5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole | 89144-73-0

• 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-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole
• 英文别名: 5-(4-chlorophenyl)-3-phenyl-2-pyrazoline；1H-Pyrazole, 5-(4-chlorophenyl)-4,5-dihydro-3-phenyl-
• CAS: 89144-73-0
• 化学式: C₁₅H₁₃ClN₂
• mdl: MFCD06254466
• 分子量: 256.735
• InChiKey: RXULPLUJSOLALC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole 在 三乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.33h， 生成 2-(5-{2-[5-(4-chlorophenyl)-3-phenyl-4,5-dihydropyrazol-1-yl]-2-oxoethylidene}-2,4-dioxothiazolidin-3-yl)-N-p-tolylacetamide
  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：

  4-氯查耳酮 在 肼 作用下， 生成 5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  基于靛红的吡唑啉和噻唑烷共轭物的合成和抗癌活性

  摘要：

  进行了具有噻唑烷和吡唑啉部分的新型靛红基缀合物的合成和抗肿瘤活性筛选。3,5-二芳基-4,5-二氢吡唑与氯乙酰氯反应生成起始的2-氯-1-（3,5-二芳基-4,5-二氢吡唑-1-基）-乙酮，用于靛红的烷基化和 5-溴皂苷。因此，得到了相应的1-[2-(3,5-二芳基-4,5-二氢吡唑-1-基)-2-氧乙基]-1H-吲哚-2,3-二酮(1a-1d)。化合物 1a-1d 已用于与 4-噻唑烷酮的 Knoevenagel 缩合反应，得到一系列 5-亚苯基衍生物 2a-2f 和 3a-3d。测试合成的化合物在 NCI60 细胞系中的抗癌活性。被测化合物中，5-溴-1-{2-[5-(4-氯苯基)-3-(4-甲氧基苯基)-4,5-二氢吡唑-1-基]-2-氧乙基}-1H-吲哚-2,

  DOI：

  10.1002/ardp.201100055

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
• SOCl&lt;sub&gt;2&lt;/sub&gt; catalyzed cyclization of chalcones: Synthesis and spectral studies of some bio-potent &lt;sup&gt;1&lt;/sup&gt;&lt;i&gt;H&lt;/i&gt; pyrazoles
  作者：K. Ranganathan、R. Suresh、G. Vanangamudi、K. Thirumurthy、P. Mayavel、G. Thirunarayanan

  DOI：10.4314/bcse.v28i2.11

  日期：——

  Some aryl-aryl 1H pyrazoles have been synthesised by cyclization of aryl chalcones and hydrazine hydrate in the presence of SOCl2. The yields of the pyrazoles are more than 85%. These pyrazoles are characterized by their physical constants and spectral data. The infrared, NMR spectral group frequencies of these pyrazolines have been correlated with Hammett substituent constants, F and R parameters. From the results of statistical analyses the effects of substituent on the spectral frequencies have been studied. The antimicrobial activities of all synthesised pyrazolines have been studied using Bauer-Kirby method.

  一些芳基-芳基1H吡唑通过在SOCl2存在下对芳香醛和水合肼进行环化合成。吡唑的得率超过85%。这些吡唑通过其物理常数和谱学数据进行了表征。这些吡唑频率的红外和核磁共振（NMR）光谱组频率与Hammett取代基常数、F和R参数相关联。通过统计分析结果，研究了取代基对光谱频率的影响。所有合成的吡唑的抗微生物活性通过Bauer-Kirby方法进行了研究。
• SAR studies of differently functionalized chalcones based hydrazones and their cyclized derivatives as inhibitors of mammalian cathepsin B and cathepsin H
  作者：Neera Raghav、Mamta Singh

  DOI：10.1016/j.bmc.2014.05.037

  日期：2014.8

  recognized as most potent inhibitors of cathepsin B in this study with Ki values of 0.042 μM, 0.053 μM and 0.131 μM whereas 1b (Ki = 1.111 μM), 2b (Ki = 1.174 μM) and 4b (Ki = 1.562 μM) inhibited cathepsin H activity effectively. And, preeminent cathepsin B inhibitors were –NO2 functionalized however, –Cl substituted moieties were the most persuasive inhibitors for cathepsin H among all the designed

  组织蛋白酶已成为黑素瘤治疗的潜在药物靶标，并引起研究人员的关注，以开发和评估半胱氨酸组织蛋白酶抑制剂作为癌症治疗剂。在这个方向上，我们设计，合成和体外分析了查尔酮的30种低分子量功能化类似物的小文库，用于评估结构-活性关系以及对组织蛋白酶B和H的抑制效力。查尔酮hydr，其为开链类似物，其后为环化衍生物吡唑啉和吡唑。所有合成的化合物均被确立为这些酶的可逆抑制剂。组织蛋白酶B被各系列化合物选择性抑制。化合物1d，2d和4d被认为是组织蛋白酶B最有效的抑制剂，其K i值为0.042μM，0.053μM和0.131μM，而1b（K i  = 1.111μM），2b（K i  = 1.174μM）和4b（K i  = 1.562μM）有效抑制组织蛋白酶H活性。而且，出色的组织蛋白酶B抑制剂被–NO 2功能化，但是–Cl取代的部分是所有设计化合物中最有说服力的组织蛋白酶H抑制剂。使用iGemdock进行的分子对接研究提供了宝贵的见解。
• 一种二氢吡唑类化合物及其制备方法和用途
  申请人：合肥工业大学

  公开号：CN109912574A

  公开（公告）日：2019-06-21

  本发明公开了一种二氢吡唑类化合物及其制备方法和用途，其中二氢吡唑类化合物的结构通式如下：其中，R1选自H、4‑CH3、4‑O 、4‑Br或4‑Cl；R2选自4‑Cl、4‑F、4‑O 或4‑ 。本发明二氢吡唑类衍生物作为BRAF/P13K双靶点抑制剂，对vemuRAfenib有耐药性的黑色素瘤细胞A375R有良好的抗增殖活性。
• 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。