4-hydroxy-3-(4-methoxyphenyl)-2H-chromen-2-one | 26151-95-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4-hydroxy-3-(4-methoxyphenyl)-2H-chromen-2-one
• 英文别名: 4-hydroxy-3-(4-methoxyphenyl)coumarin；Coumarin, 4-hydroxy-3-(p-methoxyphenyl)-；4-hydroxy-3-(4-methoxyphenyl)chromen-2-one
• CAS: 26151-95-1
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: CERHCYIDWGTRQA-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：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(4-methoxyphenyl)-2H-chromen-2-one 在 iron(III) chloride 、 silica gel 、 三溴化硼 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 9-hydroxy-6H-benzofuro[3,2-c]chromen-6-one
  参考文献：
  名称：

  Coumestan Inhibits Radical-Induced Oxidation of DNA: Is Hydroxyl a Necessary Functional Group?

  摘要：

  Coumestan is a natural tetracycle with a C═C bond shared by a coumarin moiety and a benzofuran moiety. In addition to the function of the hydroxyl group on the antioxidant activity of coumestan, it is worth exploring the influence of the oxygen-abundant scaffold on the antioxidant activity as well. In this work, seven coumestans containing electron-withdrawing and electron-donating groups were synthesized to evaluate the abilities to trap 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(•+)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively, and to inhibit the oxidations of DNA mediated by (•)OH, Cu(2+)/glutathione (GSH), and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH), respectively. It was found that all of the coumestans used herein can quench the aforementioned radicals and can inhibit (•)OH-, Cu(2+)/GSH-, and AAPH-induced oxidations of DNA. In particular, substituent-free coumestan exhibits higher ability to quench DPPH and to inhibit AAPH-induced oxidation of DNA than Trolox. In addition, nonsubstituted coumestan shows a similar ability to inhibit (•)OH- and Cu(2+)/GSH-induced oxidations of DNA relative to that of Trolox. The antioxidant effectiveness of the coumestan can be attributed to the lactone in the coumarin moiety and, therefore, a hydroxyl group may not be a necessary functional group for coumestan to be an antioxidant.

  DOI：

  10.1021/jf500013v
• 作为产物：
  描述：

  (Z)-4'-methoxyaurone 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 生成 4-hydroxy-3-(4-methoxyphenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Brady, Brian A.; Healy, Mary M.; O'Sullivan, W. Ivo, Journal of the Chemical Society. Perkin transactions I, 1983, p. 1151 - 1156

  摘要：

  DOI：

文献信息

• 3-Substituted-4-aminoalkoxy-5,6-condensed ring-2-pyranones
  申请人：LIPHA, Lyonnaise Industrielle Pharmaceutique

  公开号：US04230850A1

  公开（公告）日：1980-10-28

  Novel 3-substituted-4-aminoalkoxy-5,6-condensed ring-2-pyranones are disclosed as having utility as pharmacologically active compounds, in particular vasodilatory, hypotensive, anti-ischemic and anti-tussive activity. The compounds may be 3-phenyl-4-morpholinoalkoxy-coumarins. Administration may be by the oral or parenteral route. Intermediates useful in the production of these compounds are also disclosed.

  新颖的3-取代-4-氨基烷氧基-5,6-环化-2-吡喃酮被披露为具有药理活性化合物的效用，特别是血管扩张、降压、抗缺血和镇咳活性。这些化合物可能是3-苯基-4-吗啡基烷氧基-香豆素。可以通过口服或静脉注射途径进行给药。还披露了在这些化合物生产中有用的中间体。
• 3-芳基-4-芳香胺-香豆素衍生物及其制备方法和医药用途
  申请人：中国药科大学

  公开号：CN105801544A

  公开（公告）日：2016-07-27

  本发明涉及药物化学领域，具体涉及一系列3?芳基?4?芳香胺?香豆素衍生物、其制备方法及医药用途，特别是用于治疗肿瘤方面的药物，如乳腺癌等。本发明中涉及化合物的结构通式如下，通式中各基团定义详见说明书。
• Design, synthesis and biological evaluation of novel 3-substituted 4-anilino-coumarin derivatives as antitumor agents
  作者：Guoshun Luo、Moses Muyaba、Weiting Lyu、Zhichao Tang、Ruheng Zhao、Qian Xu、Qidong You、Hua Xiang

  DOI：10.1016/j.bmcl.2017.01.013

  日期：2017.2

  Various 3-substituted 4-anilino-coumarin derivatives have been designed, synthesized and their anti-proliferative properties have been studied. The in vitro cytotoxicity screening was performed against MCF-7, HepG2, HCT116 and Panc-1 cancer cell lines by MTT assay. Most of the synthesized compounds exhibited comparable anti-proliferative activity to the positive control 5-Fluorouracil against these

  已经设计，合成了各种3-取代的4-苯胺基香豆素衍生物，并且已经研究了它们的抗增殖性能。通过MTT测定法针对MCF-7，HepG2，HCT116和Panc-1癌细胞系进行了体外细胞毒性筛选。大多数合成的化合物对这四种测试的癌细胞系表现出与阳性对照5-氟尿嘧啶相当的抗增殖活性。在香豆素骨架的C-3位的不同取代基中，3-三氟乙酰基显示出最有希望的结果。特别是化合物33d（IC50 = 16.57、5.45、4.42和5.16μM）和33e（IC50 = 20.14、6.71、4.62和5.62μM）对MCF-7，HepG2，HCT116和Panc-1细胞系表现出优异的抗增殖活性分别。此外，细胞周期分析和细胞凋亡激活表明，33d诱导MCF-7细胞G2 / M期阻滞和细胞凋亡呈剂量依赖性。观察到化合物33d和33e对人脐静脉内皮细胞（HUVEC）的低毒性，表明它们在正常细胞中的可接受安全性。此外，计
• The Rhodium Carbenoid Route to 3-Aryl-4-hydroxycoumarins: Synthesis of Derrusnin
  作者：Stefano Tollari、Giovanni Palmisano、Luca Goldoni、Giancarlo Cravotto、Andrea Penoni

  DOI：10.1055/s-2005-864808

  日期：——

  3-Aryl-4-hydroxycoumarins have been obtained in satisfactory yields and selectivity through a Rh(II)-mediated arylation of diazocoumarin. The utility of this approach is demonstrated by ­synthesis of the natural product derrusnin.

  3-芳基-4-羟基香豆素通过Rh(II)介导的二氮香豆素芳基化反应获得了令人满意的产率和选择性。这种方法的实用性通过天然产物德鲁斯宁的合成得到了证明。
• Metal-free C(3)–H arylation of coumarins promoted by catalytic amounts of 5,10,15,20-tetrakis(4-diethylaminophenyl)porphyrin
  作者：Masahiro Kojima、Kounosuke Oisaki、Motomu Kanai

  DOI：10.1039/c5cc02349a

  日期：——

  Metal-free, Meerwein-type C(3)–H arylation of coumarins was achieved in the presence of catalytic amounts of 5,10,15,20-tetrakis(4-diethylaminophenyl)porphyrin.

  在存在催化量的5,10,15,20-四(4-二乙基氨基苯基)卟啉的情况下，实现了无金属、Meerwein型C(3)-H芳基化香豆素。