S(+)-N-benzyl-O-acetyl mandelamide | 188025-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S(+)-N-benzyl-O-acetyl mandelamide
• 英文别名: (S)-O-acetyl-N-benzylmandelamide；(S)-(benzylcarbamoyl)(phenyl)methyl acetate；[(1S)-2-(benzylamino)-2-oxo-1-phenylethyl] acetate
• CAS: 188025-26-5
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: HZUAABDZTNOQFU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S(+)-N-benzyl-O-acetyl mandelamide 在 甲醇 、 sodium hydroxide 、 盐酸 、 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 以73%的产率得到(S)-N-benzylmandelamide
  参考文献：
  名称：

  SUBSTITUTED (S)-BENZOXAZINONES

  摘要：

  本发明提供了对映纯的取代(S)-苯并噁嗪酮化合物及这些化合物的缓释制剂。这些化合物表现出强效的肾素抑制活性和改善的生物利用度。

  公开号：

  US20090311318A1
• 作为产物：
  描述：

  L-(+)-扁桃酸乙酯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 S(+)-N-benzyl-O-acetyl mandelamide
  参考文献：
  名称：

  The anticonvulsant activities of functionalized N-benzyl 2-acetamidoacetamides. The importance of the 2-acetamido substituent

  摘要：

  Recent studies have demonstrated that substituted N-benzyl 2-acetamidoacetamides provide significant protection against maximal electroshock (MES)-induced seizures in mice and rats. In this study, we investigated whether the 2-acetamido moiety was necessary for anticonvulsant activity. Ten derivatives of the known anticonvulsant, N-benzyl 2-acetamido-2-phenyl acetamide were prepared in which the 2-acetamido group was replaced by hydrogen, methyl, oxygen, and halogen substituents. Evaluation of these compounds in the MES-induced seizure test demonstrated that both the hydroxy and the methoxy compounds provided full protection against MES-induced seizures in mice given ip at 100 mg/kg. Moreover, evaluation of the individual stereoisomers for the hydroxy compound showed that the principal activity resided in the (R)-isomer. These findings demonstrated that the 2-acetamido substituent is important but not obligatory for the prevention of MES-induced seizures. Further supporting evidence was provided by comparing the pharmacological activities of N-benzyl 2,3-dimethoxypropionamide with N-benzyl 2-acetamido-3-methoxypropionamide. The ED(50) value for the former in the MES test was 30 mg/kg (ip), which compared favorably with phenobarbital (ED(50) = 22 mg/kg), but the ED(50) value for N-benzyl 2-acetamido-3-methoxypropionamide was 8.3 mg/kg. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00225-8

文献信息

• SUBSTITUTED BENZOXAZINONES
  申请人：Holsworth Daniel

  公开号：US20090215763A1

  公开（公告）日：2009-08-27

  The present invention provides substituted oxazinone compounds, such as substituted benzoxazinones, which exhibit potent renin inhibition activities.

  本发明提供了取代的噁唑酮化合物，例如取代的苯并噁唑酮，表现出强大的肾素抑制活性。
• Stereoselective formation of optically active 2-oxy-1,3-oxazolidin-4-ones from chiral O-acylmandelamides or lactamides
  作者：Akio Kamimura、Yoji Omata、Akikazu Kakehi、Masashi Shirai

  DOI：10.1016/s0040-4020(02)01057-8

  日期：2002.10

  (-)-O-Acyllactamides or mandelamides in the presence of TBSOTf underwent cyclization reaction to give optically active 2-oxy-1,3-oxazolidin-4-ones, a novel nitrogen analog of orthoesters, in good yields. An X-ray analysis and NOE studies indicated that the absolute configuration at the newly formed chiral carbon was S. For their synthetic application, the 1,3-dipolar cycloaddition of nitrile oxide was examined. The cycloadducts were obtained in a stereoselective manner. Subsequent treatment of the adduct with TBAF resulted in the one-step removal of mandelamide, giving optically active 4,5-dihydroisoxazole and mandelamide in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  (-)-O-Acyllactamides 或 mandelamides 在 TBSOTf 存在下发生环化反应，生成具有光学活性的 2-oxy-1,3-oxazolidin-4-ones（一种新型氮类似物），产率良好。X 射线分析和 NOE 研究表明，新形成手性碳的绝对构型为 S。在合成应用方面，研究了硝基氧化物的 1,3-偶极环加成反应。环加成产物以立体选择性方式获得。随后，用 TBAF 处理加成物，一步去除了 mandelamide，生成具有光学活性的 4,5-dihydroisoxazole 和 mandelamide，产率良好。 (C) 2002 Elsevier Science Ltd. 保留所有权利。
• Stereoselective formation of optically active 2-oxy-1,3-oxazolidin-4-ones and an efficient synthesis of optically active secondary 2-pyrrolidones
  作者：Yoji Omata、Akikazu Kakehi、Masashi Shirai、Akio Kamimura

  DOI：10.1016/s0040-4039(02)01632-5

  日期：2002.9

  Treatment of (−)-O-acyllactamides or mandelamides with TBSOTf in the presence of base gives optically active 2-oxy-1,3-oxazolidin-4-ones stereoselectively, which serve as useful precursors for the preparation of optically active secondary 2-pyrrolidones via radical cyclization and subsequent one-step removal of mandelic acid.

  在碱存在下，用TBSOTf处理（-）- O-酰基酰胺或扁桃酰胺，可以立体选择性地产生旋光的2-氧基-1,3-恶唑烷丁-4-酮，它们可用作制备旋光的仲2-羟基的有用前体。吡咯烷酮通过自由基环化和随后的一步去除扁桃酸的步骤。
• Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes
  作者：P Saravanan、Alakesh Bisai、S Baktharaman、M Chandrasekhar、Vinod K Singh

  DOI：10.1016/s0040-4020(02)00376-9

  日期：2002.6

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.
• [EN] SUBSTITUTED BENZOXAZINONES<br/>[FR] BENZOXAZINONES SUBSTITUÉES
  申请人：P & H THERAPEUTICS INC

  公开号：WO2009108722A2

  公开（公告）日：2009-09-03

  The present invention provides substituted oxazinone compounds, such as substituted benzoxazinones, which exhibit potent renin inhibition activities.