7,8-dihydroxy-3-(4'-methylphenyl)-2H-chromen-2-one

• 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: 7,8-dihydroxy-3-(4'-methylphenyl)-2H-chromen-2-one
• 英文别名: 7,8-dihydroxy-3-(4-methylphenyl)-coumarin；DHMPC；7,8-Dihydroxy-3-(4-methylphenyl) coumarin；7,8-dihydroxy-3-(4-methylphenyl)chromen-2-one
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: IINCUCBAKKWVAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7,8-dihydroxy-3-(4'-methylphenyl)-2H-chromen-2-one 、 1,2-bis(3-tosyloxypropoxy)benzene 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 120.0h， 以17%的产率得到7,8-[6,7-benzo-1,5,8,12-tetraoxadecylene]-3-[4'-methylphenyl]-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis of Some Benzo-14-crown-4 Ethers Substituted to 7,8-Dihydroxy-3-phenylcoumarin Derivatives

  摘要：

  7,8-Dihydroxy-3-phenylcoumarin derivatives reacted with 1,2-bis-(3-tosyloxypropoxy)benzene in CH3CN/alkali carbonate to furnish 3-phenylchromenone-14-crown-4 ether derivatives, which were identified with elemental analysis, IR, H-1 NMR, C-13 NMR and MS spectroscopy.

  DOI：

  10.3987/com-05-10581
• 作为产物：
  描述：

  3-(2,3,4-trimethoxyphenyl)-2-(4-methylphenyl)acrylonitrile 在 吡啶盐酸盐 作用下， 生成 7,8-dihydroxy-3-(4'-methylphenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Yuce, Basak; Danis, Ozkan; Ogan, Ayse, Arzneimittel-Forschung/Drug Research, 2009, vol. 59, # 3, p. 129 - 134

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of 3-arylcoumarins as potential anti-Alzheimer's disease agents
  作者：Jie Yang、Pingping Zhang、Yuheng Hu、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1080/14756366.2019.1574297

  日期：2019.1.1

  the extremely complex pathogenesis. Accumulating evidence indicates there is a close relationship between several enzymes and Alzheimer's disease. Various substituted 3-arylcoumarin derivatives were synthesised, and their in vitro activity, including cholinesterase inhibitory activity, monoamine oxidase inhibitory activity, and antioxidant activity were investigated. Most of the compounds exhibited

  抽象的 阿尔茨海默氏病是一种神经退行性疾病，其发病机理极为复杂。越来越多的证据表明，几种酶与阿尔茨海默氏病之间存在密切的关系。合成了各种取代的3-芳基香豆素衍生物，并研究了它们的体外活性，包括胆碱酯酶抑制活性，单胺氧化酶抑制活性和抗氧化活性。大多数化合物表现出高活性。因此3-芳基香豆素类化合物具有治疗阿尔茨海默氏病的潜力。
• Synthesis and biological evaluation of 3-arylcoumarin derivatives as potential anti-diabetic agents
  作者：Yuheng Hu、Bing Wang、Jie Yang、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1080/14756366.2018.1518958

  日期：2019.1.1

  Abstract A variety of substituted 3-arylcoumarin derivatives were synthesised through microwave radiation heating. The method has characteristics of environmental friendliness, economy, simple separation, and purification process, less by-products and high reaction yield. Those 3-arylcoumarin derivatives were screened for antioxidant, α-glucosidase inhibitory and advanced glycation end-products (AGEs)

  抽象的 通过微波辐射加热合成了多种取代的3-芳基香豆素衍生物。该方法具有环境友好，经济，分离纯化工艺简单，副产物少，反应收率高的特点。筛选了那些3-芳基香豆素衍生物的抗氧化剂，α-葡萄糖苷酶抑制物和晚期糖基化终产物（AGEs）形成抑制物。大多数化合物表现出显着的抗氧化剂和AGEs形成抑制活性。抗糖尿病活性研究表明，化合物11和17在体内与标准药物glibenclamide等效。根据实验结果，目标化合物35可用作开发抗糖尿病新药的先导化合物。整个实验表明，抗糖尿病活性在3-芳基香豆素中普遍存在，为抗糖尿病活性药物的开发增加了新的天然骨架。
• Investigation of HMG‐CoA reductase inhibitory and antioxidant effects of various hydroxycoumarin derivatives
  作者：Lalehan Ozalp、Özkan Danış、Basak Yuce‐Dursun、Serap Demir、Cihan Gündüz、Ayse Ogan

  DOI：10.1002/ardp.201900378

  日期：2020.10

  low‐density lipoprotein cholesterol level is critical for treating these diseases, the inhibition of 3‐hydroxy‐3‐methyl‐glutaryl coenzyme A (HMG‐CoA) reductase, which is essentially responsible for cholesterol biosynthesis, stands out as a key solution to lower plasma cholesterol levels. In this study, we synthesized several dihydroxycoumarins and investigated their antioxidant and in vitro HMG‐CoA reductase

  心血管疾病是世界范围内死亡的主要原因之一，动脉粥样硬化的发展与高胆固醇血症密切相关。由于低密度脂蛋白胆固醇水平的降低对于治疗这些疾病至关重要，因此主要负责胆固醇生物合成的 3-羟基-3-甲基-戊二酰辅酶 A (HMG-CoA) 还原酶的抑制作用突出降低血浆胆固醇水平的关键解决方案。在这项研究中，我们合成了几种二羟基香豆素，并研究了它们的抗氧化和体外 HMG-CoA 还原酶抑制作用。此外，我们进行了计算机研究并检查了香豆素衍生物的量子化学性质。我们还进行了分子对接实验并分析了每种香豆素衍生物的结合强度。我们的结果表明，化合物 IV 在体外表现出最高的 HMG-CoA 还原酶抑制活性 (IC50 = 42.0 µM)。铜还原抗氧化能力和铁还原抗氧化能力测定表明香豆素衍生物表现出有效的抗氧化活性。此外，发现最低未占分子轨道能级与抗氧化活性之间存在密切关系。
• COUMARIN DERIVATIVE AND USE THEREOF
  申请人：MORINAGA MILK INDUSTRY CO., LTD.

  公开号：EP0645382A1

  公开（公告）日：1995-03-29

  The invention provides a compound having a 12-lipoxygenase inhibitory effect and a drug selectively inhibiting 12-lipoxygenase and relates to a novel coumarin derivative represented by general formula (1) and a drug comprising said compound as the active ingredient. In formula (1) R¹ represents hydrogen or lower alkyl; R² and R³ represent each hydrogen or hydroxyl provided that R² and R³ do not represent hydrogen atoms at the same time; and Ar represents (a) (b), (c) etc.; and R⁴ represents lower alkyl, lower alkoxy, halogen, trifluoromethyl or cyano. It further provides a compound which can be converted into another compound capable of selectively inhibiting 12-lipoxygenase activity through cleavage and breakage of its modifying moiety in vivo and a drug which selectively inhibits 12-lipoxygenase and relates to a novel coumarin derivative having an acyl group as the modifying moiety and a drug containing said compound as the active ingredient. The invention compound, which can potently inhibit 12-lipoxygenase at a high selectivity, is useful as a drug for preventing and treating circulatory diseases such as arteriosclerosis and vasoconstriction and preventing the metastasis of certain cancers. It has a low toxicity and little exhibits side effects.

  本发明提供了一种具有12-脂氧合酶抑制作用的化合物和一种选择性抑制12-脂氧合酶的药物，并涉及一种由通式(1)表示的新型香豆素衍生物和一种以上述化合物为活性成分的药物。在式(1)中，R¹代表氢或低级烷基；R²和R³分别代表氢或羟基，条件是R²和R³不同时代表氢原子；Ar代表(a)(b)、(c)等；R⁴代表低级烷基、低级烷氧基、卤素、三氟甲基或氰基。本发明进一步提供了一种化合物，该化合物可通过其修饰基团在体内的裂解和断裂转化为另一种能够选择性抑制 12-脂氧合酶活性的化合物，以及一种选择性抑制 12-脂氧合酶的药物，并涉及一种以酰基为修饰基团的新型香豆素衍生物和一种含有上述化合物作为活性成分的药物。本发明化合物能以高选择性有效抑制 12-脂氧合酶，可用作预防和治疗动脉硬化和血管收缩等循环系统疾病以及防止某些癌症转移的药物。它毒性低，副作用小。
• Danis, Ozkan; Yuce-Dursun, Basak; Gunduz, Cihan, Arzneimittel-Forschung/Drug Research, 2010, vol. 60, # 10, p. 617 - 620
  作者：Danis, Ozkan、Yuce-Dursun, Basak、Gunduz, Cihan、Ogan, Ayse、Sener, Goksel、Bulut, Mustafa、Yarat, Aysen

  DOI：——

  日期：——