Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India.
Eur J Med Chem. 2013 Aug;66:146-52. doi: 10.1016/j.ejmech.2013.05.036. Epub 2013 Jun 5.
A small library of structurally diverse α-aminophosphonates has been synthesized by reacting alkyl/aryl aldehydes, alkyl/aryl amines and alkyl/aryl phosphites in one-pot catalyzed by Amberlite-IR 120 resin (acidic). All the synthesized α-aminophosphonates were assayed for their in vitro cytotoxic activities against a panel of five human cancer cell lines including A-549, NCI-H23 (Lung), Colo 320DM (Colon), MG-63 (Bone marrow) and Jurkat (Blood T lymphocytes). Compound 4n having (R)-1-phenylethanamine was found to be the most active amongst all the synthesized α-aminophosphonates against all the five cancer cell lines, most prominent being against Jurkat cell line with an IC50 value of 4 μM. Surprisingly, compound 4o having (S)-1-phenylethanamine was found to be devoid of any cytotoxicity. Our finding suggests that these chemical entities could further serve as interesting template for the design of potential anticancer agents.
已通过 Amberlite-IR 120 树脂（酸性）一锅法催化反应，合成了结构多样的α-氨基膦酸酯的小库，反应原料为烷基/芳基醛、烷基/芳基胺和烷基/芳基亚磷酸酯。对所有合成的α-氨基膦酸酯进行了体外细胞毒性测试，以评估它们对包括 A-549、NCI-H23（肺）、Colo 320DM（结肠）、MG-63（骨髓）和 Jurkat（血液 T 淋巴细胞）在内的五种人类癌细胞系的活性。在所有合成的α-氨基膦酸酯中，具有（R）-1-苯乙胺的化合物 4n 对所有五种癌细胞系均表现出最强的活性，对 Jurkat 细胞系的抑制活性最为显著，IC50 值为 4 μM。令人惊讶的是，具有（S）-1-苯乙胺的化合物 4o 则没有表现出任何细胞毒性。我们的发现表明，这些化学实体可能进一步作为潜在抗癌药物设计的有趣模板。
