Synthesis and biological evaluation of 2-chloro-3-[(thiazol-2-yl)amino]-1,4-naphthoquinones

• Published in: Bioorganic & medicinal chemistry letters Vol. 29; no. 13; pp. 1572 - 1575
• Main Authors: Olawode, Emmanuel O., Tandlich, Roman, Prinsloo, Earl, Isaacs, Michelle, Hoppe, Heinrich, Seldon, Ronnett, Warner, Digby F., Steenkamp, Vanessa, Kaye, Perry T.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.07.2019; Elsevier
• Subjects: 2-Chloro-3-[(thiazol-2-yl)amino]-1,4-naphthoquinones; Anti-bacterial; Anti-malarial; Anti-tuberculosis; Chemistry; Chemistry, Medicinal; Chemistry, Organic; Cytotoxicity; HeLa cells; Life Sciences & Biomedicine; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; HeLa cells; Cytotoxicity; 2-Chloro-3-[(thiazol-2-yl)amino]-1,4-naphthoquinones; Anti-bacterial; Anti-malarial; Anti-tuberculosis; NAD(P)H-QUINONE OXIDOREDUCTASE-1; DESIGN; 1,4-NAPHTHOQUINONE; CRIBROSTATIN-6; ANTINEOPLASTIC AGENTS; CANCER; 2-Chloro-3-(thiazol-2-yl)amino]-1,4-naphthoquinones; ANTITUMOR AGENTS; NAPHTHOQUINONES; ANTIFUNGAL
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2019.05.001

[Display omitted] A series of novel, substituted 2-chloro-3-[(thiazol-2-yl)amino]-1,4-naphthoquinones have been prepared and shown to exhibit promising concentration-dependent activity against human SH-SY5Y cells, Plasmodium falciparum, Mycobacterium tuberculosis and P. aeruginosa. Substituent effects on observed bioactivity have been explored; the para-fluorophenyl derivative 3d exhibited activity across the range of the bioassays employed, indicating the potential of the 2-chloro-3-[(4-arylthiazol-2-yl)amino]-1,4-naphthoquinone scaffold in the development of novel, broad spectrum therapeutics.