast to THIP, thio-THIP (4,5,6,7-tetrahydroisothiazolo[5,4-c]pyridin-3-ol, 5) was only a weak GABA agonist. Thio-THPO (4,5,6,7-tetrahydroisothiazolo[4,5-c]pyridin-3-ol, 10) was slightly weaker than THPO as an inhibitor of GABA uptake in vitro, and these two compounds were approximately equipotent in enhancing the inhibition of the firing of cat spinal neurons by GABA. Like THAZ and structurally related bicyclic isoxazole zwitterions, thio-THAZ (5,6,7,8-tetrahydro-4H-isothiazolo[4,5-d]azepin-3-ol, 15) was an antagonist at glycine receptors on cat spinal neurons. The I/U ratios, which reflect the ability of neutral amino acids to penetrate the blood-brain barrier (BBB), were calculated for 5 (I/U = 16), 10 (63), and 15 (200). These low I/U ratios, compared with the findings that THIP (I/U = 500 or 1500) and THPO (I/U = 2500) enter the brain after systemic administration, suggest that the thio analogues may penetrate the BBB very easily.

  DOI：

  10.1021/jm00360a020

文献信息

• THAZ derivatives for enhancement of cerebral function
  申请人：Bristol-Myers Company

  公开号：US04859666A1

  公开（公告）日：1989-08-22

  Tetrahydro-isoxazolo[4,5-d]azepine derivatives possess antiamnesic properties and are cognition enhancers.

  四氢异噁唑[4,5-d]氮杂环庚烷衍生物具有抗遗忘特性，是认知增强剂。
• FISON, MICHAEL S.;KROGSGAARD-LARSEN, POVL
  作者：FISON, MICHAEL S.、KROGSGAARD-LARSEN, POVL

  DOI：——

  日期：——