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新型烷基酰胺官能化三氟甲基取代吡唑并[3,4-b]吡啶衍生物的合成与生物评价作为潜在的抗癌剂。

Synthesis and biological evaluation of novel alkyl amide functionalized trifluoromethyl substituted pyrazolo[3,4-b]pyridine derivatives as potential anticancer agents.

机构信息

Fluoroorganic Division, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.

出版信息

Bioorg Med Chem Lett. 2013 Nov 1;23(21):5893-5. doi: 10.1016/j.bmcl.2013.08.089. Epub 2013 Sep 3.

Abstract

A series of novel alkyl amide functionalized trifluoromethyl substituted pyrazolo[3,4-b]pyridine derivatives 5, 6 and 7 were prepared starting from 6-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-3-amine 3 via selective N-alkylation, followed by reaction with different primary aliphatic amines, cyclic secondary amines or l-amino acids under different set of conditions. All the synthesized compounds 5, 6 and 7 were screened for anticancer activity against four cancer cell lines such as A549-Lung cancer (CCL-185), MCF7-Breast cancer (HTB-22), DU145-Prostate cancer (HTB-81) and HeLa-Cervical cancer (CCL-2). The compounds 5i and 6e are found to have promising bioactivity at micro molar concentration.

摘要

一系列新型的烷基酰胺官能化三氟甲基取代的吡唑并[3,4-b]吡啶衍生物 5、6 和 7 是从 6-苯基-4-(三氟甲基)-1H-吡唑并[3,4-b]吡啶-3-胺 3 通过选择性 N-烷基化反应制备的,然后在不同的条件下与不同的伯脂肪族胺、环状仲胺或 L-氨基酸反应。所有合成的化合物 5、6 和 7 都对四种癌细胞系(A549-肺癌(CCL-185)、MCF7-乳腺癌(HTB-22)、DU145-前列腺癌(HTB-81)和 HeLa-宫颈癌(CCL-2))进行了抗癌活性筛选。化合物 5i 和 6e 在微摩尔浓度下表现出有希望的生物活性。

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