1-(2-furyl)-3-(3,5-trimethoxyphenyl)prop-2-en-1-one | 105686-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-furyl)-3-(3,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(Furan-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 105686-93-9
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: RJHRFPAQAZJXDX-UHFFFAOYSA-N

物化性质

• 熔点：
  154 °C
• 沸点：
  429.9±45.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-磺酰胺基苯肼盐酸盐 、 1-(2-furyl)-3-(3,5-trimethoxyphenyl)prop-2-en-1-one 以 乙醇 为溶剂， 反应 36.0h， 以62%的产率得到4-[3-furan-2-yl-5-(3,4,5-trimethoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-benzenesulfonamide
  参考文献：
  名称：

  Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1,3,5-triarylpyrazoline and 1,5-diarylpyrazole derivatives as selective COX-2 inhibitors

  摘要：

  Two new series of 1,3,5-triarylpyrazolines 10a-m and 1,5-diarylpyrazoles 14a-d were synthesized. All prepared compounds were evaluated for their in vitro COX-1/COX-2 inhibitory activity and the in vivo anti-inflammatory activity. All compounds were more selective for COX-2 isozyme and showed good in vivo anti-inflammatory activity. Compound 10k was the most COX-2 selective compound (S.I. = 5.91) and the most potent anti-inflammatory derivative (ED50 = 99 mu mol/kg) which is approximately five folds more potent than ibuprofen (ED50 = 499 mu mol/kg) and had half potency of celecoxib (ED50 = 47 mu mol/kg). All compounds were less ulcerogenic (Ulcer Indexes = 1.20-5.00) than ibuprofen (Ulcer Index = 20.25) and comparable to celecoxib (Ulcer Index = 2.90). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.105
• 作为产物：
  描述：

  2-乙酰基呋喃 、 3,4,5-三甲氧基苯甲醛 以 甲醇 为溶剂， 生成 1-(2-furyl)-3-(3,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  具有甲磺酰基药效团的新型 1,3,5-三芳基吡唑啉衍生物的合成、环氧合酶抑制、抗炎评价和致溃疡性

  摘要：

  合成了一系列新的 1,3,5-三芳基吡唑啉 13a-l，并评估了所有制备的化合物的体外 COX-1/COX-2 抑制活性和体内抗炎活性。所有测试化合物对 COX-2 同工酶的选择性更高，并显示出良好的体内抗炎活性。与塞来昔布（COX-2 SI = 9.29 和ED50 = 81.4 µmol/kg)。与阿司匹林 (UI = 2.33) 相比，所有筛选化合物的致溃疡性 (溃疡指数 (UI) = 0.33–1.33) 均低于塞来昔布 (UI = 0.33)。

  DOI：

  10.1002/ardp.201600145

文献信息

• Synthesis and biological evaluation of naphthalene, furan and pyrrole based chalcones as cytotoxic and antimicrobial agents
  作者：Abhishek Budhiraja、Kanika Kadian、Mandeep Kaur、Vikas Aggarwal、Atul Garg、Sameer Sapra、Kunal Nepali、O. P. Suri、K. L. Dhar

  DOI：10.1007/s00044-011-9733-y

  日期：2012.9

  but in the present study we report the reactions of 1-acetylnaphthalene, 2-acetylfuran and 2-acetylpyrrole with aldehydes, thus getting compounds akin to chalcones. 31 analogues have been synthesised and evaluated for cytotoxic potential against PC-3, OVCAR, IMR-32 and HEP-2. Compound 9 was found to be the most cytotoxic with inhibition ranging from 72 to 88% against the cell lines employed. The synthetics

  摘要查耳酮是一种芳香族酮，可形成多种重要生物化合物（统称为查耳酮）的核心。它们显示出抗菌，抗真菌，抗肿瘤和抗炎特性，并且是类黄酮生物合成的中间体，类黄酮是植物中广泛存在的具有一系列生物活性的物质。这些联芳基丙烯酮对几种癌细胞显示出强力毒性，并在其秋水仙碱结合位点与微管蛋白相互作用。微管蛋白结合分子干扰微管的动态不稳定性，从而破坏微管，诱导细胞周期停滞在M期，形成异常纺锤体并最终导致凋亡性细胞死亡。基本上，Chalcones由C 6 –C 3 –C 6组成单位，但在本研究中，我们报道了1-乙酰基萘，2-乙酰基呋喃和2-乙酰基吡咯与醛的反应，从而得到类似于查耳酮的化合物。已合成了31种类似物，并评估了其对PC-3，OVCAR，IMR-32和HEP-2的细胞毒性。发现化合物9对细胞毒性最大，对所用细胞系的抑制作用范围为72％至88％。还评估了合成物的抗菌活性，发现化合物25最有效。 图形概要合成
• 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。
• 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 .
• Singhal, R. K.; Mishra, Naresh K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 1079 - 1080
  作者：Singhal, R. K.、Mishra, Naresh K.

  DOI：——

  日期：——
• Synthesis, Cyclooxygenase Inhibition, Anti-Inflammatory Evaluation, and Ulcerogenic Liability of New 1,3,5-Triarylpyrazoline Derivatives Possessing a Methanesulfonyl Pharmacophore
  作者：Khaled R. A. Abdellatif、Wael A. A. Fadaly、Amany A. Azouz

  DOI：10.1002/ardp.201600145

  日期：2016.10

  A new series of 1,3,5‐triarylpyrazolines 13a–l was synthesized and all prepared compounds were evaluated for their in vitro COX‐1/COX‐2 inhibitory activity and in vivo anti‐inflammatory activity. All test compounds were more selective for the COX‐2 isozyme and showed good in vivo anti‐inflammatory activity. Compound 13h was the most COX‐2 selective compound (COX‐2 selectivity index (SI) = 10.23) and

  合成了一系列新的 1,3,5-三芳基吡唑啉 13a-l，并评估了所有制备的化合物的体外 COX-1/COX-2 抑制活性和体内抗炎活性。所有测试化合物对 COX-2 同工酶的选择性更高，并显示出良好的体内抗炎活性。与塞来昔布（COX-2 SI = 9.29 和ED50 = 81.4 µmol/kg)。与阿司匹林 (UI = 2.33) 相比，所有筛选化合物的致溃疡性 (溃疡指数 (UI) = 0.33–1.33) 均低于塞来昔布 (UI = 0.33)。