4-Methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one | 105290-13-9

• 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
• 英文名称: 4-Methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one
• 英文别名: 7-methyl-9H-benzofuro<3,2-g> <1> benzopyran-9-one；4-methyl-2H-benzofuro[3,2-g]-1-benzopyran-2-one；2H-Benzofuro(3,2-g)-1-benzopyran-2-one, 4-methyl-；4-methyl-[1]benzofuro[3,2-g]chromen-2-one
• CAS: 105290-13-9
• 化学式: C₁₆H₁₀O₃
• 分子量: 250.254
• InChiKey: MOTTUNALIBKKNF-UHFFFAOYSA-N

物化性质

• 熔点：
  228-230 °C(Solv: methanol (67-56-1))
• 沸点：
  457.6±30.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one 在 selenium(IV) oxide 作用下， 以 乙醇 、 xylene 为溶剂， 反应 26.0h， 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：

  羟甲香豆素 在 sodium hydroxide 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 4-Methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one
  参考文献：
  名称：

  A QSAR Model for in Silico Screening of MAO-A Inhibitors. Prediction, Synthesis, and Biological Assay of Novel Coumarins

  摘要：

  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.

  DOI：

  10.1021/jm0509849

文献信息

• 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。
• Ahluwalia, Vinod Kumar; Adhikari, Raju; Singh, Rishi Pal, Acta Chimica Hungarica, 1987, vol. 124, # 3, p. 427 - 430
  作者：Ahluwalia, Vinod Kumar、Adhikari, Raju、Singh, Rishi Pal

  DOI：——

  日期：——
• AHLUWALIA, VINOD KUMAR;ADHIKARI, RAJU;SINGH, RISHI PAL, ACTA CHIM. HUNG., 124,(1987) N 3, 427-429
  作者：AHLUWALIA, VINOD KUMAR、ADHIKARI, RAJU、SINGH, RISHI PAL

  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.
• 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.