7-hydroxy-8-((2E)-3-(3-nitrophenyl)-1-oxo-2-propen-1-yl)-4-methyl-2H-1-benzopyran-2-one | 749863-00-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 7-hydroxy-8-((2E)-3-(3-nitrophenyl)-1-oxo-2-propen-1-yl)-4-methyl-2H-1-benzopyran-2-one
• 英文别名: (E)-7-hydroxy-4-methyl-8-(3-(3-nitrophenyl)acryloyl)-2H-chromen-2-one；7-hydroxy-4-methyl-8-[(E)-3-(3-nitrophenyl)prop-2-enoyl]chromen-2-one
• CAS: 749863-00-1
• 化学式: C₁₉H₁₃NO₆
• 分子量: 351.315
• InChiKey: RHXCYOLHMNKUGD-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-hydroxy-8-((2E)-3-(3-nitrophenyl)-1-oxo-2-propen-1-yl)-4-methyl-2H-1-benzopyran-2-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到8-(4,5-dihydro-5-(3-nitrophenyl)-1H-pyrazol-3-yl)-7-hydroxy-4-methyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety to scavenge radicals and to protect DNA

  摘要：

  A series of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety were synthesized and their antioxidant activities were evaluated in AAPH (2,2'-azobis(2-amidinopropane hydrochloride))-induced oxidation of DNA, and in trapping DPPH (2,2'-diphenyl-1-picrylhydrazyl) and ABTS(+center dot) (2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical), respectively. Among coumarin derivatives, 3a-d and 4a-c exhibited the termination of radical propagation-chains in AAPH-induced oxidation of DNA. The ortho dihydroxyphenyl substitution at 5 position and 1-unsubstitution of the 4,5-dihydroxylpyrazole was found enhancing the antioxidant activities of these coumarin derivatives. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.052
• 作为产物：
  描述：

  间苯二酚 在 哌啶 、 aluminum (III) chloride 、 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 60.0h， 生成 7-hydroxy-8-((2E)-3-(3-nitrophenyl)-1-oxo-2-propen-1-yl)-4-methyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Coumarin moiety can enhance abilities of chalcones to inhibit DNA oxidation and to scavenge radicals

  摘要：

  Coumarin and chalcone are naturally occurring compounds, and coumarin as a functional group was combined with chalcone in this work, aiming to test the inhibitory effects of coumarin-substituted chalcones on the oxidation of DNA and on scavenging radicals. It was found that the antioxidant activity of hydroxyl group attaching to coumarin can be increased by hydroxyl groups attaching to chalcone. The double hydroxyl groups at adjacent position exhibited high abilities to inhibit Cu2+/glutathione-induced oxidation of DNA and to trap 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS.) as well as 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH). Especially, the double hydroxyl groups in chalcone were able to protect DNA against 2,2'-azobis(2-amidinopropanehydrochloride) (AAPH)-induced oxidation significantly. On the other hand, the hydroxyl group attaching to coumarin exhibited high ability to inhibit (OH)-O-center dot-induced oxidation of DNA. Therefore, coumarin-appended chalcones exhibited higher antioxidant effectiveness with only single or double phenolic hydroxyl groups contained. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.08.063

文献信息

• SYNTHESIS OF SOME NEW 1,5-BENZOTHIAZEPINES CONTAINING 2H-1- BENZOPYRAN-2-ONE HETEROCYCLE
  作者：A. Prashant、S. Srinivas Rao、K.S. Chowdary、V.S.H. Krishnan

  DOI：10.1515/hc.2001.7.1.61

  日期：2001.1
• Yarapathi, Venkat Reddy, Heterocyclic Communications, 2004, vol. 10, # 1, p. 59 - 62
  作者：Yarapathi, Venkat Reddy

  DOI：——

  日期：——
• SHARAN, P.;GIRI, S.;NIZAMUDDIN, J. INDIAN CHEM. SOC., 66,(1989) N, C. 393-394
  作者：SHARAN, P.、GIRI, S.、NIZAMUDDIN

  DOI：——

  日期：——
• Synthesis of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety to scavenge radicals and to protect DNA
  作者：Chuan Xiao、Xu-Yang Luo、De-Jun Li、Hang Lu、Zai-Qun Liu、Zhi-Guang Song、Ying-Hua Jin

  DOI：10.1016/j.ejmech.2012.03.052

  日期：2012.7

  A series of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety were synthesized and their antioxidant activities were evaluated in AAPH (2,2'-azobis(2-amidinopropane hydrochloride))-induced oxidation of DNA, and in trapping DPPH (2,2'-diphenyl-1-picrylhydrazyl) and ABTS(+center dot) (2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical), respectively. Among coumarin derivatives, 3a-d and 4a-c exhibited the termination of radical propagation-chains in AAPH-induced oxidation of DNA. The ortho dihydroxyphenyl substitution at 5 position and 1-unsubstitution of the 4,5-dihydroxylpyrazole was found enhancing the antioxidant activities of these coumarin derivatives. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Coumarin moiety can enhance abilities of chalcones to inhibit DNA oxidation and to scavenge radicals
  作者：Gao-Lei Xi、Zai-Qun Liu

  DOI：10.1016/j.tet.2014.08.063

  日期：2014.11

  Coumarin and chalcone are naturally occurring compounds, and coumarin as a functional group was combined with chalcone in this work, aiming to test the inhibitory effects of coumarin-substituted chalcones on the oxidation of DNA and on scavenging radicals. It was found that the antioxidant activity of hydroxyl group attaching to coumarin can be increased by hydroxyl groups attaching to chalcone. The double hydroxyl groups at adjacent position exhibited high abilities to inhibit Cu2+/glutathione-induced oxidation of DNA and to trap 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS.) as well as 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH). Especially, the double hydroxyl groups in chalcone were able to protect DNA against 2,2'-azobis(2-amidinopropanehydrochloride) (AAPH)-induced oxidation significantly. On the other hand, the hydroxyl group attaching to coumarin exhibited high ability to inhibit (OH)-O-center dot-induced oxidation of DNA. Therefore, coumarin-appended chalcones exhibited higher antioxidant effectiveness with only single or double phenolic hydroxyl groups contained. (C) 2014 Elsevier Ltd. All rights reserved.