Gangadhar Y. Meti

Expedient synthesis of benzimidazoles using amides

In the present report an efficient, rapid, facile and inexpensive route for the synthesis of benzimidazoles using 1,2-arylenediamines and N,N-dimethylformamide in acidic medium under thermal/microwave condition is developed. This reaction was further explored with the different amides to afford a library of 2-substituted benzimidazoles. The advantage of the present synthetic method includes shorter reaction time, easy work up and excellent yields without using catalysts.

Synthesis of novel imidazo[2,1-b][1,3,4]thiadiazoles appended to sydnone as anticancer agents

A novel series of 3-aryl-4{6′-(6′′-substituted-coumarin-3′′-yl) imidazo[2,1-b][1,3,4]thiadiazol-2′-yl}-sydnones 5h–5s were synthesized and screened for their anticancer and DNA cleavage activities and analyzed for pharmacological parameters such as toxicity, drug-likeliness, and drug score for oral bioavailability. In vitro toxicity assay was carried out by assessing the survival E. coli AB1157 (wild type) cultures. Some of the compounds have shown significant anticancer activities also.

Facile synthesis of novel quinoline derivatives as anticancer agents

Convenient and efficient synthesis of novel N-(4-acetyl-4,5-dihydro-5-(7,8,9-substituted-tetrazolo[1,5-a]-quinolin-4-yl)-1,3,4-thiadiazol-2-yl)acetamides 4a–j and their in vitro anticancer activity against two cell lines viz., human breast cancer cell line MCF7 and human cervix cancer cell line HeLa were carried out. GI50, LC50, TGI values were evaluated. Two of the compounds 4e and 4i with halogen substituent at 7th position of the target molecules have shown potent activity against human cervix cancer cell line HeLa. DNA cleavage studies revealed that most of these compounds show partial cleavage and few of them show complete cleavage of DNA.

Synthesis of Novel 1,2,4-Triazole Derivatives as Antimicrobial Agents via the Japp-Klingemann Reaction: Investigation of Antimicrobial Activities

In the present investigation, 1,2,4-triazole appended to pyrazoline and pyrazole rings (4a–g) using N-arylsydnone as synthon was prepared. The title compounds were subjected to Osiris property explorer for the oral bioavailability to analyze their drug likeness and drug score. Further, the compounds were subjected to the antimicrobial activity and analyzed the IC 50 and MIC values.

Synthesis of biphenyl derivatives as ACE and α-amylase inhibitors

Angiotensin converting enzyme (ACE) and α-amylase inhibitors were synthesized using 4′-(bromomethyl)-biphenyl-2-carbonitrile 1 and various cyclic secondary amines (a–h). The nitrile group appended to biphenyl was converted into tetrazole 3a–3h and the tetrazole was ring transformed into 1,3,4-oxadiazole derivatives 4a–4h. Some of the compounds have exhibited significant ACE and α-amylase inhibition.

2-[4-(Morpholin-4-ylmeth­yl)phen­yl]benzonitrile

In the title compound, C18H18N2O, the morpholine ring adopts a chair conformation with the exocyclic N—C bond in an equatorial orientation. The dihedral angles between the central benzene ring and the morpholine ring (all atoms) and the cyanobenzene ring are 87.87 (7) and 52.54 (7)°, respectively. No significant intermolecular interactions are observed in the crystal structure.

5-{4'-[(5-Benzyl-2H-tetra-zol-2-yl)meth-yl]biphenyl-2-yl}-1H-tetra-zole monohydrate.

In the title compound, C22H18N8·H2O, the dihedral angle between the tetrazole rings is 69.58 (1)° while the terminal phenyl ring makes dihedral angles of 26.98 (8) and 39.75 (8)° with the other benzene rings. The rings of the biphenyl unit subtend a dihedral angle of 55.23 (8)°. In the crystal, the solvent water molecule is linked to the main molecule via an N—H⋯O hydrogen bond. In addition, C—H⋯N and O—H⋯N hydrogen bonds link the components into chains along [010]. The crystal structure also features C—H⋯π and π–π interactions, with centroid–centroid distances of 3.6556 (9) and 3.826 (1) Å.

Synthesis and Anti-Proliferative Activity of Biphenyl Derived 5-Substituted-Indolin-2-Ones

A series of novel biphenyl derived 5-substituted-indolin-2-one derivatives were synthesized by the reaction of 6-chloro-5-(2-chloroethyl)-indolin-2-one 1 with cyclic secondary amines 2a-h followed by condensation of bromomethylcyanobiphenyl to afford the compounds 5a-h. The nitrile group of 5a-h was converted into tetrazole to obtain the compounds 7a-h and tetrazole of 7a-h was further ring transformed into oxadiazole to get compounds 8a-h. Molecular docking study of these previously unknown molecules was performed on PDB: 453D to analyze the interaction and preferred binding mode of synthesized molecules with DNA. Anti-proliferative activity of these newly synthesized compounds were evaluated against a panel of 60 human cancer cell lines at National Cancer Institute (NCI), Bethesda USA. Among these, seven (07) compounds were evaluated for their anti-cancer activity. Some of the compounds displayed potent anti-proliferative activity at 10 µM.

Crystal structure of 6-chloro-5-(2-chloro­eth­yl)-3-(propan-2-yl­idene)indolin-2-one

The title compound, C13H13Cl2NO, has a 3-(propan-2-ylidene)indolin-2-one core with a Cl atom and a chloroethyl substituent attached to the aromatic ring. Two atoms of the aromatic ring and the chloroethyl substituent atoms are disordered over two sets of sites with a refined occupancy ratio of 0.826 (3):0.174 (3). In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif.