1,3-bis({[(3Z)-5-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene]amino})urea | 1431458-76-2

• 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: 1,3-bis({[(3Z)-5-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene]amino})urea
• 英文别名: 1,3-bis[(5-methyl-2-oxoindol-3-yl)amino]urea
• CAS: 1431458-76-2；1452580-00-5
• 化学式: C₁₉H₁₆N₆O₃
• 分子量: 376.374
• InChiKey: QHKJYDGFGJRGEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  124.05
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  5-甲基靛红 、 碳酰肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 1,3-bis({[(3Z)-5-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene]amino})urea
  参考文献：
  名称：

  作为可能的生物活性剂的硫代碳酰肼和碳酰肼衍生物的合成

  摘要：

  摘要5-取代靛红与硫代卡巴肼或碳酰肼缩合合成了一系列新的β-靛红醛-N、N′-硫代羰腙、双-β-靛红硫代羰腙、双-β-靛红羰腙。新合成化合物的化学结构经FT-IR、1 H NMR和质谱分析证实。评估了合成的化合物对各种 DNA 和 RNA 病毒株的体外抗病毒活性，但与参考化合物相比显示出中等的抗病毒活性。在所有化合物中，6c在两阶段小鼠皮肤致癌试验中表现出最高的化学预防活性。 图形概要

  DOI：

  10.1007/s00044-013-0684-3

文献信息

• Microwave Assisted Synthesis, Characterization of Some New Isatin and Thiophene Derivatives as Cytotoxic and Chemopreventive Agents
  作者：Kiran Gangarapu、Sarangapani Manda、Sreekanth Thota、Rajeshwar Yerra、Subhas S. Karki、Jan Balzarini、Erik De Clercq、Harukuni Tokuda

  DOI：10.2174/157018012804586950

  日期：2012.12.1

  In obtaining some new cytotoxic and chemopreventive agents with potent antiproliferative activity against cancer cells, a series of new beta-isatin aldehyde-N,N'-thiocarbohydrazone, bis-beta-isatin thiocarbohydrazones, bis-beta-isatin carbohydrazones, N,2-bis(thiophen-2-ylmethylidene) thiocarbohydrazone and N,2-bis(thiophen-2-ylmethylidene) carbohydrazone derivatives was synthesized by microwave oriented reaction and evaluated for their in vitro cytotoxic activity. The newly synthesized compounds were characterized based on spectral (FT-IR, NMR, MS) analyses. The inhibitory effects of synthesized compounds on the proliferation of murine leukemia cells (L1210), human T-lymphocyte cells (CEM) and human cervix carcinoma cells (HeLa) were assayed by using MTT assay. The compounds were also tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). In vitro evaluation of these schiff bases revealed mild to moderate cytotoxic activity in a dose dependent manner. The results of the in vitro inhibitory activities of synthetic compounds against EBV-EA activation with IC50 ranges from 485-535 (mol ratio/32pmol/TPA). Chlorine group containing derivatives did not show increased inhibitory activity against tumor promoter TPA induction. Sulphur containing derivatives also did not show a high inhibitory potency in this system.