6-cyano-4,9-dimethoxy-5-methyl-7H-furo-<3,2-g><1>benzopyran-7-one | 5712-05-0

• 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: 6-cyano-4,9-dimethoxy-5-methyl-7H-furo-<3,2-g><1>benzopyran-7-one
• 英文别名: 4,9-dimethoxy-5-methyl-7-oxo-7H-furo[3,2-g]chromene-6-carbonitrile；4,9-Dimethoxy-5-methyl-7-oxofuro[3,2-g]chromene-6-carbonitrile
• CAS: 5712-05-0
• 化学式: C₁₅H₁₁NO₅
• 分子量: 285.256
• InChiKey: RGMIGLPPYXZTBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-cyano-4,9-dimethoxy-5-methyl-7H-furo-<3,2-g><1>benzopyran-7-one 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以75%的产率得到4,9-dimethoxy-5-methyl-7-oxo-7H-furo[3,2-g]chromene-6-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and docking studies of new furobenzopyranones and pyranobenzopyranones as photoreagent towards DNA and as antimicrobial agents

  摘要：

  A number of new furobenzopyranones and pyranobenzopyranones carrying an electron- withdrawing function at the position 3 are synthesized in order to obtain new photoreagents towards DNA. Our interest in this study is to investigate the effect of introduction of electron withdrawing function on the position 3 of the benzo-a-pyrranone ring of linear furobenzo-a-pyranone (5,8-dimethoxypsoralen) or angular pyranobenzo-a-pyranone on the biological activity, by preparing 3-cyano, carboxylic acid, carboxylic acid ester, acid hydrazide, thiosemicarbazide, or mercaptotriazole derivatives. 5-acetyl-6-hydroxybenzofuran, and 8-acetyl-7-hydroxy-4-phenylbenzopyranone are the key starting compounds on which 3-cyano-4-methylfurobenzopyranone and 3-cyano-4-methyl pyranobenzopyranone moieties were built respectively. The photobiological activity of the newly synthesized compounds was evaluated. It looks most promising for enhancement of photoreactivity of compounds towards DNA, and a certain effect was observed in the dark determining the antimicrobial activity.Compounds 5, 6, 7, 13, 14 exhibit potential photoreactivity, towards DNA, while 3-mercaptotriazole derivatives 7,14 possess only photosensitizing activity.To investigate the antimicrobial data on structural basis, molecular modelling and docking studies of the tested compounds into the crystal structure of topoisomerase II DNA Gyrase B complexed with the natural inhibitor bearing the coumarin moiety clorobiocin (1kzn), using Molsoft ICM 3.4-8C program was performed in order to predict the affinity and orientation of the synthesized compounds at the active site. The ICM score values and hydrogen bonds formed with the surrounding amino acids show good agreement with predicted binding affinities obtained by molecular docking studies as verified by antimicrobial screening, where compounds 5, 6,13 were the most active compounds against Bacillus subtilis, Staphylococcus aureus, and Escherichia coli. Compound 13 has good affinity with the receptor and forms six hydrogen bonds with Asp-73. and two bonds with Thr-165, compound 6 has ICM score value -85.66 and forms one hydrogen bond with Asp-73, and three with Thr-165, and compound 5 has ICM score value -53 but forms one hydrogen bond with Asp-73, and four bonds with Thr-165 which may reveal the potent antimicrobial activity referred to the natural antimicrobial Clorobiocin which forms two hydrogen bonds with Asp-73 and three with Thr-165. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.016
• 作为产物：
  描述：

  凯林酮 在 ammonium acetate 、 溶剂黄146 作用下， 反应 3.0h， 生成 6-cyano-4,9-dimethoxy-5-methyl-7H-furo-<3,2-g><1>benzopyran-7-one
  参考文献：
  名称：

  Hishmat, O. H.; Zohair, M. M. Y.; Miky, J. A. A., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 12, p. 1690 - 1694

  摘要：

  DOI：

文献信息

• HISHMAT, O. H.;ZOHAIR, M. M. Y.;MIKY, J. A. A., Z. NATURFORSCH., 1983, 38, N 12, 1690-1694
  作者：HISHMAT, O. H.、ZOHAIR, M. M. Y.、MIKY, J. A. A.

  DOI：——

  日期：——
• Hishmat, O. H.; Zohair, M. M. Y.; Miky, J. A. A., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 12, p. 1690 - 1694
  作者：Hishmat, O. H.、Zohair, M. M. Y.、Miky, J. A. A.

  DOI：——

  日期：——
• Design, synthesis and docking studies of new furobenzopyranones and pyranobenzopyranones as photoreagent towards DNA and as antimicrobial agents
  作者：Nahla A.H. Farag、Wafaa El-Tayeb

  DOI：10.1016/j.ejmech.2009.10.016

  日期：2010.1

  A number of new furobenzopyranones and pyranobenzopyranones carrying an electron- withdrawing function at the position 3 are synthesized in order to obtain new photoreagents towards DNA. Our interest in this study is to investigate the effect of introduction of electron withdrawing function on the position 3 of the benzo-a-pyrranone ring of linear furobenzo-a-pyranone (5,8-dimethoxypsoralen) or angular pyranobenzo-a-pyranone on the biological activity, by preparing 3-cyano, carboxylic acid, carboxylic acid ester, acid hydrazide, thiosemicarbazide, or mercaptotriazole derivatives. 5-acetyl-6-hydroxybenzofuran, and 8-acetyl-7-hydroxy-4-phenylbenzopyranone are the key starting compounds on which 3-cyano-4-methylfurobenzopyranone and 3-cyano-4-methyl pyranobenzopyranone moieties were built respectively. The photobiological activity of the newly synthesized compounds was evaluated. It looks most promising for enhancement of photoreactivity of compounds towards DNA, and a certain effect was observed in the dark determining the antimicrobial activity.Compounds 5, 6, 7, 13, 14 exhibit potential photoreactivity, towards DNA, while 3-mercaptotriazole derivatives 7,14 possess only photosensitizing activity.To investigate the antimicrobial data on structural basis, molecular modelling and docking studies of the tested compounds into the crystal structure of topoisomerase II DNA Gyrase B complexed with the natural inhibitor bearing the coumarin moiety clorobiocin (1kzn), using Molsoft ICM 3.4-8C program was performed in order to predict the affinity and orientation of the synthesized compounds at the active site. The ICM score values and hydrogen bonds formed with the surrounding amino acids show good agreement with predicted binding affinities obtained by molecular docking studies as verified by antimicrobial screening, where compounds 5, 6,13 were the most active compounds against Bacillus subtilis, Staphylococcus aureus, and Escherichia coli. Compound 13 has good affinity with the receptor and forms six hydrogen bonds with Asp-73. and two bonds with Thr-165, compound 6 has ICM score value -85.66 and forms one hydrogen bond with Asp-73, and three with Thr-165, and compound 5 has ICM score value -53 but forms one hydrogen bond with Asp-73, and four bonds with Thr-165 which may reveal the potent antimicrobial activity referred to the natural antimicrobial Clorobiocin which forms two hydrogen bonds with Asp-73 and three with Thr-165. (C) 2009 Elsevier Masson SAS. All rights reserved.