1-(呋喃-2-基)-3-(3-羟基苯基)丙-2-烯-1-酮 | 105904-51-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 1-(呋喃-2-基)-3-(3-羟基苯基)丙-2-烯-1-酮
• 中文别名: 2-丙烯-1-酮,1-(2-呋喃基)-3-(3-羟基苯基)-
• 英文名称: 1-(furan-2-yl)-3-(3-hydroxyphenyl)prop-2-en-1-one
• CAS: 105904-51-6
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: ZNRZXBKRQBQRRO-UHFFFAOYSA-N

物化性质

• 熔点：
  144.5-146 °C(Solv: benzene (71-43-2))
• 沸点：
  396.7±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：

  1-(呋喃-2-基)-3-(3-羟基苯基)丙-2-烯-1-酮 、 溶剂黄146 在 一水合肼 作用下， 反应 3.0h， 生成 1-[3-(furan-2-yl)-4,5-dihydro-5-(3-hydroxyphenyl)pyrazol-1-yl]ethanone
  参考文献：
  名称：

  Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones

  摘要：

  Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C-6-C-3-C-6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines.All the synthesized compounds were evaluated for in vitro cytotoxicity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Compound 68 was found to be the most potent showing broad spectrum of cytotoxicity against all the cell lines .

  DOI：

  10.1007/s00044-011-9824-9
• 作为产物：
  描述：

  3-(tetrahydro-2H-2-pyranyloxy)benzaldehyde 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 1-(呋喃-2-基)-3-(3-羟基苯基)丙-2-烯-1-酮
  参考文献：
  名称：

  Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent

  摘要：

  In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-gamma/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r (2) = 0.989 and a good cross validated value, q (2) = 0.583.

  DOI：

  10.1007/s00044-011-9706-1

文献信息

• Thieny/Furanyl-hydroxyphenylpropenones as Inhibitors of LPS-induced ROS and NO Production in RAW 264.7 Macrophages, and Their Structure-Activity Relationship Study
  作者：Tara Man Kadayat、Mi Jin Kim、Tae-Gyu Nam、Pil-Hoon Park、Eung-Seok Lee

  DOI：10.5012/bkcs.2014.35.8.2481

  日期：2014.8.20

  Twelve thienyl/furanyl-hydroxyphenylpropenones were systematically designed and synthesized, and evaluated for their inhibitory effect on LPS-induced ROS and NO production in RAW 264.7 macrophages. Compound 11 displayed the most significant inhibitory activity of LPS-induced ROS and NO production in RAW 264.7 macrophages. Structure-activity relationship study indicated that para-hydroxyphenyl moiety plays an important role for inhibitory activities on both LPS-induced ROS and NO production as well as 3-thienyl moiety on molecule.

  系统设计并合成了十二种噻吩/呋喃羟基苯丙烯酮，并评估其对LPS诱导的RAW 264.7巨噬细胞中ROS和NO产生的抑制作用。化合物11在抑制LPS诱导的RAW 264.7巨噬细胞中ROS和NO产生方面表现出最显著的抑制活性。结构-活性关系研究表明，para-羟基苯基部分在抑制LPS诱导的ROS和NO产生方面起着重要作用，而分子中的3-噻吩部分也同样关键。
• A rational approach for the design and synthesis of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles as a new class of potential non-purine xanthine oxidase inhibitors
  作者：Kunal Nepali、Gurinderdeep Singh、Anil Turan、Amit Agarwal、Sameer Sapra、Raj Kumar、Uttam C. Banerjee、Prabhakar K. Verma、Naresh K. Satti、Manish K. Gupta、Om P. Suri、K.L. Dhar

  DOI：10.1016/j.bmc.2011.01.058

  日期：2011.3

  Xanthine oxidase is a complex molybdoflavoprotein that catalyses the hydroxylation of xanthine to uric acid. Fifty three analogues of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles were rationally designed and synthesized and evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Some notions about structure activity relationships are presented. Six compounds 41, 42, 44, 46,

  黄嘌呤氧化酶是一种复杂的钼黄素蛋白，可催化黄嘌呤羟化为尿酸。合理设计和合成了1-乙酰基3,5-二芳基-4,5-二氢（1 H）吡唑的53种类似物，并首次评估了其体外黄嘌呤氧化酶抑制活性。提出了有关结构活动关系的一些概念。六种化合物41，42，44，46，55和59被认为是最有效对抗XO带IC 50范围为5.3μM至15.2μM。化合物59成为最有效的XO抑制剂（IC 50 = 5.3μM）。通过分子模拟已经确定了59与XO活性位点氨基酸残基的一些重要相互作用。
• Synthesis and Evaluation of Chalcone Derivatives as Inhibitors of Neutrophils' Chemotaxis, Phagocytosis and Production of Reactive Oxygen Species
  作者：Syed N. A. Bukhari、Yasmin Tajuddin、Vannessa J. Benedict、Kok W. Lam、Ibrahim Jantan、Juriyati Jalil、Malina Jasamai

  DOI：10.1111/cbdd.12226

  日期：2014.2

  Inhibitory effects on neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species (ROS) are among the important targets in developing anti‐inflammatory agents and immunosuppressants. Eight series of chalcone derivatives including five newly synthesized series were assessed for their inhibitory effects on chemotaxis, phagocytosis and ROS production in human polymorphonuclear neutrophils (PMNs). Inhibition of PMNs' chemotaxis and phagocytosis abilities were investigated using the Boyden chamber technique and the Phagotest kit, respectively, while ROS production was evaluated using luminol‐ and lucigenin‐based chemiluminescence assay. The new derivatives (4d and 8d), which contain 4‐methylaminoethanol functional group were active in all the assays performed. It was also observed that some of the compounds were active in inhibiting chemotaxis while others suppressed phagocytosis and ROS production. The information obtained gave new insight into chalcone derivatives with the potential to be developed as immunomodulators.
• Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones
  作者：Kunal Nepali、Kanika Kadian、Ritu Ojha、Rajni Dhiman、Atul Garg、Gagandip Singh、Abhishek Buddhiraja、Preet Mohinder Singh Bedi、Kanaya Lal Dhar

  DOI：10.1007/s00044-011-9824-9

  日期：2012.10

  Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C-6-C-3-C-6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines.All the synthesized compounds were evaluated for in vitro cytotoxicity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Compound 68 was found to be the most potent showing broad spectrum of cytotoxicity against all the cell lines .
• Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent
  作者：Kok Wai Lam、Reaz Uddin、Choi Yi Liew、Chau Ling Tham、Daud A. Israf、Ahmad Syahida、Mohd. Basyaruddin Abdul Rahman、Zaheer Ul-Haq、Nordin H. Lajis

  DOI：10.1007/s00044-011-9706-1

  日期：2012.8

  In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-gamma/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r (2) = 0.989 and a good cross validated value, q (2) = 0.583.