(E)-1-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one

• 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: (E)-1-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(4-Chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: IATZESCYNFYSEI-KRXBUXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one 在 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.75h， 生成 4-[5-(4-Chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid
  参考文献：
  名称：

  METHANOGEN INHIBITORS

  摘要：

  The present invention relates to a new class of methanogen inhibitors for ruminants. The invention also extends to the use of such compounds in ruminants to reduce methane production in the rumen and/or to enhance productivity in the ruminant.

  公开号：

  WO2024039250A1
• 作为产物：
  描述：

  异香兰素 、 对氯苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 (E)-1-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  研究一系列合成查耳酮对酵母白色念珠菌的取代基作用。

  摘要：

  合成了大量查耳酮，并研究了其对白色念珠菌的活性。SAR分析表明，抗真菌活性高度依赖于芳基环的取代方式，并在很大程度上与化合物与巯基相互作用的能力有关。最具活性的是羟基化查耳酮，因为它们的活性与芳基环B中酚基的位置有关，如下所示：o-OH> p-OH约为3,4-di-OH> m-OH。获得的这些相关性和其他相关性极大地有助于设计抗候选查耳酮。

  DOI：

  10.1016/j.ejmech.2006.08.012

文献信息

• [EN] PYRIMIDINONE DERIVATIVES AND USES THEREOF TO NEUTRALIZE THE BIOLOGICAL ACTIVITY OF CHEMOKINES<br/>[FR] DÉRIVÉS DE PYRIMIDINONE ET LEURS UTILISATIONS POUR NEUTRALISER L'ACTIVITÉ BIOLOGIQUE DES CHIMIOKINES
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENT - CNRS -

  公开号：WO2018011376A1

  公开（公告）日：2018-01-18

  A subject of the present invention is a compound having the general formula (I) a pharmaceutically acceptable salt thereof or a tautomeric form thereof, wherein A, B3, B4, B5, Y, X, B1 and B2 are as defined in any one of claims 1 to 10. Another subject of the invention is the compound as defined above for use as a medicament, in particular for preventing and/or treating inflammation and inflammatory diseases, immune and auto-immune diseases, pain related diseases, genetic diseases and/or cancer.

  本发明的一个主题是具有通式（I）的化合物，其药学上可接受的盐或其互变异构体，其中A、B3、B4、B5、Y、X、B1和B2如权利要求1至10中的任一所定义。本发明的另一个主题是上述定义的化合物作为药物的用途，特别用于预防和/或治疗炎症和炎症性疾病、免疫和自身免疫疾病、与疼痛有关的疾病、遗传疾病和/或癌症。
• Synthesis and biological evaluation of oleanolic acid derivative–chalcone conjugates as α-glucosidase inhibitors
  作者：Chu Tang、Linhui Zhu、Yu Chen、Rui Qin、ZhiNan Mei、Jing Xu、Guangzhong Yang

  DOI：10.1039/c3ra46492j

  日期：——

  α-Glucosidase is a promising target for the treatment of obesity and diabetes mellitus. A series of oleanolic acid derivative–chalcone conjugates were designed and synthesized as α-glucosidase inhibitors. Their structures were determined by spectroscopic analysis and their α-glucosidase inhibitory activities were investigated in vitro. Most conjugates exhibited moderate inhibitory activity against

  α-葡萄糖苷酶是治疗肥胖症和糖尿病的有希望的靶标。设计并合成了一系列齐墩果酸衍生物-查耳酮共轭物，作为α-葡萄糖苷酶抑制剂。通过光谱分析确定其结构，并在体外研究其对α-葡萄糖苷酶的抑制活性。大多数缀合物对α-葡萄糖苷酶表现出中等的抑制活性。其中，缀合物1b（IC 50= 3.2±0.2μM）具有最强的α-葡萄糖苷酶抑制活性，初步的构效关系表明，缀合物查尔酮单元中的呋喃环或噻吩环具有增强活性的趋势。Lineweaver-Burk图分析表明1b，6b，5c和4d竞争性抑制了α-葡萄糖苷酶的活性。它们的抑制常数（K i）分别为16.6、29.3、14.6和20.6μM。结合物和α-葡萄糖苷酶之间的相互作用力是氢键和范德华力。
• Pyrimidinone derivatives and uses thereof to neutralize the biological activity of chemokines
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：US11046657B2

  公开（公告）日：2021-06-29

  A subject of the present invention is a compound having the general formula (I): a pharmaceutically acceptable salt thereof or a tautomeric form thereof, wherein A, B3, B4, B5, Y, X, B1 and B2 are as defined in any one of claims 1 to 10. Another subject of the invention is the compound as defined above for use as a medicament, in particular for preventing and/or treating inflammation and inflammatory diseases, immune and auto-immune diseases, pain related diseases, genetic diseases and/or cancer.

  本发明的一个主题是具有通式 (I) 的化合物： 其药学上可接受的盐或其同分异构体、 其中 A、B3、B4、B5、Y、X、B1 和 B2 如权利要求 1 至 10 中任一项所定义。 本发明的另一个主题是上文定义的化合物，可用作药物，特别是用于预防和/或治疗炎症和炎症性疾病、免疫和自身免疫性疾病、疼痛相关疾病、遗传性疾病和/或癌症。
• Synthesis and anticancer activity of chalcones derived from vanillin and isovanillin
  作者：Saiharish Raghavan、Prasath Manogaran、Balasubramanian Kalpattu Kuppuswami、Ganesh Venkatraman、Krishna Kumari Gadepalli Narasimha

  DOI：10.1007/s00044-015-1453-2

  日期：2015.12

  An array of chalcones from vanillin/isovanillin and differently substituted acetophenones were synthesized and assessed for their anticancer activity against A549, MCF7 and MIA PaCa-2 cell lines using MTT assay. Some of the chalcones exhibited good anticancer activity with IC50 values below 10 mu M. Compound 5f with IC50 values 5.4 +/- A 0.7, 10.45 +/- A 2.15 and 13.0 +/- A 1.68 A mu M on MIA PaCa-2, A549 and MCF7, respectively, was more potent than curcumin and hence was analyzed for changes in cell morphology, inhibition of cell migration, mechanism of cell death and arrest of cell cycle progression on MIA PaCa-2 cells.
• Antifungal activity of chalcones: A mechanistic study using various yeast strains
  作者：K.L. Lahtchev、D.I. Batovska、St.P. Parushev、V.M. Ubiyvovk、A.A. Sibirny

  DOI：10.1016/j.ejmech.2007.12.027

  日期：2008.10

  We reported the synthesis, antifungal evaluation and study on substituent effects of 21 chalcones. A lot of genetically defined strains belonging to different yeast genera and species, namely Saccharomyces cerevisiae, Hansenula polymorpha and Kluyveromyces lactis, were used as test organisms. Concerning the mode of the antifungal action of chalcones it was shown that DNA was probably not the main target for the chalcones. It was revealed that the yeast's intracellular glutathione and cysteine molecules play significant role as defence barrier against the chalcone action. It was also shown that chalcones may react with some proteins involved in cell separation. (C) 2008 Elsevier Masson SAS. All fights reserved.