2-(benzo[d][1,3]dioxol-5-yl)-3-hydroxy-4H-chromen-4-one | 19275-69-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(benzo[d][1,3]dioxol-5-yl)-3-hydroxy-4H-chromen-4-one
• 英文别名: 2-(1,3-benzodioxol-5-yl)-3-hydroxy-4H-chromen-4-one；3′,4′-methylenedioxy-3-hydroxyflavone；3',4'-methylenedioxy-3-hydroxyflavone；3-Hydroxy-3',4'-methylenedioxyflavone；3-hydroxy-3,4-methylenedioxyflavone；2-benzo[1,3]dioxol-5-yl-3-hydroxy-chromen-4-one；2-(1,3-benzodioxol-5-yl)-3-hydroxychromen-4-one
• CAS: 19275-69-5
• 化学式: C₁₆H₁₀O₅
• 分子量: 282.252
• InChiKey: RQYDCAXLKOYPFU-UHFFFAOYSA-N

物化性质

• 熔点：
  214-215 °C
• 沸点：
  453.6±45.0 °C(Predicted)
• 密度：
  1.522±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(benzo[d][1,3]dioxol-5-yl)-3-hydroxy-4H-chromen-4-one 以 甲醇 为溶剂， 以6%的产率得到3-benzo[1,3]dioxol-5-yl-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Photochemistry of flavonoids. III. Photorearrangement of flavonols.

  摘要：

  在甲醇中辐照黄酮醇（1）可得到 3-芳邻苯酞（3），后者通过二酮（4）形成。金属离子（Cu2+、Ni2+、Fe3+、Co2+ 和 Be2+）抑制了这种重排。

  DOI：

  10.1248/cpb.29.894
• 作为产物：
  描述：

  2'-羟基-2-戊烯基对苯二酚 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以71%的产率得到2-(benzo[d][1,3]dioxol-5-yl)-3-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  SAR Studies and Biological Characterization of a Chromen-4-one Derivative as an Anti-Trypanosoma brucei Agent

  摘要：

  Chemical modulation of the flavonol 2-(benzo[d] [1,3]dioxo1-5-y1)-chromen-4-one (1), a promising anti-Trypanosomatid agent previously identified, was evaluated through a phenotypic screening approach. Herein, we have performed structure activity relationship studies around hit compound 1. The pivaloyl derivative (13) showed significant anti-T. brucei activity (EC50 = 1.1 1iM) together with a selectivity index higher than 92. The early in vitro ADME-tox properties (cytotoxicity, mitochondria] toxicity, cytochrome P450 and hERG inhibition) were determined for compound 1 and its derivatives, and these led to the identification of some liabilities. The 1,3-benzodioxole moiety in the presented compounds confers better in vivo pharmacokinetic properties than those of classical flavonols. Further studies using different delivery systems could lead to an increase of compound blood levels.

  DOI：

  10.1021/acsmedchemlett.8b00565

文献信息

• Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis
  作者：Yuanyuan Zheng、Wenchen Pu、Jiao Li、Xianyan Shen、Qiang Zhou、Xin Fan、Sheng-Yong Yang、Yamei Yu、Qiang Chen、Chun Wang、Xin Wu、Yong Peng

  DOI：10.1002/asia.201801461

  日期：2019.1.4

  isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7‐(benzyloxy)‐3,5‐dihydroxy‐2‐(4‐methoxyphenyl)‐8‐(3‐methylbut‐2‐en‐1‐yl)‐4H‐chromen‐4‐one (AF‐39) was identified as a novel Pin1

  肽脯氨酰顺-反异构酶中Pin1在人类癌症的发展至关重要的作用。最近，我们披露了Pin1调节miRNA的生物发生，miRNA在HCC中异常表达并促进HCC进展，表明Pin1在HCC治疗中的治疗作用。在此，7-（苄氧基）-3,5-二羟基-2-（4-甲氧基苯基）-8-（3-甲基丁-2-烯-1-基）-4H-铬-4--1（AF-39）被鉴定为新型的Pin1抑制剂。生化试验表明，AF-39有效抑制中Pin1活性，其IC 50的1.008μ值米，并且还显示中肽基脯氨酰异构酶对中Pin1高选择性。此外，AF‐39以剂量和时间依赖性方式显着抑制HCC细胞的细胞增殖。从机制上讲，AF-39调节XPO5的亚细胞分布并增加HCC细胞中miRNA的生物发生。这项工作为HCC治疗提供了有希望的先导化合物，突出了基于miRNA的疗法对人类癌症的治疗潜力。
• An Expeditious Synthesis of Flavonols Promoted by Montmorillonite KSF Clay and Assisted by Microwave Irradiation under Solvent-Free Conditions
  作者：Mariappan Babu、Kasi Pitchumani、Penugonda Ramesh

  DOI：10.1002/hlca.201200336

  日期：2013.7

  A simple, efficient, rapid, and ecofriendly synthesis of flavonols in >90% yield from 2′‐(mesyloxy)epoxychalcones (=2‐(3‐aryl‐2,3‐epoxypropanoyl)phenyl methanesulfonates) promoted by montmorillonite KSF clay and assisted by microwave irradiation has been described.

  蒙脱石KSF粘土促进并辅助合成的2'-（甲氧基）环氧查尔酮（= 2-（3-芳基-2,3-环氧丙酰基）苯基甲磺酸盐）以简单，有效，快速且环保的方式合成黄酮醇，收率> 90％已经描述了通过微波辐射。
• Effect of an Electron-Donating Substituent at the 3′,4′-position of 3-Hydroxyflavone: Photophysics in Bulk Solvents
  作者：Deborin Ghosh、Giasuddin Ahamed、Shaikh Batuta、Naznin Ara Begum、Debabrata Mandal

  DOI：10.1021/acs.jpca.5b09681

  日期：2016.1.14

  was stabilized in relatively polar solvents, whereupon the enol → tautomer excited state intramolecular proton-transfer (ESIPT) rate decreased. Hydrogen-bonding solvents caused further retardation by interfering with the intramolecular hydrogen bond that promotes ESIPT. Among these solvents, hydrogen bond donors appear to be more efficient ESIPT inhibitors than hydrogen bond acceptors. Femtosecond fluorescence

  与3-羟基黄酮的3'，4'-位引入亚甲基二氧基取代基对其质子转移反应产生重大影响，就像众所周知的4'- N，N-二烷基氨基。取代基的潜在电子给体性质有助于在分子的激发烯醇形式中维持高度的电荷分离，该电荷分离在相对极性的溶剂中稳定，于是烯醇→互变异构体激发态分子内质子转移（ESIPT）速率降低。氢键键合剂通过干扰促进ESIPT的分子内氢键而引起进一步的阻滞作用。在这些溶剂中，氢键供体似乎比氢键受体更有效的ESIPT抑制剂。飞秒荧光实验表明，即使在后者中，随着溶剂氢键碱性的增加，ESIPT的时间常数也会稳定地变长。
• LACTATE DEHYDROGENASE INHIBITOR AND ANTIEPILEPTIC DRUG CONTAINING SAME
  申请人：National University Corporation Okayama University

  公开号：EP3257510A1

  公开（公告）日：2017-12-20

  The invention provides a lactate dehydrogenase inhibitor that makes it possible to suppress refractory epilepsy in which conventional antiepileptic drugs are ineffective, and an antiepileptic drug containing said inhibitor. The lactate dehydrogenase inhibitor of the invention contains a compound represented by formula (III); i.e., isosafrole or a compound having isosafrole as a scaffold, and the antiepileptic drug of the invention has these compounds as an active ingredient.

  本发明提供了一种乳酸脱氢酶抑制剂，可以抑制常规抗癫痫药物无效的难治性癫痫，以及一种含有上述抑制剂的抗癫痫药物。本发明的乳酸脱氢酶抑制剂含有由式（III）代表的化合物；即异黄樟素或以异黄樟素为支架的化合物，本发明的抗癫痫药物以这些化合物为有效成分。
• Dhoubhadel, S. P.; Tuladhar, Sudersan M.; Tuladhar, Sarbajna M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 6, p. 511 - 512
  作者：Dhoubhadel, S. P.、Tuladhar, Sudersan M.、Tuladhar, Sarbajna M.、Wagley, Pradyumna P.

  DOI：——

  日期：——

表征谱图