(S)-4-trityl-2-hydroxymethylmorpholine | 132073-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-4-trityl-2-hydroxymethylmorpholine
• 英文别名: [(2S)-4-tritylmorpholin-2-yl]methanol
• CAS: 132073-84-8
• 化学式: C₂₄H₂₅NO₂
• 分子量: 359.468
• InChiKey: WPMOUGZXSDONLS-QHCPKHFHSA-N

物化性质

• 沸点：
  467.9±40.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-trityl-2-hydroxymethylmorpholine 在 吡啶 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.33h， 生成 (S)-(-)-2-({[3-(morpholinomethyl)-2H-chromen-8-yl]oxy}methyl)morpholine
  参考文献：
  名称：

  (R)-(+)-2-[[[3-(Morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine Methanesulfonate:  A New Selective Rat 5-Hydroxytryptamine_1B Receptor Antagonist

  摘要：

  In the search for new 5-hydroxytryptamine (5-HT) receptor antagonists it was found that the compound (R)-(+)-2-[[[3-(morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine methanesulfonate, (R)-25, is a selective rat 5-hydroxytryptamine(1B) (r5-HT1B) receptor antagonist. The binding profile showed a 13-fold preference for r5-HT1B (K-i = 47 +/- 5 nM; n = 3) vs bovine 5-HT1B (K-i = 630 nM; n = 1) receptors. The compound had very low affinity for other monoaminergic receptors examined. The r5-HT1B receptor antagonism was demonstrated by the potentiation of the K+-stimulated release of [H-3]-5-HT from superfused rat brain slices in vitro, an effect that was antagonized by addition of 5-HT to the superfusion fluid. (R)-25 at 20 mg/kg sc enhanced the 5-HT turnover in four rat brain regions (hypothalamus, hippocampus, striatum, and frontal cortex) with about 40% measured as the 5-HTP accumulation after decarboxylase inhibition with 3-hydroxybenzylhydrazine. At 3 mg/kg sc (R)-25 produced a significant increase in the number of wet dog shakes in rats, a 5-HT2A/5-HT2C response that was abolished by depletion of 5-HT after pretreatment with the tryptophan hydroxylase inhibitor p-chlorophenylalanine. These observations show that (R)-25, by inhibiting terminal r5-HT1B autoreceptors, increases the 5-HT turnover and the synaptic concentration of 5-HT.

  DOI：

  10.1021/jm970806i
• 作为产物：
  描述：

  (S)-2-[(苯基甲氧基)甲基]-4-(苯基甲基)吗啉 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 (S)-4-trityl-2-hydroxymethylmorpholine
  参考文献：
  名称：

  (R)-(+)-2-[[[3-(Morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine Methanesulfonate:  A New Selective Rat 5-Hydroxytryptamine_1B Receptor Antagonist

  摘要：

  In the search for new 5-hydroxytryptamine (5-HT) receptor antagonists it was found that the compound (R)-(+)-2-[[[3-(morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine methanesulfonate, (R)-25, is a selective rat 5-hydroxytryptamine(1B) (r5-HT1B) receptor antagonist. The binding profile showed a 13-fold preference for r5-HT1B (K-i = 47 +/- 5 nM; n = 3) vs bovine 5-HT1B (K-i = 630 nM; n = 1) receptors. The compound had very low affinity for other monoaminergic receptors examined. The r5-HT1B receptor antagonism was demonstrated by the potentiation of the K+-stimulated release of [H-3]-5-HT from superfused rat brain slices in vitro, an effect that was antagonized by addition of 5-HT to the superfusion fluid. (R)-25 at 20 mg/kg sc enhanced the 5-HT turnover in four rat brain regions (hypothalamus, hippocampus, striatum, and frontal cortex) with about 40% measured as the 5-HTP accumulation after decarboxylase inhibition with 3-hydroxybenzylhydrazine. At 3 mg/kg sc (R)-25 produced a significant increase in the number of wet dog shakes in rats, a 5-HT2A/5-HT2C response that was abolished by depletion of 5-HT after pretreatment with the tryptophan hydroxylase inhibitor p-chlorophenylalanine. These observations show that (R)-25, by inhibiting terminal r5-HT1B autoreceptors, increases the 5-HT turnover and the synaptic concentration of 5-HT.

  DOI：

  10.1021/jm970806i

文献信息

• 1,2-ethanediol derivative and salt thereof, process for producing the
  申请人：Toyama Chemical Co., Ltd.

  公开号：US05280032A1

  公开（公告）日：1994-01-18

  This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.

  本发明涉及一种1,2-乙二醇衍生物及其盐，制备该衍生物的方法，以及包含该衍生物的改善脑功能的药剂。本发明的改善脑功能药剂对治疗脑血管性痴呆、老年性痴呆、阿尔茨海默症、缺血性脑病后遗症和脑卒中等方面具有用处。
• 1,2-ethanediol derivative and salt thereof process for producing the
  申请人：Toyama Chemical Co., Ltd.

  公开号：US05612381A1

  公开（公告）日：1997-03-18

  This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.

  本发明涉及一种1,2-乙二醇衍生物及其盐，其制备方法以及包含该物质的脑功能改善剂。本发明的脑功能改善剂可用于治疗脑血管性痴呆、老年性痴呆、阿尔茨海默病性痴呆、缺血性脑病后遗症和脑卒中。
• 1,2-ethanediol derivative and salt thereof and cerebral
  申请人：Toyama Chemical Co., Ltd.

  公开号：US05472984A1

  公开（公告）日：1995-12-05

  This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.

  本发明涉及一种1,2-乙二醇衍生物及其盐，制备方法以及包含该衍生物的脑功能改善剂。本发明的脑功能改善剂对于治疗脑血管性痴呆、老年性痴呆、阿尔茨海默病、缺血性脑病后遗症和脑卒中等疾病有用。
• 1,2-ethanediol derivative and salt thereof, process for producing the same, and cerebral function-improving agent comprising the same
  申请人：TOYAMA CHEMICAL CO., LTD.

  公开号：EP0383281A1

  公开（公告）日：1990-08-22

  This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.

  本发明涉及一种1,2-乙二醇衍生物及其盐、一种生产该衍生物的工艺以及一种包含该衍生物的脑功能改善剂。本发明的脑功能改善剂可用于治疗脑血管性痴呆、老年性痴呆、阿尔茨海默氏痴呆、缺血性脑病后遗症和脑中风。
• 1,2-Ethanediol derivative and salt thereof, process for producing the same, and cerebral function-improving agent comprising the same
  申请人：TOYAMA CHEMICAL CO., LTD.

  公开号：EP0587193A1

  公开（公告）日：1994-03-16

  This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.

  本发明涉及一种1,2-乙二醇衍生物及其盐、一种生产该衍生物的工艺以及一种包含该衍生物的脑功能改善剂。本发明的脑功能改善剂可用于治疗脑血管性痴呆、老年性痴呆、阿尔茨海默氏痴呆、缺血性脑病后遗症和脑中风。