1,3-diphenylpyrazole-4-carboxylic acid chloride | 373627-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-diphenylpyrazole-4-carboxylic acid chloride
• 英文别名: 1,3-Diphenyl-1h-pyrazole-4-carbonyl chloride；1,3-diphenylpyrazole-4-carbonyl chloride
• CAS: 373627-25-9
• 化学式: C₁₆H₁₁ClN₂O
• mdl: MFCD03421616
• 分子量: 282.729
• InChiKey: ADIAVEGZGDQOSA-UHFFFAOYSA-N

物化性质

• 沸点：
  454.4±33.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-diphenylpyrazole-4-carboxylic acid chloride 在 叠氮基三甲基硅烷 作用下， 以 甲苯 为溶剂， 以52%的产率得到4-Isocyanato-1,3-diphenyl-1H-pyrazole
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1013982203774
• 作为产物：
  描述：

  苯肼,盐酸盐 在 potassium permanganate 、 氯化亚砜 、 sodium acetate 、 三氯氧磷 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 14.0h， 生成 1,3-diphenylpyrazole-4-carboxylic acid chloride
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking studies of pyrazole derivatives coupling with a thiourea moiety as novel CDKs inhibitors

  摘要：

  It was discovered that a number of cyclin dependent kinase inhibitors containing the pyrazole core structure exhibited high inhibitory potency against broad-range CDKs and corresponding anti-proliferative activities. This information guided us to design and synthesize a series of 1,3-diphenyl-N-(phenylcarbamothioyl)-1H-pyrazole-4-carboxamide derivatives (5a-10d), and evaluate their biological activities as CDKs inhibitors. Among all the synthesized compounds, compound 10b inhibited CDK2 with an IC50 value of 25 nM, counteracting tumor cell proliferation of three cancer cell lines (H460, MCF-7, A549) in the micromolar range (from 0.75 mu M to 4.21 mu M), In addition, flow cytometry indicated that compound 10b could induce cycle G(0)/G(1) phase arrest in A549 cells with a dose dependent. Taken together, compound 10b could be selected for further preclinical evaluation. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.003

文献信息

• Discovery of N-(benzyloxy)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives as potential antiproliferative agents by inhibiting MEK
  作者：Xian-Hai Lv、Zi-Li Ren、Ben-Guo Zhou、Qing-Shan Li、Ming-Jie Chu、Dao-Hong Liu、Kai Mo、Li-Song Zhang、Xiao-Kang Yao、Hai-Qun Cao

  DOI：10.1016/j.bmc.2016.08.002

  日期：2016.10

  inhibitor has been demonstrated significant clinical benefit for blocking MAPK pathway activation and possibly could block reactivation of the MAPK pathway at the time of BRAF inhibitor resistance. Twenty N-(benzyloxy)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives have been designed and synthesized as MEK inhibitors, and their biological activities were evaluated. Among these compounds, compound 7b

  丝裂原活化蛋白激酶（MAPK）信号转导途径已被证明在肿瘤发生和癌症发展中起重要作用。已经证明MEK抑制剂对于阻断MAPK途径活化具有显着的临床益处，并且可能在BRAF抑制剂抵抗时阻断MAPK途径的再活化。设计并合成了二十种N-（苄氧基）-1,3-二苯基-1H-吡唑-4-羧酰胺衍生物作为MEK抑制剂，并对其生物学活性进行了评估。在这些化合物中，化合物7b表现出最强的抑制活性，对MEK1的IC50为91nM，对A549细胞的GI50为0.26μM。进行了SAR分析和对接模拟，以提供可用于进一步结构优化的关键药效​​团线索。
• Urea derivatives of piperazine doped with pyrazole‐4‐carboxylic acids: Synthesis and antimicrobial evaluation
  作者：Harshita Phougat、Vandana Devi、Sanjay Rai、T. Shreedhar Reddy、Karan Singh

  DOI：10.1002/jhet.4325

  日期：2021.10

  A series of novel N-cycloalkyl/aryl-4-(1,3-diphenyl-1H-pyrazole-4-carbonyl)piperazine-1-carboxamides 9a-g has been synthesized for biological interest by simple base catalyzed reaction of various N-cycloalkyl/aryl isocyanates with (1,3-diphenyl-1H-pyrazol-4-yl)(piperazin-1-yl)methanone hydrochloride 8. The compound 8 was synthesized in excellent yield by the reaction of 1,3-diphenyl-1H-pyrazole-4-carbonyl

  通过各种N 的简单碱催化反应合成了一系列新型N-环烷基/芳基-4-(1,3-二苯基-1H-吡唑-4-羰基)哌嗪-1-甲酰胺9a-g用于生物学研究。-环烷基/芳基异氰酸酯与(1,3-二苯基-1H-吡唑-4-基)(哌嗪-1-基)甲酮盐酸盐8。通过1,3-二苯基-1H-吡唑-4-碳酰氯与boc-哌嗪反应，然后用二恶烷-HCl脱保护boc基团，以优异的收率合成了化合物8。所有新的中间体和尿素衍生物都已经过抗微生物活性的筛选。化合物9a被发现是一种极好的化合物，对所有革兰氏 (-ve) 和革兰氏 (+ve) 细菌菌株E.coli、Y. enterocolitica、B. cereus和S. aureus都有活性。与参考标准咪康唑相比，它还显示出类似的抗白色念珠菌活性，MIC 为 78.1 μg/ml。
• Solvent-free Microwave-assisted Synthesis of 1-(1,3-diphenyl-1H-pyrazol-4-yl)-3-( 2-hydroxyphenyl) propane-1,3-dione Using K2CO3 as Green Solid Support
  作者：Navnath R. Dalvi、Namdeo T. Dhokale、Satish B. Kale、Sadashiv S. Nagre、Shankaraiah G. Konda

  DOI：10.2174/1570178620666230329104520

  日期：2023.3.29

  We herein present the synthesis of 1-(1,3-diphenyl-1H-pyrazol-4-yl)-3-(2-hydroxy-substituted phenyl) propane-1,3-dione using microwave irradiation. Reactions were carried out by employing a solvent-free path using K2CO3 as green solid support. The results were compared with those of the conventional method. This microwave-assisted synthesis avoids hazardous solvents and reduces the number of steps and time, providing increased yields. The synthesized products were characterized by IR, 1H NMR, and mass spectrometry.

  摘要：： 我们在此介绍利用微波辐照合成 1-(1,3-二苯基-1H-吡唑-4-基)-3-(2-羟基取代苯基)丙烷-1,3-二酮。以 K2CO3 为绿色固体支持物，通过无溶剂途径进行了反应。结果与传统方法进行了比较。这种微波辅助合成法避免了有害溶剂，减少了步骤和时间，提高了产率。合成产物通过红外光谱、1H NMR 和质谱进行了表征。
• Investigation of the action of 1,3-diphenylpyrazolecarboxylic acids on the liver cytochrome P-450 system
  作者：T. G. Khlopushina、A. V. Krinskaya、Z. D. Kirsanova、D. A. Zykov、V. A. Zagorevskii

  DOI：10.1007/bf00767251

  日期：1991.11
• Adamantylamides of 1,3-diphenylpyrazole-4-carboxylic acids
  作者：I. S. Morozov、N. V. Klimova、N. P. Bykov、N. M. Zaitseva、G. V. Pushkar'、É. D. Dvalishvili、A. A. Khranilov、B. M. Pyatin

  DOI：10.1007/bf00772017

  日期：1991.3