Half-sandwich d6 metal complexes comprising of 2-substituted-1,8-napthyridine ligands with unexpected bonding modes

Synthesis, structural and anti-cancer studies

Sanjay Adhikari, Omar Hussain, Roger M. Phillips, Mohan Rao Kollipara

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The Friedländer condensation reaction between 2-aminonicotinealdehyde and acetophenone derivatives in presence of potassium hydroxide yielded 2-substituted-1,8-napthyridine derivatives viz. 2-(1,8-napthyridin-2-yl)phenol (PHNp), 2-(1,8-napthyridin-2-yl)aniline (AnNp) and 2-(pyridine-4-yl)-1,8-napthyridine (PyNp). Treatment of the chloro-bridged dimers [(arene)MCl2]2 [arene = p-cymene, Cp*; M = Ru, Rh and Ir] with two equivalents of napthyridine ligands (PHNp, AnNp and PyNp) allowed the formation of mononuclear napthyridine complexes having formula [(arene)M(PHNp)Cl2] (1–3), [(arene)M(AnNp)Cl]PF6 (4–6) and [(arene)M(PyNp)Cl2] (7–9). These napthyridine compounds were isolated as neutral and cationic complexes which were further characterized by analytical and spectroscopic techniques. The molecular structures of some of the respective napthyridine complexes were established by carrying out the single crystal X-ray analysis. Single crystal X-ray studies revealed the coordination of the napthyridine ligands to the metal center wherein AnNp ligand coordinated metal in a bidentate chelating NN′ manner and PHNp and PyNp ligand coordinated metal in a monodentate fashion. In case of PHNp complexes the coordination occurs through napthyridine nitrogen N(1) whereas in case of PyNp complexes the coordination takes place through pyridine nitrogen N(1). These napthyridine complexes possessed cytotoxicity against HCT-116 (human colorectal cancer) and MIA-PaCa-2 (pancreatic carcinoma) cancer cell lines as compared to non-cancer cell line ARPE-19.

Original languageEnglish
Pages (from-to)27-37
Number of pages11
JournalJournal of Organometallic Chemistry
Volume854
Early online date13 Nov 2017
DOIs
Publication statusPublished - 1 Jan 2018

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Coordination Complexes
Metal complexes
Pyridine
pyridines
cancer
Ligands
ligands
synthesis
metals
Neoplasms
Metals
cultured cells
Nitrogen
Cells
X-Rays
Single crystals
Derivatives
nitrogen
potassium hydroxides
Cell Line

Cite this

@article{cb65ff938c544621962513d592f7796d,
title = "Half-sandwich d6 metal complexes comprising of 2-substituted-1,8-napthyridine ligands with unexpected bonding modes: Synthesis, structural and anti-cancer studies",
abstract = "The Friedl{\"a}nder condensation reaction between 2-aminonicotinealdehyde and acetophenone derivatives in presence of potassium hydroxide yielded 2-substituted-1,8-napthyridine derivatives viz. 2-(1,8-napthyridin-2-yl)phenol (PHNp), 2-(1,8-napthyridin-2-yl)aniline (AnNp) and 2-(pyridine-4-yl)-1,8-napthyridine (PyNp). Treatment of the chloro-bridged dimers [(arene)MCl2]2 [arene = p-cymene, Cp*; M = Ru, Rh and Ir] with two equivalents of napthyridine ligands (PHNp, AnNp and PyNp) allowed the formation of mononuclear napthyridine complexes having formula [(arene)M(PHNp)Cl2] (1–3), [(arene)M(AnNp)Cl]PF6 (4–6) and [(arene)M(PyNp)Cl2] (7–9). These napthyridine compounds were isolated as neutral and cationic complexes which were further characterized by analytical and spectroscopic techniques. The molecular structures of some of the respective napthyridine complexes were established by carrying out the single crystal X-ray analysis. Single crystal X-ray studies revealed the coordination of the napthyridine ligands to the metal center wherein AnNp ligand coordinated metal in a bidentate chelating NN′ manner and PHNp and PyNp ligand coordinated metal in a monodentate fashion. In case of PHNp complexes the coordination occurs through napthyridine nitrogen N(1) whereas in case of PyNp complexes the coordination takes place through pyridine nitrogen N(1). These napthyridine complexes possessed cytotoxicity against HCT-116 (human colorectal cancer) and MIA-PaCa-2 (pancreatic carcinoma) cancer cell lines as compared to non-cancer cell line ARPE-19.",
keywords = "Cytotoxicity, Iridium, Napthyridine's, Rhodium, Ruthenium",
author = "Sanjay Adhikari and Omar Hussain and Phillips, {Roger M.} and Kollipara, {Mohan Rao}",
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Half-sandwich d6 metal complexes comprising of 2-substituted-1,8-napthyridine ligands with unexpected bonding modes : Synthesis, structural and anti-cancer studies. / Adhikari, Sanjay; Hussain, Omar; Phillips, Roger M.; Kollipara, Mohan Rao.

In: Journal of Organometallic Chemistry, Vol. 854, 01.01.2018, p. 27-37.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Half-sandwich d6 metal complexes comprising of 2-substituted-1,8-napthyridine ligands with unexpected bonding modes

T2 - Synthesis, structural and anti-cancer studies

AU - Adhikari, Sanjay

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AU - Kollipara, Mohan Rao

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N2 - The Friedländer condensation reaction between 2-aminonicotinealdehyde and acetophenone derivatives in presence of potassium hydroxide yielded 2-substituted-1,8-napthyridine derivatives viz. 2-(1,8-napthyridin-2-yl)phenol (PHNp), 2-(1,8-napthyridin-2-yl)aniline (AnNp) and 2-(pyridine-4-yl)-1,8-napthyridine (PyNp). Treatment of the chloro-bridged dimers [(arene)MCl2]2 [arene = p-cymene, Cp*; M = Ru, Rh and Ir] with two equivalents of napthyridine ligands (PHNp, AnNp and PyNp) allowed the formation of mononuclear napthyridine complexes having formula [(arene)M(PHNp)Cl2] (1–3), [(arene)M(AnNp)Cl]PF6 (4–6) and [(arene)M(PyNp)Cl2] (7–9). These napthyridine compounds were isolated as neutral and cationic complexes which were further characterized by analytical and spectroscopic techniques. The molecular structures of some of the respective napthyridine complexes were established by carrying out the single crystal X-ray analysis. Single crystal X-ray studies revealed the coordination of the napthyridine ligands to the metal center wherein AnNp ligand coordinated metal in a bidentate chelating NN′ manner and PHNp and PyNp ligand coordinated metal in a monodentate fashion. In case of PHNp complexes the coordination occurs through napthyridine nitrogen N(1) whereas in case of PyNp complexes the coordination takes place through pyridine nitrogen N(1). These napthyridine complexes possessed cytotoxicity against HCT-116 (human colorectal cancer) and MIA-PaCa-2 (pancreatic carcinoma) cancer cell lines as compared to non-cancer cell line ARPE-19.

AB - The Friedländer condensation reaction between 2-aminonicotinealdehyde and acetophenone derivatives in presence of potassium hydroxide yielded 2-substituted-1,8-napthyridine derivatives viz. 2-(1,8-napthyridin-2-yl)phenol (PHNp), 2-(1,8-napthyridin-2-yl)aniline (AnNp) and 2-(pyridine-4-yl)-1,8-napthyridine (PyNp). Treatment of the chloro-bridged dimers [(arene)MCl2]2 [arene = p-cymene, Cp*; M = Ru, Rh and Ir] with two equivalents of napthyridine ligands (PHNp, AnNp and PyNp) allowed the formation of mononuclear napthyridine complexes having formula [(arene)M(PHNp)Cl2] (1–3), [(arene)M(AnNp)Cl]PF6 (4–6) and [(arene)M(PyNp)Cl2] (7–9). These napthyridine compounds were isolated as neutral and cationic complexes which were further characterized by analytical and spectroscopic techniques. The molecular structures of some of the respective napthyridine complexes were established by carrying out the single crystal X-ray analysis. Single crystal X-ray studies revealed the coordination of the napthyridine ligands to the metal center wherein AnNp ligand coordinated metal in a bidentate chelating NN′ manner and PHNp and PyNp ligand coordinated metal in a monodentate fashion. In case of PHNp complexes the coordination occurs through napthyridine nitrogen N(1) whereas in case of PyNp complexes the coordination takes place through pyridine nitrogen N(1). These napthyridine complexes possessed cytotoxicity against HCT-116 (human colorectal cancer) and MIA-PaCa-2 (pancreatic carcinoma) cancer cell lines as compared to non-cancer cell line ARPE-19.

KW - Cytotoxicity

KW - Iridium

KW - Napthyridine's

KW - Rhodium

KW - Ruthenium

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