苯乙酰胺,N-(3,5-二甲氧苯基)- | 176696-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯乙酰胺,N-(3,5-二甲氧苯基)-
• 英文名称: N-(3,5-dimethoxyphenyl)-2-phenylacetamide
• 英文别名: N-(3,5-dimethoxyphenyl)-phenylacetamide；Cambridge id 6376045
• CAS: 176696-11-0
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: IZUPVBJGUXDAGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯乙酰胺,N-(3,5-二甲氧苯基)- 在 potassium tert-butylate 、 四氯化锡 作用下， 以 1,2-二氯乙烷 、 叔丁醇 为溶剂， 反应 21.5h， 生成
  参考文献：
  名称：

  Antimitotic Activity of 5-Hydroxy-7-methoxy-2-phenyl-4-quinolones

  摘要：

  We report the synthesis of 5-hydroxy-7-methoxy-2-phenyl-4-quinolones and their biological activity as antitumor agents. These molecules were initially evaluated for their ability to induce cell cycle arrest in the G2/M phase. Compounds that showed significant G2/M cell cycle arrest were tested for antiproliferative activity using both the MTT assay and the NCI in vitro 60 cell line human tumor screen. The 5-hydroxy-7-methoxy-2-phenyl-4-quinolone (3a) and 2-(3-fluorophenyl)-5-hydroxy-7-methoxy-4-quinolone (3f) were the most active in the cell cycle arrest test whereas 3f was found to be the most active in the MTT assay. In terms of structural requirements, we found that the presence of a 5-hydroxyl group, a 7-methoxy group, and an unsubstituted N1 were essential for the antimitotic activity. In accordance with the literature, a fluoro group at the 3'- or 2'-position and a methoxy or a chloro group at the 3'-position were found to be highly advantageous for both the cell cycle arrest and the antiproliferative activities.

  DOI：

  10.1021/jm049876x
• 作为产物：
  描述：

  3,5-二甲氧基苯胺 、 苯乙酰氯 以 甲苯 为溶剂， 以1.55 g (87%)的产率得到苯乙酰胺,N-(3,5-二甲氧苯基)-
  参考文献：
  名称：

  Pharmaceutical compositions comprising 2-quinolones

  摘要：

  这项发明涉及一种对肿瘤中克隆性细胞增殖具有活性的药物组合物，包括所述式(I)和(Ia)中选择的化合物之一的有效量，其中：X，R1，R2，R3，R4，R5，R6如权利要求书中所定义。

  公开号：

  US06593342B1

文献信息

• Synthesis of 7-indolyl-imines by the reaction of 4,6-dimethoxyindoles with secondary amides and phosphoryl chloride
  作者：David StC. Black、Michael C. Bowyer、Andrew J. Ivory、Katrina A. Jolliffe、Naresh Kumar

  DOI：10.1016/0040-4020(96)00140-8

  日期：1996.3

  4,6-Dimethoxy-2,3-diphenylindole 1 undergoes reaction with formanilide, acetanilide, benzanilide and several dimethoxy analogs in the presence of phosphoryl chloride to give the corresponding 7-imino derivatives 2–6. This reaction has been extended to include the synthesis of 7-indolyl-pyrrolines and tetrahydropyridines 7–9, 11 and oxazolines 14,15.

  4,6-二甲氧基-2,3-二苯基吲哚1在磷酰氯存在下与甲酰苯胺，对乙酰苯胺，苯甲酰苯胺和几种二甲氧基类似物反应，得到相应的7-亚氨基衍生物2-6。该反应已扩展到包括7-吲哚基-吡咯啉和四氢吡啶7-9、11和恶唑啉14,15的合成。
• Synthesis of Dimethoxy Activated Benzimidazoles and Bisbenzimidazoles
  作者：David StC. Black、Mahiuddin Alamgir、Glenn C. Condie、Vesna Martinovic、Joanne Wood、Hayat Sholihin、Paul K. Bowyer、Naresh Kumar

  DOI：10.3987/com-20-14278

  日期：——
• 3-Aryl-2-Quinolone Derivatives:  Synthesis and Characterization of In Vitro and In Vivo Antitumor Effects with Emphasis on a New Therapeutical Target Connected with Cell Migration
  作者：Benoît Joseph、Francis Darro、Aurélie Béhard、Brigitte Lesur、Françoise Collignon、Christine Decaestecker、Armand Frydman、Gérald Guillaumet、Robert Kiss

  DOI：10.1021/jm010978m

  日期：2002.6.1

  Among 25 3-aryl-2-quinolone derivatives synthesized, the antitumor activity of some of them was characterized both in vitro and in vivo. In this series, no compound appeared to be cytotoxic in vitro, as was known by the colorimetric MTT assay carried out on 12 distinct human cancer cell lines obtained from the American Type Culture Collection. Indeed, the concentration values decreasing the growth of the 12 cell lines by at least 50% (IC50 index) were always higher than 10(-5) M. We then made use of a computer-assisted phase-contrast videomicroscopy system to quantitatively determine in vitro the level of migration of living MCF-7 human breast cancer cells. For example, at 10(-7) M, compounds 7, 13, 16, and 28 markedly decreased the migration level of these MCF-7 human breast cancer cells. The in vivo determination of the maximum tolerated dose showed that all compounds tested were definitively nontoxic. When the nontoxic, antimigratory compound 16 was combined with either doxorubicin or etoposide, two cytotoxic compounds routinely used in the clinic, this led to additive in vivo benefits from this treatment (as compared to individual administrations of the drugs) when the MXT mouse mammary adenocarcinoma was used. Thus, nontoxic antimigratory compounds, including the 2-quinolone derivatives synthesized here, can actually improve the efficiency of antitumor treatment when combined with conventional cytotoxic agents.
• COMPOSITIONS PHARMACEUTIQUES COMPRENANT DES 2-QUINOLONES
  申请人：LABORATOIRE L. LAFON

  公开号：EP1097138B1

  公开（公告）日：2005-12-07
• US6593342B1
  申请人：——

  公开号：US6593342B1

  公开（公告）日：2003-07-15