3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylpropenone | 380450-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylpropenone
• 英文别名: 3-[3-(4-Chlorophenyl)-1-phenylpyrazol-4-yl]-1-phenylprop-2-en-1-one
• CAS: 380450-07-7
• 化学式: C₂₄H₁₇ClN₂O
• 分子量: 384.865
• InChiKey: SHQYDKFVJHGZEG-UHFFFAOYSA-N

物化性质

• 沸点：
  577.1±50.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 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：
  2

反应信息

• 作为反应物：
  描述：

  3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylpropenone 在 吡啶 、 mercury(II) diacetate 作用下， 以 neat (no solvent) 为溶剂， 反应 6.0h， 以94%的产率得到2-((3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Ashok; Radhika, Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 3, p. 291 - 292

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯乙酮 在 硫酸 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylpropenone
  参考文献：
  名称：

  作为癌症相关选择性 COX-2 抑制剂的吡唑-吡唑啉杂化物的设计和合成

  摘要：

  继续我们之前在癌症和炎症方面的工作，合成并充分表征了 15 种新型吡唑-吡唑啉杂化物（WSPP1-15）。吡唑啉环的形成通过在 1H 核磁共振谱中出现的三个双峰证实了吡唑啉环的三个质子（HA、HM 和 HX）的 AMX 模式。使用 MTT 生长抑制试验筛选了所有合成的化合物对五种细胞系，即 MCF-7、A549、SiHa、COLO205 和 HepG2 细胞的体外抗癌活性。本研究以 5-氟尿嘧啶作为阳性对照。据观察，其中 WSPP11 对 A549、SiHa、COLO205 和 HepG2 细胞具有活性，IC50 值为 4.94、4.54、4.86 和 2.09 µM。还评估了所有衍生物对 HaCaT 细胞的细胞毒性。还发现 WSPP11 对正常细胞（细胞系 HaCaT）无毒，IC50 值超过 50 µM。还使用双氯芬酸钠和塞来昔布作为标准品，通过蛋白质（卵白蛋白）变性试验和红细胞膜稳定试

  DOI：

  10.1002/ardp.202000116

文献信息

• A Facile Synthesis of Some New 1-Benzothiazolyl-3-aryl/Hetaryl-5-(3-aryl-1-phenyl-4-pyrazolyl) Pyrazoles and Their Antimicrobial Activity
  作者：Sushma Singh、Vijaykiran Punia、Chetan Sharma、K. R. Aneja、Om Prakash、Rashmi Pundeer

  DOI：10.1002/jhet.1505

  日期：2015.11

  Some new derivatives of 1‐benzothiazolyl‐3‐aryl/hetaryl‐5‐(3‐aryl‐1‐phenyl‐4‐pyrazolyl) pyrazoles were synthesized by the cyclocondensation of 1‐aryl/hetaryl‐3‐(3‐aryl‐1‐phenyl‐1H‐pyrazole‐4‐yl)prop‐2‐en‐1‐ones (pyrazolyl chalcones) and 6‐substituted‐2‐hydrazinobenzothiazoles.

  1-苯并噻唑基-3-芳基/杂芳基-5-（3-芳基-1-苯基-4-吡唑基）吡唑的一些新衍生物是通过1-芳基/杂芳基-3-（3-芳基-1）的环缩合反应合成的-苯基-1 H-吡唑-4-基）丙-2-烯-1-酮（吡唑基查耳酮）和6-取代-2-肼基苯并噻唑。
• 1,3-Disubstitutedpyrazole-4-caboxaldehyde in Heterocyclic Synthesis: A Novel Synthesis of Pyridine-2(1<i>H</i>)-thione and Fused Nitrogen and/or Sulfur Heterocyclic Derivatives
  作者：Mohamed A. A. Elneairy

  DOI：10.1080/10426500902814049

  日期：2010.1.29

  Pyridine-2(1H)-thione 5 was synthesized from the reaction of 3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylpropenone (3) and cynothioacetamide (4). Compound 5 reacted with halogented compounds 6a–e to give 2-S-alkylpyridine derivatives 7a–e, which could be in turn cyclized into the corresponding thieno[2,3-b]-pyridine derivatives 8a–e. Compound 8a reacted with hydrazine hydrate to give 9

  Pyridine-2(1H)-thone 5 由 3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylpropenone (3) 和cynothioacetamide (4) 反应合成. 化合物 5 与卤代化合物 6a-e 反应生成 2-S-烷基吡啶衍生物 7a-e，其可以依次环化为相应的噻吩并 [2,3-b]-吡啶衍生物 8a-e。化合物 8a 与水合肼反应得到 9。后一种化合物与乙酸酐 (10a)、甲酸 (10b)、乙酸、乙酰乙酸乙酯和戊烷-2,4-二酮反应得到相应的吡啶并[3'， 2':4,5]噻吩并[3,2-d]嘧啶13a,b，吡唑并[3',4':4,5]噻吩并[3,2-d]吡啶14和噻吩并[2,3- b]-吡啶衍生物分别为18和20。或者，8c与10a,b和亚硝酸反应得到相应的吡啶并[3',2':4,5]噻吩并[3,2-d]嘧啶24a
• Novel pyrazole–pyrazoline hybrids endowed with thioamide as antimalarial agents: their synthesis and 3D-QSAR studies
  作者：Akranth Marella、Mohammad Shaquiquzzaman、Mymoona Akhter、Garima Verma、Mohammad Mumtaz Alam

  DOI：10.3109/14756366.2014.958081

  日期：2015.7.4

  One of the most viable options to tackle the growing resistance to the antimalarial drugs is hybrid molecules. It involves combination of different scaffolds in one frame that may lead to compounds with diverse biological profiles. In this context, new hybrids of three different scaffolds viz pyrazole, pyrazoline and thiosemicarbazone moiety were incorporated into one single compound and evaluated for their in vitro schizontocidal activity against the CQ-sensitive 3D7 strain of Plasmodium falciparum. Compounds with significant in vitro antimalarial activity were further evaluated for cytotoxicity against VERO cell lines. The best active compound 48 exhibited an IC50 of 1.13 mu M. The in vitro results were further validated by quantitative structure-activity relationship (QSAR).
• Synthesis and antimicrobial activity of some (3-phenyl-5-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanones: new derivatives of 1,3,5-trisubstituted pyrazolines
  作者：Satyender Kumar、Meenakshi、Sunil Kumar、Parvin Kumar

  DOI：10.1007/s00044-012-0045-7

  日期：2013.1

  A series of (3-phenyl-5-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl) methanones was synthesized by condensing suitably substituted chalcones, i.e., 3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-ones, and isoniazid in acetic acid. The structure of newly synthesized compounds has been established on the basis of analytical and spectral data. The new compounds were screened for antimicrobial activity and most of them showed good activity comparable with that of standard drugs ciprofloxacin and fluconazole. Compounds containing methoxy group showed high antimicrobial activity.
• Design and synthesis of pyrazole–pyrazoline hybrids as cancer‐associated selective COX‐2 inhibitors
  作者：Wasim Akhtar、Akranth Marella、Mohammad Mumtaz Alam、Mohemmed F. Khan、Mymoona Akhtar、Tariq Anwer、Farah Khan、Md. Naematullah、Faizul Azam、Moshahid A. Rizvi、Mohammad Shaquiquzzaman

  DOI：10.1002/ardp.202000116

  日期：2021.1

  activities were further studied for COX‐2 inhibition. The manifestation of a higher COX‐2 selectivity index of WSPP11 as compared with other derivatives and an in vitro anticancer activity against four cell lines further established that compounds that were more selective toward COX‐2 also exhibited a better spectrum of activity against various cancer cell lines.

  继续我们之前在癌症和炎症方面的工作，合成并充分表征了 15 种新型吡唑-吡唑啉杂化物（WSPP1-15）。吡唑啉环的形成通过在 1H 核磁共振谱中出现的三个双峰证实了吡唑啉环的三个质子（HA、HM 和 HX）的 AMX 模式。使用 MTT 生长抑制试验筛选了所有合成的化合物对五种细胞系，即 MCF-7、A549、SiHa、COLO205 和 HepG2 细胞的体外抗癌活性。本研究以 5-氟尿嘧啶作为阳性对照。据观察，其中 WSPP11 对 A549、SiHa、COLO205 和 HepG2 细胞具有活性，IC50 值为 4.94、4.54、4.86 和 2.09 µM。还评估了所有衍生物对 HaCaT 细胞的细胞毒性。还发现 WSPP11 对正常细胞（细胞系 HaCaT）无毒，IC50 值超过 50 µM。还使用双氯芬酸钠和塞来昔布作为标准品，通过蛋白质（卵白蛋白）变性试验和红细胞膜稳定试