Fazlur-Rahman Nawaz Khan

Solvent-free synthesis and antibacterial studies of some quinolinones

Solvent-free, microwave-induced condensation of 2-aminoaryl alkyl ketones and ethyl 3-oxobutanoate in the presence of amberlite Na sr1L gave quinolinones in high yield when compared to other catalysts. Further, N-alkylation of the quinolinones was carried out effectively with various halides using amberlite Na sr1L. An N-alkylated quinolinone exhibited enhanced activities against B. subtilis, E. coli, and P. aeruginosa, similar to standard drug ampicillin. Two compounds showed effective activity against S. aureus, and one resulted in moderate activity against E. coli.Graphical abstract

Synthesis of Methoxy‐substituted Chalcones and in vitro Evaluation of their Anticancer Potential

Methoxy‐substituted chalcones, 3 were obtained using simple, efficient method from 2‐naphtylethanone, 1 and aromatic aldehydes, 2. The in vitro cytotoxicity activities of the chalcones against a panel of three human cancer cell lines were explored. The tested compounds were found to possess significant cytotoxic activity. The DNA strand break and damage was quantified through alkaline comet assay, flow cytometric analysis, and chromatin condensation studies, which revealed the apoptotic nature of the compounds. Compound 3c, (3‐(3,4,5‐trimethoxyphenyl)‐1‐(2‐naphthyl) prop‐2‐en‐1‐one) showed highest cytotoxicity of 0.019 μm against HeLa, 0.020 μm against HCT15 and 0.022 μm against A549. Compound 3e, (3‐(3,5‐dimethoxyphenyl)‐1‐(2‐naphthyl) prop‐2‐en‐1‐one) showed better IC50 values against all the three cell lines employed for the study.

Nicotinic acid conjugates of nonsteroidal anti-inflammatory drugs (NSAID’s) and their anti-inflammatory properties

A series of nicotinic acid conjugates with non-steroidal anti-inflammatory drugs (NSAIDs) have been effectively synthesized using TBTU in high yield and purity. All the synthesized conjugates were evaluated for their in vitro anti-inflammatory activity.

Quinoline-3-carboxylates as potential antibacterial agents

AbstractThe ethyl-2-chloroquinoline-3-carboxylates, 4, were achieved from o-aminobenzophenones in two steps. i.e. initially, the ethyl-2-oxoquinoline-3-carboxylates, 3, were obtained by base-catalyzed Friedlander condensations of o-aminobenzophenones, 1, and diethylmalonate, 2. The 2-chloroquinoline-3-carboxylates, 4, were then obtained by the reaction with POCl3 in good yields. The chemical structures were confirmed by FTIR, mass and 1H-NMR spectroscopic techniques. All the synthesized compounds were tested for their in vitro antibacterial activity against Bacillus subtilis and Vibrio cholera and found to possess moderate activity.

3-Phenyl-1-[2-(3-phenyl-isoquinolin-1-yl)-diselan-yl]isoquinoline.

The complete molecule of the title compound, C(30)H(20)N(2)Se(2), is generated by a crystallographic inversion centre at the mid-point of the Se-Se bond. The dihedral angle between the isoquinoline-1-selenol group and the phenyl ring is 14.92 (2)°. The herringbone-like packing of the structure is supported by inter-molecular π-π stacking inter-actions with a shortest perpendicular distance between isoquinoline groups of 3.514 Å; the slippage between these ring systems is 0.972 Å, and the distance between the centroids of the six-membered carbon rings is 3.645 (3) Å.

Organoiodine(III) mediated intramolecular oxidative cyclization of 1-(3-arylisoquinolin-1-yl)-2-(arylmethylene)hydrazines to 5-aryl-3-(aryl)-[1,2,4]triazolo[3,4-a] isoquinolines

A series of 5-aryl-3-(aryl)-[1,2,4]triazolo[3,4-a]isoquinolines, 4 were obtained by oxidative cyclization of 1-(3-arylisoquinolin-1-yl)-2-(arylmethylene)hydrazines, 3, in the presence of a hypervalent iodine oxidant (iodobenzene diacetate, IDB) and dichloromethane at ambient temperature. This methodology involves a proficient metal-free intramolecular C–N bond formation, facilitated by a hypervalent iodine reagent.

Flower-shaped ZnO nanoparticles as an efficient, heterogeneous and reusable catalyst in the synthesis of N-arylhomophthalimides and benzannelated isoquinolinones

A simple and green protocol, developed utilizing an efficient, heterogeneous and recyclable catalyst, i.e. zinc oxide nanoparticles (ZnO NPs)-mediated synthesis of N-arylhomophthalimides and benzannelated isoquinolinones, is reported. The structures of the desired products were characterized by FTIR, 1H NMR, 13C NMR, and HRMS techniques. The ZnO NPs exhibited excellent catalytic activity and the proposed methodology is capable of providing the desired products in good yield and purity.

Environmentally benign one-pot synthesis and antimicrobial activity of 1-methyl-2,6-diarylpiperidin-4-ones

An efficient and environmentally benign one-pot method for the synthesis of 1-methyl-2,6-diarylpiperidin-4-ones using montmorillonite K-10 as a catalyst has been developed. Antimicrobial activity of the compounds has been tested against selected representatives of Gram-positive and Gram-negative bacteria and fungi.

Facile synthesis of 3-aryl-1-((4-aryl-1,2,3-selenadiazol-5-yl)sulfanyl)isoquinolines

A new series of 1,2,3-selenadiazoles containing an aryl or a 3-arylisoquinoline sulfanyl moiety at carbons 4 and 5, respectively, was prepared by cyclization of the respective semicarbazones in the presence of selenium(II) oxide and tetrahydrofuran at 70–75°C. Semicarbazones required for the reaction were obtained from 2-((3-arylisoquinolin-1-yl)sulfanyl)-1-phenylethanones, I, by a reaction with semicarbazide hydrochloride in ethanol/water mixture and potassium acetate base.

N-Phenyl-nicotinamide.

In the title compound, C12H10N2O, the dihedral angle between the phenyl and pyridine rings is 64.81 (1)°. Intermolecular N—H⋯O hydrogen bonds connect the molecules into chains running along the b axis.