(S)-2-phthalimido-6-hydroxyhexanoic acid | 84688-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (S)-2-phthalimido-6-hydroxyhexanoic acid
• 英文别名: N-phthaloyl-L-ε-hydroxynorleucine；(S)-6-hydroxy-2-phthalimidohexanoic acid；(S)-2-(1,3-dioxoisoindolin-2-yl)-6-hydroxyhexanoic acid；6-Hydroxy-2(S)-phthalimidohexanoic acid；(2S)-2-(1,3-dioxoisoindol-2-yl)-6-hydroxyhexanoic acid
• CAS: 84688-11-9
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: IMPSXCFIPHVJQN-NSHDSACASA-N

物化性质

• 沸点：
  497.5±40.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-phthalimido-6-hydroxyhexanoic acid 在 palladium on activated charcoal sodium hydroxide 、 草酰氯 、 叠氮基三甲基硅烷 、 三氟化硼乙醚 、 氢气 、 四氯化钛 、 1-羟基苯并三唑 、 caesium carbonate 、 一水合肼 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 242.58h， 生成 [14C]-Gemopatrilat
  参考文献：
  名称：

  Vasopeptidase Inhibitors:  Incorporation of Geminal and Spirocyclic Substituted Azepinones in Mercaptoacyl Dipeptides

  摘要：

  A series of 7-(di)alkyl and spirocyclic substituted azepinones were generated and incorporated as conformationally restricted dipeptide surrogates in mercaptoacyl dipeptides. Clear structure-activity relationships with respect to both angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP) activity in vitro were observed. The best in this series, compound 1g, a geminally dimethylated C-7-substituted azepinone, demonstrated excellent blood pressure lowering in animal models. Compound 1g (BMS-189921) is characterized by a good duration of activity and excellent oral efficacy in models relevant to ACE or NEP inhibition, and its activity is comparable to that of the clinically efficacious agent omapatrilat. Consequently this inhibitor has been advanced clinically for the treatment of hypertension and congestive heart failure.

  DOI：

  10.1021/jm980542f
• 作为产物：
  描述：

  5-D-羟基丁基海因 在 barium dihydroxide 、 acylase 1 、 sodium carbonate 作用下， 以 水 为溶剂， 生成 (S)-2-phthalimido-6-hydroxyhexanoic acid
  参考文献：
  名称：

  Hydroxyoxazolidines as α-aminoacetaldehyde equivalents: Novel inhibitors of calpain

  摘要：

  The synthesis of [1-[(5-hydroxy-4-(phenylmethyl)-3-oxazolidinyl)carbonyl]-2-ethylpropyl] carbamic acid phenylmethyl ester (2; MDL 104,903), a potent inhibitor of calpain, is described. Synthesis of related compounds, which offer insights into the mechanism of action for 2, are also described, as is an O-acetyl prodrug derivative of 2. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00391-1

文献信息

• N-formyl hydroxylamine containing compounds useful as ACE inhibitors and/or NEP inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US06777550B1

  公开（公告）日：2004-08-17

  N-formyl hydroxylamines are provided which have the structure wherein R is H, alkyl, alkenyl, aryl-(CH2)p—, heteroaryl-(CH2)p— or cycloheteroalkyl-(CH2)p— R1 is H or COR2 where R2 is alkyl, aryl-(CH2)p—, cycloheteroalkyl-(CH2)p—, heteroaryl-(CH2)p—, alkoxy or cycloalkyl-(CH2)p—, p is 0 to 8, and A is a dipeptide derived from an amino acid or is a conformationally restricted dipeptide mimic. The above compounds are useful in treating hypertension congestive heart failure, renal failure, and hepatic cirrhosis.

  提供了具有以下结构的N-甲酰羟胺，其中R为H，烷基，烯基，芳基-(CH2)p—，杂芳基-(CH2)p—或环杂芳基-(CH2)p—；R1为H或COR2，其中R2为烷基，芳基-(CH2)p—，环杂芳基-(CH2)p—，杂芳基-(CH2)p—，烷氧基或环烷基-(CH2)p—；p为0至8，A为来源于氨基酸的二肽或是具有构象限制的二肽模拟物。上述化合物在治疗高血压、充血性心力衰竭、肾功能衰竭和肝硬化方面具有用途。
• Substituted azepinone dual inhibitors of angiotensin converting enzyme
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05552397A1

  公开（公告）日：1996-09-03

  Compounds of the formula ##STR1## are disclosed as possessing inhibitory activity against angiotensin converting enzyme (ACE) and neutral endopeptidase (NEP) and thus being useful as cardiovascular agents. Processes for preparing these compounds are also disclosed.

  公式##STR1##的化合物被披露具有抑制血管紧张素转换酶（ACE）和中性内肽酶（NEP）活性的特性，因此可用作心血管药物。同时也披露了制备这些化合物的方法。
• Method for producing lysine derivative
  申请人：AJINOMOTO CO., INC.

  公开号：US20020042537A1

  公开（公告）日：2002-04-11

  The present invention provides a method for industrially producing an optically active lysine derivative useful as a pharmaceutical intermediate. More particularly, the present invention provides a production method including protecting an amino group or an amino group and carboxyl group of optically active 2-amino-6-methyl-6-nitroheptanoic acid with a protecting group, reducing a nitro group to synthesize a 6,6-dimethyl lysine derivative and reacting the 6,6-dimethyl lysine derivative with an acetic acid derivative.

  本发明提供一种用作制药中间体的光学活性赖氨酸衍生物的工业生产方法。更具体地，本发明提供一种生产方法，包括保护光学活性2-氨基-6-甲基-6-硝基庚酸的氨基或氨基和羧基与保护基结合，还包括还原硝基以合成6,6-二甲基赖氨酸衍生物，以及将6,6-二甲基赖氨酸衍生物与乙酸衍生物发生反应。
• Compounds containing a fused bicycle ring and processes therefor
  申请人：Bristol-Myers Squibb Company

  公开号：US05508272A1

  公开（公告）日：1996-04-16

  Compounds of the formula ##STR1## wherein X is O or S--(O).sub.t ; n is one or two; m is zero or one; Y is CH.sub.2, O, or S--(O).sub.t provided that Y is O or S--(O).sub.t only when m is one; and A is ##STR2## are dual inhibitors of NEP and ACE. Compounds wherein A is ##STR3## are selective ACE inhibitors. Also disclosed are methods of preparation and intermediates.

  式为##STR1##的化合物，其中X为O或S--(O).sub.t；n为一或二；m为零或一；Y为CH.sub.2、O或S--(O).sub.t，前提是当m为一时，Y仅为O或S--(O).sub.t；A为##STR2##的双重NEP和ACE抑制剂。其中A为##STR3##的化合物是选择性ACE抑制剂。还公开了制备方法和中间体。
• Bicyclic lactams
  申请人：Merck & Co., Inc.

  公开号：US04415496A1

  公开（公告）日：1983-11-15

  The invention relates to bicyclic lactams and related compounds which are useful as antihypertensives.

  该发明涉及双环内酰胺和相关化合物，其可作为降压药物。