Synthesis of novel naphthoquinone aliphatic amides and esters and their anticancer evaluation

• Published in: European journal of medicinal chemistry Vol. 60; pp. 271 - 284
• Main Authors: Kongkathip, Boonsong, Akkarasamiyo, Sunisa, Hasitapan, Komkrit, Sittikul, Pichamon, Boonyalai, Nonlawat, Kongkathip, Ngampong
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.02.2013; Elsevier
• Subjects: Amides - chemical synthesis; Amides - chemistry; Amides - pharmacology; Animals; Anticancer activity; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Cancer; Cell Proliferation - drug effects; Cercopithecus aethiops; Chemistry, Medicinal; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Esters - chemical synthesis; Esters - chemistry; Esters - pharmacology; Humans; KB Cells; Life Sciences & Biomedicine; Models, Molecular; Molecular Structure; Naphthoquinone aliphatic amide; Naphthoquinone aliphatic ester; Naphthoquinones - chemistry; Pharmacology & Pharmacy; Science & Technology; Structure-Activity Relationship; Topoisomerase II; Vero Cells; Naphthoquinone aliphatic ester; Naphthoquinone aliphatic amide; Topoisomerase II; Anticancer activity; Cancer; APOPTOSIS; CELLS; RHINACANTHUS-NASUTUS; INDUCTION

Fourteen new naphthoquinone aliphatic amides and seventeen naphthoquinone aliphatic esters were synthesized in nine to ten steps from 1-hydroxy-2-naphthoic acid with 9–25% overall yield for the amides, and 16–21% overall yield for the esters. The key step of the amide synthesis is a coupling reactio...