6-butyl-2-methoxy-2,5-cyclohexadiene-1,4-dione | 57855-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-butyl-2-methoxy-2,5-cyclohexadiene-1,4-dione
• 英文别名: 2-methoxy-6-n-butyl-1,4-benzoquinone；2-Methoxy-6-butyl-1,4-benzoquinone；2,5-Cyclohexadiene-1,4-dione, 2-butyl-6-methoxy-；2-butyl-6-methoxycyclohexa-2,5-diene-1,4-dione
• CAS: 57855-18-2
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: JTNZEYFXPDFBBF-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• 沸点：
  301.5±31.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  6-butyl-2-methoxy-2,5-cyclohexadiene-1,4-dione 在 sodium dithionite 作用下， 生成 2-methoxy-4-hydroxy-6-n-butylphenol
  参考文献：
  名称：

  primin和miconidin及其衍生物的生物合成

  摘要：

  许多具有有趣生物活性的 2-甲氧基-6-n-烷基-1,4-苯醌已被发现作为植物和植物种子的成分。最突出的是 primin，一种正戊基衍生物，它储存在 Primula obconica 叶和茎上的毛状体中，是引起报春花皮炎的原因。通过用放射性标记的前体和未标记的同系物进料实验来研究 primin 的生物合成。

  DOI：

  10.1016/0031-9422(95)00590-0
• 作为产物：
  描述：

  6-butyl-2-methoxyphenol 在 salcomine 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以82%的产率得到6-butyl-2-methoxy-2,5-cyclohexadiene-1,4-dione
  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

文献信息

• Koenig, Wilfried A.; Faasch, Holger; Heitsch, Holger, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1993, vol. 48, # 3, p. 387 - 393
  作者：Koenig, Wilfried A.、Faasch, Holger、Heitsch, Holger、Colberg, Cornelia、Hausen, Bjoern M.

  DOI：——

  日期：——
• 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