5,6,7,8-tetrahydro-4H-isothiazolo<4,5-d>azepin-3-ol dihydrobromide | 85250-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 5,6,7,8-tetrahydro-4H-isothiazolo<4,5-d>azepin-3-ol dihydrobromide
• CAS: 85250-69-7
• 化学式: 2BrH*C₇H₁₀N₂OS
• 分子量: 332.059
• InChiKey: OOHOGZHNBKAAKT-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  methyl 3-hydroxy-4,5,7,8-tetrahydro-6H-isothiazolo[4,5-d]azepine-6-carboxylate 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 22.0h， 以36%的产率得到5,6,7,8-tetrahydro-4H-isothiazolo<4,5-d>azepin-3-ol dihydrobromide
  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