2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-6,8-dimethylchromen-4-one | 95273-01-1

• 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: 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-6,8-dimethylchromen-4-one
• 英文别名: 5,7-dihydroxy-4'-methoxy-6,8-dimethylflavanon；matteucinol；5,7-dihydroxy-2-(4-methoxy-phenyl)-6,8-dimethyl-chroman-4-one；5,7-Dihydroxy-2-(4-methoxy-phenyl)-6,8-dimethyl-chroman-4-on；2,7-Dihydroxy-6,8-dimethyl-4'-methoxyflavanon (Matteucinol)；(+/-)-Matteucinol；5,7-dihydroxy-2-(4-methoxyphenyl)-6,8-dimethyl-2,3-dihydrochromen-4-one
• CAS: 95273-01-1
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: DZTRDRPCROOSOG-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  552.7±50.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)
• 保留指数：
  2881.2

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-6,8-dimethylchromen-4-one 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 5,7-dihydroxy-4'-methoxy-6,8-dimethylanthocyanidin
  参考文献：
  名称：

  Tanaka, Nobutoshi; Sada, Takuro; Murakami, Takao, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 2, p. 490 - 496

  摘要：

  DOI：
• 作为产物：
  描述：

  二甲基均苯三酚 、 p-methoxycinnamoyl chloride 在 三氯化铝 、 乙醚 、 硝基苯 作用下， 生成 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-6,8-dimethylchromen-4-one
  参考文献：
  名称：

  Fujise, Scientific Papers of the Institute of Physical and Chemical Research (Japan), vol. 11, p. 111

  摘要：

  DOI：

文献信息

• Asymmetric Cyclization of 2′-Hydroxychalcones to Flavanones: Catalysis by Chiral Brønsted Acids and Bases
  作者：Claudia Dittmer、Gerhard Raabe、Lukas Hintermann

  DOI：10.1002/ejoc.200700682

  日期：2007.12

  the realization of an asymmetric flavanone synthesis by means of camphorsulfonic acid as chiral Bronsted acid catalysts were reinvestigated using accurate HPLC methods for quantification of enantiomer ratios. The previous claims of asymmetric induction were thus shown to be untenable. On the other hand, cinchona alkaloids serve as chiral Bronsted base mediators for the asymmetric cyclization of either

  2'-羟基查尔酮不对称环化为黄烷酮是类黄酮天然产物生物合成中的基本酶催化步骤，但对小分子催化剂的不对称催化造成了长期存在的问题。先前关于通过樟脑磺酸作为手性布朗斯台德酸催化剂实现不对称黄烷酮合成的声明使用准确的 HPLC 方法对对映异构体比率进行量化，重新研究。因此，先前关于不对称归纳的主张被证明是站不住脚的。另一方面，金鸡纳生物碱作为手性布朗斯台德碱介体用于 6'-取代的 2'-羟基查耳酮或 2',6'-二羟基查耳酮的不对称环化。例如，2',6'-二羟基-4,4'-二甲氧基查尔酮环化得到天然存在的柚皮素-4'，7-二甲醚的 ee 高达 64%，转化率为 81%。催化剂显示产物的对映体过量对催化剂、溶剂和反应物浓度的显着依赖性。基于这些 2'-羟基查尔酮不对称环化为黄烷酮的成功实例，可以定义对活性更高的不对称催化剂的要求。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451
• Pharmaceutical compositions containing compounds with a flavanone skeleton and process for the preparation of said compounds
  申请人：INVERNI DELLA BEFFA S.P.A.

  公开号：EP0122053A2

  公开（公告）日：1984-10-17

  Compounds with a flavanone skeleton having the formula I in which R1 and R2, which may be the same or different, represent hydrogen, hydroxyl, methoxyl, thiomethyl, amino or substituted amino, are endowed with expectorant, mucolytic, mucopoietic, chloretic and hypolipaemia-producing activity.

  具有式 I 的黄烷酮骨架的化合物，其中 R1 和 R2（可以相同或不同）代表氢、羟基、甲氧基、硫甲基、氨基或取代氨基，具有祛痰、粘液溶解、粘液造血、软化胆囊和降血脂活性。
• Pharmaceutical composition containing substance inhibiting HSP47 production
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：EP0742012A2

  公开（公告）日：1996-11-13

  A pharmaceutical composition comprising a substance inhibiting HSP47 production, selected from the group consisting of a malt extract, a flavonoid compound, a protein-bound-polysaccharide obtained from a fungus belonging to Coriolus versicolor, a paeoniflorin derivative, a tocopherol derivative, and a ferulic acid derivative, and a pharmaceutically acceptable carrier is disclosed. The substance inhibiting HSP47 production can efficiently improve physiological conditions of a patient suffering from diseases exhibiting pathosis of overproduction of the extracellular matrix, and efficiently treat such diseases. Further, the substance is useful for preventing or treating various diseases accompanied with abnormal growth of the vascularization.

  本发明公开了一种药物组合物，该组合物包含一种抑制 HSP47 生成的物质，该物质选自麦芽提取物、黄酮类化合物、从属于 Coriolus versicolor 的真菌中获得的蛋白结合多糖、芍药苷衍生物、生育酚衍生物和阿魏酸衍生物组成的组，以及一种药学上可接受的载体。这种抑制 HSP47 生成的物质可以有效改善患有细胞外基质过度生成病症的患者的生理状况，并有效治疗此类疾病。此外，该物质还可用于预防或治疗伴有血管异常生长的各种疾病。
• Synthesis and biological activity of flavanone derivatives
  作者：Lei Shi、Xiu E Feng、Jing Rong Cui、Lian Hua Fang、Guan Hua Du、Qing Shan Li

  DOI：10.1016/j.bmcl.2010.07.090

  日期：2010.9

  A series of new flavanone derivatives of farrerol was synthesized by a convenient method. The in vitro anti-tumor activity of these compounds was evaluated against human Bel-7402, HL-60, BGC-823 and KB cell lines, the protein tyrosine kinase (PTK) inhibitor activity was also tested. Their cytoprotective activity was tested using hydrogen peroxide (H2O2)-induced injury in human umbilical vein endothelial cells. Their in vitro anti-atherosclerosis activity was tested on vascular smooth muscle cells by the MTT method using tetrandrine as a positive contrast drug. The structures of all compounds synthesized were confirmed by H-1, C-13 NMR and ESI-MS. Most of the compounds exhibited good pharmacological activity and the preliminary structure-activity relationships were described. (c) 2010 Elsevier Ltd. All rights reserved.
• JP2002173424A
  申请人：——

  公开号：JP2002173424A

  公开（公告）日：2002-06-21