4-(1-oxo-1,3-dihydroisoindol-2-yl)butyric acid | 101004-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(1-oxo-1,3-dihydroisoindol-2-yl)butyric acid
• 英文别名: 4-(1-Oxoisoindolin-2-yl)butanoic acid；4-(3-oxo-1H-isoindol-2-yl)butanoic acid
• CAS: 101004-97-1
• 化学式: C₁₂H₁₃NO₃
• mdl: MFCD07528335
• 分子量: 219.24
• InChiKey: VZHAWKBRFXIGPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1-oxo-1,3-dihydroisoindol-2-yl)butyric acid 在 硫酸 、 palladium on activated charcoal 、 氢气 、 硝酸 作用下， 以 甲醇 、 硫酸 、 水 为溶剂， 反应 16.0h， 生成 4-(6-amino-1-oxo-1,3-dihydroisoindol-2-yl)butyric acid methyl ester
  参考文献：
  名称：

  Synthesis, biological evaluation, X-ray molecular structure and molecular docking studies of RGD mimetics containing 6-amino-2,3-dihydroisoindolin-1-one fragment as ligands of integrin αIIbβ3

  摘要：

  A series of novel RGD mimetics containing phthalimidine fragment was designed and synthesized. Their antiaggregative activity determined by Born's method was shown to be due to inhibition of fibrinogen binding to alpha(IIb)beta(3). Molecular docking of RGD mimetics to alpha(IIb)beta(3) receptor showed the key interactions in this complex, and also some correlations have been observed between values of biological activity and docking scores. The single crystal X-ray data were obtained for five mimetics. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.019
• 作为产物：
  描述：

  4-(1,3-二氧代异吲哚啉-2-基)丁酸 在 amalgamated zinc 作用下， 反应 4.0h， 生成 4-(1-oxo-1,3-dihydroisoindol-2-yl)butyric acid
  参考文献：
  名称：

  RGD mimetics containing phthalimidine fragment as novel ligands of fibrinogen receptor

  摘要：

  The novel RGD mimetics with phthalimidine central fragment were synthesized with the use of 4-piperidine-4-yl-butyric, 4-piperidine-4-yl-butyric, 4-piperazine-4-yl-benzoic and 1,2,3,4-tetrahydroiso-quinoline-7-carboxylic acids as surrogates of Arg motif. The synthesized compounds potently inhibited platelet aggregation in vitro and blocked FITC-Fg binding to alpha(IIb)beta(3) integrin in a suspension of washed human platelets. The key alpha(IIb)beta(3) protein-ligand interactions were determined in docking experiments. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.063

文献信息

• A simple one-step synthesis of N-substituted isoindolin-1-ones. Diastereofacially selective protonation of an intermediate isoindolinol
  作者：Ronald Grigg、H. Q. Nimal Gunaratne、Visuvanathar Sridharan

  DOI：10.1039/c39850001183

  日期：——

  substituted aliphatic amines, react with o-phthaldialdehyde in the presence of acetic acid to give N-substituted isoindolin-1-ones in excellent yield; deuteriation studies implicate an isoindolinol intermediate and, when α-amino acids are used, provide evidence of its diastereofacially selective protonation.

  α-氨基酸及其甲基酯，芳基胺，杂环胺，以及效率较低的芳基取代的脂族胺，在乙酸存在下与邻苯二甲醛反应，以优异的收率得到N-取代的异吲哚啉-1-酮。氘化研究涉及异吲哚酚中间体，并且当使用α-氨基酸时，提供了其非对面选择性质子化的证据。
• Compounds having a renin-inhibiting activity
  申请人：BEECHAM GROUP PLC

  公开号：EP0375451A2

  公开（公告）日：1990-06-27

  Compounds of formula (I) and pharmaceutically acceptable salts thereof: wherein Z₁, Z₂, Z₃ and the carbon atoms to which Z₁ and Z₃ are attached, form a 5-membered non-aromatic heterocyclic ring; E is absent or is (CH₂)n or CH(CH₂)n-1 wherein n is 1 to 4; A is -CONH-, -NHCO-, -COO- -S(O)r- wherein r is 0, 1, or 2, or -CH₂-; p is 0, 1 or 2; q is 0 or 1; s is 0, 1, 2, 3 or 4; Rz is hydrogen, C₁₋₆ alkyl or, when A is -CH₂-, hydroxy; Ra and Rb are independently selected from hydrogen or a substituent; R₁ is CH₂R₉ wherein R₉ is optionally substituted aryl or heteroaryl; R₂ is CHR₁₀R₁₁ wherein R₁₀ is hydrogen or methyl and R₁₁ is C₁₋₆ alkyl, C₃₋₈ cycloalkyl, optionally substituted aryl or heteroaryl, or R₁₁ is amino, C₂₋₇ alkanoylamino, 2-oxopyrrolidinyl, 2-oxopiperidinyl or C₁₋₆ alkoxycarbonylamino; R₃ is CH₂R₁₂ wherein R₁₂ is C₁₋₆ alkyl, C₃₋₈ cycloalkyl or phenyl; and R₄ is a saturated or unsaturated heterocyclic ring linked through carbon, hydroxy, C₁₋₆ alkoxy, C₁₋₇ alkanoyloxy, amino, C₁₋₇ alkanoylamino, amino substituted by one or two C₁₋₆ alkyl groups, C₁₋₆ alkylsulphonyl, carboxy, C₁₋₆ alkoxycarbonyl, benzyloxycarbonyl, aminocarbonyl or CH(NHR₁₃)CO₂R₁₄ wherein R₁₃ is hydrogen or C₁₋₆ alkanoyl and R₁₄ is hydrogen or C₁₋₆ alkyl; or (when s is 2 to 4) R₄ is a saturated or unsaturated heterocyclic ring linked through nitrogen; and the dashed line represents an optional bond (when E is present); which are renin inhibitors, a process for their preparation and their use as pharmaceuticals.

  式 (I) 的化合物及其药学上可接受的盐类： 其中 Z₁、Z₂、Z₃ 和连接 Z₁ 和 Z₃ 的碳原子形成 5 元非芳杂环； E 不存在或为 (CH₂)n 或 CH(CH₂)n-1，其中 n 为 1 至 4； A 是-CONH-、-NHCO-、-COO- -S(O)r- 其中 r 是 0、1 或 2，或 -CH₂-； p 是 0、1 或 2 q 是 0 或 1； s 是 0、1、2、3 或 4； Rz 是氢、C₁₋₆烷基或（当 A 是-CH₂-时）羟基； Ra 和 Rb 分别独立地选自氢或取代基； R₁ 是 CH₂R₉，其中 R₉ 是任选取代的芳基或杂芳基； R₂ 是 CHR₁₀R₁₁ 其中 R₁₀ 是氢或甲基，R₁₁ 是 C₁₋₆ 烷基、C₃₋₈ 环烷基、R₁₁是氨基、C₂₋₇烷酰氨基、2-氧代吡咯烷基、2-氧代哌啶基或 C₁₋₆烷氧羰基氨基； R₃ 是 CH₂R₁₂，其中 R₁₂ 是 C₁₋₆ 烷基、C₃₋₈ 环烷基或苯基；以及 R₄ 是通过碳、羟基、C₁₋₆ 烷氧基、C₁₋₇ 烷酰氧基、氨基、C₁₋₇ 烷酰氨基、氨基取代的一个或两个 C₁₋₆烷基连接的饱和或不饱和杂环、C₁₋₆ 烷基磺酰基、羧基、C₁₋₆ 烷氧基羰基、苄氧羰基、氨基羰基或 CH(NHR₁₃)CO₂R₁₄ 其中 R₁₃ 是氢或 C₁₋₆ 烷酰基，R₁₄ 是氢或 C₁₋₆ 烷基；或（当 s 为 2 至 4 时）R₄ 是通过氮连接的饱和或不饱和杂环；以及 虚线代表任选键（当 E 存在时）； 它们是肾素抑制剂、其制备过程以及作为药物的用途。
• GRIGG, R.;GUNARATNE, H. Q. N.;SRIDHARAN, VLAUVANATHAR, J. CHEM. SOC. CHEM. COMMUN., 1985, N 17, 1183-1184
  作者：GRIGG, R.、GUNARATNE, H. Q. N.、SRIDHARAN, VLAUVANATHAR

  DOI：——

  日期：——