4'-(4-methoxyphenyl)-3-[(4-methoxyphenyl)methylidene]-1'-methyl-1"-[(1-piperidinyl)methylene]-dispiro[cyclohexane-1,3'-pyrrolidine-2',3"-[3H]indole]-2,2"(1"H)-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4'-(4-methoxyphenyl)-3-[(4-methoxyphenyl)methylidene]-1'-methyl-1"-[(1-piperidinyl)methylene]-dispiro[cyclohexane-1,3'-pyrrolidine-2',3"-[3H]indole]-2,2"(1"H)-dione
• 化学式: C₃₈H₄₃N₃O₄
• 分子量: 605.777
• InChiKey: BLWXQMFGFDPBKH-WJBJUIIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  肌氨酸 、 (2E,6E)-2,6-bis(4-methoxybenzylidene)cyclohexanone 、 1-(哌啶-1-基甲基)吲哚-2,3-二酮 以 乙醇 为溶剂， 反应 20.0h， 以60%的产率得到4'-(4-methoxyphenyl)-3-[(4-methoxyphenyl)methylidene]-1'-methyl-1"-[(1-piperidinyl)methylene]-dispiro[cyclohexane-1,3'-pyrrolidine-2',3"-[3H]indole]-2,2"(1"H)-dione
  参考文献：
  名称：

  Design, synthesis and QSAR studies of dispiroindole derivatives as new antiproliferative agents

  摘要：

  A variety of 4'-ary1-3-(arylmethylidene)-1 ''-[(cyclic-amino)methylene]-1'-methyl-dispiro[cyclohexane-1,3'-pyrrolidine-2',3 ''-[3H]indole]-2,2 ''(1"H)-diones 4a-u were prepared via reaction of 2E,6E-bis(arylidene)-1-cyclohexanones 1a-i with azomethine ylides, generated in situ via a decarboxylative condensation of isatins 2a-c and sarcosine (3). Single crystal X-ray study of 4a, revealed structural and stereochemical features of these derivatives. While most of the synthesized compounds exhibit mild antitumor properties when tested against various human tumor cell lines (HEPG2 "liver", HELA "cervical" and PD "prostate" cancers), three of them, 4d and 4p (active against HEPG2), and compound 4g (active against HELA), demonstrated higher activities, that were close or even higher than that of the reference standard Doxorubicin. QSAR studies revealed good predictive and statistically significant 3 descriptor models (r(2) = 0.903-0.812, r(adjusted)(2) = 0.855-0.672, r(prediction)(2) = 0.773-0.605). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.035

文献信息

• Design, synthesis and QSAR studies of dispiroindole derivatives as new antiproliferative agents
  作者：Riham F. George、Nasser S.M. Ismail、Jacek Stawinski、Adel S. Girgis

  DOI：10.1016/j.ejmech.2013.07.035

  日期：2013.10

  A variety of 4'-ary1-3-(arylmethylidene)-1 ''-[(cyclic-amino)methylene]-1'-methyl-dispiro[cyclohexane-1,3'-pyrrolidine-2',3 ''-[3H]indole]-2,2 ''(1"H)-diones 4a-u were prepared via reaction of 2E,6E-bis(arylidene)-1-cyclohexanones 1a-i with azomethine ylides, generated in situ via a decarboxylative condensation of isatins 2a-c and sarcosine (3). Single crystal X-ray study of 4a, revealed structural and stereochemical features of these derivatives. While most of the synthesized compounds exhibit mild antitumor properties when tested against various human tumor cell lines (HEPG2 "liver", HELA "cervical" and PD "prostate" cancers), three of them, 4d and 4p (active against HEPG2), and compound 4g (active against HELA), demonstrated higher activities, that were close or even higher than that of the reference standard Doxorubicin. QSAR studies revealed good predictive and statistically significant 3 descriptor models (r(2) = 0.903-0.812, r(adjusted)(2) = 0.855-0.672, r(prediction)(2) = 0.773-0.605). (C) 2013 Elsevier Masson SAS. All rights reserved.