Indian Institution of Science Education and Research

Pune, India

Indian Institution of Science Education and Research

Pune, India

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PubMed | Indian Institution of Science Education and Research and University of Veterinary Medicine Hannover
Type: Journal Article | Journal: Nanoscale | Year: 2016

Multivalent glycodendrimers make promising tools to tackle the basic and translational research in the field of carbohydrate-mediated interactions. Despite advances in glycodendrimers and glycopolymers, the multivalent probes available to date are still far from being ideal biological mimics. This work demonstrates the inherent chirality of glycodendrimers to be one of the promising factors to generate different spatial carbohydrate micro-environments to modulate specific carbohydrate-protein interactions. By exploiting the host-guest strategy, chiral Ru(ii) complexes ( and ) and mannose capped -cyclodextrin (-CD), we generated a library of homologous metallo-glycodendrimers (MGDs) with sizes of 50-70 nm. These nanoclusters can enantioselectively bind to specific C-type lectins and displayed selectivity in cellular uptake. We also discovered their potential clathrin-mediated endocytotic pathway in DC-SIGN and SIGNR3-transfected cell lines. Finally, in vivo biodistribution and sequestration of MGDs was determined to understand the role of chirality mediated spatial arrangement in carbohydrate-mediated interactions.


Manoharan R.,Indian Institution of Science Education and Research | Jeganmohan M.,Indian Institution of Science Education and Research
Organic and Biomolecular Chemistry | Year: 2015

A regioselective synthesis of substituted pyrroloquinolinones via a ruthenium-catalyzed oxidative cyclization of substituted N-carbamoyl indolines with alkynes is described. The cyclization reaction was compatible with various symmetrical and unsymmetrical alkynes including substituted propiolates. Later, we performed the aromatization of pyrroloquinolinones into indole derivatives in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). © The Royal Society of Chemistry 2015.


Padala K.,Indian Institution of Science Education and Research | Jeganmohan M.,Indian Institution of Science Education and Research
Chemistry - A European Journal | Year: 2014

A highly regioselective ortho-benzoxylation of N-alkyl benzamides with aromatic acids in the presence of [{RuCl2(p-cymene)}2], AgSbF6, and (NH4)2S2O8 in 1,2-dichloroethane at 100°C for 24 h affording ortho-benzoxylated N-alkyl benzamides by C-H bond activation is described. Further, Ru-catalyzed alkenylation is done at the ortho C-H bond of benzoxylated N-alkyl benzamides with alkenes in water solvent. Subsequently, the benzoxyl moiety of N-alkyl benzamides was converted into a hydroxyl group in the presence of base or acid. A possible reaction mechanism was proposed to account for the present coupling reaction. C-H bond activation: A highly regioselective ortho-benzoxylation of benzamides with substituted benzoic acids in the presence of a ruthenium catalyst is described. Further, Ru-catalyzed alkenylation is carried out at the ortho C-H bond of benzoxylated N-alkyl benzamides with alkenes in water solvent. Subsequently, the benzoxyl moiety of N-alkyl benzamides was converted into the hydroxyl group in the presence of base or acid (see scheme). © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


More N.Y.,Indian Institution of Science Education and Research | Jeganmohan M.,Indian Institution of Science Education and Research
Chemistry (Weinheim an der Bergstrasse, Germany) | Year: 2015

A regioselective synthesis of symmetrical and unsymmetrical benzopinacolones through aerobic dehydrogenative α-arylation at the tertiary sp(3) C-H bond of substituted 1,1-diphenylketones with aromatic and heteroaromatic compounds, in the presence of K2S2O8 in CF3COOH at room temperature, is described. The reaction is proposed to go via a carbocation intermediate, which could be generated directly from cleavage of the sp(3) C-H bond of 1,1-diphenylketone. Subsequent α-arylation was achieved at the methene sp(3) carbon atom of the substituted ketone. A variety of substituted aromatic and heteroaromatic compounds were compatible with this reaction. In addition, benzopinacolones were converted into sterically hindered, tetrasubstituted alkenes and polycyclic aromatic compounds. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Manikandan R.,Indian Institution of Science Education and Research | Jeganmohan M.,Indian Institution of Science Education and Research
Organic and Biomolecular Chemistry | Year: 2016

Substituted aromatic amides reacted efficiently with allylic acetates in the presence of a cationic ruthenium complex in ClCH2CH2Cl at room temperature providing ortho allylated benzamides in a highly regioselective manner without any oxidant and base. The whole catalytic reaction occurred in a Ru(ii) oxidation state and thus the oxidation step is avoided. By tuning the reaction temperature, ortho allyl and vinyl benzamides were prepared exclusively. Later, ortho allyl and vinylated benzamides were converted into biologically useful six- and five-membered benzolactones in the presence of HCl. © 2016 The Royal Society of Chemistry.


Misra R.,Indian Institution of Science Education and Research | Reja R.M.,Indian Institution of Science Education and Research | Narendra L.V.,Indian Institute of Science | George G.,Indian Institute of Science | And 2 more authors.
Chemical Communications | Year: 2016

We are reporting the influence of foldamer structures on their self-assembled architectures. In a sharp contrast to the ordered α,γ-hybrid 12-helix obtained from 11 alternating Aib and γ-Phe, the α,γ-hybrid peptides constituted with α-Phe and 4,4-dimethyl γ-amino acid (Aic) displayed the extended sheet type of conformations in solution and spontaneously self-assembled into thermally and proteolytically stable capsules. In contrast, the conformationally ordered 12-helix self-assembled into a three-dimensional supramolecular polyhedron. © 2016 The Royal Society of Chemistry.


PubMed | Indian Institution of Science Education and Research and Indian Institute of Science
Type: Journal Article | Journal: Chemical communications (Cambridge, England) | Year: 2016

We are reporting the influence of foldamer structures on their self-assembled architectures. In a sharp contrast to the ordered ,-hybrid 12-helix obtained from 1:1 alternating Aib and -Phe, the ,-hybrid peptides constituted with -Phe and 4,4-dimethyl -amino acid (Aic) displayed the extended sheet type of conformations in solution and spontaneously self-assembled into thermally and proteolytically stable capsules. In contrast, the conformationally ordered 12-helix self-assembled into a three-dimensional supramolecular polyhedron.


PubMed | Indian Institution of Science Education and Research
Type: Journal Article | Journal: Organic & biomolecular chemistry | Year: 2015

A regioselective synthesis of substituted pyrroloquinolinones via a ruthenium-catalyzed oxidative cyclization of substituted N-carbamoyl indolines with alkynes is described. The cyclization reaction was compatible with various symmetrical and unsymmetrical alkynes including substituted propiolates. Later, we performed the aromatization of pyrroloquinolinones into indole derivatives in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ).


PubMed | Indian Institution of Science Education and Research
Type: Journal Article | Journal: Chemistry (Weinheim an der Bergstrasse, Germany) | Year: 2015

A regioselective synthesis of symmetrical and unsymmetrical benzopinacolones through aerobic dehydrogenative -arylation at the tertiary sp(3) C-H bond of substituted 1,1-diphenylketones with aromatic and heteroaromatic compounds, in the presence of K2S2O8 in CF3COOH at room temperature, is described. The reaction is proposed to go via a carbocation intermediate, which could be generated directly from cleavage of the sp(3) C-H bond of 1,1-diphenylketone. Subsequent -arylation was achieved at the methene sp(3) carbon atom of the substituted ketone. A variety of substituted aromatic and heteroaromatic compounds were compatible with this reaction. In addition, benzopinacolones were converted into sterically hindered, tetrasubstituted alkenes and polycyclic aromatic compounds.


PubMed | Indian Institution of Science Education and Research
Type: Journal Article | Journal: Chemistry (Weinheim an der Bergstrasse, Germany) | Year: 2014

A highly regioselective ortho-benzoxylation of N-alkyl benzamides with aromatic acids in the presence of [{RuCl2(p-cymene)}2], AgSbF6 , and (NH4)2S2O8 in 1,2-dichloroethane at 100C for 24h affording ortho-benzoxylated N-alkyl benzamides by C-H bond activation is described. Further, Ru-catalyzed alkenylation is done at the ortho C-H bond of benzoxylated N-alkyl benzamides with alkenes in water solvent. Subsequently, the benzoxyl moiety of N-alkyl benzamides was converted into a hydroxyl group in the presence of base or acid. A possible reaction mechanism was proposed to account for the present coupling reaction.

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