5-(4-methoxyphenyl)-cyclohexane-1,3-dione | 111945-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-methoxyphenyl)-cyclohexane-1,3-dione
• 英文别名: 3-Hydroxy-5-(4-methoxyphenyl)cyclohex-2-en-1-one
• CAS: 111945-85-8
• 化学式: C₁₃H₁₄O₃
• mdl: MFCD00778544
• 分子量: 218.252
• InChiKey: VMWQNDYIARTQTB-UHFFFAOYSA-N

物化性质

• 熔点：
  171-173 °C
• 沸点：
  369.5±42.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-methoxyphenyl)-cyclohexane-1,3-dione 在 甲烷 、 palladium dichloride sodium hydroxide 、 氢气 、 sodium methylate 、 sodium hydride 作用下， 以 盐酸 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 [3-(4-Methoxy-phenyl)-cyclohex-(E)-ylidene]-acetic acid
  参考文献：
  名称：

  Kuchar, Miroslav; Brunova, Bohumila; Grimova, Jaroslava, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 12, p. 2896 - 2908

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 alkaline medium 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 5-(4-methoxyphenyl)-cyclohexane-1,3-dione
  参考文献：
  名称：

  Kuchar, Miroslav; Brunova, Bohumila; Grimova, Jaroslava, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 12, p. 2896 - 2908

  摘要：

  DOI：

文献信息

• Colchicine Models: Synthesis and Binding to Tubulin of Tertamethoxybiphenyls
  作者：Yoshikuni Itoh、Arnold Brossi、Ernest Hamel、Chii M. Lin

  DOI：10.1002/hlca.19880710531

  日期：1988.8.10

  analogs 28, 29, and 31 were evaluated for antitubulin activity and as antimitotic agents with L1210 murine leukemia cells. Compounds 31 and 34 had significant effects on the in-vitro polymerization of tubulin. Compound 31 was the most cytotoxic of the six new biphenyls studied (IC50 for cell growth, 0.6M) and caused the accumulation of cells in metaphase arrest.

  四甲氧基的Syntheis 21，从4- phenylcylohexane -1,3-二酮完成13通过芳构化联苯19和还原去除酚的OH基作为phenyltetrazolyl醚。四甲氧基联苯34和40是通过酯27从4-苯基环己烯酮26中获得的。的tetramethoxybiphenyls 21,34，和40，和类似物28,29和31用于抗微管蛋白活性和与抗有丝分裂剂进行了评价L1210小鼠白血病细胞。化合物31和34有上显著影响在-体外微管蛋白的聚合。在研究的六种新联苯中，化合物31具有最大的细胞毒性（细胞生长的IC 50为0.6M），并导致细胞在中期停滞中积累。
• Chandrasekharan,V. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1978, vol. 16, p. 970 - 972
  作者：Chandrasekharan,V. et al.

  DOI：——

  日期：——
• KUCHAR M.; BRUNOVA B.; GRIMOVA J.; VANECEK S.; HOLUBEK J., COLLECT. CZECHOSL. CHEM. COMMUN., 51,(1986) N 12, 2896-2908
  作者：KUCHAR M.、 BRUNOVA B.、 GRIMOVA J.、 VANECEK S.、 HOLUBEK J.

  DOI：——

  日期：——
• Identification of substituted 3-hydroxy-2-mercaptocyclohex-2-enones as potent inhibitors of human lactate dehydrogenase
  作者：Peter S. Dragovich、Benjamin P. Fauber、Jason Boggs、Jinhua Chen、Laura B. Corson、Charles Z. Ding、Charles Eigenbrot、HongXiu Ge、Anthony M. Giannetti、Thomas Hunsaker、Sharada Labadie、Chiho Li、Yichin Liu、Yingchun Liu、Shuguang Ma、Shiva Malek、David Peterson、Keith E. Pitts、Hans E. Purkey、Kirk Robarge、Laurent Salphati、Steve Sideris、Mark Ultsch、Erica VanderPorten、Jing Wang、BinQing Wei、Qing Xu、Ivana Yen、Qin Yue、Huihui Zhang、Xuying Zhang、Aihe Zhou

  DOI：10.1016/j.bmcl.2014.06.076

  日期：2014.8

  A novel class of 3-hydroxy-2-mercaptocyclohex-2-enone-containing inhibitors of human lactate dehydrogenase (LDH) was identified through a high-throughput screening approach. Biochemical and surface plasmon resonance experiments performed with a screening hit (LDHA IC50 = 1.7 mu M) indicated that the compound specifically associated with human LDHA in a manner that required simultaneous binding of the NADH co-factor. Structural variation of this screening hit resulted in significant improvements in LDHA biochemical inhibition activity (best IC50 = 0.18 mu M). Two crystal structures of optimized compounds bound to human LDHA were obtained and explained many of the observed structure-activity relationships. In addition, an optimized inhibitor exhibited good pharmacokinetic properties after oral administration to rats (F = 45%). (C) 2014 Elsevier Ltd. All rights reserved.
• Kuchar, Miroslav; Brunova, Bohumila; Grimova, Jaroslava, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 12, p. 2896 - 2908
  作者：Kuchar, Miroslav、Brunova, Bohumila、Grimova, Jaroslava、Vanecek, Stanislav、Holubek, Jiri

  DOI：——

  日期：——