3,4-methylenedioxy-3',4'-dimethoxy-2'-hydroxychalcone | 919094-32-9

• 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: 3,4-methylenedioxy-3',4'-dimethoxy-2'-hydroxychalcone
• 英文别名: 3-benzo[1,3]dioxol-5-yl-1-(2-hydroxy-3,4-dimethoxy-phenyl)-propenone；3-Benzo[1,3]dioxol-5-yl-1-(2-hydroxy-3,4-dimethoxy-phenyl)-propenon；3-(Benzo[1,3]dioxol-5-yl)-1-(2-hydroxy-3,4-dimethoxyphenyl)-2-propen-1-one；(E)-3-(1,3-benzodioxol-5-yl)-1-(2-hydroxy-3,4-dimethoxyphenyl)prop-2-en-1-one
• CAS: 919094-32-9
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: MUXCTCMFOCZAHT-ZZXKWVIFSA-N

物化性质

• 熔点：
  172-173 °C(Solv: ethanol (64-17-5))
• 沸点：
  530.3±50.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-methylenedioxy-3',4'-dimethoxy-2'-hydroxychalcone 在 硫酸 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 生成 4H-1-Benzopyran-4-one,2-(1,3-benzodioxol-5-yl)-2,3-dihydro-7,8-dimethoxy-
  参考文献：
  名称：

  Gao, Jin-Ming; Lu, Jia-Wen; Zhang, An-Ling, Journal of Chemical Research, 2006, # 3, p. 163 - 164

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-羟基-3',4'-二甲氧基苯乙酮 、 胡椒醛 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以85%的产率得到3,4-methylenedioxy-3',4'-dimethoxy-2'-hydroxychalcone
  参考文献：
  名称：

  Singh, Om V.; Muthukrishnan; Sunderavadivelu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 12, p. 2575 - 2581

  摘要：

  DOI：

文献信息

• Differential effects of synthesized 2′-oxygenated chalcone derivatives: modulation of human cell cycle phase distribution
  作者：Yerra Koteswara Rao、Shih-Hua Fang、Yew-Min Tzeng

  DOI：10.1016/j.bmc.2004.03.014

  日期：2004.5

  Ten structurally related T-oxygenated chalcone derivatives, bearing either hydroxy and/or methoxy substituents oil the A and B rings, were synthesized through Claisen-Schmidt condensation. The synthesis procedure was relatively easy and had an acceptable yield. The in vitro cytotoxicities of these compounds against the human tumor cells such as Jurkat, U937 cells, and normal cells PHA stimulated PBMCs were investigated. Among those, compounds 1 (IC50 = 2.5 muM), 2 (1.7 muM), and 8 (3.2 muM) showed potent inhibitory activity toward Jurkat cell line. In parallel, compounds 1 (6.7 muM), 2 (1.5 muM), and 10 (5.3 muM) showed the highest activity against U937 cell line. However, the chalcones also inhibit the PHA stimulated PBMCs cells, but the IC50 values were relatively high when compared to the tumor cell line values. Studies were also on the effect of synthesized chalcones on the cell cycle phase distribution. In Jurkat cell line, compounds 7 and 9 showed the highest activity and the most striking effect in reduction of the percentage of cells in the S phase, which was associated with an increase of cells in G2/M phase. In U937 cell line, compound 3 increased the proportion of cells in the G0/G1 phase and reduced the proportion in S phase. In contrast, compounds 1, 9, and 10 showed a decrease effect on the percentage of cells in S phase and an increase effect on the percentage of cells in the G2/M phase of the cell cycle. Whereas in the case of PHA stimulated PBMCs, compounds 1, 4, 8, and 10 increased the percentage of cells in G2/M phase, which was associated with a decrease effect in the :S phase of the cell cycle. (C) 2004 Elsevier Ltd. All rights reserved.
• Pfeiffer; Emmer, Chemische Berichte, 1920, vol. 53, p. 949
  作者：Pfeiffer、Emmer

  DOI：——

  日期：——
• NOVEL CDK INHIBITORS HAVING FLAVONE STRUCTURE
  申请人：LG CHEMICAL LIMITED

  公开号：EP1109800A1

  公开（公告）日：2001-06-27
• US6500846B1
  申请人：——

  公开号：US6500846B1

  公开（公告）日：2002-12-31
• [EN] NOVEL CDK INHIBITORS HAVING FLAVONE STRUCTURE<br/>[FR] NOUVEAUX INHIBITEURS DE KINASE DEPENDANTE DES CYCLINES (CDK) PRESENTANT UNE STRUCTURE FLAVONE
  申请人：LG CHEMICAL LTD

  公开号：WO2000012496A1

  公开（公告）日：2000-03-09

  The present invention relates to a novel flavone derivative, pharmaceutically acceptable salt, hydrate, solvate and isomer thereof which is useful as an inhibitor against Cyclin Dependent Kinase (CDK), a process for preparation thereof, and a composition of anti-cancer agent or agent for treating neurodegenerative disease comprising this compound as an active ingredient.