(1S,4S)-2-oxa-5-azabicyclo<2.2.1>heptane-3-one nonohydrobromide salt | 81075-58-3

• 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: (1S,4S)-2-oxa-5-azabicyclo<2.2.1>heptane-3-one nonohydrobromide salt
• 英文别名: cis-4-hydroxy-L-proline-lactone; hydrobromide；cis-4-Hydroxy-L-prolin-lacton; Hydrobromid；cis-4-hydroxy-L-proline lactone HBr salt；(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-3-one;hydrobromide
• CAS: 81075-58-3
• 化学式: BrH*C₅H₇NO₂
• 分子量: 194.028
• InChiKey: DLMSCPHXEHNONK-MMALYQPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (S)-2-<oxy>-6-<(trifluoroacetyl)amino>hexanoic acid 、 (1S,4S)-2-oxa-5-azabicyclo<2.2.1>heptane-3-one nonohydrobromide salt 生成 (2S,4S)-4-hydroxy-1-[(2S)-2-[hydroxy(4-phenylbutyl)phosphoryl]oxy-6-[(2,2,2-trifluoroacetyl)amino]hexanoyl]pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  KARANEWSKY, DONALD S.;BADIA, MICHAEL C.;CUSHMAN, DAVID W.;DEFORREST, JACK+, J. MED. CHEM., 33,(1990) N, C. 1459-1469

  摘要：

  DOI：

文献信息

• Carboxyacyl, mercapto and acylmercapto derivatives of heterobicyclo
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04303662A1

  公开（公告）日：1981-12-01

  A compound of the formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, phenyl lower alkyl or halo substituted lower alkyl; R.sub.2 is hydrogen, lower alkyl, phenyl lower alkyl or halo substituted lower alkyl; n is 0, 1 or 2; X is--(CH.sub.2).sub.m Z--; Z is oxygen, sulfur or imino; m is 0 or 1; Y is S-R or ##STR2## R is hydrogen, lower alkyl, ##STR3## R.sub.3 is lower alkyl, phenyl or phenyl lower alkyl; and R.sub.4 is hydroxy, amino, hydroxyamino or lower alkoxy. These compounds are useful as hypotensive agents.

  化合物的化学式为##STR1##其中R.sub.1是氢、低碳基、苯基低碳基或卤代低碳基；R.sub.2是氢、低碳基、苯基低碳基或卤代低碳基；n为0、1或2；X为--(CH.sub.2).sub.m Z--；Z为氧、硫或亚胺基；m为0或1；Y为S-R或##STR2## R为氢、低碳基、##STR3##R.sub.3为低碳基、苯基或苯基低碳基；R.sub.4为羟基、氨基、羟胺基或低烷氧基。这些化合物可用作降压剂。
• (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oxy]-1-oxohexyl]-L-proline (1, SQ 29,852) in which the terminal proline residue has been replaced by a variety of substituted and heteroatom-substituted prolines, N-arylglycines, N-cycloalkylglycines, and bicyclic amino acids have been synthesized and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.
• KARANEWSKY, DONALD S.;BADIA, MICHAEL C.;CUSHMAN, DAVID W.;DEFORREST, JACK+, J. MED. CHEM., 33,(1990) N, C. 1459-1469
  作者：KARANEWSKY, DONALD S.、BADIA, MICHAEL C.、CUSHMAN, DAVID W.、DEFORREST, JACK+

  DOI：——

  日期：——