(E)-1-[2,5-bis(oxan-2-yloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 1026981-46-3

• 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: (E)-1-[2,5-bis(oxan-2-yloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1026981-46-3
• 化学式: C₂₈H₃₄O₈
• 分子量: 498.573
• InChiKey: DUJQPUWMPYGHGX-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-1-[2,5-bis(oxan-2-yloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以65%的产率得到(E)-1-(2,5-dihydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Cytotoxic 2′,5′-dihydroxychalcones with unexpected antiangiogenic activity

  摘要：

  A series of 2',5'-dihydroxychalcones were synthesized and evaluated for cytotoxicity against tumor cell lines and human umbilical venous endothelial cells (HUVEC). It was found that chalcones with electron-withdrawing substituents on the B ring exhibited potent cytotoxicity against a variety of tumor cell lines while compounds with electron-releasing groups ere less potent in general. Those compounds with B ring replaced by extended or heteroaromatic rings exhibited significant bioactivity. Several compounds were shown to have marked cytotoxic selectivity towards HUVECs. Especially, among the synthesized compounds. 2-chloro-2'.5'dihydroxychalcone (2-3) showed the highest selectivity index up to 66 in comparison to HCT 116 cells. This Compound also exhibited strong inhibitory effects on the HUVEC tube formation in an in vitro model. When administered into BDF1 mice bearing Lewis lung carcinoma cells at 50 mg kg(-1) day (-1), 2-3 was found to inhibit the growth of tumor mass by 60.5%. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01443-5
• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 barium dihydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (E)-1-[2,5-bis(oxan-2-yloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Cytotoxic 2′,5′-dihydroxychalcones with unexpected antiangiogenic activity

  摘要：

  A series of 2',5'-dihydroxychalcones were synthesized and evaluated for cytotoxicity against tumor cell lines and human umbilical venous endothelial cells (HUVEC). It was found that chalcones with electron-withdrawing substituents on the B ring exhibited potent cytotoxicity against a variety of tumor cell lines while compounds with electron-releasing groups ere less potent in general. Those compounds with B ring replaced by extended or heteroaromatic rings exhibited significant bioactivity. Several compounds were shown to have marked cytotoxic selectivity towards HUVECs. Especially, among the synthesized compounds. 2-chloro-2'.5'dihydroxychalcone (2-3) showed the highest selectivity index up to 66 in comparison to HCT 116 cells. This Compound also exhibited strong inhibitory effects on the HUVEC tube formation in an in vitro model. When administered into BDF1 mice bearing Lewis lung carcinoma cells at 50 mg kg(-1) day (-1), 2-3 was found to inhibit the growth of tumor mass by 60.5%. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01443-5

文献信息

• Cytotoxic 2′,5′-dihydroxychalcones with unexpected antiangiogenic activity
  作者：Nguyen-Hai Nam、Yong Kim、Young-Jae You、Dong-Ho Hong、Hwan-Mook Kim、Byung-Zun Ahn

  DOI：10.1016/s0223-5234(02)01443-5

  日期：2003.2

  A series of 2',5'-dihydroxychalcones were synthesized and evaluated for cytotoxicity against tumor cell lines and human umbilical venous endothelial cells (HUVEC). It was found that chalcones with electron-withdrawing substituents on the B ring exhibited potent cytotoxicity against a variety of tumor cell lines while compounds with electron-releasing groups ere less potent in general. Those compounds with B ring replaced by extended or heteroaromatic rings exhibited significant bioactivity. Several compounds were shown to have marked cytotoxic selectivity towards HUVECs. Especially, among the synthesized compounds. 2-chloro-2'.5'dihydroxychalcone (2-3) showed the highest selectivity index up to 66 in comparison to HCT 116 cells. This Compound also exhibited strong inhibitory effects on the HUVEC tube formation in an in vitro model. When administered into BDF1 mice bearing Lewis lung carcinoma cells at 50 mg kg(-1) day (-1), 2-3 was found to inhibit the growth of tumor mass by 60.5%. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.