4-carboxy-2',5'-dimethoxychalcone | 849524-16-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-carboxy-2',5'-dimethoxychalcone
• 英文别名: 4-carboxyl-2',5'-dimethoxychalcone；4-[3-(2,5-Dimethoxyphenyl)-3-oxoprop-1-enyl]benzoic acid
• CAS: 849524-16-9
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: BSAROFRSKAPDHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-甲基-2-羟基乙胺 、 4-carboxy-2',5'-dimethoxychalcone 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以79.1%的产率得到4-(2-hydroxyethyl)methylcarbamoyl-2',5'-dimethoxychalcone
  参考文献：
  名称：

  Synthesis and biological evaluation of 2′,5′-dimethoxychalcone derivatives as microtubule-targeted anticancer agents

  摘要：

  A series of novel 2',5'-dimethoxylchalcone derivatives including 18 new compounds were synthesized and evaluated for cytotoxicities against two human cancer cell lines, NTUB1 ( human bladder cancer cell line) and PC3 ( human prostate cancer cell line). All these derivatives except for 21 exhibited significant cytotoxic effect against NTUB1 and PC3 cell lines. Compounds 13 and 17 with 4-carbamoyl moiety showed potent inhibitory effect on growth of NTUB1 and PC3 cells. Flow cytometric analysis demonstrated that treatment of NTUB1 cells with 1 mu M 13 and 17 induced G1 phase arrest accompanied by an increase in apoptotic cell death of NTUB1 cells after 24 h. Treatment of PC3 cells with 1 mu M and 3 mu M 13, and 1 mu M and 3 mu M 17 induced S and G1, and G1 and G2/M phase arrests, respectively, accompanied by an increase in apoptotic cell death. These data suggested that 13 and 17 with different 4-carbamoyl moiety displayed same cell cycle arrest in NTUB1 cells while different doses of 13 and 17 revealed different cell cycle arrest in PC3 cells. Cell morphological study of 17 indicated that more cells rounding up or dead associated with tubulin polymerization. Compound 17 showed an increased alpha-tubulin level in polymerized microtubule fraction in a dose-dependent manner while 500 nM paclitaxel also showed similar effect in NTUB1 cells by Western blot analysis. The result suggested that 17 may be used as microtubule-targeted agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.012
• 作为产物：
  描述：

  2,5-二甲氧基苯乙酮 、 对甲酰基苯甲酸甲酯 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以63%的产率得到4-carboxy-2',5'-dimethoxychalcone
  参考文献：
  名称：

  SYNTHESIS AND BIOLOGICAL EVALUATION OF 2',5'-DIMETHOXYCHALCONE DERIVATIVES AS MICROTUBULE-TARGETED ANTICANCER AGENTS

  摘要：

  揭示了一系列治疗癌症的2′,5′-二甲氧基茴香酮衍生物，其中2,5-二甲氧基苯乙酮和甲基4-甲醛苯甲酸酯缩合形成4-羧基-2′,5′-二甲氧基茴香酮（化合物1），进一步与烷基卤化物或胺反应以合成化合物2-17的茴香酮衍生物。此外，2,5-二甲氧基苯乙酮与5-甲醛-2-噻吩羧酸反应形成化合物18（3-（3-噻吩）羧基-1-（2,5-二甲氧基苯基）丙-2-烯-1-酮）。合成的2′,5′-二甲氧基茴香酮衍生物可作为微管靶向的微管蛋白聚合剂。

  公开号：

  US20110306775A1

文献信息

• Synthesis and biological evaluation of 2′,5′-dimethoxychalcone derivatives as microtubule-targeted anticancer agents
  作者：Huang-Yao Tu、A-Mei Huang、Tzyh-Chyuan Hour、Shyh-Chyun Yang、Yeong-Shiau Pu、Chun-Nan Lin

  DOI：10.1016/j.bmc.2010.02.012

  日期：2010.3

  A series of novel 2',5'-dimethoxylchalcone derivatives including 18 new compounds were synthesized and evaluated for cytotoxicities against two human cancer cell lines, NTUB1 ( human bladder cancer cell line) and PC3 ( human prostate cancer cell line). All these derivatives except for 21 exhibited significant cytotoxic effect against NTUB1 and PC3 cell lines. Compounds 13 and 17 with 4-carbamoyl moiety showed potent inhibitory effect on growth of NTUB1 and PC3 cells. Flow cytometric analysis demonstrated that treatment of NTUB1 cells with 1 mu M 13 and 17 induced G1 phase arrest accompanied by an increase in apoptotic cell death of NTUB1 cells after 24 h. Treatment of PC3 cells with 1 mu M and 3 mu M 13, and 1 mu M and 3 mu M 17 induced S and G1, and G1 and G2/M phase arrests, respectively, accompanied by an increase in apoptotic cell death. These data suggested that 13 and 17 with different 4-carbamoyl moiety displayed same cell cycle arrest in NTUB1 cells while different doses of 13 and 17 revealed different cell cycle arrest in PC3 cells. Cell morphological study of 17 indicated that more cells rounding up or dead associated with tubulin polymerization. Compound 17 showed an increased alpha-tubulin level in polymerized microtubule fraction in a dose-dependent manner while 500 nM paclitaxel also showed similar effect in NTUB1 cells by Western blot analysis. The result suggested that 17 may be used as microtubule-targeted agents. (C) 2010 Elsevier Ltd. All rights reserved.
• SYNTHESIS AND BIOLOGICAL EVALUATION OF 2',5'-DIMETHOXYCHALCONE DERIVATIVES AS MICROTUBULE-TARGETED ANTICANCER AGENTS
  申请人：Lin Chun-Nan

  公开号：US20110306775A1

  公开（公告）日：2011-12-15

  Disclosed are a serious of 2′,5′-dimethoxychalcone derivatives for treating cancer, wherein 2,5-dimethoxyacetophenone and methyl 4-formylbenzoate are condensed to form 4-carboxyl-2′,5′-dimethoxychalcone (compound 1), which is further reacted with alkyl halides or amines to synthesize the chalcone derivatives of compounds 2-17. In addition, 2,5-dimethoxyacetophenone is reacted with 5-formyl-2-thiophenecarboxylic acid to form compound 18 (3-(3-thiophene)carboxyl-1-(2,5-dimethoxyphenyl)prop-2-en-1-one). The synthesized 2′,5′-dimethoxychalcone derivatives can be acted as microtubule-targeted tubulin-polymerizing agents.

  揭示了一系列治疗癌症的2′,5′-二甲氧基茴香酮衍生物，其中2,5-二甲氧基苯乙酮和甲基4-甲醛苯甲酸酯缩合形成4-羧基-2′,5′-二甲氧基茴香酮（化合物1），进一步与烷基卤化物或胺反应以合成化合物2-17的茴香酮衍生物。此外，2,5-二甲氧基苯乙酮与5-甲醛-2-噻吩羧酸反应形成化合物18（3-（3-噻吩）羧基-1-（2,5-二甲氧基苯基）丙-2-烯-1-酮）。合成的2′,5′-二甲氧基茴香酮衍生物可作为微管靶向的微管蛋白聚合剂。