Synthesis, characterization and anticancer activity of 3-formylchromone benzoylhydrazone metal complexes

Abstract

A new Schiff base derived from 3-formylchromone and benzohydrazide (Hfcbh) and its Ni(II), Zn(II), Ru(II), Ru(III), Pd(II), Pt(II) and Ag(I) complexes were synthesized. These compounds were characterized on the basis of physicochemical and spectroscopic methods. Two modes of chelation for Hfcbh are reported: (1) neutral tridentate ligand through the chromone carbonyl oxygen, hydrazonic carbonyl oxygen and azomethine nitrogen atoms and (2) mononegative tridentate ligand via the chromone carbonyl oxygen, hydrazonic deprotonated hydroxy oxygen and azomethine nitrogen atoms. Free Hfcbh and its Ni(II), Zn(II), Ag(I), Pd(II) and Pt(II) complexes have been tested as anticancer agents against the human breast cancer (MDA-MB231) and human ovarian cancer (OVCAR-8) cell lines. The [Ag(fcbh)(PPh 3 )] complex shows the highest efficacy with a mean IC 50 values of 1.0 (MDA-MB231) and 0.87 (OVCAR-8) lM, respectively.

Novel metal complexes of 3‐acetylcoumarin‐2‐hydrazinobenzothiazole Schiff base: Design, structural characterizations, DNA binding, DFT calculations, molecular docking and biological studies

“…The absorption band due to the ν(C‐S‐C) vibration does not change in the complexes revealing the non‐involvement of the sulfur atom in coordination and this agrees with the reported data on benzothiazole and 2‐substituted benzothiazoles 58, 59 . The appearance of new bands in the 431–460 cm −1 range are due to ν(M‐N), while in the Ru (II) and Cu (II) complexes, the ν(M‐O) band appears at 514 and 536 cm −1 , respectively 60 . All the FT‐IR spectra of the ligand and complexes are presented in the Supporting Information section (Figure S1A‐f).…”

“…The UV–Vis spectra of the Zn (II) and Ag (1) complexes (d 10 configuration) show similar behavior to that of the ligand with slight red shifts to the higher wavelengths (~ 5 nm) owing to coordination to the metal ion 52, 66 . In the paramagnetic Ru (III) complex (μ eff = 1.90 BM), the bands associated with (4d 5 ) configuration are located at 280, 479 and 748 nm and these can be assigned to π‐π*, LMCT (ligand‐to‐metal charge transfer) and d‐d transitions, respectively 60, 67 . The spectrum of the square‐planar Pd (II) complex (d 8 configuration) shows electronic bands at 384 and 486 nm due to the ( 1 A 1 g → 1 B 1 g) and ( 1 A 1 g → 1 E 1 g) transitions, 64 respectively.…”

Physico-chemical, Antioxidant and Antimicrobial Investigation on New Mixed Ligand Complexes Containing bis(2,4,4-trimethylpentyl)dithiophosphinic acid and 2,2′-bipyridine

“…The molecular ion peak of metal complex 1-6 was appeared in the FAB mass spectra at m/z = 570.1, m/z = 571.1, m/z = 573.9, m/z = 577.9, m/z = 578.8 and m/z = 626.2, respectively. Moreover, the complexes (1-6) were showed another characteristic peak at m/z = 535.1, m/z = 536.2, m/z = 538.9, m/z = 542.9, m/z = 543.8 and m/z = 591.2, respectively due to the loss of one chloride ligand 48 . Both molecular ion and characteristic peak of metal complexes were in good agreement with their assigned molecular formula.…”

Cobalt(II) coordination complex with 2,5-bis(pyridine-2-yl)-1,3,4-thiadiazole and thiocyanate as co-ligand: Synthesis, crystal structure, Hirshfeld surface analysis, spectroscopic, thermal and magnetic properties

“…Since the nitrogen atom is present in many natural molecules or in those of pharmacological interest [6,10], research has been devoted to the synthesis of transition metal complexes with hetero-atom and chelating ligands [11][12][13]. It is also well established that some of these organic molecules (drugs) are much more effective when administered linked to a metal [14][15][16]. The 1,3,4-thiadiazole derivatives such as 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole (L) have been studied and have allowed access essentially to mono and bimetallic complexes [17][18][19][20][21][22].…”