methyl 4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethoxybenzoate | 134178-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethoxybenzoate
• 英文别名: methyl 4-O-tert-butyldimethylsilyl-3,5-dimethoxybenzoate；Methyl 4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxybenzoate
• CAS: 134178-07-7
• 化学式: C₁₆H₂₆O₅Si
• 分子量: 326.465
• InChiKey: RSVCHJNXMWCPBB-UHFFFAOYSA-N

物化性质

• 沸点：
  377.0±42.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethoxybenzoate 在 硫酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 72.0h， 生成 苜蓿素
  参考文献：
  名称：

  Increased Bioavailability of Tricin−Amino Acid Derivatives via a Prodrug Approach

  摘要：

  Tricin (4',5,7-trihydroxy-3',5'-dimethoxyflavone) has demonstrated diverse biological activities. This compound has a high anti-human cytomegalovirus (HCMV) activity; however, its oral availability is low. To improve its bioavailability, we synthesized tricin-amino acid derivatives as prodrugs and investigated their cell permeability, stability in vitro, and oral availability in vivo. The results demonstrated that the tricin-alanine-glutamic acid conjugate exhibited enhanced permeability, stability in MDCK cells, and excellent bioavailability after oral administration in Crl:CD (SD) male rats. Tricin-alanine-glutamic acid conjugate is a potential new anti-HCMV drug.

  DOI：

  10.1021/jm1015457
• 作为产物：
  描述：

  丁香酸甲酯 、 叔丁基二甲基氯硅烷 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethoxybenzoate
  参考文献：
  名称：

  Increased Bioavailability of Tricin−Amino Acid Derivatives via a Prodrug Approach

  摘要：

  Tricin (4',5,7-trihydroxy-3',5'-dimethoxyflavone) has demonstrated diverse biological activities. This compound has a high anti-human cytomegalovirus (HCMV) activity; however, its oral availability is low. To improve its bioavailability, we synthesized tricin-amino acid derivatives as prodrugs and investigated their cell permeability, stability in vitro, and oral availability in vivo. The results demonstrated that the tricin-alanine-glutamic acid conjugate exhibited enhanced permeability, stability in MDCK cells, and excellent bioavailability after oral administration in Crl:CD (SD) male rats. Tricin-alanine-glutamic acid conjugate is a potential new anti-HCMV drug.

  DOI：

  10.1021/jm1015457

文献信息

• COMPOUND OR SALT THEREOF, ANTIVIRAL AGENT, AND PHARMACEUTICAL COMPOSITION
  申请人：TSUCHIDA YUUZO

  公开号：US20200079750A1

  公开（公告）日：2020-03-12

  The present invention addresses the problem of providing a tricin derivative having higher antiviral activity. The compound according to the present invention is a compound represented by formula (I) or a salt thereof. (In formula (I), at least one of R 1 -R 5 represents a fluorine atom, and the rest of R 1 -R 5 , which are not fluorine atoms, represent a hydrogen atom or a hydroxy group.)

  本发明解决了提供具有更高抗病毒活性的三环素衍生物的问题。根据本发明的化合物是由式（I）表示的化合物或其盐。（在式（I）中，R1-R5中至少一个表示氟原子，其余的R1-R5不是氟原子的表示氢原子或羟基。）
• A short and facile synthetic route to hydroxylated flavones. New syntheses of apigenin, tricin, and luteolin
  作者：Dhanapalan Nagarathnam、Mark Cushman

  DOI：10.1021/jo00016a015

  日期：1991.8

  Reaction of the lithium polyanions generated from omicron-hydroxyacetophenones 3a-f with O-silyloxylated benzoates 2a-d gave 1-aryl-3-(2-hydroxyphenyl)-1,3-propanediones 4a-n, which on treatment with acetic acid containing 0.5% H2SO4 at 95-100-degrees-C afforded hydroxylated flavones 5-18 in high yields (76-92%).