2-(3-benzyloxy-4-methoxy-phenyl)-6-hydroxy-3,5,7-trimethoxy-chromen-4-one | 124909-82-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3-benzyloxy-4-methoxy-phenyl)-6-hydroxy-3,5,7-trimethoxy-chromen-4-one
• 英文别名: 2-(3-Benzyloxy-4-methoxy-phenyl)-6-hydroxy-3,5,7-trimethoxy-chromen-4-on；6-Hydroxy-3,5,7-trimethoxy-2-(4-methoxy-3-phenylmethoxyphenyl)chromen-4-one
• CAS: 124909-82-6
• 化学式: C₂₆H₂₄O₈
• 分子量: 464.472
• InChiKey: MOJFZRWHDSWXCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(3-benzyloxy-4-methoxy-phenyl)-6-hydroxy-3,5,7-trimethoxy-chromen-4-one 生成 3,5,6,7,4'-Pentamethoxy-3'-benzyloxy-flavon
  参考文献：
  名称：

  HORIE, TOKUNARU;KAWAMURA, YASUHIKO;TSUKAYAMA, MASAO;YOSHIZAKI, SHIRO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1216-1220

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3,6-dihydroxy-2,4-dimethoxy-phenyl)-2-methoxy-ethanone 生成 2-(3-benzyloxy-4-methoxy-phenyl)-6-hydroxy-3,5,7-trimethoxy-chromen-4-one
  参考文献：
  名称：

  HORIE, TOKUNARU;KAWAMURA, YASUHIKO;TSUKAYAMA, MASAO;YOSHIZAKI, SHIRO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1216-1220

  摘要：

  DOI：

文献信息

• Studies of the Selective<i>O</i>-Alkylation and Dealkylation of Flavonoids. XIV. A Convenient Method for Synthesizing 5,6,7-Trihydroxy-3-methoxyflavones from 6-Hydroxy-3,5,7-trimethoxyflavones
  作者：Tokunaru Horie、Hideaki Tominaga、Isao Yoshida、Yasuhiko Kawamura

  DOI：10.1246/bcsj.66.877

  日期：1993.3

  acetonitrile afforded the 5,6,7-trihydroxyflavone as a main product without cleavage of the 4′-methoxyl group and the reaction was more conveniently applicable for the synthesis of the 5,6,7-trihydroxyflavones. The method, however, was not adapted to the synthesis of the flavones with methoxyl groups adjacent to the hydroxyl group on the B ring, since the benzyloxyl gro...

  研究了 6-羟基-3,5,7-三甲氧基黄酮及其乙酸酯的去甲基化，并发现了以下结果。6-羟基-3,4',5,7-四甲氧基黄酮与 30% 无水氯化铝的乙腈溶液脱甲基反应得到 5,6-二羟基-3,4',7-三甲氧基黄酮和 5,6,7-三羟基的混合物-3,4'-二甲氧基黄酮，但其乙酸酯的去甲基化形成了 5,6,7-三羟基黄酮作为主要产物。后一反应可用作合成 5,6,7-三羟基-3-甲氧基黄酮的一般方法。另一方面，6-羟基-3,4',5,7-四甲氧基黄酮与 10% 无水溴化铝在乙腈中的脱甲基反应得到 5,6,7-三羟基黄酮作为主要产物，4'-甲氧基，该反应更适用于合成5,6,7-三羟基黄酮。
• Structure−Activity Requirements for Flavone Cytotoxicity and Binding to Tubulin
  作者：John A. Beutler、Ernest Hamel、Arnold J. Vlietinck、Achiel Haemers、Padinchare Rajan、James N. Roitman、John H. Cardellina、Michael R. Boyd

  DOI：10.1021/jm970842h

  日期：1998.6.1

  A series of 79 flavones related to centaureidin (3,6,4'-trimethoxy-5,7,3'-trihydroxyflavone 1) was screened for cytotoxicity in the NCI in vitro 60-cell line human tumor screen. The resulting cytotoxicity profiles of these flavones were compared for degree of similarity to the profile of 1. Selected compounds were further evaluated with in vitro assays of tubulin polymerization and [H-3]colchicine binding to tubulin. Maximum potencies for tubulin interaction and production of differential cytotoxicity profiles characteristic of 1 were observed only with compounds containing hydroxyl substituents at C-3' and C-5 and methoxyl groups at C-3 and C-4'.
• Goel et al., Journal of the Chemical Society, 1956, p. 1369
  作者：Goel et al.

  DOI：——

  日期：——
• Horie, Tokunaru; Kawamura, Yasuhiko; Tsukayama, Masao, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 5, p. 1216 - 1220
  作者：Horie, Tokunaru、Kawamura, Yasuhiko、Tsukayama, Masao、Yoshizaki, Shiro

  DOI：——

  日期：——
• HORIE, TOKUNARU;KAWAMURA, YASUHIKO;TSUKAYAMA, MASAO;YOSHIZAKI, SHIRO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1216-1220
  作者：HORIE, TOKUNARU、KAWAMURA, YASUHIKO、TSUKAYAMA, MASAO、YOSHIZAKI, SHIRO

  DOI：——

  日期：——