(3E,5E)-3,5-bis(2,3,4-trimethoxybenzylidene)-tetrahydrothiopyran-4-one | 1360119-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3E,5E)-3,5-bis(2,3,4-trimethoxybenzylidene)-tetrahydrothiopyran-4-one
• 英文别名: (3Z,5Z)-3,5-bis[(2,3,4-trimethoxyphenyl)methylidene]thian-4-one
• CAS: 1360119-20-5
• 化学式: C₂₅H₂₈O₇S
• 分子量: 472.559
• InChiKey: ZMHGZRIEKXTPDW-JYFOCSDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  97.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  四氢噻喃-4-酮 、 2,3,4-三甲氧基苯甲醛 在 盐酸 、 溶剂黄146 作用下， 以61%的产率得到(3E,5E)-3,5-bis(2,3,4-trimethoxybenzylidene)-tetrahydrothiopyran-4-one
  参考文献：
  名称：

  Synthesis and evaluation of curcumin-related compounds for anticancer activity

  摘要：

  Sixty-one curcumin-related compounds were synthesized and evaluated for their anticancer activity toward cultured prostate cancer PC-3 cells, pancreas cancer Panc-1 cells and colon cancer HT-29 cells. Inhibitory effects of these compounds on the growth of PC-3. Panc-1 and HT-29 cells were determined by the MTT assay. Compounds E10, F10, FN1 and FN2 exhibited exceptionally potent inhibitory effects on the growth of cultured PC-3, Panc-1 and HT-29 cells. The IC50 for these compounds was lower than 1 mu M in all three cell lines. E10 was 72-, 46- and 117-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. F10 was 69-, 34- and 72-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. FN1 and FN2 had about the same inhibitory effect as E10 and F10 toward Panc-1 cells but were less active than E10 and F10 toward PC-3 and HT-29 cells. The active compounds were potent stimulators of apoptosis. The present study indicates that E10, F10, FN1 and FN2 may have useful anticancer activity. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.005

文献信息

• [EN] COMPOUNDS FOR TREATING INFLAMMATORY AND HYPERPROLIFERATIVE DISEASES<br/>[FR] COMPOSÉS POUR TRAITER DES MALADIES INFLAMMATOIRES ET HYPERPROLIFÉRATIVES
  申请人：UNIV TEXAS

  公开号：WO2014160339A1

  公开（公告）日：2014-10-02

  Compounds are provided that can exhibit anti-cancer and/or anti-inflammatory properties, in some aspects, methods of treating an inflammatory disease or a hyperproliferative disease, such as cancer, with the compounds are provided.

  提供了一些化合物，可以展示抗癌和/或抗炎特性，在某些方面，提供了使用这些化合物治疗炎症性疾病或过度增殖性疾病（如癌症）的方法。
• Compounds for treating inflammatory and hyperproliferative diseases
  申请人：Board of Regents, The University of Texas System

  公开号：US10208012B2

  公开（公告）日：2019-02-19

  Compounds are provided that can exhibit anti-cancer and/or anti-inflammatory properties, in some aspects, methods of treating an inflammatory disease or a hyperproliferative disease, such as cancer, with the compounds are provided.

  所提供的化合物具有抗癌和/或抗炎特性，在某些方面，还提供了用这些化合物治疗炎症性疾病或过度增殖性疾病（如癌症）的方法。
• COMPOUNDS FOR TREATING INFLAMMATORY AND HYPERPROLIFERATIVE DISEASES
  申请人：BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM

  公开号：US20160016931A1

  公开（公告）日：2016-01-21

  Compounds are provided that can exhibit anti-cancer and/or anti-inflammatory properties, in some aspects, methods of treating an inflammatory disease or a hyperproliferative disease, such as cancer, with the compounds are provided.
• Synthesis and evaluation of curcumin-related compounds for anticancer activity
  作者：Xingchuan Wei、Zhi-Yun Du、Xi Zheng、Xiao-Xing Cui、Allan H. Conney、Kun Zhang

  DOI：10.1016/j.ejmech.2012.04.005

  日期：2012.7

  Sixty-one curcumin-related compounds were synthesized and evaluated for their anticancer activity toward cultured prostate cancer PC-3 cells, pancreas cancer Panc-1 cells and colon cancer HT-29 cells. Inhibitory effects of these compounds on the growth of PC-3. Panc-1 and HT-29 cells were determined by the MTT assay. Compounds E10, F10, FN1 and FN2 exhibited exceptionally potent inhibitory effects on the growth of cultured PC-3, Panc-1 and HT-29 cells. The IC50 for these compounds was lower than 1 mu M in all three cell lines. E10 was 72-, 46- and 117-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. F10 was 69-, 34- and 72-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. FN1 and FN2 had about the same inhibitory effect as E10 and F10 toward Panc-1 cells but were less active than E10 and F10 toward PC-3 and HT-29 cells. The active compounds were potent stimulators of apoptosis. The present study indicates that E10, F10, FN1 and FN2 may have useful anticancer activity. (C) 2012 Elsevier Masson SAS. All rights reserved.