4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid | 501421-94-9

• 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: 4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid
• 英文别名: 4-benzoyl-1-(3-nitrophenyl)-5-phenylpyrazole-3-carboxylic acid
• CAS: 501421-94-9
• 化学式: C₂₃H₁₅N₃O₅
• 分子量: 413.389
• InChiKey: UYVNKYQBCMCHNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid 在 氯化亚砜 作用下， 反应 5.0h， 以65%的产率得到4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride
  参考文献：
  名称：

  环状草酰化合物与肼或的反应研究：4-苯甲酰基-1-（3-硝基苯基）-5-苯基-1H-吡唑-3-羧酸的合成与反应

  摘要：

  由呋喃-2,3-二酮1和N-苄叉基-N '-（3-硝基苯基）肼制得的1 H-吡唑-3-羧酸2通过其酰氯3与各种醇的反应而转化。或N-亲核试剂分别变成相应的酯或酰胺衍生物4或5。腈6和苯胺基吡唑酸7个的衍生物2也通过脱水而获得图5A中的SOCl的混合物2用DMF和减少2与多硫化钠分别。而环缩合反应2或7与苯基肼或水合肼和6与仅无水肼分别导致吡唑并[3,4- d ]-哒嗪酮8和吡唑并[3,4- d ]哒嗪胺9的衍生物。2与2-肼基吡啶并reaction反应生成并吡唑酸衍生物10，将其脱羧得到to并吡唑衍生物11。吡唑并[4,3- d ]恶嗪酮12和2-喹啉基吡唑并[3,4- d ]哒嗪13衍生物也通过环戊二烯的缩合反应制备。分别与盐酸羟胺和乙醛分别为2和7。

  DOI：

  10.1002/jhet.5570390503
• 作为产物：
  描述：

  4-benzoyl-5-phenyl-furan-2,3-dione 、 benzaldehyde p-nitrophenylhydrazone 反应 1.0h， 以55%的产率得到4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  环状草酰化合物与肼或的反应研究：4-苯甲酰基-1-（3-硝基苯基）-5-苯基-1H-吡唑-3-羧酸的合成与反应

  摘要：

  由呋喃-2,3-二酮1和N-苄叉基-N '-（3-硝基苯基）肼制得的1 H-吡唑-3-羧酸2通过其酰氯3与各种醇的反应而转化。或N-亲核试剂分别变成相应的酯或酰胺衍生物4或5。腈6和苯胺基吡唑酸7个的衍生物2也通过脱水而获得图5A中的SOCl的混合物2用DMF和减少2与多硫化钠分别。而环缩合反应2或7与苯基肼或水合肼和6与仅无水肼分别导致吡唑并[3,4- d ]-哒嗪酮8和吡唑并[3,4- d ]哒嗪胺9的衍生物。2与2-肼基吡啶并reaction反应生成并吡唑酸衍生物10，将其脱羧得到to并吡唑衍生物11。吡唑并[4,3- d ]恶嗪酮12和2-喹啉基吡唑并[3,4- d ]哒嗪13衍生物也通过环戊二烯的缩合反应制备。分别与盐酸羟胺和乙醛分别为2和7。

  DOI：

  10.1002/jhet.5570390503

文献信息

• Effects of new 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives on human carbonic anhydrase isozymes
  作者：Rahmi Kasımoğulları、Metin Bülbül、Hatice Günhan、Hülya Güleryüz

  DOI：10.1016/j.bmc.2009.03.048

  日期：2009.5

  Pyrazole carboxylic acid amides of 5-amino-1,3,4-thiadiazole-2-sulfonamide 1 (inhibitor 1) were synthesized from 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride and 4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride compounds. Human carbonic anhydrase isoenzymes (hCA-I and hCA-II) were purified from erythrocyte cells by the affinity chromatography. The inhibitory effects of inhibitor 1, acetazolamide (AAZ), and of 16 newly synthesized amides (8-11, 12a-f, 13a-c, 14a-b, and 15) on hydratase and esterase activities of these isoenzymes have been studied in vitro. The average IC50 values of the new compounds (8-11,12a-f, 13a-c, 14a-b, and 15) for hydratase activity ranged from 3.25 to 4.75 mu M for hCA-I and from 0.055 to 2.6 mu M for hCA-II. The mean IC50 values of the same inhibitors for esterase activity were in the range of 2.7-6.6 mu M for hCA-I ( with the exception of inhibitor 10, which did not inhibit the esterase activity of hCA-I) and of 0.013-4.2 mu M for hCA-II. The K-i values for new compounds (8-11, 12a-f, 13a-c, 14a-b, and 15) were observed well below that of the parent compound inhibitor 1 and were also comparable to that of AAZ under the same experimental conditions. The comparison of newly synthesized amides to inhibitor 1 and to AAZ indicated that the new derivatives preferentially inhibit hCA-II and are more potent inhibitors of hCA-II than the parent inhibitor 1 and AAZ. (C) 2009 Elsevier Ltd. All rights reserved.
• Kasimoʇullari, Rahmi; Maden, Makbule; Yaglioglu, Ayse Sahin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 9, p. 1134 - 1139
  作者：Kasimoʇullari, Rahmi、Maden, Makbule、Yaglioglu, Ayse Sahin、Mert, Samet、Demirtaş, Ibrahim

  DOI：——

  日期：——
• Design, synthesis, characterization, and antiproliferative activity of novel pyrazole-3-carboxylic acid derivatives
  作者：Rahmi Kasımoğulları、Hamdiye Duran、Ayşe Şahin Yağlıoğlu、Samet Mert、İbrahim Demirtaş

  DOI：10.1007/s00706-015-1450-7

  日期：2015.10

  In this study several novel 4-substituted-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid derivatives were synthesized. The structures of these pyrazole-3-carboxylic acid derivatives were characterized by FT-IR, H-1 NMR, C-13 NMR, and elemental analysis methods. Synthesized molecules were screened to evaluate their antiproliferative activities against Vero (African green monkey kidney), C6 (rat brain tumor), and HeLa (human uterus carcinoma) cells as in vitro. The tests were carried out as dose-dependent assay starting from 100 to 500 mu g/cm(3). Ethyl 1-(3-nitrophenyl)-5-phenyl-3-(phenylcarbamoyl)-1H-pyrazole-4-carboxylate exhibited the highest performance against HeLa, Vero, and C6 cells among the synthesized derivatives. Also, it showed better antiproliferative activity compared with 5-fluorouracil (5-FU) against Vero cell. Two compounds showed moderate antiproliferative activities against C6 cell line when compared with 5-FU. Also moderate antiproliferative activities against Vero and HeLa cell lines were found.