title: Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and their anticancer properties.
abstract: A series of 2-amino-3-cyano-4H-chromen-4-ylphosphonates have been synthesized by reacting substituted salicylaldehydes, malononitrile, and dialkylphosphites using a catalytic amount of dibutylamine as an organocatalyst employing Knoevenagel, Pinner, and phospha-Michael reactions simultaneously in ethanol. This protocol is an environmentally friendly procedure and gives high yields of the desired compounds (85-96%). In addition, no extraction or chromatography steps are needed to obtain the desired products. The compounds are tested against the viability of adenocarcinomic human alveolar basal epithelial (A549) and human epidermoid cancer (KB) cell lines using an MTT assay. Among these, diethyl 2-amino-3-cyano-4H-chromen-4-ylphosphonate and diethyl 2-amino-6-bromo-3-cyano-4H-chromen-4-ylphosphonate showed promising anticancer activity against the two tested cell lines.
authors.affiliation: BK21 PLUS Center for Advanced Chemical Technology, Department of Polymer Science and Engineering, Pusan National University, Pusan 609-735, Republic of Korea.
authors.forename: Reddi Mohan Naidu
authors.initials: RM
authors.lastname: Kalla
authors.affiliation: College of Pharmacy, Pusan National University, Pusan 609-735, Republic of Korea; Department of Food & Drug, Chosun University, Gwangju 501-759, Republic of Korea.
authors.forename: Jin-Seok
authors.initials: JS
authors.lastname: Choi
authors.affiliation: College of Pharmacy, Pusan National University, Pusan 609-735, Republic of Korea.
authors.forename: Jin-Wook
authors.initials: JW
authors.lastname: Yoo
authors.affiliation: BK21 PLUS Center for Advanced Chemical Technology, Department of Polymer Science and Engineering, Pusan National University, Pusan 609-735, Republic of Korea.
authors.forename: Seong Jin
authors.initials: SJ
authors.lastname: Byeon
authors.affiliation: BK21 PLUS Center for Advanced Chemical Technology, Department of Polymer Science and Engineering, Pusan National University, Pusan 609-735, Republic of Korea.
authors.forename: Min Seon
authors.initials: MS
authors.lastname: Heo
authors.affiliation: BK21 PLUS Center for Advanced Chemical Technology, Department of Polymer Science and Engineering, Pusan National University, Pusan 609-735, Republic of Korea. Electronic address: ilkim@pusan.ac.kr.
authors.forename: Il
authors.initials: I
authors.lastname: Kim
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D063065:Organophosphonates
keywords: Anticancer activity; Chromenylphosphonates; Dibutylamine; Multicomponent reactions; One-pot synthesis; Organocatalyst