Hetero-annulation reaction between 2-acylnaphthoquinones and 2-aminobenzothiazoles. A new synthetic route to antiproliferative benzo[g]benzothiazolo[2, 3-b]quinazoline-7, 12-quinones. Issue 36 (2nd September 2015)

• Record Type: Journal Article
• Authors: Valderrama, Jaime A.; Ríos, David; Muccioli, Giulio G.; Buc Calderon, Pedro; Brito, Iván; Benites, Julio
• Is Part Of: Tetrahedron letters. Volume 56:Issue 36(2015)
• Page Start: 5103
• Page End: 5105
• Publication Date: 2015-09-02
• Subjects: Acylnaphthoquinones -- Aminobenzothiazoles -- Hetero-annulation -- Antiproliferative activity -- MTT assay; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.07.034
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A simple approach to form benzo[ g ]benzothiazolo[2, 3- b ]quinazolinequinones. The structure of the compounds is supported by X-rays crystallography. Some compounds of the series showed significant antiproliferative properties. Abstract: A convenient two-step method is developed for the preparation of benzo[ g ]benzothiazolo[2, 3- b ]quinazoline-7, 12-quinones from 2-acylnaphthohydroquinones and 2-aminobenzothiazoles. The structure of the heterocyclic quinones is supported by X-ray crystallography. This protocol provides an operationally simple strategy to prepare the title compounds and shows good functional flexibility and easily available starting materials. Evidences are reported on the significant in vitro antiproliferative activities of some of the obtained heterocyclic quinones on prostate, bladder, and breast human-derived tumor cell lines.