3-(naphthalen-2-yl)-5-(4-chlorophenyl)-2-pyrazoline | 114346-59-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphthalen-2-yl)-5-(4-chlorophenyl)-2-pyrazoline
• 英文别名: 5-(4-chlorophenyl)-3-naphthalen-2-yl-4,5-dihydro-1H-pyrazole
• CAS: 114346-59-7
• 化学式: C₁₉H₁₅ClN₂
• 分子量: 306.794
• InChiKey: CJZWCKORYUGTNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  24.39
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(naphthalen-2-yl)-5-(4-chlorophenyl)-2-pyrazoline 以 乙醇 为溶剂， 反应 2.0h， 生成 5-[5-(4-chlorophenyl)-3-naphthalen-2-yl-4,5-dihydropyrazol-1-yl]-3-(4-ethylpiperazin-1-ylmethyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones

  摘要：

  A series of novel 5-pyrazoline substituted 4-thiazolidinones have been synthesized. Target compounds were evaluated for their anticancer activity in vitro within DTP NCI protocol. Among the tested compounds, the derivatives 4d and 4f were found to be the most active, which demonstrated certain sensitivity profile toward the leukemia subpanel cell lines with GI(50) value ranges of 2.12-4.58 mu M (4d) and 1.64-3.20 mu M (4f). The screening of antitrypanosomal and antiviral activities of 5-(3-naphthalen-2yl-5-aryl-4,5-dihydropyrazol-1-yl)-thiazolidine-2,4-diones was carried out with the promising influence of the mentioned compounds on Tiypanosoma brucei, but minimal effect on SARS coronavirus and influenza types A and B viruses. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.044
• 作为产物：
  描述：

  3-(4-chlorophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 以82 %的产率得到3-(naphthalen-2-yl)-5-(4-chlorophenyl)-2-pyrazoline
  参考文献：
  名称：

  新型吡唑啉衍生物抗氧化和酶抑制活性的机理见解和治疗意义

  摘要：

  药物化学的主要特征之一是新化合物的合成，以及评估其生物活性以用于潜在的治疗应用。作为对该领域的贡献，目前的工作研究了新合成的吡唑啉衍生物的作用。为此，合成了四种吡唑啉衍生物，并评估了它们的抗氧化活性和体外对乙酰胆碱酯酶（AChE）和酪氨酸酶的酶抑制作用。所有合成的化合物2a-2d均表现出中等至强效的抗氧化活性。对于酶抑制活性，化合物2a发挥最有效的乙酰胆碱酯酶抑制作用，IC 50值为 (IC 50=3.93±0.52 µM），是标准药物加兰他敏（IC 50 =6.27±1.15 µM）的两倍，而化合物 2a 被确定为合成化合物中最好的酪氨酸酶抑制剂，其 IC 50值为(32.65±2.30μM)。进行密度泛函理论 (DFT) 计算以确定化合物的性质，并进行分子对接研究以讨论最活跃的化合物之间的潜在相互作用 ( 2a) 以及蛋白质 AchE (PDB: 1ACL) 和酪氨酸酶 (PDB: 2Y9X)

  DOI：

  10.1016/j.molstruc.2023.136761

文献信息

• Synthesis of New 4-Thiazolidinone-, Pyrazoline-, and Isatin-Based Conjugates with Promising Antitumor Activity
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Olexandr Vasylenko、Andrzej Gzella、Roman Lesyk

  DOI：10.1021/jm300789g

  日期：2012.10.25

  The synthesis and antitumor activity screening of novel 3-[2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene]-2,3-dihydro-1H-indol-2-ones 1–23 and 3-(3,5-diarylpyrazol-1-yl)-2,3-dihydro-1H-indol-2-ones 24–39 are performed. In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute. Most of them displayed anticancer activity on leukemia

  新型3- [2-（3,5-二芳基-4,5-二氢吡唑-1-基）-4-氧代-4,5-二氢-1,3-噻唑-5-亚烷基的合成及抗肿瘤活性的筛选] -2,3-dihydro-1 H-吲哚-2-ones 1 – 23和3-（3,5-diarylpyrazol-1-yl）-2,3-dihydro-1 H -indol-2-ones 24 –执行39次。美国国家癌症研究所测试了合成化合物的体外抗癌活性。他们中的大多数对白血病，黑素瘤，肺癌，结肠癌，中枢神经系统，卵巢癌，肾癌，前列腺癌和乳腺癌细胞系均表现出抗癌活性。讨论了构效关系。发现最有效的抗癌化合物10具有平均GI 50的活性TGI值分别为0.071μM和0.76μM。它显示出对非小细胞肺癌细胞HOP-92（GI 50 <0.01μM），结肠癌细胞系HCT-116（GI 50 = 0.018μM），CNS癌细胞SNB-75（ GI 50 = 0.0159μM），卵巢癌细胞系NCI
• 5-Ene-4-thiazolidinones induce apoptosis in mammalian leukemia cells
  作者：Julia Senkiv、Nataliya Finiuk、Danylo Kaminskyy、Dmytro Havrylyuk、Magdalena Wojtyra、Iryna Kril、Andrzej Gzella、Rostyslav Stoika、Roman Lesyk

  DOI：10.1016/j.ejmech.2016.03.089

  日期：2016.7

  structure and purity of compounds were confirmed by analytical and spectral data including X-ray analysis. Target compounds were screened for their anticancer activity and selective antileukemic action was confirmed. 5-[5-(2-Hydroxyphenyl)-3-phenyl-4,5-dihydropyrazol-1-ylmethylene]-3-(3-acetoxyphenyl)-2-thioxothiazolidin-4-one (compound 1) was selected as most active agent against HL-60 and HL-60/ADR

  本文介绍了以烯胺基连接吡唑核心的5-ene-4-thiazolidinone衍生物的合成方法。化合物的结构和纯度通过包括X射线分析在内的分析和光谱数据进行了确认。筛选目标化合物的抗癌活性，并确认了选择性抗白血病作用。选择5- [5-（2-羟基苯基）-3-苯基-4,5-二氢吡唑-1-基亚甲基] -3-（3-乙酰氧基苯基）-2-硫代噻唑烷-4-（化合物1）作为最有效的化合物抗HL-60和HL-60 / ADR细胞系的药物; IC 50  = 118 nM / HL-60，对伪正常细胞毒性低。线粒体依赖性细胞凋亡被认为是1作用的主要模式。另外，化合物的作用诱发了G 0 / G 1。 抑制所处理的细胞并引起细胞分裂的抑制，并且与ROS产生的活化有关。
• Synthesis of pyrazoline–thiazolidinone hybrids with trypanocidal activity
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Olexandr Karpenko、Philippe Grellier、Roman Lesyk

  DOI：10.1016/j.ejmech.2014.07.103

  日期：2014.10

  A series of novel 4-thiazolidinone-pyrazoline conjugates have been synthesized and tested for anti-Trypanosoma brucei activity. Screening data allowed us to identify five thiazolidinone-pyrazoline hybrids, which possess promising trypanocidal activity, with IC50 <= 1.2 mu M. The highest active thiazolidinone-pyrazoline conjugates 3c and 6b (IC50 values of 0.6 mu M and 0.7 mu M, respectively) were 6-times more potent antitrypanosomal agents than nifurtimox. In addition, these compounds, as well as 6d and 6e had selectivity index higher than 50, and were more selective than nifurtimox. SAR study included substituent variations at the pyrazoline moiety, modifications of N3 position of the thiazolidinone portion, elongation of the linker between the heterocycles, as well as rhodanine-isorhodanine isomerism. It was also shown that methyl or aryl substitution at the thiazolidinone N3-position is crucial for trypanocidal activity. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis and evaluation of biological activity of rhodanine-pyrazoline hybrid molecules with 2-(2,6-dichlorophenylamino)-phenylacetamide fragment
  作者：Yu. L. Shepeta、A. V. Lozynskyi、Z. V. Tomkiv、P. Grellier、R. B. Lesyk

  DOI：10.7124/bc.000a27

  日期：2020.4.30
• EL-BAYOUKI, KHAIRY A. M.;IBRAHIM, I. H.;LATIF, N., EGYPT. J. CHEM., 29,(1986) N 1, 129-137
  作者：EL-BAYOUKI, KHAIRY A. M.、IBRAHIM, I. H.、LATIF, N.

  DOI：——

  日期：——