4-甲基-7-(2-氧代环己基氧基)-色烯-2-酮 | 86048-54-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 4-甲基-7-(2-氧代环己基氧基)-色烯-2-酮
• 英文名称: 4-Methyl-7-(2'-oxocyclohexyloxy)coumarin
• 英文别名: 4-methyl-7-[(2-oxocyclohexyl)oxy]-2H-chromen-2-one；4-methyl-7-(2-oxocyclohexyl)oxychromen-2-one
• CAS: 86048-54-6
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: VLZYGOANNLHKCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  4-甲基-7-(2-氧代环己基氧基)-色烯-2-酮 在 palladium on activated charcoal sodium hydroxide 、 selenium(IV) oxide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 甲苯 、 xylene 为溶剂， 反应 35.0h， 生成 4-((phenylimino)methyl)-2H-benzofuro[3,2-g]chromen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors

  摘要：

  Three series of functionalized coumarin compounds were designed and prepared as cholinesterase (AChE and BuChE) inhibitors. The biological profile against AChE and BuChE of the prepared compounds was determined. Compound 7b exhibited a mixed-type of AChE inhibitor with IC50 value for the AChE inhibition of 0.19 +/- 0.01 mu M and a high selectivity for AChE/BuChE, and compound 6b acted as 0 non-competitive AChE inhibitor with IC50 value of 0.43 +/- 0.02 mu M. Structure-activity, relationships (SARs) of prepared compounds were discussed. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.014
• 作为产物：
  描述：

  2-溴环己酮 、 羟甲香豆素 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以61%的产率得到4-甲基-7-(2-氧代环己基氧基)-色烯-2-酮
  参考文献：
  名称：

  四氢苯并呋喃香豆素和苯并呋喃香豆素的甲基x衍生物，一类新的潜在的脱氧核糖核酸光试剂

  摘要：

  合成了许多具有线性结构或具有各种角度排列的新的四环呋喃香豆素衍生物。新化合物的特征在于在呋喃香豆素核的呋喃环的4'，5'双键上稠合了一个额外的环己烯或苯环。从合适的羟基香豆素开始进行合成，在该羟基香豆素上建立了四氢苯并呋喃或苯并呋喃部分。甲基被引入到看起来最有希望增强化合物对DNA的光反应性的位置。

  DOI：

  10.1002/jhet.5570230530

文献信息

• A QSAR Model for in Silico Screening of MAO-A Inhibitors. Prediction, Synthesis, and Biological Assay of Novel Coumarins
  作者：Lourdes Santana、Eugenio Uriarte、Humberto González-Díaz、Giuseppe Zagotto、Ramón Soto-Otero、Estefanía Méndez-Álvarez

  DOI：10.1021/jm0509849

  日期：2006.2.1

  This work explores the potential of the MARCH-INSIDE methodology to seek a QSAR for MAO-A inhibitors from a heterogeneous series of compounds. A Markov model was used to quickly calculate the molecular electron delocalization, polarizability, refractivity, and n-octanol/water partition coefficients for a series of 1406 active/nonactive compounds. LDA was subsequently used to fit a classification function. The model showed 92.8% and 91.8% global accuracy and predictability in training and validation studies. This QSAR model was validated through a virtual screening of a series of cournarin derivatives. The 15 selected compounds were prepared and evaluated as in vitro MAO-A inhibitors. The theoretical prediction was' compared with the experimental results and the model correctly predicted 13 compounds with only two mistakes on compounds with activities very close to the cutoff point established for the model. Consequently, this method represents a useful tool for the "in silico" screening of MAO-A inhibitors.
• Kelkar, Shriniwas L.; Patil, Sharadbala D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 1, p. 91 - 92
  作者：Kelkar, Shriniwas L.、Patil, Sharadbala D.

  DOI：——

  日期：——
• KELKAR, S. L.;PATIL, S. D., INDIAN J. CHEM., 1983, 22, N 1, 91-92
  作者：KELKAR, S. L.、PATIL, S. D.

  DOI：——

  日期：——
• Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors
  作者：Qiong Shen、Quan Peng、Jialiang Shao、Xufeng Liu、Zhishu Huang、Xianzhang Pu、Lin Ma、Yue-Ming Li、Albert S.C. Chan、Lianquan Gu

  DOI：10.1016/j.ejmech.2005.07.014

  日期：2005.12

  Three series of functionalized coumarin compounds were designed and prepared as cholinesterase (AChE and BuChE) inhibitors. The biological profile against AChE and BuChE of the prepared compounds was determined. Compound 7b exhibited a mixed-type of AChE inhibitor with IC50 value for the AChE inhibition of 0.19 +/- 0.01 mu M and a high selectivity for AChE/BuChE, and compound 6b acted as 0 non-competitive AChE inhibitor with IC50 value of 0.43 +/- 0.02 mu M. Structure-activity, relationships (SARs) of prepared compounds were discussed. (c) 2005 Elsevier SAS. All rights reserved.
• Methylx derivatives of tetrahydrobenzo- and benzofurocoumarins, a new class of potential photoreagents toward dna
  作者：P. Rodighiero、M. Palumbo、S. Marciani Magno、P. Manzini、O. Gia、R. Piro、A. Guiotto

  DOI：10.1002/jhet.5570230530

  日期：1986.9

  A number of new tetracyclic furocoumarin derivatives with a linear structure or with various angular arrangements, were synthetized. The new compounds are characterized for having an additional cyclohexene or phenyl ring condensed at the 4′,5′ double bond of the furan ring of the furocoumarin nucleus. The syntheses were performed starting from the appropriate hydroxycoumarins on which the tetrahydrobenzofuran

  合成了许多具有线性结构或具有各种角度排列的新的四环呋喃香豆素衍生物。新化合物的特征在于在呋喃香豆素核的呋喃环的4'，5'双键上稠合了一个额外的环己烯或苯环。从合适的羟基香豆素开始进行合成，在该羟基香豆素上建立了四氢苯并呋喃或苯并呋喃部分。甲基被引入到看起来最有希望增强化合物对DNA的光反应性的位置。