methyl 4-[[3-[(Z)-(2-imino-3-methyl-5-oxoimidazolidin-4-ylidene)methyl]indol-1-yl]methyl]benzoate | 1207733-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-[[3-[(Z)-(2-imino-3-methyl-5-oxoimidazolidin-4-ylidene)methyl]indol-1-yl]methyl]benzoate
• CAS: 1207733-65-0
• 化学式: C₂₂H₂₀N₄O₃
• 分子量: 388.426
• InChiKey: GZPRMGUFQDSMBC-ODLFYWEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  肌酸酐 、 (9ci)-4-[(3-甲酰基-1H-吲哚-1-基)甲基]-苯甲酸甲酯 在 sodium acetate 、 溶剂黄146 作用下， 反应 0.02h， 以87%的产率得到methyl 4-[[3-[(Z)-(2-imino-3-methyl-5-oxoimidazolidin-4-ylidene)methyl]indol-1-yl]methyl]benzoate
  参考文献：
  名称：

  Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines

  摘要：

  The synthesis of several novel substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones structurally related to aplysinopsin have been carried out under microwave irradiation and conventional heating methods. The analogs 3a, 3b, 3d-3g, 3k and 3l were evaluated for their in vitro cytotoxic activity against an NCI 60 human tumor cell line panel. Compound 3f exhibited good growth inhibitory properties against all but four of the human cancer cell lines examined, and afforded LC50 values < 10 mu M for 30% of the cell lines in the panel. Compound 3e was an effective inhibitor of leukemia, CNS, melanoma, and breast cancer cell growth, but generally less effective as a cytotoxic agent. Thus, the aplysinopsin analog 3f was regarded as a useful lead compound for further structural optimization. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.083

文献信息

• Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines
  作者：Narsimha Reddy Penthala、Thirupathi Reddy Yerramreddy、Peter A. Crooks

  DOI：10.1016/j.bmcl.2009.11.083

  日期：2010.1

  The synthesis of several novel substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones structurally related to aplysinopsin have been carried out under microwave irradiation and conventional heating methods. The analogs 3a, 3b, 3d-3g, 3k and 3l were evaluated for their in vitro cytotoxic activity against an NCI 60 human tumor cell line panel. Compound 3f exhibited good growth inhibitory properties against all but four of the human cancer cell lines examined, and afforded LC50 values < 10 mu M for 30% of the cell lines in the panel. Compound 3e was an effective inhibitor of leukemia, CNS, melanoma, and breast cancer cell growth, but generally less effective as a cytotoxic agent. Thus, the aplysinopsin analog 3f was regarded as a useful lead compound for further structural optimization. (C) 2009 Elsevier Ltd. All rights reserved.