dihydromyricetin pentamethyl ether

• 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: dihydromyricetin pentamethyl ether
• 英文别名: (2R,3R)-3-hydroxy-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-4-one；(2R,3R)-3-hydroxy-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrochromen-4-one
• 化学式: C₂₀H₂₂O₈
• 分子量: 390.39
• InChiKey: YZLYYHZJNOAWHF-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  dihydromyricetin pentamethyl ether 以77%的产率得到
  参考文献：
  名称：

  ONDA, MASAYUKI;LI, SHAOSHUN;LI, XIAN;HARIGAYA, YOSHIHIRO;TAKAHASHI, HIROS+, J. NATUR. PROD., 52,(1989) N, C. 1100-1106

  摘要：

  DOI：
• 作为产物：
  描述：

  二氢杨梅素 、 重氮甲烷 以40%的产率得到
  参考文献：
  名称：

  ONDA, MASAYUKI;LI, SHAOSHUN;LI, XIAN;HARIGAYA, YOSHIHIRO;TAKAHASHI, HIROS+, J. NATUR. PROD., 52,(1989) N, C. 1100-1106

  摘要：

  DOI：

文献信息

• Dihydroflavonols from Cedrus deodara
  作者：P.K. Agrawal、S.K. Agarwal、R.P. Rastogi

  DOI：10.1016/0031-9422(80)85133-8

  日期：——

  The identification of taxifolin and structure elucidation of cedeodarin (6-methyltaxifolin), dihydromyricetin, cedrin (6-methyldihydromyricetin) and cedrinoside from cedar wood are described.

  描述了来自雪松木的紫杉叶素的鉴定和雪松素（6-甲基紫杉叶素）、二氢杨梅素、雪松素（6-甲基二氢杨梅素）和雪松苷的结构解析。
• Li, Shaoshun; Onda, Masayuki; Kagawa, Hitoshi, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 2029 - 2035
  作者：Li, Shaoshun、Onda, Masayuki、Kagawa, Hitoshi、Kawase, Hiromi、Iguchi, Mieko、Harigaya, Yoshihiro

  DOI：——

  日期：——
• Potent and Nontoxic Chemosensitizer of P-Glycoprotein-Mediated Multidrug Resistance in Cancer: Synthesis and Evaluation of Methylated Epigallocatechin, Gallocatechin, and Dihydromyricetin Derivatives
  作者：Iris L. K. Wong、Bao-Chao Wang、Jian Yuan、Liang-Xing Duan、Zhen Liu、Tao Liu、Xue-Min Li、Xuesen Hu、Xiao-Yu Zhang、Tao Jiang、Sheng-Biao Wan、Larry M. C. Chow

  DOI：10.1021/acs.jmedchem.5b00085

  日期：2015.6.11

  We are interested in developing novel natural product-derived P-gp inhibitors to reverse cancer drug resistance. Here, we have synthesized 55 novel derivatives of methylated epigallocatechin (EGC), gallocatechin (GC), and dihydromyricetin (DHM). Three EGC derivatives (23, 35, and 36) and three GC derivatives (50, 51, and 53) are significantly better than epigallocatechin gallate (EGCG) with a relative fold (RF) ranging from 31.4 to 53.6. The effective concentration (EC50) of 23 and 51 ranges from 102 to 195 nM. Compounds 23 and 51 are noncytotoxic to fibroblasts with IC50 > 100 mu M. Compound 23 is specific for P-gp without modulating activity toward MITI or BCRP. Compounds 23 and 51 are non-P-gp substrates. Important pharmacophores for P-gp modulation were identified. In summary, methylated EGC and GC derivatives represent a new class of potent, specific, noncytotoxic, and nonsubstrate P-gp modulators.
• ONDA, MASAYUKI;LI, SHAOSHUN;LI, XIAN;HARIGAYA, YOSHIHIRO;TAKAHASHI, HIROS+, J. NATUR. PROD., 52,(1989) N, C. 1100-1106
  作者：ONDA, MASAYUKI、LI, SHAOSHUN、LI, XIAN、HARIGAYA, YOSHIHIRO、TAKAHASHI, HIROS+

  DOI：——

  日期：——
• LI, SHAOSHUN;ONDA, MASAYUKI;KAGAWA, HITOSHI;KAWASE, HIROMI;IGUCHI, MIEKO;+, J. HETEROCYCL. CHEM., 27,(1990) N, C. 2029-2035
  作者：LI, SHAOSHUN、ONDA, MASAYUKI、KAGAWA, HITOSHI、KAWASE, HIROMI、IGUCHI, MIEKO、+

  DOI：——

  日期：——