(S)-2-hydroxy-6<(trifluoroacetyl)amino>hexanoic acid | 116287-37-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-hydroxy-6<(trifluoroacetyl)amino>hexanoic acid
• 英文别名: (S)-2-hydroxy-6-[(trifluoroacetyl)amino]hexanoic acid；(S)-2-hydroxy-6[(trifluoroacetyl)amino]hexanoic acid；(2S)-2-hydroxy-6-(trifluoroacetamido)hexanoic acid；(2S)-2-hydroxy-6-[(2,2,2-trifluoroacetyl)amino]hexanoic acid
• CAS: 116287-37-7
• 化学式: C₈H₁₂F₃NO₄
• 分子量: 243.183
• InChiKey: MWFJJOFIBGGADK-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxy-6<(trifluoroacetyl)amino>hexanoic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium periodate 、 氢气 、 potassium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 32.5h， 生成 <1(R^*),2α,4β>-1-<2-<oxy>-1-oxo-6-<(trifluoroacetyl)amino>hexyl>-4-(phenylthio)-L-proline methyl ester
  参考文献：
  名称：

  (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

  摘要：

  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oxy]-1-oxohexyl]-L-proline (1, SQ 29,852) in which the terminal proline residue has been replaced by a variety of substituted and heteroatom-substituted prolines, N-arylglycines, N-cycloalkylglycines, and bicyclic amino acids have been synthesized and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.

  DOI：

  10.1021/jm00167a028
• 作为产物：
  描述：

  (2S)-6-氨基-2-羟基己酸 生成 (S)-2-hydroxy-6<(trifluoroacetyl)amino>hexanoic 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

• Substituted aminoalkanoylaminoalkyl phosphonate angiotensin converting
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04849414A1

  公开（公告）日：1989-07-18

  Compounds of the formula ##STR1## wherein X is various amino or imino acids and esters are disclosed. These compounds are useful as anti-hypertensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.

  公式为##STR1##的化合物中，X是各种氨基或亚氨基酸和酯。这些化合物由于其抑制血管紧张素转化酶的活性而可用作降压药物，根据X的定义，它们也可能由于其脑啡肽酶抑制活性而用作镇痛药。
• Phosphonate angiotensin converting enzyme inhibitors
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0239109A2

  公开（公告）日：1987-09-30

  Compounds of the formula wherein Z is and X is various amino or imino acids and esters are disclosed. These compounds are useful as anti-hypertensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.

  这些化合物具有抑制血管紧张素转换酶的活性，因此可用作抗高血压药；根据 X 的定义，它们还具有抑制脑啡肽酶的活性，因此也可用作镇痛药。
• Substituted aminoalkanoylaminoalkyl phosphonate angiotensin converting enzyme inhibitors
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0249445A2

  公开（公告）日：1987-12-16

  Compounds of the formula wherein X is various amino or imino acids and esters are disclosed. These compounds are useful as anti-hypertensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.

  式中的化合物 其中 X 为各种氨基酸或亚胺酸及酯类。由于具有血管紧张素转换酶抑制活性，这些化合物可用作抗高血压药，而且根据 X 的定义，由于具有脑啡肽酶抑制活性，这些化合物还可用作镇痛药。
• US4849414A
  申请人：——

  公开号：US4849414A

  公开（公告）日：1989-07-18