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

New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis andIn VitroAntiproliferative Activities on Breast and Prostate Human Cancer Cells

“…Acylquinones are highly reactive towards nucleophiles due to the confluence of electrophilic centers at the quinone nucleus and the 2-carbonyl substituents. The relatively close location of these electrophilic centers in the acylquinone scaffold enables reactions with diverse mono- and binucleophiles such as arylamines [ 17 ], azaenamines [ 18 ], enaminones [ 19 ], and 2-aminobenzothiazoles [ 20 ] to give a diversity of substances shown in Figure 1 such as 2,3-disubstituted 1,4-naphthoquinones (a, b) and heterocyclic fused 1,4-naphthoquinones (c–e).…”

Synthetic approaches and in vitro cytotoxic evaluation of 2-acyl-3-(3,4,5-trimethoxyanilino)-1,4-naphthoquinones

“…[5][6][7][8][9][10][11][12][13] The 2-acyl-1,4-benzo-and 1,4-naphthoquinones exhibit remarkable features in terms of their reactivity with nucleophiles due to the fact that the electrophilic centers at the quinone nucleus and acyl substituent are suitably located, thus enabling reactions with compounds such as arylamines [14][15][16] azaenamines 17 enaminones 18,19 and 2-aminobenzothiazoles 20 to give rise to a broad variety of quinonoid compounds such as those depicted in Fig. 1.…”

In Vitro Inhibition of Hsp90 Protein by Benzothiazoloquinazolinequinones Is Enhanced in The Presence of Ascorbate. A Preliminary In Vivo Antiproliferative Study

“…In this context, we have induced the alteration of intracellular redox homeostasis of cancer cells by using redox-cycler quinones as a new strategy in the research and development of new antitumor drugs. To this end, numerous quinone derivatives have been synthesized and assessed for their biological activity in order to optimize this redox-cycling approach [11,[14][15][16].…”

“…Recently, we have reported results on the synthesis and preliminary in vitro cytotoxic evaluation of a coplanar heteroaromatic scaffold namely benzo[g]benzothiazolo [2,3-b]quinazoline-7,12-quinones [16]. The synthetic accessibility to these heterocycles as well as the encouraging cytotoxic activities of some members of the series on cancer cells suggest that these heterocyclic quinones might be good antitumor compound candidates.…”