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一系列带有4-芳氧基-7-氯喹啉片段的新型2-吡唑啉衍生物的合成及其体外抗肿瘤活性

Synthesis and in vitro antitumor activity of a novel series of 2-pyrazoline derivatives bearing the 4-aryloxy-7-chloroquinoline fragment.

作者信息

Montoya Alba, Quiroga Jairo, Abonia Rodrigo, Nogueras Manuel, Cobo Justo, Insuasty Braulio

机构信息

Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Apartado Aéreo 25360, Colombia.

Department of Inorganic and Organic Chemistry, Universidad de Jaén, Jaén 23071, Spain.

出版信息

Molecules. 2014 Nov 14;19(11):18656-75. doi: 10.3390/molecules191118656.

DOI:10.3390/molecules191118656
PMID:25405285
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6271490/
Abstract

A new series of NH-pyrazoline derivatives 6 was synthesized by cyclocondensation reaction of novel [(7-chloroquinolin-4-yl)oxy]chalcones 5 with hydrazine hydrate. The treatment of pyrazolines 6 with acetic anhydride or formic acid yielded the N-acetyl- or N-formylpyrazoline derivatives 7-8, respectively. These novel 2-pyrazoline derivatives 6-8 were evaluated by the U.S. National Cancer Institute (NCI). Compounds 7b,d,f and 8c,f showed remarkable antitumor activity against 58 cancer cell lines, with the most important GI50 values from in vitro assays ranging from 0.48 to 1.66 μM. The 2-pyrazoline derivatives bearing the 4-aryloxy-7-chloroquinoline fragment are thus considered to be useful leads for the rational design of new antitumor agents.

摘要

通过新型[(7-氯喹啉-4-基)氧基]查耳酮5与水合肼的环缩合反应合成了一系列新的NH-吡唑啉衍生物6。用乙酸酐或甲酸处理吡唑啉6分别得到N-乙酰基-或N-甲酰基吡唑啉衍生物7-8。美国国立癌症研究所（NCI）对这些新型2-吡唑啉衍生物6-8进行了评估。化合物7b、d、f和8c、f对58种癌细胞系显示出显著的抗肿瘤活性，体外试验中最重要的GI50值范围为0.48至1.66μM。因此，带有4-芳氧基-7-氯喹啉片段的2-吡唑啉衍生物被认为是合理设计新型抗肿瘤药物的有用先导化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03a3/6271490/7a5845db412d/molecules-19-18656-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03a3/6271490/882f05dfcdaa/molecules-19-18656-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03a3/6271490/95bbeace439d/molecules-19-18656-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03a3/6271490/7a5845db412d/molecules-19-18656-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03a3/6271490/882f05dfcdaa/molecules-19-18656-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03a3/6271490/95bbeace439d/molecules-19-18656-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03a3/6271490/7a5845db412d/molecules-19-18656-g003.jpg

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