4,5,6,7-tetrahydroisothiazolo<4,5-c>pyridin-3-ol hydrobromide | 85250-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4,5,6,7-tetrahydroisothiazolo<4,5-c>pyridin-3-ol hydrobromide
• 英文别名: 4,5,6,7-tetrahydro-[1,2]thiazolo[4,5-c]pyridin-2-ium-3-ol;bromide
• CAS: 85250-65-3
• 化学式: BrH*C₆H₈N₂OS
• 分子量: 237.12
• InChiKey: KAKOROXIEAAWGS-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrahydroisothiazolo<4,5-c>pyridin-3-ol hydrobromide 在 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3-Prop-2-ynyloxy-6,7-dihydro-4H-isothiazolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  一系列槟榔碱的4,5,6,7-四氢异噻唑并[4,5-c]吡啶生物等位基因的合成及毒蕈碱受体药理作用。

  摘要：

  通过处理适当取代的4-苄基氨基-1,2,5,6，合成了4,5,6,7-四氢异噻唑并[4,5-c]吡啶-3-醇的一系列O-和环烷基化衍生物-四氢吡啶-3-甲酰胺与硫化氢，然后通过用溴氧化来闭环。使用大鼠脑膜和许多ti化的毒蕈碱受体配体测定了该系列双环槟榔碱生物等排物的毒蕈碱受体亲和力以及估计的相对功效和亚型选择性。使用受体选择和扩增技术（R-SAT）研究了已建立的绝对立体化学对选定系列手性类似物的五个克隆的人毒蕈碱受体亚型的影响。效力，相对功效，

  DOI：

  10.1016/s0968-0896(99)00033-4
• 作为产物：
  描述：

  1-(methoxycarbonyl)-4-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxamide 在 molecular sieve 、 硫化氢 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 146.0h， 生成 4,5,6,7-tetrahydroisothiazolo<4,5-c>pyridin-3-ol hydrobromide
  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