N-(2,3-dihydro-1 H-inden-2-yl)-glycine benzyl ester hydrochloride | 83356-18-7

• 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: N-(2,3-dihydro-1 H-inden-2-yl)-glycine benzyl ester hydrochloride
• 英文别名: N-(Indan-2-yl)glycine benzyl ester hydrochloride；benzyl 2-(2,3-dihydro-1H-inden-2-ylamino)acetate;hydrochloride
• CAS: 83356-18-7
• 化学式: C₁₈H₁₉NO₂*ClH
• 分子量: 317.815
• InChiKey: FGSXZICHCOAEOO-UHFFFAOYSA-N

物化性质

• 熔点：
  186-189 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,3-dihydro-1 H-inden-2-yl)-glycine benzyl ester hydrochloride 生成 N-chloroacetyl-N-(indan-2-yl)glycine benzyl ester
  参考文献：
  名称：

  OKA, YOSHIKAZU;NISHIKAWA, KOHEL;MIYAKE, AKIO

  摘要：

  DOI：
• 作为产物：
  描述：

  2-茚酮 生成 N-(2,3-dihydro-1 H-inden-2-yl)-glycine benzyl ester hydrochloride
  参考文献：
  名称：

  OKA, YOSHIKAZU;NISHIKAWA, KOHEI;MIYAKE, AKIO

  摘要：

  DOI：

文献信息

• [EN] PROCESS FOR THE PREPARATION OF AMIDES OF N-[1-(S)-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALANINE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AMIDES DE N-[1-(S)-(ÉTHOXYCARBONYL)-3-PHÉNYLPROPYL]-L-ALANINE
  申请人：SANOFI AVENTIS DEUTSCHLAND

  公开号：WO2014202659A1

  公开（公告）日：2014-12-24

  A process for the production of amides of N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine is described. The process can be used for the production of key intermediates and finally the ACE inhibitors such as Ramipril, Enalapril, Quinapril, Trandolapril, Delapril and Moexipril starting from N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine by the reaction with the appropriate amines.

  描述了一种制备N-[1-(S)-(乙氧羰基)-3-苯基丙基]-L-丙氨酸酰胺的方法。该工艺可用于从N-[1-(S)-(乙氧羰基)-3-苯基丙基]-L-丙氨酸出发，通过与适当的胺类反应，生产关键中间体，最终生产ACE抑制剂，如雷米普利、依那普利、喹那普利、群多普利、地拉普利和莫昔普利。
• L-Alanyl-N-(indan-2-yl)glycine, its esters and salts thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04474692A1

  公开（公告）日：1984-10-02

  Useful intermediates for the preparation of hypotensives and inhibitors of angiotensin converting enzymes are L-alanyl-N-(indan-2-yl)glycine, its lower alkyl esters and the salts thereof.

  L-丙氨酸-N-(茚-2-基)甘氨酸及其较低的烷基酯和盐是制备降压药和血管紧张素转换酶抑制剂的有用中间体。
• Bicycle compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04822818A1

  公开（公告）日：1989-04-18

  New bicyclic compounds, inclusive of salts thereof, of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each represents hydrogen, hydroxyl or lower alkoxy, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is hydrogen, lower alkyl, amino-lower-alkyl or acylamino-lower-alkyl, R.sup.5 is hydrogen, lower alkyl or aralkyl which may be substituted, R.sup.6 is hydroxyl, lower alkoxy, amino or lower alkylamino, and m and n each means 1 or 2, have inhibitory activities of angiotensin converting enzyme and bradykinin decomposing enzyme, and are useful as antihypertensive agents.

  新的双环化合物，包括其盐，化学式如下：##STR1## 其中，R.sup.1和R.sup.2相同或不同，分别代表氢、羟基或较低的烷氧基，R.sup.3代表氢或较低的烷基，R.sup.4代表氢、较低的烷基、氨基-较低-烷基或酰胺基-较低-烷基，R.sup.5代表氢、较低的烷基或可能被取代的芳基烷基，R.sup.6代表羟基、较低的烷氧基、氨基或较低的烷基氨基，m和n分别表示1或2，具有抑制血管紧张素转化酶和缓激肽降解酶的活性，并且可用作降压剂。
• Process for preparation of bicyclic compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05098892A1

  公开（公告）日：1992-03-24

  New bicyclic compounds, inclusive of salts thereof, of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each represents hydrogen, hydroxyl or lower alkoxy, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is hydrogen, lower alkyl, amino-lower-alkyl or acylamino-lower-alkyl, R.sup.5 is hydrogen, lower alkyl or aralkyl which may be substituted, R.sup.6 is hydroxyl, lower alkoxy, amino or lower alkylamino, and m and n each means 1 or 2, have inhibitory activities of angiotensin converting enzyme and bradykinin decomposing enzyme, and are useful as antihypertensive agents.

  新的双环化合物，包括其盐，化学式如下：##STR1## 其中R.sup.1和R.sup.2相同或不同，分别代表氢，羟基或低级烷氧基，R.sup.3代表氢或低级烷基，R.sup.4代表氢，低级烷基，氨基-低级烷基或酰胺基-低级烷基，R.sup.5代表氢，低级烷基或可能被取代的芳基烷基，R.sup.6代表羟基，低级烷氧基，氨基或低级烷基氨基，m和n分别表示1或2，具有抑制血管紧张素转换酶和缓激肽降解酶的活性，并可用作降压剂。
• (Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme. 2. Terminal amino acid analogs of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L-proline
  作者：Donald S. Karanewsky、Michael C. Badia、David W. Cushman、Jack M. DeForrest、Tamara Dejneka、Ving G. Lee、Melanie J. Loots、Edward W. Petrillo

  DOI：10.1021/jm00167a028

  日期：1990.5

  Analogues of (S)-1-[6-amino-2[[hydroxy(4-phenylbutyl)phosphinyl] oxy]-1-oxohexyl]-L-proline (1, SQ 29,852) in which the terminal proline residue has been replaced by a variety of substituted and heteroatom-substituted prolines, N-arylglycines, N-cycloalkylglycines, and bicyclic amino acids have been synthesized and evaluated as inhibitors of angiotensin converting enzyme in vitro and in vivo. In general, the addition of lipophilic substituents to the 4-position of proline of the parent phosphonate 1 resulted in substantial increases in in vitro activity. The largest improvements were observed in the case of cis-benzyl (36-fold) and dithioketal (24-fold) analogues 2r and 2x, respectively. These enhancements of in vitro activity were accompanied by modest increases (2-3.5-fold) in in vivo (iv) activity. Among the various terminal amino acid replacements examined in this study, the indoline-based analogue 2i was by far the most potent compound on iv administration in the normotensive rat.