ethyl 3-acetyl-1,5-diphenyl-1H-pyrazole-4-carboxylate | 478407-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-acetyl-1,5-diphenyl-1H-pyrazole-4-carboxylate
• 英文别名: ethyl 3-acetyl-1-phenyl-5-phenyl-1H-pyrazole-4-carboxylate；3-acetyl-1,5-diphenyl-1H-pyrazole-4-carboxylate
• CAS: 478407-68-0
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: PECIEAYWEBXVRW-UHFFFAOYSA-N

物化性质

• 沸点：
  528.1±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  61.19
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-acetyl-1,5-diphenyl-1H-pyrazole-4-carboxylate 在 水 、 溶剂黄146 、 sodium hydroxide 作用下， 反应 0.25h， 生成 ethyl 3-(4-oxo-5-phenyl-2-thioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-7-yl)-1,5-diphenyl-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  新型吡唑并嘧啶和吡咯并三唑并嘧啶酮并入吡唑部分的合成及抑菌活性

  摘要：

  在催化量的乙酸存在下，通过1-（吡唑-3-基）-2-丙烯酮与多种杂环胺的反应合成了一系列新的并入吡唑基的嘧啶嘧啶衍生物。还讨论了产物的形成机理，并根据元素和光谱分析数据阐明了分配的结构。此外，还使用了7-（吡唑基）-2-硫代-2--5-苯基-1,3-二氢吡啶并[2,3 - d ]嘧啶-4-酮作为原料，通过反应制备一系列新的吡啶并三唑并嘧啶用三乙胺作为催化剂在二恶烷中与各种酰氯酰氯一起使用。这些产品的指定结构还通过元素分析和光谱技术证明（IR，11 H NMR和质量。此外，评估了新产品的一些选定实例的抗微生物活性，并且获得的结果表明化合物20a对革兰氏阳性细菌金黄色葡萄球菌和革兰氏阴性细菌肺炎克雷伯菌具有高活性。所有测试的化合物均无抗真菌活性。

  DOI：

  10.1002/jhet.2968
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 1-氯-1-(2-苯基亚肼基)乙酮 以 乙醇 为溶剂， 生成 ethyl 3-acetyl-1,5-diphenyl-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  吡唑类化合物对人肺癌和肝细胞癌的合成，结构鉴定和生物学活性

  摘要：

  合成了两个新的吡唑和联吡唑系列，并根据光谱和元素分析的所有数据结果阐明了它们的结构。讨论了新联吡唑衍生物的形成途径。此外，还对所有合成的衍生物针对人肺（A-549）和肝细胞癌（HepG-2）细胞系的抗肿瘤活性进行了筛选。抗肿瘤筛选的结果表明，几种衍生物比参考药物更有效。

  DOI：

  10.1002/jhet.3257

文献信息

• Ecofriendly one-pot synthesis and antiviral evaluation of novel pyrazolyl pyrazolines of medicinal interest
  作者：Sobhi GOMHA、Magda ABDALLAH、Mohamad ABD EL-AZIZ、Nany SERAG

  DOI：10.3906/kim-1510-25

  日期：——

  Ethyl 3-acetyl-1,5-diphenyl-1$H$-pyrazole-4-carboxylate reacts with a variety of arylaldehydes by grinding method in the presence of a catalytic amount of sodium hydroxide at ambient temperature to give the respective chalcones. The latter compounds react also by grinding method with nitrogen nucleophiles such as hydrazine hydrate, phenylhydrazine, and thiosemicarbazide to afford the corresponding pyrazol-3-yl pyrazolines. A series of 6-pyrazolylpyrimidine-2-thione derivatives were prepared by reaction of the above chalcones with thiourea by grinding method in the presence of a catalytic amount of sodium hydroxide at room temperature. In addition, 7-pyrazolylpyridopyrimidine-3-thione was prepared by reaction of chalcone with 6-aminothiouracil. All the newly synthesized compounds were characterized on the basis of elemental analysis and spectral data (IR, $^1}$H and $^13}$C NMR, mass). Moreover, some of the products were evaluated for their antiviral activity against the herpes virus at different concentrations. The results obtained indicated that compounds 4a, 4b, 4f, 5a, 5b, and 5c have promising activity.

  乙基3-乙酰基-1,5-二苯基-1$H$-吡唑-4-羧酸酯在室温下，以少量氢氧化钠为催化剂，通过研磨法与各种芳香醛反应，得到相应的查耳酮。这些查耳酮化合物同样通过研磨法与氮亲核试剂如水合肼、苯肼和硫半卡巴腙反应，生成相应的吡唑-3-基吡唑啉。一系列6-吡唑基嘧啶-2-硫酮衍生物是通过上述查耳酮在室温下，以少量氢氧化钠为催化剂，通过研磨法与硫脲反应制备的。此外，7-吡唑基吡啶并嘧啶-3-硫酮是通过查耳酮与6-氨基硫尿嘧啶反应制备的。所有新合成的化合物都基于元素分析和光谱数据（IR，$^1}$H和$^13}$C NMR，质谱）进行了表征。此外，部分产品在不同浓度下对其抗病毒活性进行了评估，针对疱疹病毒。结果表明，化合物4a、4b、4f、5a、5b和5c具有良好的活性。
• Synthesis and evaluation of some novel thiazoles and 1,3-thiazines as potent agents against the rabies virus
  作者：Magda ABDALLA、Sobhi GOMHA、Mohamad ABD EL-AZIZ、Nany SERAG

  DOI：10.3906/kim-1506-13

  日期：——

  A series of novel thiazoles and 1,3-thiazine derivatives were synthesized in good yield via reaction of ethyl 3-(1-(2-thiocarbamoylhydrazono)ethyl)-1,5-diphenyl-1$H$-pyrazole-4-carboxylate with hydrazonoyl halides and arylidenemalononitriles, respectively. The structure of the newly synthesized products was elucidated via elemental analysis, spectral data, and alternative routes whenever possible. Moreover, the antiviral screening of the products was evaluated and the results revealed that some of them have strong to moderate potency against the rabies virus compared with the reference drug.

  一系列新型噻唑和1,3-噻嗪衍生物通过乙基3-(1-(2-硫代氨基脲基)乙基)-1,5-二苯基-1H-吡唑-4-羧酸酯与氮杂烯基卤化物和芳基亚甲二腈的反应，合成了良好的产率。新合成产品的结构通过元素分析、光谱数据和尽可能的替代路线进行阐明。此外，产品的抗病毒活性进行了评估，结果显示其中一些对狂犬病毒具有强到中等的活性，与参考药物相比。
• Synthesis of Some Novel Thiadiazoles and Thiazoles Linked to Pyrazole Ring
  作者：Sobhi M. Gomha、Magda A. Abdallah、Mohamad R. Abdelaziz、Nany S. Eldin Serag

  DOI：10.3987/com-15-13370

  日期：——

  The novel compound namely ethyl 3-(1-(2-(2-cyanoacetyl)-hydrazono)ethyl)-1,5-diphenyl-1H-pyrazole-4-carboxylate 3 was used as key intermediate for synthesizing the thioanilide derivative 4 and the arylidene derivatives 6. The reaction of 4 with a number of haloketones and haloesters furnished the respective thiazole derivatives 8, 10 and 11a,b. Moreover, the reaction of 4 with N-aryl-2-oxopropane hydrazonoyl chloride 13 and ethyl (N-arylhydrazono)chloroacetate 17 in absolute ethanol in the presence of triethylamine at reflux afforded a new series of thiadiazoles 15 and 19, respectively. The mechanisms that account for formation of products 15 and 19 were discussed. Also, the structures of all the newly synthesized products were confirmed based on elemental analysis, spectral data and by alternative methods.
• Site-selectivity in hydrazinolysis of 3,4'-bis-(functionalized carbonyl)-4,3'-bis(pyrazolyl)ketones. A convenient synthesis of 4-(pyrazol-3-yl)-2H-pyrazolo[3,4-d]-pyridazines
  作者：Ahmad Sami Shawali、Adel J. M. Haboub

  DOI：10.3998/ark.5550190.0013.525

  日期：——

  Reaction of hydrazine hydrate with 3,4-bis-(functionalized carbonyl)-4,3-bis(pyrazolyl)ketones proceeds regioselectively affording the corresponding 4-(pyrazol-3-yl)-2H-pyrazolo[3,4-d]pyridazine derivatives in high yields. The structures of the products were determined by spectroscopic and elemental analyses and supported by comparison with the possible isomers prepared by an independent route.