Synthesis, preliminary cytotoxicity evaluation of new 3-formylchromone hydrazones and phosphorohydrazone derivatives of coumarin and chromone

Abstract

Reactions of chromone derivatives 1-4 with N-substituted hydrazines were described. Hydrazones (6, 7a, 8a-c, 9b-e, 10e, 11e, 12) were evaluated for cytotoxicity (MTT test) against HL-60 and NALM-6 leukemia cells. Phosphorohydrazone of 3-formylchromone 8a and hydrazone of 2-amino-3-chromone derivative 11e showed appreciable cytotoxicity. The cytotoxicity indices of 8a, 11e, and 12 were higher on drug-resistant HL-60 ADR cells in comparison to HL-60. Compounds 8a and 11e were tested for their ability to induce cytochrome c translocation from mitochondria to cytosol.

Chemistry of 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehydes

“…34 The hydrazone 76 (R = 2,4-dichlorophenyl, CO 2 Me, CH 2 CH 2 OH) and the bis-hydrazone 78, derived from 1 and benzophenone hydrazone, have been evaluated for cytotoxicity (MTT test) against H2-60 and NALM-6 leukemia cells. 35 The hydrazone 76 (R = CO 2 Et), obtained from 1 and ethyl carbazate, on heating with ethyl chloroformate gives the carbazate 79 instead of any cyclized product. 36 The hydrazone 80 obtained by heating the amine 1 with 5,6-diphenyl-1,2,4-triazin-3-ylhydrazine in CF 3 COOH acts as a fluorophore.…”

3-Formylchromones as diverse building blocks in heterocycles synthesis

“…Treatment of 3-formylchromone 1a with substituted hydrazines 222a-c in absolute ethanol or toluene afforded the corresponding hydrazones 223a-c (Scheme 104) [152,153].…”

Synthesis and evaluation of pyridinium‐hydrazone derivatives as potential antitumoral agents

“…Recently, researchers focus on discovering effective molecules targeting cell death pathways, such as apoptosis, necrosis, and autophagy. [8][9][10] Many researchers have reported hydrazones as promising anticancer agents. [3] Apoptosis is the best-characterized type of PCD, and it has been targeted to prevent and treat cancer for decades.…”

“…Hydrazone derivatives have important biological activities, and this functional group is found as a core structure in many chemotherapeutic agents having antimicrobial, antimalarial, antileishmanial, antiviral, and anticancer effects. [8][9][10] Many researchers have reported hydrazones as promising anticancer agents. [11][12][13][14][15][16][17][18] According to the reports, these hydrazone compounds display anticancer activity via diverse molecular mechanisms.…”