(-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(R)-mandelamide | 121216-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(R)-mandelamide
• 英文别名: N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(R)-mandelamide；(2R)-2-hydroxy-N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl]-2-phenylacetamide
• CAS: 121216-33-9
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: DCKGATCXENEYCB-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(R)-mandelamide 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-7-((R)-2-Hydroxy-2-phenyl-ethylamino)-5,6,7,8-tetrahydro-naphthalen-2-ol
  参考文献：
  名称：

  Synthesis and β-adrenergic activity of atypical β-adrenergic phenylethanolaminotetralin stereoisomers

  摘要：

  A series of substituted phenylethanolaminotetralins were synthesized as pure stereoisomers and their ability to stimulate atypical beta-adrenoceptors selectively was evaluated. The compounds in vitro relative potencies were assessed using the atypical beta response of inhibition of rat proximal colon motility and the typical beta 1 (increase in guinea-pig right atrial frequency) and beta 2 (guinea-pig tracheal relaxation and rat uterus motility inhibition) responses. Compound 42 (SR 58611A) was found to be the most potent and selective.

  DOI：

  10.1016/0223-5234(94)90095-7
• 作为产物：
  描述：

  2-氨基-7-甲氧基四氢萘 在 ammonium hydroxide 、 TEA 、 氢溴酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(R)-mandelamide
  参考文献：
  名称：

  Synthesis and β-adrenergic activity of atypical β-adrenergic phenylethanolaminotetralin stereoisomers

  摘要：

  A series of substituted phenylethanolaminotetralins were synthesized as pure stereoisomers and their ability to stimulate atypical beta-adrenoceptors selectively was evaluated. The compounds in vitro relative potencies were assessed using the atypical beta response of inhibition of rat proximal colon motility and the typical beta 1 (increase in guinea-pig right atrial frequency) and beta 2 (guinea-pig tracheal relaxation and rat uterus motility inhibition) responses. Compound 42 (SR 58611A) was found to be the most potent and selective.

  DOI：

  10.1016/0223-5234(94)90095-7

文献信息

• Process for the preparation of phenylethanolaminotetralins
  申请人：Sanofi

  公开号：US05198586A1

  公开（公告）日：1993-03-30

  A process for the preparation of phenylethanolaminotetralins of formula ##STR1## wherein X is hydrogen, a halogen, a trifluoromethyl or a lower alkyl group and R.degree. is hydrogen or a methyl group substituted by a carboxy or a lower carbalkoxy group, which comprises treating a mandelic acid with a 2-amino-7-hydroxytetralin, optionally alkylating with a lower alkyl haloacetate and reducing the amido group of the mandelamide into a methyleneamino group. The mandelamides intermediates are novel.

  一种制备式为##STR1##的苯乙醇胺四氢萘的过程，其中X是氢、卤素、三氟甲基或低碳基，R°是氢或被羧基或低碳基卡尔博基基取代的甲基基团，包括将苯乙酸与2-氨基-7-羟基四氢萘处理，可选择用低碳基卤代乙酸酯进行烷基化，并将苯乙酰胺的酰胺基还原为亚甲基胺基。苯乙酰胺中间体是新颖的。
• Procédé pour la préparation de phényléthanolaminotétralines
  申请人：ELF SANOFI

  公开号：EP0303545B1

  公开（公告）日：1992-06-17
• US5198586A
  申请人：——

  公开号：US5198586A

  公开（公告）日：1993-03-30
• US5235103A
  申请人：——

  公开号：US5235103A

  公开（公告）日：1993-08-10
• Synthesis and β-adrenergic activity of atypical β-adrenergic phenylethanolaminotetralin stereoisomers
  作者：R Cecchi、T Croci、R Boigegrain、S Boveri、M Baroni、G Boccardi、JP Guimbard、U Guzzi

  DOI：10.1016/0223-5234(94)90095-7

  日期：1994.1

  A series of substituted phenylethanolaminotetralins were synthesized as pure stereoisomers and their ability to stimulate atypical beta-adrenoceptors selectively was evaluated. The compounds in vitro relative potencies were assessed using the atypical beta response of inhibition of rat proximal colon motility and the typical beta 1 (increase in guinea-pig right atrial frequency) and beta 2 (guinea-pig tracheal relaxation and rat uterus motility inhibition) responses. Compound 42 (SR 58611A) was found to be the most potent and selective.