5-hydroxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-2-phenyl-4H-chromen-4-one

• 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: 5-hydroxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-2-phenyl-4H-chromen-4-one
• 英文别名: 5-hydroxy-7-[3-(4-methyl-piperazin-1-yl)-propoxy]-2-phenyl chromen-4-one；5-hydroxy-7-[3-(4-methylhexahydro-1-pyrazinyl)propyloxy]-2-p henyl-4H-4-chromenone；5-hydroxy-7-[3-(4-methylpiperazin-1-yl)propoxy]-2-phenylchromen-4-one
• 化学式: C₂₃H₂₆N₂O₄
• 分子量: 394.47
• InChiKey: ZLXGCJYBWWEVOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  62.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  白杨素 在 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 5-hydroxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel C (7) modified chrysin analogues as antibacterial agents

  摘要：

  The natural product, chrysin (5,7-dihydroxy flavone), obtained from Oroxylum indicum, exhibits numerous biological activities including anticancer, anti-inflammatory, and antiallergic activities. Three series of chrysin analogues were prepared, in which chrysin and heterocyclic moieties are separated by 3-carbon, 4-carbon, and 6-carbon spacers. All the derivatives were screened for antibacterial activity against a panel of susceptible and resistant Gram-positive and Gram-negative organisms. It was observed that most of the derivatives displayed significant activity as compared to their parent compound (chrysin). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.009

文献信息

• Synthesis of C(7) modified chrysin derivatives designing to inhibit β-ketoacyl-acyl carrier protein synthase III (FabH) as antibiotics
  作者：Huan-Qiu Li、Lei Shi、Qing-Shan Li、Peng-Gang Liu、Yin Luo、Jing Zhao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2009.07.046

  日期：2009.9.1

  synthase III (FabH) catalyzes the initial step of fatty acid biosynthesis via a type II fatty acid synthase in most bacteria. The important role of this essential enzyme combined with its unique structural features and ubiquitous occurrence in bacteria has made it an attractive new target for the development of antibacterial agents. We first used a structure-based approach to develop 18 novel chrysin analogues

  作为天然分布的黄酮，菊花素具有多种生物活性，包括抗癌，抗炎和抗菌活性。β-酮酰基-酰基载体蛋白合酶III（FabH）在大多数细菌中通过II型脂肪酸合酶催化脂肪酸生物合成的起始步骤。这种必不可少的酶的重要作用，加上其独特的结构特征和在细菌中的普遍存在，使其成为开发抗菌剂的有吸引力的新目标。我们首先使用基于结构的方法来开发针对FabH的18种新的菊花素类似物，以开发新的抗生素。基于结构的设计方法被用于扩展菊花链衍生物，包括分子对接和SAR研究。根据结果​​，3克）显示出与1.56-6.25微克/毫升的MIC的最有效的抗菌活性对测试细菌的污渍，和对接模拟进行到位置化合物3克到大肠埃希氏 杆菌的FabH活性位点，以确定可能的结合构象。该生物测定表明，化合物3克是的有效抑制剂E. 大肠杆菌的FabH如抗生素。
• Natural agent for treatment of gastrointestinal toxicity, associated symptoms and ulcers
  申请人：Rao Madusudana Janaswamy

  公开号：US20070213281A1

  公开（公告）日：2007-09-13

  The present invention relates to identification of Oroxylum indicum , Indian medicinal plant as a rich source for flavanoid compounds. Mucoprotective and antigastric ulcer properties in the flavone class of compounds isolated therefrom have been identified along with a flavanoids mixture in substantial yields from hexane and acetone extracts. The hexane extract was fractionated, purified and the compounds identified as Oroxylin A, Chrysin and Baicalein. The acetone extract was purified and the compounds obtained identified as methoxy chrysin, Oroxyloside methyl ester and chrysin-7-O-methyl glycoside.

  本发明涉及将印度药用植物印度酸枝鉴定为一种丰富的类黄酮化合物来源。从中分离出的黄酮类化合物中已确定具有粘膜保护和抗胃溃疡特性，同时还从己烷和丙酮提取物中获得了大量的类黄酮混合物。己烷提取物经过分级、纯化，鉴定出的化合物为千里光素A、槲皮素和黄芩素。丙酮提取物经过纯化，获得的化合物被鉴定为甲氧基黄芩素、千里光苷甲酯和黄芩-7-O-甲基糖苷。
• [EN] FLAVANOID COMPOUNDS AND PROCESS FOR PREPARATION THEREOF<br/>[FR] COMPOSÉS FLAVANOÏDES ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2010097816A1

  公开（公告）日：2010-09-02

  The present invention relates to flavanoid compounds of general formula (X1) wherein: R1 is selected from a group consisting of morpholinyl, N-methyl piperizinyl, piperidinyl and N,N'-dimethylamino groups, and n ranges from 3 to 6, and process for preparation thereof. The present invention relates to the demonstration of anti Helicobacter pylori activity and gastric antisecretory activity of semisynthetically designed flavonoid compounds, to be used for the prevention and treatment of gastroduodenal disorders in general and peptic ulcer diseases in particular. The present invention also relates to a hetero-dimeric bi-functional molecule that can be used as monotherapy substituting/replacing/overcoming currently used triple/quadruple therapy, thereby implicating/ anticipating/envisaging its commercial applicability.

  本发明涉及一般式为（X1）的黄酮类化合物，其中：R1从包括吗啡啶基、N-甲基哌嗪基、哌啶基和N,N'-二甲基氨基等基团中选择，n的范围为3至6，并涉及其制备方法。本发明涉及半合成设计的黄酮类化合物展示抗幽门螺杆菌活性和胃分泌抑制活性，可用于预防和治疗胃十二指肠疾病，特别是消化性溃疡。本发明还涉及一种异源二聚体双功能分子，可用作单疗法替代/取代/克服目前使用的三联/四联疗法，从而暗示/预期/设想其商业适用性。
• COMPOSITIONS AND METHODS FOR THE TREATMENT OF GASTROINTESTINAL INDICATIONS
  申请人：RAO Janaswamy Madusudana

  公开号：US20110059913A1

  公开（公告）日：2011-03-10

  The present invention relates to identification of Oroxylum indicum, Indian medicinal plant as a rich source for flavanoid compounds. Mucoprotective and antigastric ulcer properties in the flavone class of compounds isolated therefrom have been identified along with a flavanoids mixture in substantial yields from hexane and acetone extracts. The hexane extract was fractionated, purified and the compounds identified as Oroxylin A, Chrysin and Baicalein. The acetone extract was purified and the compounds obtained identified as methoxy chrysin, Oroxyloside methyl ester and chrysin-7-O-methyl glycoside.
• Flavanoid Compounds and Process for Preparation Thereof
  申请人：Dab Pratap Kumar

  公开号：US20120022062A1

  公开（公告）日：2012-01-26

  The present invention relates to flavanoid compounds of general formula (X 1 ) wherein: R 1 is selected from a group consisting of morpholinyl, N-methyl piperizinyl, piperidinyl and N,N′-dimethylamino groups, and n ranges from 3 to 6, and process for preparation thereof. The present invention relates to the demonstration of anti Helicobacter pylori activity and gastric antisecretory activity of semisynthetically designed flavonoid compounds, to be used for the prevention and treatment of gastroduodenal disorders in general and peptic ulcer diseases in particular. The present invention also relates to a hetero-dimeric bi-functional molecule that can be used as monotherapy substituting/replacing/overcoming currently used triple/quadruple therapy, thereby implicating/anticipating/envisaging its commercial applicability.