Department of Chemistry, Krishna University, Machilipatnam-521 001, Andhra Pradesh, India.
Department of Chemistry, Amritasai Institute of Science and Technology, Paritala, Krishna Dist., -521 180, Andhra Pradesh, India.
Anticancer Agents Med Chem. 2020;20(8):932-940. doi: 10.2174/1871520620666200311102304.
Compounds containing furo[3,2-b]pyridine framework have shown interesting pharmacological properties, including anticancer activities. Though these compounds are generally synthesized via the heteroannulation processes involving acetylenic derivatives, some of them are complex.
The study aimed to explore a series of 2-substituted furo[3,2-b]pyridines for their cytotoxic properties against cancer cell lines in vitro.
We developed a convenient synthesis of 2-substituted furo[3,2-b]pyridines via sequential (i) C-C coupling followed by (ii) C-O bond-forming reactions in a single pot. The reactions were performed under ultrasound irradiation in the presence of Pd/C as an inexpensive, stable and widely used catalyst. A range of 2- substituted furo[3,2-b]pyridines were synthesized via coupling of 3-chloro-2-hydroxy pyridine with terminal alkynes in the presence of 10% Pd/C-CuI-PPh3-Et3N in EtOH. The in vitro evaluation of all these compounds was carried out against MDA-MB-231 and MCF-7 cell lines and subsequently against SIRT1.
The furo[3,2-b]pyridine derivative 3b showed encouraging growth inhibition of both MDAMB-231 and MCF-7 cell lines and inhibition of SIRT1. The compound 3b also showed apoptosis-inducing potential when tested against MCF-7 cells.
The Pd/C-Cu catalysis under ultrasound accomplished a one-pot and direct access to 2-substituted furo[3,2-b]pyridine derivatives, some of which showed anticancer properties.
含有呋喃并[3,2-b]吡啶骨架的化合物表现出有趣的药理学性质，包括抗癌活性。尽管这些化合物通常通过涉及炔属衍生物的杂环化过程合成，但其中一些化合物较为复杂。
本研究旨在探索一系列 2-取代的呋喃并[3,2-b]吡啶类化合物的体外细胞毒性，评估它们对癌细胞系的抑制活性。
我们开发了一种通过连续（i）C-C 偶联和（ii）C-O 键形成反应在一锅法中合成 2-取代的呋喃并[3,2-b]吡啶的简便方法。在超声辐射下，在 Pd/C 作为一种廉价、稳定且广泛使用的催化剂存在下进行反应。通过在 10% Pd/C-CuI-PPh3-Et3N 的存在下，用 3-氯-2-羟基吡啶与末端炔烃偶联，合成了一系列 2-取代的呋喃并[3,2-b]吡啶。所有这些化合物的体外评估均针对 MDA-MB-231 和 MCF-7 细胞系进行，随后针对 SIRT1 进行评估。
呋喃并[3,2-b]吡啶衍生物 3b 对 MDAMB-231 和 MCF-7 细胞系均显示出令人鼓舞的生长抑制作用，并抑制 SIRT1。当在 MCF-7 细胞中测试时，该化合物 3b 还显示出诱导细胞凋亡的潜力。
在超声下使用 Pd/C-Cu 催化实现了一锅法和直接合成 2-取代的呋喃并[3,2-b]吡啶衍生物的方法，其中一些具有抗癌特性。
