3-cyano-4,5-dimethyl-2-hydroxyacetophenone | 89638-56-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-cyano-4,5-dimethyl-2-hydroxyacetophenone
• 英文别名: 3-Acetyl-2-hydroxy-5,6-dimethylbenzonitrile；3-acetyl-2-hydroxy-5,6-dimethylbenzonitrile
• CAS: 89638-56-2
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: FWFWVGJTMFBYDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cyano-4,5-dimethyl-2-hydroxyacetophenone 在 吡啶 、 三乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 6,7-dimethyl-4-oxo-2-(4'-trifluoromethylphenyl)-4H-1-benzopyran-8-carboxylic acid
  参考文献：
  名称：

  Cell death triggered by synthetic flavonoids in human leukemia cells is amplified by the inhibition of extracellular signal-regulated kinase signaling

  摘要：

  A new class of methyl esters of flavonoids, with different substituents on the B ring were synthesized and evaluated for their antiproliferative activity against the human leukemia cell line HL-60. The presence of either a methyl group (1f) or a chlorine atom (1o) at position 2' of the B ring played an important role in affecting antiproliferative activity. The cytotoxic effects of these compounds were accompanied by the concentration- and time-dependent appearance of DNA- and nuclear-fragmentation, increase in the percentage of sub-G(1) cells, and processing of multiple caspases and poly(ADP-ribose)polymerase cleavage. Pretreatment of cells with the specific mitogen-activated extracellular kinases (MEK) 1/2 inhibitor PD98059, together with if and 1o, resulted in an important enhancement of cell death, which might have clinical implications for the use of both compounds in combination with MEK 1/2 inhibitors as potential therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.028
• 作为产物：
  描述：

  6-Acetyl-1-amino-3,4-dimethyl-7-oxa-bicyclo[2.2.1]hept-2-ene-2-carbonitrile 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 生成 3-cyano-4,5-dimethyl-2-hydroxyacetophenone
  参考文献：
  名称：

  Cutler, Stephen J.; El-Kabbani, Fiesal M.; Keane, Charlene, Heterocycles, 1990, vol. 31, # 4, p. 651 - 661

  摘要：

  DOI：

文献信息

• Synthesis of previously inaccessible quinazolines and 1,4-benzodiazepines as potential anticonvulsants
  作者：Aqeel A. Fatmi、Niteen A. Vaidya、W. B. Iturrian、C. DeWitt Blanton

  DOI：10.1021/jm00372a012

  日期：1984.6

  method. Selected compounds were also evaluated for benzodiazepine receptor binding properties and in vivo antagonist potential. Although the compounds lack potency, the data suggest that previously inaccessible substituted analogues may be useful to segregate the proconvulsant , anticonvulsant, and antagonist actions of benzodiazepines and quinazolines.

  一系列4,6,7,8-四取代的3,4-二氢喹唑啉，喹唑啉，喹唑啉-2-酮，1,2,3,4-四氢喹唑啉-2-酮和5,7,8,9-四取代通过利用呋喃邻氨基腈与各种烷基或芳基乙烯基酮二亲二烯物之间的狄尔斯-阿尔德反应合成1，4-苯并二氮杂卓，以获得邻氨基苯甲酸前体。在小鼠中评估所有新合成的目标化合物的抗惊厥活性。通过定时静脉内戊四氮癫痫发作阈值方法对促惊厥作用和抗惊厥作用进行定量。还评估了所选化合物的苯并二氮杂receptor受体结合特性和体内拮抗剂潜力。尽管这些化合物缺乏药效，但数据表明，以前难以获得的取代类似物可能对分离前惊厥药，
• Synthesis of flavone-8-carboxylic acid analogues as potential antitumor agents
  作者：SJ Cutler、FM El-Kabbani、C Keane、SL Fisher-Shore、FL McCabe、RK Johnson、C De Witt Blanton

  DOI：10.1016/0223-5234(93)90127-z

  日期：1993.1

  Furan o-aminonitriles may be utilized as precursors in the synthesis of flavone-8-carboxylic acids. Some results from in vivo evaluation against P388 leukemia, colon carcinoma 38, and B16 melanoma models suggest that selected examples of the acids are potentially as effective as the antitumor compound, flavone acetic acid. The flavone-8-carboxylic acids did not exhibit significant activity against an in vitro HIV screen or an in vitro antitumor screen consisting of a cell panel of 60 lines.
• Cutler, Stephen J.; El-Kabbani, Fiesal M.; Keane, Charlene, Heterocycles, 1990, vol. 31, # 4, p. 651 - 661
  作者：Cutler, Stephen J.、El-Kabbani, Fiesal M.、Keane, Charlene、Fisher-Shore, Sherri L.、Blanton, C. DeWitt

  DOI：——

  日期：——
• Cell death triggered by synthetic flavonoids in human leukemia cells is amplified by the inhibition of extracellular signal-regulated kinase signaling
  作者：Sara Rubio、Francisco León、José Quintana、Stephen Cutler、Francisco Estévez

  DOI：10.1016/j.ejmech.2012.07.028

  日期：2012.9

  A new class of methyl esters of flavonoids, with different substituents on the B ring were synthesized and evaluated for their antiproliferative activity against the human leukemia cell line HL-60. The presence of either a methyl group (1f) or a chlorine atom (1o) at position 2' of the B ring played an important role in affecting antiproliferative activity. The cytotoxic effects of these compounds were accompanied by the concentration- and time-dependent appearance of DNA- and nuclear-fragmentation, increase in the percentage of sub-G(1) cells, and processing of multiple caspases and poly(ADP-ribose)polymerase cleavage. Pretreatment of cells with the specific mitogen-activated extracellular kinases (MEK) 1/2 inhibitor PD98059, together with if and 1o, resulted in an important enhancement of cell death, which might have clinical implications for the use of both compounds in combination with MEK 1/2 inhibitors as potential therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.