3-(furan-2-yl)-1-(3-hydroxyphenyl)prop-2-en-1-one | 24089-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(furan-2-yl)-1-(3-hydroxyphenyl)prop-2-en-1-one
• 英文别名: 3-(furan-2-yl)-1-(3-hydroxyphenyl)propenone；3-(Furan-2-yl)-1-(3-hydroxyphenyl)prop-2-en-1-one
• CAS: 24089-96-1
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: HQVKSSBNWSCWHD-UHFFFAOYSA-N

物化性质

• 沸点：
  396.9±42.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 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：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(furan-2-yl)-1-(3-hydroxyphenyl)prop-2-en-1-one 、 1-[2-(4-chloro-phenyl)-2-oxo-ethyl]-pyridinium iodide 在 ammonium acetate 、 溶剂黄146 作用下， 以73.5%的产率得到3-(6-(4-chlorophenyl)-4-(furan-2-yl)pyridin-2-yl)phenol
  参考文献：
  名称：

  一系列新的2-酚-4-芳基-6-氯苯基吡啶衍生物作为双拓扑异构酶I / II抑制剂：合成，生物学评估和3D-QSAR研究

  摘要：

  为了不断开发新型抗肿瘤药，我们合成了一系列新的四十五种2-苯酚-4-芳基-6-氯苯基吡啶化合物，并评估了其对四种不同的人类癌细胞系（DU145，HCT15，T47D，和HeLa），以及拓扑异构酶I和II的抑制活性。几种化合物（10 - 15，20，22，24，28，42，和49）表现出强烈的，中度双拓扑异构酶I，并在100μMII抑制活性。观察到间位或对位的羟基和氯部分苯环的位置有利于双重拓扑异构酶的抑制活性和细胞毒性。与所有针对HCT15和T47D细胞系的阳性对照相比，大多数化合物显示出更强的细胞毒性。为了研究结构-活性关系，进行了使用比较分子场分析（CoMFA）方法的3D-QSAR分析。生成的3D等高线图可用于进一步合理设计新型三联吡啶衍生物，作为高度选择性和有效的细胞毒剂。

  DOI：

  10.1016/j.ejmech.2016.02.050
• 作为产物：
  描述：

  糠醛 、 3-羟基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以93.4%的产率得到3-(furan-2-yl)-1-(3-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  一系列新的2-酚-4-芳基-6-氯苯基吡啶衍生物作为双拓扑异构酶I / II抑制剂：合成，生物学评估和3D-QSAR研究

  摘要：

  为了不断开发新型抗肿瘤药，我们合成了一系列新的四十五种2-苯酚-4-芳基-6-氯苯基吡啶化合物，并评估了其对四种不同的人类癌细胞系（DU145，HCT15，T47D，和HeLa），以及拓扑异构酶I和II的抑制活性。几种化合物（10 - 15，20，22，24，28，42，和49）表现出强烈的，中度双拓扑异构酶I，并在100μMII抑制活性。观察到间位或对位的羟基和氯部分苯环的位置有利于双重拓扑异构酶的抑制活性和细胞毒性。与所有针对HCT15和T47D细胞系的阳性对照相比，大多数化合物显示出更强的细胞毒性。为了研究结构-活性关系，进行了使用比较分子场分析（CoMFA）方法的3D-QSAR分析。生成的3D等高线图可用于进一步合理设计新型三联吡啶衍生物，作为高度选择性和有效的细胞毒剂。

  DOI：

  10.1016/j.ejmech.2016.02.050

文献信息

• Silica-supported heterogeneous catalysts-mediated synthesis of chalcones as potent urease inhibitors: in vitro and molecular docking studies
  作者：Aeysha Sultan、Shanavas Shajahan、Tansir Ahamad、Saad M. Alshehri、Noreen Sajjad、Mehr-un-Nisa、Mian Habib Ur Rehman、Lokman Torun、Muhammad Khalid、Roberto Acevedo

  DOI：10.1007/s00706-019-02534-z

  日期：2020.1

  potent urease inhibition activity. The chalcone 3-(3-hydroxyphenyl)-1-phenylpropenone was found to be the most potent with percentage inhibition 86.17 ± 0.89 and half maximal inhibitory concentration (IC50) value 11.51 ± 0.03 µM. The molecular docking study emphasized that the same congeners 3-(furan-2-yl)-1-(4-hydroxyphenyl)propenone, 3-(4-hydroxyphenyl)-1-(4-methoxyphenyl)propanone, and 3-[4-(dim

  摘要我们在此报告了二氧化硅负载的异质催化剂介导的查耳酮合成的简便且高产率的方案。还提供了我们的合成结果与常规合成方案的比较，以评估所制备催化剂的效率。对新合成的化合物作为脲酶抑制剂进行了生物学评估。发现大多数化合物具有有效的脲酶抑制活性。发现查尔酮3-（3-羟苯基）-1-苯基丙烯酮最有效，抑制百分比为86.17±0.89，最大抑制浓度为一半（IC 50）值11.51±0.03 µM。分子对接研究强调相同的同类物3-（呋喃-2-基）-1-（4-羟苯基）丙酮，3-（4-羟苯基）-1-（4-甲氧基苯基）丙酮和3- [4 -（（二甲氨基）苯基] -1-（对甲苯基）丙酮对脲酶显示出非常好的抑制潜力，并显示出更高的对接得分5718、5940、5596和ACE--246.66，-244.79和-243.06 kJ / mol，分别比对照配体。 图形摘要
• Synthesis and Biological Evaluation of Furan-chalcone Derivatives as Protein Tyrosine Phosphatase Inhibitors
  作者：Liang-Peng Sun、Zhe Jiang、Li-Xin Gao、Li Sheng、Ying-Chun Quan、Jia Li、Hu-Ri Piao

  DOI：10.5012/bkcs.2013.34.4.1023

  日期：2013.4.20
• Synthesis and pharmacological evaluation of some novel 2-pyrazolines bearing benzenesulfonamide as anti-inflammatory and blood glucose lowering agents
  作者：Syed Ovais、Rafia Bashir、Shafiya Yaseen、Pooja Rathore、Mohammed Samim、Kalim Javed

  DOI：10.1007/s00044-012-0130-y

  日期：2013.3

  A series of novel pyrazolines (2a-l) bearing benzenesulfonamide moiety were synthesized by condensing appropriate chalcone (1a-l) with 4-hydrazinobenzenesulfonamide hydrochloride. Structure of all novel synthesized compounds was characterized on basis of elemental analysis data and spectral data (IR, (HNMR)-H-1, MS). Compounds (2a-l) were screened for in vivo anti-inflammatory action in carrageenan-induced rat paw edema model and blood glucose lowering action in glucose fed hyperglycemic normal rats. Compounds 2a, 2e, and 2l showed significant anti-inflammatory action (more than 75 %) at 5 h and also showed superior gastrointestinal safety profiles as compared to celecoxib. One compound (2i) was found to exhibit significant blood glucose lowering activity.
• Topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship study of dihydroxylated 2,6-diphenyl-4-aryl pyridines
  作者：Radha Karki、Chanju Song、Tara Man Kadayat、Til Bahadur Thapa Magar、Ganesh Bist、Aarajana Shrestha、Younghwa Na、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.bmc.2015.04.002

  日期：2015.7

  A new series of thirty-six dihydroxylated 2,6-diphenyl-4-aryl pyridines containing hydroxyl groups at the ortho, meta, or para position of 2- and 6-phenyl rings attached to the central pyridine were designed and synthesized. They were evaluated for topoisomerase I and II inhibitory activity and cytotoxicity against several human cancer cell lines for the development of novel anticancer agents. Most of the compounds with hydroxyl moiety either at the meta or para position of 2- or 6-phenyl ring in combination with thienyl or furyl group at 4-position of central pyridine displayed significant topoisomerase II inhibitory activity and cytotoxicity. Positive correlation between topoisomerase II inhibitory activity and cytotoxicity was observed for the compounds 9-11, 15-17, 19, 21-23, 28, and 41. Among all the synthesized compounds, compound 17 emerged as the most promising topoisomerase II inhibitor with significant cytotoxicity. (C) 2015 Elsevier Ltd. All rights reserved.
• [EN] NOVEL COMPOUND, AND COMPOSITION FOR PREVENTING OR TREATING HER2-POSITIVE CANCER, COMPRISING SAME<br/>[FR] NOUVEAU COMPOSÉ ET COMPOSITION POUR PRÉVENIR OU TRAITER LE CANCER HER2-POSITIF LE COMPRENANT<br/>[KO] 신규 화합물 및 이를 포함하는 HER2 양성 암 예방 또는 치료용 조성물
  申请人：[en]EWHA UNIVERSITY - INDUSTRY COLLABORATION FOUNDATION;[ko]이화여자대학교 산학협력단

  公开号：WO2024035085A1

  公开（公告）日：2024-02-15

  본 발명은 신규 화합물 및 이를 포함하는 HER2 양성 암 예방 또는 치료용 조성물에 관한 것이다. 본 발명 신규 화합물은 ELF3와 MED23의 단백질-단백질 상호작용을 억제하여 HER2의 수준을 억제할 수 있으며, 이를 통해 현저한 수준의 항암 효과를 가진다. 더욱이 기존에 암 치료제로 임상에서 사용하는 트라스트주맙에 내성을 가지는 경우에도 본 발명의 신규 화합물을 처리했을 때, 현저한 수준의 항암효과를 보여주었다. 따라서, 본 발명의 신규 화합물은 암 치료 분야에서 폭넓게 활용될 수 있을 것으로 예상된다.