P. T. Perumal

Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line.

Novel dispirooxindole-pyrrolidine derivatives have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine with the dipolarophile 3-(1H-indol-3-yl)-3-oxo-2-(2-oxoindolin-3-ylidene)propanenitrile, and also spiro compound of acenaphthenequinone obtained by the same optimized reaction condition. Synthesized compounds were evaluated for their antimicrobial activity and all the compounds shown significant activity. Anticancer activity was evaluated against A549 human lung adenocarcinoma cancer cell lines. Compounds 7b, 7g, 7i and 7r exhibit very good anticancer activity 62.96%, 62.03%, 67.67% and 60.22%, respectively, at the dose of 200μg/mL and compound 7i shows IC50 value in 50μg/mL.

Synthesis, antimicrobial and antioxidant evaluation of quinolines and bis(indolyl)methanes

An improved and practical synthesis of substituted quinolines and bis(indolyl)methanes was achieved under microwave condition using Zn(OTf)(2) as catalyst. The synthesized compounds have been screened for antimicrobial and antioxidant activities.

Novel spirooxindole–pyrrolidine compounds: Synthesis, anticancer and molecular docking studies

Novel spirooxindole-pyrrolidine compounds have been synthesised through 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or thioproline with the dipolarophile 3-(1H-imidazol-2-yl)-2-(1H-indole-3-carbonyl)acrylonitrile under the optimised reaction condition. Synthesised compounds were evaluated for their anticancer activity against A549 human lung adenocarcinoma cancer cell line. Among the 29 tested compounds 4j, 6b and 6h showed very high activity 66.3%, 64.8% and 66.3% at 25 μg/mL concentration against A549 lung adenocarcinoma cancer cell line. These spirooxindole-pyrrolidine compounds can be promising therapeutic agents for A549 lung adenocarcinoma cancer cell line.

Synthesis and antinociceptive activity of pyrazolyl isoxazolines and pyrazolyl isoxazoles.

Pyrazolyl isoxazolines and isoxazoles were synthesised in moderate to good yields using 1,3-dipolar cycloaddition of pyrazole derived nitrile oxide with various dipolarophiles such as N-substituted maleimide, diethylacetylene dicarboxylate and phenylacetylene. The synthesized compounds were evaluated for antinociceptive activities. The 3-pyrazolyl-4,5-dicarbethoxy isoxazoles (9a-c) exhibited the maximum antinociceptive activity.

Cu(OTf)2 catalyzed three component reaction: Efficient synthesis of spiro[indoline-3,4′-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines

Cu(OTf)2 catalyzed efficient synthesis of spiropyrano[3,2-b]pyran-4(8H)-ones is accomplished via one-pot three component reaction between isatin, kojic acid and active methylenes. This synthetic protocol is operationally simple and affords product with good to excellent yields at a short reaction time. The synthesized compounds were evaluated for their tumor cell growth inhibitory activity against the human lung cancer cell line (A549) and found that 13 compounds exhibited moderate to good anticancer potency. Molecular docking studies were performed for all the synthesized compounds and the results showed that compound 4e showed greater affinity for anaplastic lymphoma kinase (ALK) receptor.

A new method for the preparation of substituted 5,6,7,8-tetrahydro-4H-I-benzopyran and 4H-pyrans by Vilsmeier-Haack reagent

Abstract Substituted 5,6,7,8-tetrahydrO-4H-1-benzopyran and 4H-pyran derivatives were synthesized from their corresponding substituted 1,5 diketones with vilsmeier haack reagent in moderate yields.

DNA binding, molecular docking and apoptotic inducing activity of nickel(II), copper(II) and zinc(II) complexes of pyridine-based tetrazolo[1,5-a]pyrimidine ligands

Six mononuclear copper(II), nickel(II) and zinc(II) complexes, [ML1Cl2] (1–3) and [M(L2)2Cl2] (4–6), of two biologically active tetrazolo[1,5-a]pyrimidine core ligands, ethyl 5-methyl-7-pyridine-2-yl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate (L1) and ethyl-5-methyl-7-pyridine-4-yl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate (L2), have been synthesized and characterized. The molecular structure of the ligands (L1&2) and complex 6 were determined by single crystal X-ray diffraction. The X-ray crystal structure of 6 confirms that it has a distorted tetrahedral structure with a ZnN2Cl2 coordination environment. All of the complexes exhibit an unusually strong luminescence at room temperature. Electroparamagnetic resonance spectra of copper(II) complexes (2 and 5) show four lines, characteristic of square planar geometry, with nuclear hyperfine spin 3/2. DNA binding studies of complexes with calf-thymus DNA suggest that complexes 2 and 5 bind in the grooves of the DNA. These results were further supported by molecular docking studies. In vitro cytotoxic activities of the ligands (L1&2) and complexes (1–6) against human cancer cell lines such as lung (A549), cervical (HeLa), colon (HCT-15) and a non-cancer human embryonic kidney cell line revealed that the complexes selectively inhibit the growth of cancer cells and are inactive against non-cancer cell lines, whereas the ligands were found to be inactive with both cancer and non-cancer cell lines. The IC50 values of the complexes revealed that the copper(II) complexes (2 and 5) exhibit high cytotoxic activity against colon (HCT-15) cells when compared to the standard drug cisplatin. Furthermore, the live cell and fluorescent imaging of cancer cells show that complexes 2 and 5 induce cell death through apoptosis.

Ring opening of chalcone epoxides with vilsmeier reagent

Abstract Reaction of substituted 2,3-epoxy-1,3-diphenylpropan-1-one with Vilsmeier reagent gave substituted 3-chloro-1,3-diphenyl-2-propen-1-one 1 .

Super acid catalysed sequential hydrolysis/cycloisomerization of o-(acetylenic)benzamides under microwave condition: Synthesis, antinociceptive and antiinflammatory activity of substituted isocoumarins

AbstractSynthesis of isocoumarins and related compounds via triflic acid promoted hydrolysis/cyclization sequence of 2-(alkynyl)benzamides under microwave condition was achieved. The substrate scope of the reaction was broad to include not only aromatic but also polyaromatic and heteroaromatic motifs, thus highlighting the significance of this methodology. One-pot operation, short reaction time, good chemical yields and excellent regioselectivity are the advantages of this protocol. All the synthesized compounds were evaluated for their antinociceptive and antiinflammatory activities using in vivo rodent models. Graphical AbstractSynthesis of isocoumarins via triflic acid promoted sequential hydrolysis/cyclization of 2-(alkynyl)benzamides under microwave condition was achieved. All the synthesized compounds were evaluated for their antinociceptive and antiinflammatory activities using in vivo rodent models.

A facile synthesis of 4,5-dihydropyrazolo[4,3-c]quinolines with Vilsmeier reagent

4,5-Dihydropyrazolo[4,3-c]quinolines have been synthesised in moderate to good yields from dihydroquinolin-4-ones using the Vilsmeier reagent, under conventional and microwave irradiation conditions.