(E)-7-hydroxy-8-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)-4-methyl-2H-chromen-2-one | 148304-16-9

• 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: (E)-7-hydroxy-8-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)-4-methyl-2H-chromen-2-one
• 英文别名: 7-hydroxy-8-[3-(4-hydroxy-3-methoxyphenyl)acryloyl]-4-methyl-2H-chromen-2-one；7-hydroxy-8-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-4-methylchromen-2-one
• CAS: 148304-16-9
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: AHCFQUJHOPVTAL-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-7-hydroxy-8-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)-4-methyl-2H-chromen-2-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以93%的产率得到8-(4,5-dihydro-5-(3-methoxy-4-hydroxyphenyl)-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 、 4-二甲氨基吡啶 、 aluminum (III) chloride 、 硫酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 (E)-7-hydroxy-8-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  cinnamoyl-和pyranochromen-2-one衍生物的合成和抗增殖和c-Src激酶抑制活性

  摘要：

  合成了一系列 6- 和 8-cinnamoylchromen-2-one 和 dihydropyranochromen-2-one 衍生物，并评估了它们对三种人类癌细胞系的抗增殖活性，即卵巢腺癌 (SK-OV-3)、白血病 (CCRF) -CEM) 和乳腺癌 (MCF-7)。一般而言，与 6-肉桂酰类似物相比，8-cinnamoylchromen-2-one 衍生物对癌细胞具有更高的抗增殖活性。在所有杂合 chromen-2-one - 查尔酮/黄烷酮化合物中，发现 7-hydroxy-8-cinnamoylchromen-2-one 衍生物 35 对所有癌细胞系均具有持续活性并抑制 SK-的细胞增殖OV-3、CCRF-CEM 和 MCF-7 在孵育 72 小时后浓度为 50 μmol/L 时分别增加 63%、50% 和 43%。该化合物还表现出最高的 Src 激酶抑制 (IC50 = 14

  DOI：

  10.1139/cjc-2013-0053

文献信息

• Khan, M. S. Y.; Sharma, Poonam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 3, p. 374 - 376
  作者：Khan, M. S. Y.、Sharma, Poonam

  DOI：——

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

  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.