2-Methoxy-6-benzyl-1,4-benzoquinone | 38940-04-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methoxy-6-benzyl-1,4-benzoquinone
• 英文别名: 2-Benzyl-6-methoxy-1,4-benzochinon；2-Benzyl-6-methoxy-[1,4]benzoquinone；2-benzyl-6-methoxycyclohexa-2,5-diene-1,4-dione
• CAS: 38940-04-4
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: MAIUISBOEJPUCU-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• 沸点：
  382.4±41.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-缬氨酸 、 2-Methoxy-6-benzyl-1,4-benzoquinone 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以75%的产率得到N-(5-benzyl-3,6-dioxo-4-N-D-valine-1,4-cyclohexadienyl)-D-valine
  参考文献：
  名称：

  Development of Natural Product-Derived Receptor Tyrosine Kinase Inhibitors Based on Conservation of Protein Domain Fold

  摘要：

  Receptor tyrosine kinases (RTKs) such as Tie-2, IGF1R, Her-2/Neu, EGFR, and VEGFR1-3 play crucial roles in the control of cell growth and differentiation. Inhibition of such RTKs has become a major focus of current anticancer drug development, and therefore the discovery of new classes of inhibitors for these signal-transducing proteins is of prime importance. We have recently proposed a novel concept for improving the hit-finding process by employing natural products as biologically validated starting points in structural space for compound library development. In this concept, natural products are regarded as evolutionary chosen ligands for protein domains which are structurally conserved yet genetically mobile. Here we report on the discovery of novel and highly selective VEGFR-2 and -3, Tie-2, and IGF1R inhibitors derived from the naturally occurring Her-2/Neu kinase inhibitor nakijiquinone C and developed on the basis of this concept. Based on the structure of the natural product, a small library (74 members) was synthesized and investigated for inhibition of kinases with highly similar ATP-binding domains. The library yielded inhibitors with IC(50)s in the low micromolar range with high frequency (7 out of 74). In particular, four inhibitors of Tie-2 were found, a kinase critically involved in the formation of new blood vessels from preexisting ones (angiogenesis) and believed to be a new promising target in antitumor therapy. These results support the "domain concept". To advance the development of improved inhibitors, extensive molecular modeling studies were undertaken, including the construction of new homology models for VEGFR-2 and Tie-2. These studies revealed residues in the kinase structure which are crucial to the development of tailor-made receptor tyrosine kinase inhibitors.

  DOI：

  10.1021/jm0307943
• 作为产物：
  描述：

  2-(Hydroxy-phenyl-methyl)-6-methoxy-phenol 在 5percent Pd/C potassium nitrososulfonate 、 氢气 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 生成 2-Methoxy-6-benzyl-1,4-benzoquinone
  参考文献：
  名称：

  Isolation, Synthesis, and Structure−Activity Relationships of Bioactive Benzoquinones from Miconia lepidota from the Suriname Rainforest

  摘要：

  Bioactivity-directed fractionation of an EtOAc extract from the leaves of Miconia lepidota afforded the two benzoquinones 2-methoxy-6-heptyl-1,4-benzoquinone (1) and 2-methoxy-6-pentyl-1,4-benzoquinone (primin) (2). This is the first reported isolation of 1. Both quinones 1 and 2 exhibited activity toward mutant yeast strains based on Saccharomyces cerevisiae, indicative of their cytotoxicity and potential anticancer activity. A number of previously synthesized and new analogues were prepared and tested in the same strains. Compounds 1, 2, 2-methoxy-6-butyl-1,4-benzoquinone (5), and 2-methoxy-6-decyl-1,4-benzoquinone (6) were tested in two cytotoxicity assays. In the M109 tumor cell lines, quinones 1, 2, and 6 had an IC50 value of 10 mug/mL. In the A2780 cell line, compounds 1, 2 and 5 had IC50 values of 7.9, 2.9, and 3.2 mug/mL, respectively.

  DOI：

  10.1021/np000219r

文献信息

• BIEBER, LOTHAR W.;DE, ANDRADE CHIAPPETA ALDA;DE, MORAES E SOUZA MARIA A.;+, J. NATUR. PROD., 53,(1990) N, C. 706-709
  作者：BIEBER, LOTHAR W.、DE, ANDRADE CHIAPPETA ALDA、DE, MORAES E SOUZA MARIA A.、+

  DOI：——

  日期：——

表征谱图