α-ethyl D-glutamate | 97975-66-1

• 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: α-ethyl D-glutamate
• 英文别名: ethyl D-glutamate；H-D-Glu-Oet；(4R)-4-amino-5-ethoxy-5-oxopentanoic acid
• CAS: 97975-66-1
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: SYQNQPHXKWWZFS-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-ethyl D-glutamate 生成 (4R)-5-ethoxy-5-oxo-4-(pyridine-3-carbonylamino)pentanoic acid
  参考文献：
  名称：

  STANTON, JAMES L.;KSANDER, GARY M.

  摘要：

  DOI：
• 作为产物：
  描述：

  α-ethyl D-N-carbobenzoxyglutamate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以74%的产率得到α-ethyl D-glutamate
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors: N-substituted D-glutamic acid .gamma.-dipeptides

  摘要：

  The preparation of two series of N-carbobenzoxy-gamma-D-glutamyl secondary 2S amino acids and (N-substituted gamma-D-glutamyl)indoline-2(S)-carboxylic acid dipeptides is described. In vitro inhibition of angiotensin converting enzyme (ACE) is reported for each compound, and the structure-activity relationship is discussed. Oral and iv inhibition of AI pressor response in vivo of selected compounds in Table II is also discussed. The most potent compounds in vitro, 3 and 6a, had an ACE IC50 of 7 and 2.7 X 10(-9) M, respectively.

  DOI：

  10.1021/jm00149a011

文献信息

• Angiotensin-converting enzyme inhibitors: Synthesis and structure-activity relationships of potent N-benzyloxycarbonyl tripeptide inhibitors.
  作者：Tadahiro SAWAYAMA、Masatoshi TSUKAMOTO、Takashi SASAGAWA、Kazuya NISHIMURA、Ryuichi YAMAMOTO、Takashi DEGUCHI、Kunihiko TAKEYAMA、Kanoo HOSOKI

  DOI：10.1248/cpb.37.2417

  日期：——

  (Z) tripeptide inhibitors of angiotensin-converting enzyme (ACE) was synthesized. The effect of varying the antepenultimate amino acid residue in this series on the biological activity was studied. Introduction of Lys and Orn residues at the P1 position provided the most potent inhibitors, 25a and 25b (IC50: 3.5 and 4.9 x 10(-9) M, respectively), which exhibited an oral antihypertensive activity. This

  合成了一系列新的含γ-D-Glu的血管紧张素转化酶（ACE）的N-苄氧基羰基（Z）三肽抑制剂。研究了改变该系列中前倒数第二个氨基酸残基对生物活性的影响。在P1位置引入Lys和Orn残基可提供最有效的抑制剂25a和25b（IC50：分别为3.5和4.9 x 10（-9）M），具有口服降压活性。该结果表明，在该系列中，P1位的碱性氨基酸残基在与ACE的S1亚位点的结合中起重要作用。评价了所选化合物的口服降压活性。
• Tripeptide derivatives
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0244836A2

  公开（公告）日：1987-11-11

  A tripeptide derivative represented by the following formula wherein R1 represents a C1-10 alkyl group, a C4-7 cyclomny or C5-7 cycloalkyl-lower alkyl group, a phenyl or phenyl-lower alkyl group in which the benzene ring may optionally be substituted by a substituent selected from halogen, lower alkyl, lower alkoxy, phenyl, methylenedioxy, ethylenedioxy, amino, di(lower alkyl)amino and hydroxy, a naphthyl or naphthyl-lower alkyl group in which the naphthalene ring may optionally be substituted by a substituent selected from halogen, lower alkyl, lower alkoxy and hydroxy, a heterocyclic or heterocyclic-lower alkyl group in which the heterocycle is a saturated or unsaturated 5- or 6-membered ring containing a nitrogen, oxygen or sulfur atom as the hetero atom, and may optionally be substituted by a substituent selected from halogen, lower alkyl, lower alkoxy, amino, di(lower alkyl)amino, hydroxy, oxo and saturated 5- or 6-membered nitrogen-containing heterocyclic group, and further may optionally be fused to a benzene ring, or an imidazolylvinyl group; R2 represents a hydrogen atom, a C1-10 alkyl group or a benzyl group; R3 represents a group of the formula in which ( represents a benzene, cyclopentane or cyclohexane ring, R4 represents a hydrogen atom, a C1-10 alkyl group or a benzyl group, p is 0 or 1, q is 1, or 3, and X represents a phenyl group which may optionally be substituted by a substituent selected from halogen, lower alkoxy and hydroxy, a C4-8 cycloalkyl group, or a C5-7 cycloalkyl group which is fused to a benzene, and Y represents a hydrogen atom or a lower alkyl group, or X and Y, together with the nitrogen and carbon atoms to which they are bonded, forms a 5- or 6-membered heterocyle which may contain a nitrogen, oxygen or sulfur atom, W represents a single bond, -O- or -NH-, T represents a single bond, or-S-, and m is 2 or 3, or salts thereof; processes for production thereof; and the use thereof as a medicine, particularly an anti-hypertensive agent.

  下式所代表的三肽衍生物 其中 R1 代表 C1-10 烷基、C4-7 环烷基或 C5-7 环烷基-低级烷基、苯基或苯基-低级烷基，其中苯环可任选被选自卤素、低级烷基、低级烷氧基、苯基、亚甲基二氧基、亚乙基二氧基、氨基、二(低级烷基)氨基和羟基的取代基取代；萘基或萘基-低级烷基，其中萘环可任选被选自卤素、低级烷基、低级烷氧基和羟基的取代基取代；杂环或杂环-低级烷基，其中杂环是饱和或不饱和的 5-或 5-(低级烷基)萘环、杂环或杂环-低级烷基基团，其中杂环是饱和或不饱和的 5 或 6 元环，含氮、氧或硫原子作为杂原子，并可选择被选自卤素、低级烷基、低级烷氧基、低级烷氧基和羟基的取代基取代、低级烷基、低级烷氧基、氨基、二（低级烷基）氨基、羟基、氧代和饱和的 5 或 6 元含氮杂环基团，还可任选与苯环或咪唑乙烯基融合；R2 代表氢原子、C1-10 烷基或苄基； R3 代表如下式的基团 其中 ( 代表苯环、环戊烷环或环己烷环，R4 代表氢原子、C1-10 烷基或苄基，p 为 0 或 1，q 为 1 或 3，X 代表苯基，可任选被选自卤素、低级烷氧基和羟基的取代基取代、一个 C4-8 环烷基，或一个与苯融合的 C5-7 环烷基，Y 代表一个氢原子或一个低级烷基，或 X 和 Y 与它们所键合的氮原子和碳原子一起形成一个 5 或 6 元杂环，该杂环可包含一个氮原子、氧原子或硫原子、 W 代表单键、-O- 或-NH-，T 代表单键、 或-S-，m 为 2 或 3、 或其盐类；其生产工艺；以及其作为药物，特别是抗高血压药物的用途。
• STANTON, JAMES L.;KSANDER, GARY M.
  作者：STANTON, JAMES L.、KSANDER, GARY M.

  DOI：——

  日期：——
• US4826814A
  申请人：——

  公开号：US4826814A

  公开（公告）日：1989-05-02
• Angiotensin converting enzyme inhibitors: N-substituted D-glutamic acid .gamma.-dipeptides
  作者：Gary M. Ksander、Andrew M. Yuan、Clive G. Diefenbacher、James L. Stanton

  DOI：10.1021/jm00149a011

  日期：1985.11

  The preparation of two series of N-carbobenzoxy-gamma-D-glutamyl secondary 2S amino acids and (N-substituted gamma-D-glutamyl)indoline-2(S)-carboxylic acid dipeptides is described. In vitro inhibition of angiotensin converting enzyme (ACE) is reported for each compound, and the structure-activity relationship is discussed. Oral and iv inhibition of AI pressor response in vivo of selected compounds in Table II is also discussed. The most potent compounds in vitro, 3 and 6a, had an ACE IC50 of 7 and 2.7 X 10(-9) M, respectively.