(S)-2-(1,3-dioxoisoindolin-2-yl)-6-oxohexanoic acid methyl ester | 156479-95-7

• 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: (S)-2-(1,3-dioxoisoindolin-2-yl)-6-oxohexanoic acid methyl ester
• 英文别名: methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-6-oxohexanoate；methyl (2S)-2-(1,3-dioxoisoindol-2-yl)-6-oxohexanoate
• CAS: 156479-95-7
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: KLTLIGBOCPHNGZ-LBPRGKRZSA-N

物化性质

• 沸点：
  440.5±40.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(1,3-dioxoisoindolin-2-yl)-6-oxohexanoic acid methyl ester 生成 methyl (2S)-2-(1,3-dioxoisoindol-2-yl)-6,6-dimethoxyhexanoate
  参考文献：
  名称：

  Compounds containing a fused bicycle ring and processes therefor

  摘要：

  该化合物的分子式为 ##STR1##，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，但当m为一时，Y仅为O或S--(O).sub.t; A为 ##STR2##，是NEP和ACE的双重抑制剂。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。

  公开号：

  US05508272A1
• 作为产物：
  描述：

  L-6-羟基正亮氨酸 在 草酰氯 、 sodium carbonate 、 caesium carbonate 、 二甲基亚砜 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-(1,3-dioxoisoindolin-2-yl)-6-oxohexanoic acid methyl ester
  参考文献：
  名称：

  A synthetic route for the generation of C-7 substituted azepinones

  摘要：

  A versatile method for the synthesis of 3-amino azepinones possessing alkyl substitution at the C-7 position Is described. Compounds of this type may be viewed as conformationally restricted dipeptide surrogates.

  DOI：

  10.1016/s0040-4039(00)76227-7

文献信息

• 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.

  该化合物的分子式为 ##STR1##，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，但当m为一时，Y仅为O或S--(O).sub.t; A为 ##STR2##，是NEP和ACE的双重抑制剂。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。
• CYCLIC PEPTIDE COMPOUND HAVING HIGH MEMBRANE PERMEABILITY, AND LIBRARY CONTAINING SAME
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP3636807A1

  公开（公告）日：2020-04-15

  The present inventors have found that when screening for cyclic peptide compounds that can specifically bind to a target molecule, the use of a library including cyclic peptide compounds having a long side chain in the cyclic portion can improve the hit rate for cyclic peptide compounds that can specifically bind to the target molecule. Meanwhile, the present inventors have found that tryptophan and tyrosine residues, which have conventionally been used in oral low molecular-weight pharmaceuticals and are amino acid residues having an indole skeleton or a hydroxyphenyl group, are not suitable for peptides intended to attain high membrane permeability.

  本发明人发现，在筛选能与目标分子特异性结合的环肽化合物时，使用包括环状部分具有长侧链的环肽化合物库，可以提高能与目标分子特异性结合的环肽化合物的命中率。同时，本发明者发现色氨酸和酪氨酸残基不适合用于旨在获得高膜渗透性的肽，这两种残基通常用于口服低分子量药物，是具有吲哚骨架或羟基苯基的氨基酸残基。
• AMINO ACID HAVING FUNCTIONAL GROUP CAPABLE OF INTERMOLECULAR HYDROGEN BONDING, PEPTIDE COMPOUND CONTAINING SAME AND METHOD FOR PRODUCTION THEREOF
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP3896056A1

  公开（公告）日：2021-10-20

  It has been found that the membrane permeability of peptide compounds can be improved by making at least one of amino acids constituting the peptide compound be an amino acid having a side chain capable of forming an intramolecular hydrogen bond.

  研究发现，通过使构成多肽化合物的氨基酸中至少有一个氨基酸具有能够形成分子内氢键的侧链，可以改善多肽化合物的膜渗透性。
• Design, Synthesis, and Evaluation of Tricyclic, Conformationally Constrained Small-Molecule Mimetics of Second Mitochondria-Derived Activator of Caspases
  作者：Bin Zhang、Zaneta Nikolovska-Coleska、Yan Zhang、Longchuan Bai、Su Qiu、Chao-Yie Yang、Haiying Sun、Shaomeng Wang、Yikang Wu

  DOI：10.1021/jm801146d

  日期：2008.12.11

  A series of tricyclic, conformationally constrained Smac mimetics have been designed, synthesized, and evaluated. The most potent compound 6 (WS-5) binds to XIAP, cIAP-1, and cIAP-2 with K-i of 18, 1.1, and 4.2 nM, respectively. Compound 6 antagonizes XIAP in a functional assay, induces cIAP-1 degradation, inhibits cell growth with an IC50 of 68 nM in the MDA-MB-231 cancer cell line, and effectively induces cancer cells to undergo apoptosis.
• Robl Jeffrey A., Cimarusti Maria P., Tetrahedron Lett., 35 (1994) N 9, S 1393- 1396
  作者：Robl Jeffrey A., Cimarusti Maria P.

  DOI：——

  日期：——