Efficient Synthesis and Cytotoxic Activity of Some Symmetrical Disulfides Derived from the Quinolin‐4(1H)‐one Skeleton

Abstract

The preparation of novel organic disulfides containing the 2-(substituted phenyl)quinolin-4(1H)-one ring is described. The synthesis starts from thioanthranilic acid esterified with various bromoacetophenones. Cyclization of the resulting phenacyl thioanthranilates in trifluoroacetic acid afforded a mixture of 2-(substituted phenyl)-3-sulfanylquinolin-4(1H)ones and 3,3Ј-disulfanediylbis[2-(substituted phenyl)quinolin-4(1H)-ones]. Heating of the mixture in o-xylene gave 3,3Ј-[a]

Identification of Eukaryotic Translation Elongation Factor 1-α 1 Gamendazole-Binding Site for Binding of 3-Hydroxy-4(1H)-quinolinones as Novel Ligands with Anticancer Activity

“…1 H NMR(500 MHz, CDCl 3 ) δ ppm 7.85 (d, J = 8.6 Hz, 1H), 7.11 (d, J = 1.1 Hz, 1H), 6.86 (dd, J = 8.0, 1.7 Hz, 1H), 6.24 (s, 1H), 5.85 (s, 2H), 3.87 (s, 3H), 3.44−3.35 (m, 2H), 1.63−1.53 (m, 2H), 1.39−1.28 (m, 4H), 0.89 (t, J = 6.9 Hz, 3H). 13 Methyl 2-Amino-4-(benzylcarbamoyl)benzoate (17). The compound was prepared according to the procedure described for compound 16 with the use of benzylamine.…”

“…Several studies have reported that flavonoid aza-analogs, derivatives of 2-phenyl-3-hydroxy-4­(1 H )-quinolinone (3-HQ), exhibit significant anticancer activities. − However, until now, no study has described their molecular target. We hypothesized that 3-HQs, due to their structural similarity to other flavonoid derivatives, may serve as good ligands for interaction with eEF1A1.…”

Quinoline Derivatives in Discovery and Development of Pesticides

“…Quinolines are unique natural alkaloids that are widely found in plants, marine organisms and microorganisms. − A number of quinoline alkaloids with excellent biological activity have been commercialized (Figure ), such as quinine, camptothecin, , and berberine. − Quinoline is a bicyclic scaffold structure composed of a benzene ring and a pyridine ring. , Quinoline has many isomers or analogues (Figure ), such as 1,2,3,4-tetrahydroquinoline, 5,6,7,8-tetrahydroquinoline, decahydroquinoline, quinolin-4­(1 H )-one, quinolin-4­(3 H )-one, quinolin-2­(1 H )-one, 3,4-dihydroquinolin-2­(1 H )-one, isoquinoline, 1,2,3,4-tetrahydroisoquinoline, 5,6,7,8-tetrahydroisoquinoline, decahydroisoquinoline, isoquinolin-4­(1 H )-one, isoquinolin-1­(2 H )-one, 2,3-dihydroisoquinolin-4­(1 H )-one, 3,4-dihydroisoquinolin-1­(2 H )-one, 1,4-dihydroisoquinolin-3­(2 H )-one, and isoquinolin-3­(4 H )-one . The rich structure types and broad-spectrum biological activities greatly increase the flexibility of quinoline structure modification and derivatization and provide great potential for the discovery of new novel pesticides. − …”

Use of Phenacyl Thiosalicylates for the Preparation of 3-Hydroxybenzo[b]thiophene Derivatives

“…The same course of reaction was observed with phenacyl thioanthranilates and resulted in the formation of 3-sulfanylquinolin-4(1H)-ones II and the corresponding disulfides. 11 When the phenacylamides of anthranilic acid were subjected to acid-mediated cyclization, 3-aminoquinolin-4(1H)-ones III were obtained. 12 Finally, analogous behavior was recently described for phenacylamides of anilin-2-sulfonic acid to yield the benzothiazine-1,1-dioxides IV (Scheme 1).…”