1-furan-2-yl-3-pyridin-4-ylpropenone | 41220-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-furan-2-yl-3-pyridin-4-ylpropenone
• 英文别名: 1-furan-2-yl-3-pyridin-4-yl-propenone；2-Furyl-3-(4-pyridyl)-2-propene-1-one；1-(furan-2-yl)-3-pyridin-4-ylprop-2-en-1-one
• CAS: 41220-21-7
• 化学式: C₁₂H₉NO₂
• 分子量: 199.209
• InChiKey: GDDOEQSZYMBMAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 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：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-furan-2-yl-3-pyridin-4-ylpropenone 、 4-磺酰胺基苯肼盐酸盐 以 乙醇 为溶剂， 反应 36.0h， 以43%的产率得到4-[N'-(1-furan-2-yl-3-pyridin-4-yl-allylidene)-hydrazino]-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：

  4-吡啶甲醛 、 2-乙酰基呋喃 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 1-furan-2-yl-3-pyridin-4-ylpropenone
  参考文献：
  名称：

  设计和合成1-乙酰-3,5-二芳基-4,5-二氢（1 H）吡唑类化合物作为一种新型的潜在非嘌呤黄嘌呤氧化酶抑制剂的合理方法

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2011.01.058

文献信息

• Calcium uptake inhibitors
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05500429A1

  公开（公告）日：1996-03-19

  This invention relates to 1-aryl-3-pyridinyl-2-propene-1-ones, the use of these compounds as calcium uptake inhibitors in leukocytes and thrombocytes, and pharmaceutical compositions containing these compounds as active ingredients, and the process of their preparation.

  本发明涉及1-芳基-3-吡啶基-2-丙烯基-1-酮类化合物，这些化合物作为白细胞和血小板中钙离子吸收抑制剂的用途，以及含有这些化合物作为活性成分的药物组合物，以及它们的制备过程。
• Substituted pyrimidinone and pyridone compounds and methods of use
  申请人：Amgen Inc.

  公开号：US06096753A1

  公开（公告）日：2000-08-01

  Selected novel substituted pyrimidinone and pyridone compounds are effective for prophylaxis and treatment of diseases, such as TNF-.alpha., IL-1.beta., IL-6 and/or IL-8 mediated diseases, and other maladies, such as pain and diabetes. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving inflammation, pain, diabetes and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  选择的新型取代嘧啶酮和吡啶酮化合物可用于预防和治疗TNF-.alpha.、IL-1.beta.、IL-6和/或IL-8介导的疾病，以及其他疾病，如疼痛和糖尿病。本发明涵盖了新型化合物、类似物、前药及其药学上可接受的盐、药物组合物以及用于预防和治疗涉及炎症、疼痛、糖尿病等疾病和其他疾病或病情的方法。本发明还涉及制备这种化合物的方法以及在这些过程中有用的中间体。
• Synthesis, cyclooxygenase inhibition, and anti-inflammatory evaluation of novel diarylheterocycles with a central pyrazole, pyrazoline, or pyridine ring
  作者：Khaled R. A. Abdellatif、Eman K. A. Abdelall、Wael A. A. Fadaly、Gehan M. Kamel

  DOI：10.1007/s00044-015-1327-7

  日期：2015.6

  Five groups of diarylheterocycles with a central pyrazole ring (12a-d), pyrazoline ring (14a-d), or pyridine ring (15a-d, 16a-d and 17a-d) were synthesized and evaluated in vitro for COX-1/COX-2 inhibitory activity and in vivo for anti-inflammatory activity. All compounds that possessed anti-inflammatory activity were assessed for their ulcerogenic liability in comparison with ibuprofen and celecoxib. The pyrazole derivative 12b and the pyrazoline derivative 14b were the least ulcerogenic compounds with relative ulcerogenicities to celecoxib 0.85 and 0.90 respectively.[GRAPHICS].
• 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, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1,3,5-triarylpyrazoline and 1,5-diarylpyrazole derivatives as selective COX-2 inhibitors
  作者：Khaled R.A. Abdellatif、Eman K.A. Abdelall、Wael A.A. Fadaly、Gehan M. Kamel

  DOI：10.1016/j.bmcl.2015.11.105

  日期：2016.1

  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.