(E)-1-(4-fluorophenyl)-3-(1,3-diphenyl-1H-pyrazole-4-yl)prop-2-en-1-one | 1228954-07-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-1-(4-fluorophenyl)-3-(1,3-diphenyl-1H-pyrazole-4-yl)prop-2-en-1-one
• 英文别名: (E)-1-(4-fluorophenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-propen-1-one；(E)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-1-(4-fluorophenyl)prop-2-en-1-one；3-(1,3-diphenyl-1H-pyrazol-4-yl)-1-(4-fluorophenyl)-2-propen-1-one；(E)-3-(1,3-diphenylpyrazol-4-yl)-1-(4-fluorophenyl)prop-2-en-1-one
• CAS: 1228954-07-1
• 化学式: C₂₄H₁₇FN₂O
• 分子量: 368.41
• InChiKey: SMCSEQLZYBVMTH-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 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：
  34.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-fluorophenyl)-3-(1,3-diphenyl-1H-pyrazole-4-yl)prop-2-en-1-one 、 4-肼基苯磺酰胺 在 盐酸 作用下， 以 水 为溶剂， 以58%的产率得到4-(5-(4-fluorophenyl)-1',3'-diphenyl-3,4-dihydro-1'H,2H-[3,4'-bipyrazol]-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Pyrazole-pyrazoline as promising novel antimalarial agents: A mechanistic study

  摘要：

  A series of pyrazole-pyrazoline substituted with benzenesulfonamide were synthesized and evaluated for their antimalarial activity in vitro and in vivo. The compounds were active against both chloroquine (CQ) sensitive (3D7) and CQ resistant (RKL-9) strains of Plasmodium falciparum. Seven compounds (7e, 7i, 7j, 7l, 7m, 7o and 7p) exhibiting EC50 less than 2 mu M. A mechanistic study of compound 7o revealed that these compound act through the inhibition of beta-hematin. The study indicated that these compounds can serve as lead compounds for further development of potent antimalarial drugs. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.082
• 作为产物：
  描述：

  苯甲醛苯腙 在 sodium hydroxide 、 三氯氧磷 作用下， 反应 5.25h， 生成 (E)-1-(4-fluorophenyl)-3-(1,3-diphenyl-1H-pyrazole-4-yl)prop-2-en-1-one
  参考文献：
  名称：

  Pyrazole-pyrazoline as promising novel antimalarial agents: A mechanistic study

  摘要：

  A series of pyrazole-pyrazoline substituted with benzenesulfonamide were synthesized and evaluated for their antimalarial activity in vitro and in vivo. The compounds were active against both chloroquine (CQ) sensitive (3D7) and CQ resistant (RKL-9) strains of Plasmodium falciparum. Seven compounds (7e, 7i, 7j, 7l, 7m, 7o and 7p) exhibiting EC50 less than 2 mu M. A mechanistic study of compound 7o revealed that these compound act through the inhibition of beta-hematin. The study indicated that these compounds can serve as lead compounds for further development of potent antimalarial drugs. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.082

文献信息

• Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory–antimicrobial agents
  作者：Pawan K. Sharma、Satish Kumar、Pawan Kumar、Pawan Kaushik、Dhirender Kaushik、Yogita Dhingra、Kamal R. Aneja

  DOI：10.1016/j.ejmech.2010.01.059

  日期：2010.6

  A new series of pyrazolylpyrazolines (5a–k) was synthesized by the reaction of appropriate chalcones (3a–k) with 4-hydrazinobenzenesulfonamide hydrochloride (4) in ethanol. All the newly synthesized target compounds (5a–k) were screened for their anti-inflammatory activity using carrageenan-induced rat paw edema assay. Compounds 5g and 5j showed pronounced anti-inflammatory activity comparable to the

  通过适当的查耳酮（3a - k）与4-肼基苯磺酰胺盐酸盐（4）在乙醇中的反应合成了一系列新的吡唑基吡唑啉（5a - k）。使用角叉菜胶诱导的大鼠爪水肿试验筛选了所有新合成的目标化合物（5a - k）的抗炎活性。化合物5g和5j的抗炎活性与参考标准尼美舒利相当，而化合物5b，5d和5h显示出良好的抗炎活性。另外，评估了合成的化合物对两种革兰氏阳性细菌和两种革兰氏阴性细菌的体外抗菌活性。四种化合物5c，5h - 5j对所有测试的革兰氏阳性和革兰氏阴性细菌菌株均表现出良好的广谱活性。在这项研究中，化合物5j具有有趣的双重抗炎和抗菌特性，可以被认为是生物活性最高的成员。
• Synthesis and SARs study of novel spiro‐oxindoles as potent antiproliferative agents with CDK‐2 inhibitory activities
  作者：Refaah Mousa Al‐Jassas、Mohammad Shahidul Islam、Abdullah Mohammed Al‐Majid、Mohamed S. Nafie、Matti Haukka、A.F.M. Motiur Rahman、Abdul Majeed Abdullah Alayyaf、Assem Barakat

  DOI：10.1002/ardp.202300185

  日期：2023.8

  A series of 16 novel spirooxindole analogs 8a–p were designed and constructed via cost-effective single-step multicomponent [3+2] cycloaddition reaction of azomethine ylide (AY) generated in situ from substituted isatin (6a–d) with suitable amino acids (7a–c) and ethylene-engrafted pyrazole derivatives (5a,b). The potency of all compounds was assayed against a human breast cancer cell line (MCF-7)

  一系列 16 种新型螺吲哚类似物8a–p通过经济有效的单步多组分 [3+2] 环加成反应设计和构建，偶氮甲碱叶立德 (AY) 是由取代的靛红 (6a– d ) 与合适的氨基酸原位生成的( 7a–c ) 和乙烯接枝吡唑衍生物 ( 5a,b )。所有化合物的效力均针对人乳腺癌细胞系 (MCF-7) 和人肝细胞系 (HepG2) 进行了测定。Spiro 化合物8c是合成候选化合物中最活跃的成员，对 MCF-7 和 HepG2 细胞系具有出色的细胞毒性，IC 50值分别为 0.189 ± 0.01 和 1.04 ± 0.21 µM。候选8c表现出比标准药物 roscovitine 更有效的活性（10.10 倍和 2.27 倍）（IC 50  = 1.91 ± 0.17 µM (MCF-7) 和 2.36 ± 0.21 µM (HepG2)）。研究了化合物8c 的表皮生长因子受体 (EGFR) 抑制作用；它表现出令人鼓舞的
• Ultrasound-assisted ionic liquid-mediated green method for synthesis of 1,3-diphenylpyrazole-based spirooxindolopyrrolizidines, their anti-tubercular activity, molecular docking study and ADME predictions
  作者：Sravanthi Baddepuri、Rama Krishna Gamidi、Jyothi Kumari、Dharmarajan Sriram、Srinivas Basavoju

  DOI：10.1039/d4nj00563e

  日期：——

  in vitro anti-TB activity against Mycobacterium tuberculosis H37Rv strain. Among all, six compounds 4e (C36H29N5O4), 4g (C34H28N4O3), 4q (C36H28F2N4O2), 4r (C36H28ClFN4O2), 4y (C36H29BrN4O2) and 4z (C36H28BrFN4O2) exhibited significant anti-TB activity with MIC value 6.25 μg mL−1, when compared to the standard drug ethambutol (MIC:1.56 μg mL−1). In silico molecular docking studies were performed against

  本研究的目的是通过使用离子液体 ([Bmim] BF 4 )在超声处理下。标题化合物4a – 4ad的通式为 C a H b X (0–2) N c O d (X = F/Cl/Br)，可以在更短的反应时间内以高产率生产，并通过使用光谱技术进行了很好的表征;最后是单晶X射线衍射法( 4b )。评估了新合成的化合物对结核分枝杆菌H37Rv 菌株的体外抗结核活性。其中，6个化合物4e (C 36 H 29 N 5 O 4 )、4g (C 34 H 28 N 4 O 3 )、4q (C 36 H 28 F 2 N 4 O 2 )、4r (C 36 H 28 ClFN 4 O 2 )、4y (C 36 H 29 BrN 4 O 2 )和4z (C 36 H 28 BrFN 4 O 2 )与标准药物乙胺丁醇相比表现出显着的抗结核活性，MIC值为6.25 μg mL -1 。 (MIC：1.56μg·mL
• Kinger, Mayank; Kumar, Sushil; Kim, Sang Wook, Indian Journal of Heterocyclic Chemistry, 2016, vol. 25, # 3-4, p. 275 - 281
  作者：Kinger, Mayank、Kumar, Sushil、Kim, Sang Wook、Kumar, Raman

  DOI：——

  日期：——