Subhendu Naskar

Amberlite-IRA-402 (OH) ion exchange resin mediated synthesis of indolizines, pyrrolo [1,2-a] quinolines and isoquinolines: Antibacterial and antifungal evaluation of the products

A number of indolizines and pyrrolo[1,2-a]quinolines/isoquinolines were prepared from phenacyl pyridinium, quinolinium and isoquinolinium salts derived from the reaction of the heterocycles with 2-bromo acetophenone with alkynes and alkenes using amberlite-IRA-402 (OH) ion exchange resin as the base. Antibacterial and antifungal studies were carried out against thirteen bacterial and four fungal strains, which revealed that three derivatives (4a, 4b, 7a) out of fifteen are effective against all the thirteen strains and one derivative, 10, showed dual antibactericidal and antifungal efficacy.

Efficient synthesis of 3,3-diheteroaromatic oxindole analogues and their in vitro evaluation for spermicidal potential

Syntheses of 3,3-diheteroaromatic oxindole derivatives has been achieved by coupling indole-2,3-dione (isatin) with differently substituted indoles and pyrrole in presence of I(2) in i-PrOH. The in vitro spermicidal potentials and the mode of spermicidal action of the synthesized analogues were evaluated and the derivative, 3,3-bis (5-methoxy-1H-indol-3-yl) indolin-2-one (3d) exhibited most significant activity.

Cytotoxic Activity and Apoptosis-Inducing Potential of Di-spiropyrrolidino and Di-spiropyrrolizidino Oxindole Andrographolide Derivatives

Anticancer role of andrographolide is well documented. To find novel potent derivatives with improved cytotoxicity than andrographolide on cancer cells, two series of di-spiropyrrolidino- and di-spiropyrrolizidino oxindole andrographolide derivatives prepared by cyclo-addition of azomethine ylide along with sarcosine or proline (viz. sarcosine and proline series respectively) and substitution of different functional groups (-CH3, -OCH3 and halogens) were examined for their cytotoxic effect on a panel of six human cancer cell lines (colorectal carcinoma HCT116 cells, pancreatic carcinoma MiaPaCa-2 cells, hepatocarcinoma HepG2 cells, cervical carcinoma HeLa cells, lung carcinoma A549 and melanoma A375 cells). Except halogen substituted derivatives of proline series (viz. CY2, CY14 and CY15 for Br, Cl and I substitution respectively), none of the other derivatives showed improved cytotoxicity than andrographolide in the cancer cell lines examined. Order of cytotoxicity of the potent compounds is CY2>CY14>CY15>andrographolide. Higher toxicity was observed in HCT116, MiaPaCa-2 and HepG2 cells. CY2, induced death of HCT116 (GI50 10.5), MiaPaCa-2 (GI50 11.2) and HepG2 (GI50 16.6) cells were associated with cell rounding, nuclear fragmentation and increased percentage of apoptotic cells, cell cycle arrest at G1 phase, ROS generation, and involvement of mitochondrial pathway. Upregulation of Bax, Bad, p53, caspases-3,-9 and cleaved PARP; downregulation of Bcl-2, cytosolic NF-κB p65, PI3K and p-Akt; translocation of P53/P21, NF-κB p65 were seen in CY2 treated HCT116 cells. Thus, three halogenated di-spiropyrrolizidino oxindole derivatives of andrographolide are found to be more cytotoxic than andrographolide in some cancer cells. The most potent derivative, CY2 induced death of the cancer cells involves ROS dependent mitochondrial pathway like andrographolide.

Electron density of two bioactive oligocyclic indole and oxindole derivatives obtained from low-order X-ray data and invariom application

For two indole and oxindole bioactive molecules, low-order room-temperature X-ray data were used to generate aspherical electron density (ED) distributions by application of the invariom formalism. An analysis of the ED using the quantum theory of atoms in molecules (QTAIM) was carried out, which allowed for quantitatively examining bond orders and charge separations in various parts of the molecules. The inspection of electrostatic potentials (ESPs) and Hirshfeld surfaces provided additional information on the intermolecular interactions. Thus, reactive regions of the molecules could be identified, covalent and electrostatic contributions to interactions could be visualized, and the forces causing the crystal packing scheme could be rationalized. As the used invariom formalism needs no extra experimental effort compared to routine X-ray analysis, its wide application is recommended because it delivers information far beyond the normally obtained steric properties. In this way, complementary contributions to drug design can be given as is demonstrated for indoles in this study, which are involved in the metabolism of plants and animals as well as in cancer therapy.

NH 4 Cl-promoted synthesis of symmetrical and unsymmetrical triindolylmethanes under solvent-free conditions

The synthesis of various triindolylmethanes from indole-3-carboxaldehyde, using indole derivatives as reactants and NH4Cl as catalyst under solvent-free conditions, is described. This methodology provides access to both symmetrical and unsymmetrical triindolylmethanes in excellent yields. With N-methylindole particularly, indole-3-carboxaldehyde appears to act as a formyl donor, leading to the exclusive formation of a symmetrically trisubstituted product. The novelty of the methodology lies in its operational simplicity, environment friendly reaction conditions, and inexpensive and easy availability of the catalyst. A plausible mechanism of formation of the products is suggested.

A novel route for the synthesis of 3-(pyrrol-1-yl)-indolin-2-ones

A high yielding environmentally benign protocol has been developed for the synthesis of 3-(pyrrol-1-yl)-indolin-2-ones using a Lewis acid surfactant combined catalyst in water.

Aqueous phase supramoleculer synthesis of 3,2-and 3,3-dihetero-aromatic oxindoles catalysed by β-cyclodextrin

A high yielding green protocol is described for the synthesis of 3,2 and 3,3-diheteroaromatic oxindole involving the condensation of isatin with indole or pyrrole in an aqueous medium under neutral conditions by supramoleculer catalysis by β-cyclodextrin. The β-cyclodextrin can be easily recovered and reused without any loss of activity.

Palladium-Catalyzed 8-Exo Trig Intramolecular Heck Reaction Under Microwave Irradiation in the Presence of Basic Alumina

Abstract The Heck cross-coupling reaction has been employed for efficient conversion of quinolines to benzoxocinoquinoline through a microwave-assisted palladium-catalyzed intramolecular cyclization in the presence of basic alumina. GRAPHICAL ABSTRACT

Novel Route for the Synthesis of 3-(Pyrrol-1-yl)-indolin-2-ones in Aqueous Micellar Medium

Abstract A high-yielding environmentally benign protocol has been developed for the synthesis of 3-(pyrrol-1-yl)-indolin-2-ones from the reaction of isatin and trans-4-hydroxy-L-proline in aqueous micellar medium. The method is operationally simple and more effective than the previous methods in terms of the yield of the products and the reaction time. GRAPHICAL ABSTRACT