Synthesis and Evaluation of 9‐Anilinothiazolo[5,4‐b]quinoline Derivatives as Potential Antitumorals.

Abstract

Fused pyridine derivativesFused pyridine derivatives R 0450 Synthesis and Evaluation of 9-Anilinothiazolo[5,4-b]quinoline Derivatives as Potential Antitumorals. -Five new title derivatives, cf. (III), (VI), (IX), (XI) and (XIII), combining the general substitution pattern of potent antitumoral acridines with a thiazoloquinoline template are prepared and preliminarily evaluated for their antitumoral activity. Compounds (IX), (XI) and (XIII) are synthesized by coupling properly substituted anilines to the novel thiazoloquinoline (VII). All derivatives demonstrate DNA binding in the nanomolar range. Derivative (IX) forms the tightest intercalation complex without correlation to its cytotoxic activity. On the other hand, (VI) forms the weakest and most extensive complexes with DNA being highly cytotoxic. -(RODRIGUEZ-LOAIZA, P.; QUINTERO, A.; RODRIGUEZ-SOTRES, R.; SOLANO, J. D.; LIRA-ROCHA*, A.; Eur.

Ethyltrans-3-(2-chloro-6,7-dimethylquinolin-3-yl)-1-cyclohexylaziridine-2-carboxylate

“…2-Chloroquinolines and their derivatives, 2-aminoquinolines, 2-alkoxyquinolines or quinolin-2-(1H)-ones, occupy a prominent position in organic synthesis as key intermediates for further annelation and various functional group interconversions (Larsen & Cai, 2005). In addition, they have also attracted considerable attention due to their important biological activities as antibiotics (Mahamoud et al, 2006), anti-inflammatories (Chen et al, 2006) and antitumorals (Rodriguez-Loaiza et al, 2004). To our knowledge, no example of an aziridinoquinoline has hitherto been reported in the literature.…”

Synthesis and Antiproliferative Evaluation of 4‐Anilino‐n‐methoxyfuro[2,3‐b]quinoline Derivatives (n=6, 7). Part 5

“…These results prompted us to synthesize and evaluate furo[2,3-b]quinoline derivatives, which are structurally related to acridines by isosteric substitution of a benzene moiety for a furan ring [6 -9]. Similar approaches to this kind of compounds were also reported where a benzene moiety was isosterically replaced with a thiazole ring [10] [11].Recently, we have reported the preparation of certain 4-anilinofuro[2,3-b]quinoline derivatives, which were evaluated for their antiproliferative activities against the full panel of 60 human tumor cell lines derived from nine cancer cell types (leukemia, nonsmall-cell lung cancer, colon cancer, CNS cancer, melanoma, ovarian cancer, renal cancer, prostate cancer, and breast cancer). Among them, 1-{4- [(3-chloro-7-methoxyfuro[2,3-b]quinolin-4-yl)amino]phenyl}ethanone (1; see Scheme 1 below) exhibited an excellent antiproliferative activity, with a mean GI 50 value of 0.27 mm [4].…”

A Review on the Synthetic Methodologies of Chromones

“…A new group of 2-phenyl naphthalene type structures of 11 H-indolo[3,2-c] quinoline derivatives was designed by He et al [12] (2003). Loaiza et al [13] Ibrahim et al [34] (2017) presented a review which discusses the methods developed for the synthesis and reactions of 2-aminochromone-3-carboxaldehydes.…”