(2S)-benzyl 3-aza-4-(ethoxycarbonyl)-2-methyl-6-phenylhexanoate | 82717-95-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-benzyl 3-aza-4-(ethoxycarbonyl)-2-methyl-6-phenylhexanoate
• 英文别名: N-(1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine Benzylester；N-(1-carboethoxy-3-phenylpropyl)-(S)-alanine benzyl ester；ethyl 2-[[(2S)-1-oxo-1-phenylmethoxypropan-2-yl]amino]-4-phenylbutanoate
• CAS: 82717-95-1；90315-81-4；93836-47-6；93841-86-2；117589-32-9
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: KKMCJYRMPUGEEC-DIMJTDRSSA-N

物化性质

• 沸点：
  487.3±45.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-benzyl 3-aza-4-(ethoxycarbonyl)-2-methyl-6-phenylhexanoate 在 Pd-C 作用下， 以 乙醇 为溶剂， 生成 N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine
  参考文献：
  名称：

  Aromatic amino acid derivatives

  摘要：

  一个化合物的化学式为：##STR1## 其中n为0-5，包括0和5；R.sub.1是H或氨基酸的识别基团；R.sub.2是H、芳基烷基或烷基。

  公开号：

  US04652668A1
• 作为产物：
  描述：

  2-氧代-4-苯基丁酸乙酯 、 L-丙氨酸苄酯盐酸盐 在 sodium acetate 、 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 (2S)-benzyl 3-aza-4-(ethoxycarbonyl)-2-methyl-6-phenylhexanoate
  参考文献：
  名称：

  Nonpeptide renin inhibitors employing a novel 3-aza (or oxa)-2,4-dialkyl glutaric acid moiety as a P2/P3 amide bond replacement

  摘要：

  A new series of renin inhibitors has been developed. The inhibitors feature a novel replacement for the P2/P3 dipeptide moiety normally associated with renin inhibitors. The dipeptide replacement was a (2S,4S)-3-aza(or oxa)-2,4-di-alkylglutaric acid amide. Extensive structure-activity relationship studies determined that optimum potency was achieved when inhibitors employed a benzyl and butyl group at the C(4) and C(2) carbon position, respectively. In addition, maximum in vitro potency was obtained when the N-terminus was functionalized by incorporating a 4-(1,3-dioxabutyl)piperidine amide. SAR data suggested that the 1,3-dioxabutyl group (methoxymethyl ether) interacted by hydrogen bonding to groups in the S4 domain of renin. This hypothesis was strengthened when a 4-butylpiperidine amide was substituted and inhibitor potency decreased dramatically. Inhibitors employing this novel dipeptide mimic were prepared by coupling the glutaric acid amides with either the transition-state mimic (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (18) or the hydroxyethylene dipeptide isostere. The glutaric acid amides were prepared by two general procedures. The first procedure involved the reductive amination of alpha-amino acid esters with alpha-keto esters. The second procedure involved the displacement reaction of alpha-bromo esters or acids with alpha-amino acid amides.

  DOI：

  10.1021/jm00088a006

文献信息

• [EN] TREATING INCREASED INTRAOCULAR PRESSURE CAUSED BY STEROIDS
  申请人：SCHERING CORPORATION

  公开号：WO1987002585A2

  公开（公告）日：1987-05-07

  (EN) The rise in intraocular pressure associated with the use of steroidal anti-inflammatory drugs is controlled by use of angiotensin converting enzyme inhibitors. For the purposes of the invention, the preferred ACE inhibitor is 7-¨ADN-(1(S)-carboxy-3-phenylpropyl)-(S)-alanyl¨BD-1,4-dithia-7-azaspiro¨AD4.4¨BDnonane-8(S)-carboxylic acid.(FR) L'augmentation de la pression intra-oculaire associée à l'utilisation de médicaments stéroïdes anti-inflammatoires est contrôlée en utilisant des inhibiteurs d'une enzyme de conversion de l'angiotensine. Selon l'invention, l'inhibiteur préféré d'une enzyme de conversion de l'angiotensine est l'acide 7-¨ADN-(1(S)-carboxy-3-phénylpropyl)-(S)-alanyl¨BD-1,4-dithia-7-azaspiro¨AD4.4¨BDnonane-8(S)-carboxylique.

  使用类固醇类抗炎药物会导致眼内压力升高，但使用血管紧张素转换酶抑制剂可以控制。在本发明中，首选的血管紧张素转换酶抑制剂是7-¨ADN-(1(S)-羧基-3-苯基丙基)-(S)-丙氨酰¨BD-1,4-二硫-7-氮杂螺¨AD4.4¨BD-壬烷-8(S)-羧酸。
• Treating increased intraocular pressure by steroids
  申请人：SCHERING CORPORATION

  公开号：EP0226312A2

  公开（公告）日：1987-06-24

  The rise in intraocular pressure associated with the use of steroidal anti-inflammatory drugs is controlled by use of angiotensin converting enzyme inhibitors. For the purposes of the invention, the preferred ACE inhibitor is 7-[N-(1(S)-carboxy-3-phenylpropyl)-(S)-alanyl]-1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acid.

  使用类固醇消炎药会导致眼压升高，使用血管紧张素转换酶抑制剂可控制眼压升高。 就本发明而言，首选的血管紧张素转换酶抑制剂是 7-[N-(1(S)-羧基-3-苯基丙基)-(S)-丙氨酰]-1,4-二硫杂-7-氮杂螺[4.4]壬烷-8(S)-羧酸。
• KIM, S. H.
  作者：KIM, S. H.

  DOI：——

  日期：——
• TREATING INCREASED INTRAOCULAR PRESSURE CAUSED BY STEROIDS
  申请人：SCHERING CORPORATION

  公开号：EP0246280A1

  公开（公告）日：1987-11-25
• US4470972A
  申请人：——

  公开号：US4470972A

  公开（公告）日：1984-09-11