(Z)-3-(2,4-dihydroxyphenyl)-1-(4'-hydroxyphenyl)-2-propen-1-one | 83616-07-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-3-(2,4-dihydroxyphenyl)-1-(4'-hydroxyphenyl)-2-propen-1-one
• 英文别名: (Z)-3-(2,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one；isoliquiritigenin；(Z)-3-(2,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 83616-07-3
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: VDYSHUXENHRSOO-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2914501900

反应信息

• 作为反应物：
  描述：

  (Z)-3-(2,4-dihydroxyphenyl)-1-(4'-hydroxyphenyl)-2-propen-1-one 在 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 以 水 为溶剂， 生成 4',7-dihydroxyflavylium perchlorate
  参考文献：
  名称：

  水离子液体双相系统中4'，7-二羟基黄酮的热和光化学特性：写-读-擦除分子开关。

  摘要：

  DOI：

  10.1002/anie.200353131
• 作为产物：
  描述：

  1-苯基-3-(2,4,4-三羟基-1,5-环己二烯-1-基)-2-丙烯-1-酮 在 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 以 水 为溶剂， 生成 (Z)-3-(2,4-dihydroxyphenyl)-1-(4'-hydroxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  水离子液体双相系统中4'，7-二羟基黄酮的热和光化学特性：写-读-擦除分子开关。

  摘要：

  DOI：

  10.1002/anie.200353131

文献信息

• Hydroxychalcone inhibitors of Streptococcus mutans glucosyl transferases and biofilms as potential anticaries agents
  作者：Bhavitavya Nijampatnam、Luke Casals、Ruowen Zheng、Hui Wu、Sadanandan E. Velu

  DOI：10.1016/j.bmcl.2016.06.033

  日期：2016.8

  flavonols on S. mutans biofilms and have suggested the mechanism of action through their effect on S. mutans glucosyltransferases (Gtfs). These enzymes metabolize sucrose into water insoluble and soluble glucans, which are an integral measure of the dental caries pathogenesis. Numerous studies have shown that flavonols and polyphenols can inhibit Gtf and biofilm formation at millimolar concentrations. We have

  变形链球菌由于其形成顽强生物膜的强大能力，已被认为是龋齿发生和发展的主要病因。该疾病的理想疗法将旨在选择性地抑制生物膜形成过程，同时保留口腔的天然细菌菌群。多项研究证明了黄酮醇对变形链球菌生物膜的功效，并通过其对变形链球菌的作用提出了作用机制。葡萄糖基转移酶（Gtfs）。这些酶将蔗糖代谢为水不溶性和可溶性葡聚糖，这是龋齿发病机理的重要指标。大量研究表明，黄酮醇和多酚可以抑制毫摩尔浓度的Gtf和生物膜的形成。我们在变形链球菌生物膜测定中筛选了14种羟基黄酮，它们是黄酮醇的合成前体。这些化合物中的几种在低摩尔浓度下已成为生物膜抑制剂。在环A上含有3-OH基团的Chalcones表现出对生物膜抑制的选择性。此外，我们合成了铅化合物的6个其他类似物，并评估了它们对变形链球菌的潜在活性和选择性。生物膜。从这些研究中鉴定出的最具活性的化合物，对生物膜的IC 50值为44μM，对生长的MIC 50值为468μM，显示出对生物膜的选择性抑制>
• [EN] STREPTOCOCCUS MUTANS GLUCOSYL TRANSFERASE INHIBITORS FOR DENTAL CARIES THERAPY<br/>[FR] INHIBITEURS DE GLUCOSYLE TRANSFÉRASE DE STREPTOCOCCUS MUTANS POUR LA THÉRAPIE DES CARIES DENTAIRES
  申请人：UAB RESEARCH FOUNDATION

  公开号：WO2019195430A1

  公开（公告）日：2019-10-10

  The present invention is related to the inhibition of the formation of Streptococci biofilms through the inhibition of glucosyl transferase (Gtf). Compounds, compositions and methods for inhibiting Streptococcus biofilm formation, as well as for preventing, inhibiting and/or treating the formation of dental caries, and methods of identifying compounds that prevent, inhibit and/or treat the formation of dental caries are provided.

  本发明涉及通过抑制葡萄糖基转移酶(Gtf)来抑制链球菌生物膜形成的方法。提供了用于抑制链球菌生物膜形成的化合物、组合物和方法，以及用于预防、抑制和/或治疗龋齿形成的方法，以及用于识别能够预防、抑制和/或治疗龋齿形成的化合物的方法。
• Chalcones as positive allosteric modulators of α7 nicotinic acetylcholine receptors: A new target for a privileged structure
  作者：Beatriz Balsera、José Mulet、Asia Fernández-Carvajal、Roberto de la Torre-Martínez、Antonio Ferrer-Montiel、José G. Hernández-Jiménez、Judith Estévez-Herrera、Ricardo Borges、Andiara E. Freitas、Manuela G. López、M. Teresa García-López、Rosario González-Muñiz、María Jesús Pérez de Vega、Luis M. Valor、Lucie Svobodová、Salvador Sala、Francisco Sala、Manuel Criado

  DOI：10.1016/j.ejmech.2014.09.039

  日期：2014.10

  The alpha 7 acetylcholine nicotine receptor is a ligand-gated ion channel that is involved in cognition disorders, schizophrenia, pain and inflammation among other diseases. Therefore, the development of new agents that target this receptor has great significance. Positive allosteric modulators might be advantageous, since they facilitate receptor responses without directly interacting with the agonist binding site. Here we report the search for and further design of new positive allosteric modulators having the relatively simple chalcone structure. From the natural product isoliquiritigenin as starting point, chalcones substituted with hydroxyl groups at defined locations were identified as optimal and specific promoters of alpha 7 nicotinic function. The most potent compound (2,4,2',5'-tetrahydroxychalcone, 111) was further characterized showing its potential as neuroprotective, analgesic and cognitive enhancer, opening the way for future developments around the chalcone structure. (C) 2014 Elsevier Masson SAS. All rights reserved.
• STREPTOCOCCUS MUTANS GLUCOSYL TRANSFERASE INHIBITORS FOR DENTAL CARIES THERAPY
  申请人：UAB Research Foundation

  公开号：US20210115007A1

  公开（公告）日：2021-04-22

  The present invention is related to the inhibition of the formation of Streptococci biofilms through the inhibition of glucosyl transferase (Gtf). Compounds, compositions and methods for inhibiting Streptococcus biofilm formation, as well as for preventing, inhibiting and/or treating the formation of dental caries, and methods of identifying compounds that prevent, inhibit and/or treat the formation of dental caries are provided.