(Z)-5-[2-(4-methoxy-3-nitrophenyl)-ethenyl]-1-methylindole | 1072121-86-8

• 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: (Z)-5-[2-(4-methoxy-3-nitrophenyl)-ethenyl]-1-methylindole
• 英文别名: 5-[(Z)-2-(4-methoxy-3-nitrophenyl)ethenyl]-1-methylindole
• CAS: 1072121-86-8
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: SORCIYLTSXDRNY-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-5-[2-(4-methoxy-3-nitrophenyl)-ethenyl]-1-methylindole 在 溶剂黄146 、 锌 作用下， 反应 2.0h， 以88%的产率得到(Z)-2-methoxy-5-[2-(1-methyl-1H-indol-5-yl)-ethenyl]-phenylamine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel stilbene-based antitumor agents

  摘要：

  A series of novel stilbene derivatives has been synthesized and studied with the main goal to investigate SAR of the amino compound 1a, as well as to improve its water solubility, a potentially negative aspect of the molecule that could be a serious obstacle for a pre-clinical development. We have obtained derivatives with good cytotoxic activity, in particular, the derivatives 5c and 6b could represent two novel leads for further investigation. Compound 8b, a morpholino-carbamate derivative, prodrug of 1a, has a very good solubility in water, and is active in suppressing growth of tumor cells at a concentration of 5000 nM, which is a concentration 100 times higher than the parent stilbene 1a. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.002
• 作为产物：
  描述：

  (Z)-5-[2-(4-methoxy-3-nitrophenyl)-ethenyl]-1H-indole 、 碘甲烷 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以81%的产率得到(Z)-5-[2-(4-methoxy-3-nitrophenyl)-ethenyl]-1-methylindole
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel stilbene-based antitumor agents

  摘要：

  A series of novel stilbene derivatives has been synthesized and studied with the main goal to investigate SAR of the amino compound 1a, as well as to improve its water solubility, a potentially negative aspect of the molecule that could be a serious obstacle for a pre-clinical development. We have obtained derivatives with good cytotoxic activity, in particular, the derivatives 5c and 6b could represent two novel leads for further investigation. Compound 8b, a morpholino-carbamate derivative, prodrug of 1a, has a very good solubility in water, and is active in suppressing growth of tumor cells at a concentration of 5000 nM, which is a concentration 100 times higher than the parent stilbene 1a. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.002

文献信息

• STILBENE DERIVATIVES AS NEW CANCER THERAPEUTIC AGENTS
  申请人：Lee Ruey-min

  公开号：US20080261982A1

  公开（公告）日：2008-10-23

  Stilbene derivatives exhibit killing and suppression of growth activity against a variety of cancer cells, and are effective at suppressing tumor growth in vivo. The stilbene derivatives may be used in the treatment of diseases characterized by cell hyperproliferation including human malignancies and non-malignant diseases such as liver cirrhosis. Stilbenes may also disrupt abnormal vessels in tumor to achieve vascular disrupting effect to suppress tumor growth. Water soluble pro-drug forms of stilbene derivatives are particularly useful in suppressing tumor growth in vivo.

  Stilbene衍生物表现出对多种癌细胞的杀灭和抑制生长活性，并且在体内有效地抑制肿瘤生长。Stilbene衍生物可用于治疗以细胞过度增殖为特征的疾病，包括人类恶性肿瘤和非恶性疾病，如肝硬化。Stilbenes也可以破坏肿瘤中的异常血管，实现血管破坏效应以抑制肿瘤生长。水溶性的Stilbene衍生物前药形式在体内抑制肿瘤生长方面特别有用。
• Design, synthesis and biological evaluation of novel stilbene-based antitumor agents
  作者：Daniele Simoni、Francesco Paolo Invidiata、Marco Eleopra、Paolo Marchetti、Riccardo Rondanin、Riccardo Baruchello、Giuseppina Grisolia、Ashutosh Tripathi、Glen E. Kellogg、David Durrant、Ray M. Lee

  DOI：10.1016/j.bmc.2008.12.002

  日期：2009.1

  A series of novel stilbene derivatives has been synthesized and studied with the main goal to investigate SAR of the amino compound 1a, as well as to improve its water solubility, a potentially negative aspect of the molecule that could be a serious obstacle for a pre-clinical development. We have obtained derivatives with good cytotoxic activity, in particular, the derivatives 5c and 6b could represent two novel leads for further investigation. Compound 8b, a morpholino-carbamate derivative, prodrug of 1a, has a very good solubility in water, and is active in suppressing growth of tumor cells at a concentration of 5000 nM, which is a concentration 100 times higher than the parent stilbene 1a. (C) 2008 Elsevier Ltd. All rights reserved.