(S)-1-(苄基氨基)-3-(苄氧基)-2-丙醇 | 205242-64-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-1-(苄基氨基)-3-(苄氧基)-2-丙醇
• 英文名称: (2S)-1(benzylamino)-3-(benzyloxy)propan-2-ol
• 英文别名: (2S)-1-(benzylamino)-3-(benzyloxy)propane-2-ol；(S)-1-(benzylamino)-3-(benzyloxy)propan-2-ol；(2S)-1-(benzylamino)-3-phenylmethoxypropan-2-ol
• CAS: 205242-64-4
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: RBWDXIHJXAZLIR-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(苄基氨基)-3-(苄氧基)-2-丙醇 在 甲醇 、 lithium aluminium tetrahydride 、 sodium 作用下， 以 乙醚 为溶剂， 反应 4.67h， 生成 (S)-2-[(苯基甲氧基)甲基]-4-(苯基甲基)吗啉
  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：

  (R)-苄氧甲基环氧乙烷 、 苄胺 反应 65.0h， 以70%的产率得到(S)-1-(苄基氨基)-3-(苄氧基)-2-丙醇
  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

• HIV PROTEASE INHIBITORS
  申请人：MCCAULEY John A.

  公开号：US20170217986A1

  公开（公告）日：2017-08-03

  The present invention is directed to 2,6-morpholine derivatives of Formula (I): and pharmaceutically acceptable salts thereof, wherein Z 1 , Z 2 , V 1 , V 2 , V 3 , R 6 , R 6A , and X are defined herein. The invention also relates to methods of using the 2,6-morpholine derivatives of the invention for the inhibition of HV protease, the inhibition of HV replication, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  本发明涉及Formula (I)的2,6-吗啉衍生物及其药用盐，其中Z1、Z2、V1、V2、V3、R6、R6A和X在此被定义。该发明还涉及使用该发明的2,6-吗啉衍生物来抑制HV蛋白酶、抑制HV复制、预防HIV感染、治疗HIV感染以及预防、治疗和延缓艾滋病的发作或进展的方法。这些化合物及其盐可作为药物组合物中的成分使用，可选择性地与其他抗病毒药物、免疫调节剂、抗生素或疫苗结合使用。
• MORPHOLINE DERIVATIVE
  申请人：Akatsuka Hidenori

  公开号：US20100240644A1

  公开（公告）日：2010-09-23

  The present invention provides a morpholine derivative of the formula [I]; wherein R 1 is a substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclo group, a cycloalkyl group or an alkyl group; R 2 is a substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclo group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted heterocyclo-substituted carbonyl group or a cycloalkylcarbonyl group; T is a methylene group or a carbonyl group; R 3 , R 4 , R 5 and R 6 are the same or different and a hydrogen atom, an optionally substituted carbamoyl group or an optionally substituted alkyl group; or pharmaceutically acceptable salts thereof. These compounds are useful as a renin inhibitor.

  本发明提供了公式[I]的吗啡啶衍生物；其中R1是取代的烷基，可选取代的芳基，可选取代的杂环基，环烷基或烷基；R2是取代的烷基，可选取代的芳基，可选取代的杂环基，可选取代的烷基羰基，可选取代的芳基羰基，可选取代的杂环取代羰基或环烷基羰基；T是亚甲基或羰基；R3，R4，R5和R6相同或不同，是氢原子，可选取代的氨基甲酰基或可选取代的烷基；或其药学上可接受的盐。这些化合物可用作肾素抑制剂。
• Organic Compounds and their uses
  申请人：Britt Shawn D.

  公开号：US20100240638A1

  公开（公告）日：2010-09-23

  The present application describes macrocyclic compounds of formula (I) with NS3 protease inhibitory activity for treating hepatitis C virus infection.

  本申请描述了公式（I）的大环化合物，具有NS3蛋白酶抑制活性，用于治疗丙型肝炎病毒感染。
• Morpholine derivative
  申请人：Akatsuka Hidenori

  公开号：US08975252B2

  公开（公告）日：2015-03-10

  The present invention provides a morpholine derivative of the formula [I]; wherein R1 is a substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclo group, a cycloalkyl group or an alkyl group; R2 is a substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclo group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted heterocyclo-substituted carbonyl group or a cycloalkylcarbonyl group; T is a methylene group or a carbonyl group; R3, R4, R5 and R6 are the same or different and a hydrogen atom, an optionally substituted carbamoyl group or an optionally substituted alkyl group; or pharmaceutically acceptable salts thereof. These compounds are useful as a renin inhibitor.

  本发明提供了一种形式为[I]的吗啡啶衍生物；其中R1是取代的烷基，选修的取代芳基，选修的取代杂环基，环烷基或烷基；R2是取代的烷基，选修的取代芳基，选修的取代杂环基，选修的烷基羰基基团，选修的芳基羰基基团，选修的杂环取代羰基基团或环烷基羰基基团；T是亚甲基基团或羰基基团；R3，R4，R5和R6相同或不同，是氢原子，选修的氨基甲酰基或选修的烷基基团；或其药学上可接受的盐。这些化合物可用作肾素抑制剂。
• MORPHOLINE DERIVATIVES AS RENIN INHIBITORS
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2168952B1

  公开（公告）日：2017-02-15