(2'SR,3'RS,4'SR,5'RS)-3'-benzoyl-4',5'-diphenylspiro[indoline-3,2'-pyrrolidin]-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2'SR,3'RS,4'SR,5'RS)-3'-benzoyl-4',5'-diphenylspiro[indoline-3,2'-pyrrolidin]-2-one
• 英文别名: 3-benzoyl-4,5-diphenylspiro[pyrrolidine-2.3'-indolin]-2'-one；(3S,3'R,4'S,5'R)-3'-benzoyl-4',5'-diphenylspiro[1H-indole-3,2'-pyrrolidine]-2-one
• 化学式: C₃₀H₂₄N₂O₂
• 分子量: 444.533
• InChiKey: GUZFQMSAFCYWDX-HOSLJWMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 、 苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (2'SR,3'RS,4'SR,5'RS)-3'-benzoyl-4',5'-diphenylspiro[indoline-3,2'-pyrrolidin]-2-one
  参考文献：
  名称：

  Synthesis and biological activity of 4-aryl-3-benzoyl-5-phenylspiro[pyrrolidine-2.3′-indolin]-2′-one derivatives as novel potent inhibitors of advanced glycation end product

  摘要：

  Diabetic complications and their detrimental effects caused by sugar derived substances, have been the serious issue for the last few years and have yet not been fully combated. The key point of the present study is to synthesize some newer chemical entities which can eradicate such ailments to the maximum possible extent. So with this aim synthesis of some biologically interesting spiro-indolone-pyrrolidine derivatives was accomplished by 1,3-dipolar cycloaddition reaction of azomethine ylide 6 generated in situ from isatin and benzyl amine with the substituted alpha,beta-unsaturated carbonyl compounds 3 as dipolarophile, leading to the formation of new 4-aryl-3-benzoyl-5-phenylspiro[pyrrolidine-2.3'-indolin]2'-one derivatives 7 stereoselectively in excellent yields. The synthesized compounds have been screened for their advanced glycation end (AGE) product formation inhibitory activity on the basis of their ability to inhibit the formation of AGEs in the bovine serum albumin (BSA)-glucose assay and have been found to exhibit significant activity against AGE formation. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.022

文献信息

• Experimental and theoretical approaches to [1,5]-prototropic generation of an azomethine ylide and a 1,3-dipolar cycloaddition for novel spiropyrrolidine oxindoles synthesis
  作者：Yaghoub Sarrafi、Mahshid Hamzehloueian、Kamal Alimohammadi、Saeid Yeganegi

  DOI：10.1016/j.molstruc.2012.04.013

  日期：2012.12

  of spiropyrrolidine oxindoles was synthesized via a multicomponent 1,3-dipolar cycloaddition reaction of isatin, benzylamine and chalcone derivatives. The regio- and stereochemistry of the products were established by single crystal X-ray structure and spectroscopic techniques. The molecular mechanism of this cycloaddition has been investigated by means of a density functional theory (DFT) method. The

  摘要 通过靛红、苄胺和查耳酮衍生物的多组分1,3-偶极环加成反应合成了一系列螺吡咯烷羟吲哚。产物的区域和立体化学是通过单晶 X 射线结构和光谱技术确定的。已经通过密度泛函理论 (DFT) 方法研究了这种环加成的分子机制。评估了通过亚胺离子中的 [1,5]-H 位移制备偶氮甲碱叶立德的能量路径。基于反应物的过渡态稳定性、全局和局部反应性指数来解释区域选择性和立体选择性。环加成被假定通过一步途径发生，其中两个 C-C 键以非同步方式形成。
• Synthesis and biological activity of 4-aryl-3-benzoyl-5-phenylspiro[pyrrolidine-2.3′-indolin]-2′-one derivatives as novel potent inhibitors of advanced glycation end product
  作者：Anjandeep Kaur、Baldev Singh、Bhawna Vyas、Om Silakari

  DOI：10.1016/j.ejmech.2014.04.022

  日期：2014.5

  Diabetic complications and their detrimental effects caused by sugar derived substances, have been the serious issue for the last few years and have yet not been fully combated. The key point of the present study is to synthesize some newer chemical entities which can eradicate such ailments to the maximum possible extent. So with this aim synthesis of some biologically interesting spiro-indolone-pyrrolidine derivatives was accomplished by 1,3-dipolar cycloaddition reaction of azomethine ylide 6 generated in situ from isatin and benzyl amine with the substituted alpha,beta-unsaturated carbonyl compounds 3 as dipolarophile, leading to the formation of new 4-aryl-3-benzoyl-5-phenylspiro[pyrrolidine-2.3'-indolin]2'-one derivatives 7 stereoselectively in excellent yields. The synthesized compounds have been screened for their advanced glycation end (AGE) product formation inhibitory activity on the basis of their ability to inhibit the formation of AGEs in the bovine serum albumin (BSA)-glucose assay and have been found to exhibit significant activity against AGE formation. (c) 2014 Elsevier Masson SAS. All rights reserved.