5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole | 1611-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole
• 英文别名: 5-<4-Fluor-phenyl>-3-phenyl-Δ²-pyrazolin；1H-Pyrazole, 5-(4-fluorophenyl)-4,5-dihydro-3-phenyl-
• CAS: 1611-84-3
• 化学式: C₁₅H₁₃FN₂
• mdl: MFCD06254460
• 分子量: 240.28
• InChiKey: JTPILUYGLNFJIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole 在 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 1-(2-(5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  吡唑啉和吡咯烷-2,5-二酮杂化物作为潜在抗肿瘤剂的合成和生物学评价。

  摘要：

  为了寻找新型有效的抗肿瘤剂，设计、合成了吡唑啉取代的吡咯烷-2,5-二酮杂化物，并在计算机、体外和体内评估了其抗癌功效。所有化合物在MCF7和HT29细胞中均表现出显着的细胞毒作用。对 MCF7 (IC 50 =0.78±0.01 μM)、HT29 (IC 50 =0.92±0.15 μM) 和 K562 (IC 50 =47.25±1.24 μM) 细胞系的优异抗增殖活性，促使我们进一步研究这些细胞系的抗肿瘤作用。最好的化合物S2 (1-(2-(3-(4-fluorophenyl)-5-( p -tolyl)-4,5-dihydro- 1H -pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2, 5-二酮）。在细胞周期分析中，S2发现随着 G 1 /G 0期细胞数量增加和 G 2 /M 期细胞数量减少而破坏生长阶段。抑制抗凋亡蛋白 Bcl-2 也支持了优异的体外效果。S2在

  DOI：

  10.1002/cmdc.202000458
• 作为产物：
  描述：

  4-fluorochalcone 在 一水合肼 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  吡唑啉和吡咯烷-2,5-二酮杂化物作为潜在抗肿瘤剂的合成和生物学评价。

  摘要：

  为了寻找新型有效的抗肿瘤剂，设计、合成了吡唑啉取代的吡咯烷-2,5-二酮杂化物，并在计算机、体外和体内评估了其抗癌功效。所有化合物在MCF7和HT29细胞中均表现出显着的细胞毒作用。对 MCF7 (IC 50 =0.78±0.01 μM)、HT29 (IC 50 =0.92±0.15 μM) 和 K562 (IC 50 =47.25±1.24 μM) 细胞系的优异抗增殖活性，促使我们进一步研究这些细胞系的抗肿瘤作用。最好的化合物S2 (1-(2-(3-(4-fluorophenyl)-5-( p -tolyl)-4,5-dihydro- 1H -pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2, 5-二酮）。在细胞周期分析中，S2发现随着 G 1 /G 0期细胞数量增加和 G 2 /M 期细胞数量减少而破坏生长阶段。抑制抗凋亡蛋白 Bcl-2 也支持了优异的体外效果。S2在

  DOI：

  10.1002/cmdc.202000458

文献信息

• Design, modification and 3D QSAR studies of novel 2,3-dihydrobenzo[b][1,4]dioxin-containing 4,5-dihydro-1H-pyrazole derivatives as inhibitors of B-Raf kinase
  作者：Yu-Shun Yang、Qing-Shan Li、Shuai Sun、Yan-Bin Zhang、Xiao-Liang Wang、Fei Zhang、Jian-Feng Tang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.08.043

  日期：2012.10

  Two series of novel 2,3-dihydrobenzo[b][1,4]dioxin-containing 4,5-dihydro-1H-pyrazole derivatives C1–C15 and D1–D15 have been synthesized and evaluated for their B-Raf inhibitory and anti-proliferation activities. Compound C14 ((3-(4-bromophenyl)-5-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone) showed the most potent biological activity against B-RafV600E

  合成了两个系列的新型含2,3-二氢苯并[ b ] [1,4]二恶英的4,5-二氢-1 H-吡唑衍生物C1 - C15和D1 - D15，并评估了它们对B-Raf的抑制作用和防扩散活动。化合物C14（（3-（4-溴苯基）-5-（2-氟苯基）-4,5-二氢-1 H-吡唑-1-基）（2,3-二氢苯并[ b ] [1,4]二恶英-6-yl）methanone）对B-Raf V600E（IC 50  = 0.11μM）和WM266.4人黑素瘤细胞系（GI 50 = 0.58μM），与阳性对照厄洛替尼相当，并且比我们以前最好的化合物更有效，而D10（（2,3-dihydrobenzo [ b ] [1,4] dioxin-2-yl）（5-（3-氟苯基）-3-苯基-4,5-二氢-1 H-吡唑-1-基）甲酮在D系列中表现最好（IC 50  = 1.70μM; GI 50  = 1.45μM）。进行了对接模
• Synthesis and Evaluation of Human Monoamine Oxidase Inhibitory Activities of Some 3,5-Diaryl-N-substituted-4,5-dihydro-1H-pyrazole-1-carbothioamide Derivatives
  作者：Kerem Şentürk、Oya Unsal Tan、Samiye Yabanoğlu Çiftçi、Gülberk Uçar、Erhan Palaska

  DOI：10.1002/ardp.201100448

  日期：2012.9

  Sixteen 3‐aryl‐5‐(4‐fluorophenyl)‐N‐substituted‐4,5‐dihydro‐1H‐pyrazole‐1‐carbothioamide derivatives were synthesized and their structure were identified by UV, IR, 1H NMR, mass spectra, and microanalyses. The compounds were evaluated in vitro for their human monoamine oxidase (hMAO) inhibitory activities and their MAO‐A and ‐B selectivity. All the compounds were found to potently inhibit MAO‐A isoforms

  合成了 16 种 3-芳基-5-(4-氟苯基)-N-取代的-4,5-二氢-1H-吡唑-1-碳硫酰胺衍生物，并通过紫外、红外、1H 核磁共振、质谱和质谱鉴定了它们的结构。微量分析。体外评估了这些化合物的人单胺氧化酶 (hMAO) 抑制活性及其 MAO-A 和 MAO-B 选择性。发现所有化合物均能有效抑制 MAO-A 异构体。发现 5-(4-氟苯基)-3-(4-甲氧基苯基)-N-甲基-4,5-二氢-1H-吡唑-1-碳硫酰胺 (1.0 × 10-3 µM) 最有选择性地抑制 hMAO-A并且有力地。还使用对接研究预测了 5-(4-氟苯基)-3-(4-甲氧基苯基)-N-甲基-4,5-二氢-1H-吡唑-1-碳硫酰胺与 hMAO-A 的结合模式。
• Reductive Ring-Opening 1,3-Difunctionalizations of Arylcyclopropanes with Sodium Metal
  作者：Hideki Yorimitsu、Shuo Wang、Atsushi Kaga

  DOI：10.1055/s-0040-1706538

  日期：2021.1

  such as methoxypinacolatoborane, epoxide, oxetane, paraformaldehyde, or chlorotrimethylsilane, during the reductive ring opening event leads to the formation of 1,3-difunctionalized 1-arylalkanes by immediate trappings of the resulting two reactive carbanions. In particular, the ring-opening 1,3-diborylations of arylcyclopropanes afford 1,3-diborylalkanes with high syn selectivity.

  钠分散促进芳基环丙烷的还原开环。还原性开环过程中存在抗还原亲电子试剂，例如甲氧基频哪醇硼烷、环氧化物、氧杂环丁烷、多聚甲醛或氯三甲基硅烷，导致通过立即捕获所得两个反应性碳负离子形成 1,3-双官能化 1-芳基烷烃. 特别是，芳基环丙烷的开环 1,3-二硼基化提供了具有高顺式选择性的 1,3-二硼基烷烃。
• Development of 5-(Aryl)-3-phenyl-1H-pyrazole Derivatives as Potent Antimicrobial Compounds
  作者：B. Nagendra Chowdary、M. Umashankara、B. Dinesh、K. Girish、A. Ramesha Baba

  DOI：10.14233/ajchem.2019.21455

  日期：——

  A series of 16 chalcone compounds were synthesized by Claisen-Schmidt condensation of various aldehydes with acetophenone using KOH as a base in ethanol. The reaction affords the desired products in good yields. Then all the 16 compounds were converted into pyrazoles by treating with hydrazine hydrate in ethanol under reflux condition. Both chalcones and pyrazoles were screened for their in vitro antibacterial (Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa) and antifungal (Aspergillus flavus, Chrysosporium keratinophilum and Candida albicans) activity. Biological activities of these compounds were compared with those of commercially available antibiotic ampicillin and antifungal agent miconazole. Pyrazoles were found to be most active and effective than corresponding chalcones for antimicrobial activity. Out of the 7 pyrazole compounds tested for antibacterial and antifungal activity, 5 compounds, 4h, 4j, 4l, 4m and 4n are turned out to be potent antimicrobial agents. Therefore these derivatives could serve as a highly promising molecules for further development.

  通过克莱森-施密特冷凝反应，合成了一系列16种查尔酮化合物，使用不同的醛与乙酰苯酮在氢氧化钾的碱性条件下于乙醇中发生反应。反应获得期望产物，产率良好。随后，所有16种化合物通过在回流条件下用水合肼处理转化为吡唑。对查尔酮和吡唑进行了体外抗菌（大肠杆菌、金黄色葡萄球菌和铜绿假单胞菌）和抗真菌（青霉菌、角质毛霉和白色念珠菌）活性筛选。这些化合物的生物活性与市售抗生素氨苄青霉素和抗真菌剂米康唑进行了比较。研究发现，吡唑在抗微生物活性方面比对应的查尔酮更为活跃和有效。在测试的7种吡唑化合物中，4h、4j、4l、4m和4n五种化合物表现出很强的抗微生物活性。因此，这些衍生物有望成为进一步开发的极具潜力的分子。
• Preparation, Antiepileptic Activity, and Cardiovascular Safety of Dihydropyrazoles as Brain-Penetrant T-Type Calcium Channel Blockers
  作者：Lubos Remen、Olivier Bezençon、Lloyd Simons、Rick Gaston、Dennis Downing、John Gatfield、Catherine Roch、Melanie Kessler、Johannes Mosbacher、Thomas Pfeifer、Corinna Grisostomi、Markus Rey、Eric A. Ertel、Richard Moon

  DOI：10.1021/acs.jmedchem.6b00756

  日期：2016.9.22

  A series of dihydropyrazole derivatives was developed as potent, selective, and brain-penetrating T-type calcium channel blockers. An optimized derivative, compound 6c, was advanced to in vivo studies, where it demonstrated efficacy in the WAG/Rij rat model of generalized nonconvulsive, absence-like epilepsy. Compound 6c was not efficacious in the basolateral amygdala kindling rat model of temporal lobe epilepsy, and it led to prolongation of the PR interval in ECG recordings in rodents.