(Z)-2-amino-5-[(1-benzyl-1-H-indol-3-yl)methylene]-1-methyl-1H-imidazol-4(5H)-one | 1207733-60-5

• 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: (Z)-2-amino-5-[(1-benzyl-1-H-indol-3-yl)methylene]-1-methyl-1H-imidazol-4(5H)-one
• 英文别名: (5Z)-5-[(1-benzylindol-3-yl)methylidene]-2-imino-1-methylimidazolidin-4-one
• CAS: 1207733-60-5
• 化学式: C₂₀H₁₈N₄O
• 分子量: 330.389
• InChiKey: JEPXTMPUSZPEGO-WQRHYEAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  肌酸酐 、 1-苄基吲哚-3-甲醛 在 sodium acetate 、 溶剂黄146 作用下， 反应 0.01h， 以90%的产率得到(Z)-2-amino-5-[(1-benzyl-1-H-indol-3-yl)methylene]-1-methyl-1H-imidazol-4(5H)-one
  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

• INDOLE COMPOUNDS FOR USE IN TREATING INFLAMMATION AND CANCER
  申请人：PENTHALA Narsimha Reddy

  公开号：US20150328216A1

  公开（公告）日：2015-11-19

  Provided herein are compounds, comprising Formula (I) or Formula (II), and their pharmaceutically acceptable salts. Also provided are pharmaceutical compositions comprising a pharmaceutically acceptable excipient and at least one compound of Formula (I) and (II), singly or in combination with other pharmaceutically active ingredients, such as anti-inflammatory agents or anticancer agents. These compounds and pharmaceutical compositions are useful for treating inflammation or an inflammation related disorder in a subject via administration to the subject. These compounds and pharmaceutical compositions are also useful for inhibiting COX-2, for treating cancer, for reducing the size of a neoplasm, and for inhibiting tubulin polymerization in a cell.
• US9597316B2
  申请人：——

  公开号：US9597316B2

  公开（公告）日：2017-03-21
• 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.