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Arjunan V.,Kanchi Mamunivar Center for Post Graduate Studies | Santhanam R.,Malladi Drugs and Pharmaceuticals Ltd | Marchewka M.K.,Institute of Low Temperature And Structure Research | Mohan S.,Hawassa University
Molecular Simulation | Year: 2013

Density functional theory (DFT) (B3LYP and B3PW91) calculations have been carried out for 2,6-dimethyl-2,5-heptadien-4-one (DMHD4O) using 6-311++ G** basis set. Complete vibrational assignment and analysis of the fundamental modes of the compound were carried out from the FTIR and FT-Raman spectral data. The theoretical electronic absorption has been calculated by using time-dependent DFT (TD-DFT) methods and compared with the experimental spectra. The theoretically computed Frontier energy gaps and TD-DFT calculations are in good agreement with the experimental UV-vis spectral absorption. The chemical hardness measured from the Frontier molecular orbital energies of DMHD4O is 0.0693 eV. Electronic stability of the compound arising from hyperconjugative interactions and charge delocalisation were also investigated based on the natural bond orbital (NBO) analysis. Effective stabilisation energy E (2) associated with the interactions of the π and the lone pair of electrons was determined by the NBO analysis. 13C and 1H NMR chemical shifts of the compound have been calculated by means of Gauge-Invariant Atomic Orbital using B3LYP/6-311++ G** method. The partial ionic character of the carbonyl group due to resonance render a partially positive charge to the carbonyl carbon, and thus C4 chemical shift lie in the very downfield 191.6 ppm. Comparison between the experimental and the theoretical results indicates that B3LYP method is able to provide satisfactory results for predicting vibrational, electronic and NMR properties. © 2013 Copyright Taylor and Francis Group, LLC.


Easwaramoorthi K.,Loyola College | Easwaramoorthi K.,Malladi Drugs and Pharmaceuticals Ltd. | Rajendran A.J.,Loyola College | Rao K.C.,CSIR - Central Electrochemical Research Institute | And 9 more authors.
RSC Advances | Year: 2015

Novel 1,4-disubstituted 1,2,3-triazolo bosentan derivatives 1a-n from bosentan 2 were synthesized in good yields by sequential chlorination, azidation followed by Cu(i) catalyzed 1,3-dipolar cycloaddition. All obtained compounds 1a-n were evaluated for their antimicrobial and in vitro anticancer activities and by in silico docking studies. Among all tested compounds 1e,f and 1h-j show better antimicrobial activities against the tested bacteria and fungi. When subjected to anticancer testing, compounds 1g-j and 1n show significant activities against both A549 and SKOV-3 cell lines with IC50 values at 7.81 μg mL-1 and among them compound 1i exhibited very potent activity. In addition, no toxicity was calculated up to 2 mg mL-1 in Vero cells. In silico studies were conducted to investigate the possible bonding modes of 1a-n with target receptors namely DNA topoisomerase IV (4 EMV) and anaplastic lymphoma kinase (2XP2). Among them, compounds 1e and 1h show maximum binding energies with 4EMV and 2XP2 receptors, respectively which also exhibited good antimicrobial and potent anticancer activities. © The Royal Society of Chemistry.


Kumar B.N.H.,Malladi Drugs and Pharmaceuticals Ltd. | Kumar B.N.H.,Anna University | Murugesan V.,Anna University | Prakasam T.,Malladi Drugs and Pharmaceuticals Ltd. | And 2 more authors.
Chirality | Year: 2012

(1R,2R)-1-Phenyl-1-alkyl/arylamino-2-(N-alkylamino)propane hydrochloride salts have been synthesized with high degree of enantiomeric purity from (1S,2R)-(+)-1-phenyl-2-(N-alkylamino)-1-propanol through the corresponding chloro derivatives. This reaction sequence involves three inversions with overall inversion of configuration at C-1. Copyright © 2012 Wiley Periodicals, Inc.


Chennakesava Rao K.,CSIR - Central Leather Research Institute | Chennakesava Rao K.,Malladi Drugs and Pharmaceuticals Ltd | Easwaramoorthi K.,Malladi Drugs and Pharmaceuticals Ltd | Arun Y.,CSIR - Central Leather Research Institute | And 6 more authors.
Bioorganic and Medicinal Chemistry Letters | Year: 2015

Antimicrobial agents 4a-g and 5a-g with very good potency were synthesized with 100% ee from phenylpropanolamine (norephedrine) by BF3 catalyzed three components one pot Mannich reaction in good yields. Obtained compounds were characterized using spectral techniques. Antimicrobial study of these compounds revealed a good to very high potential activity against tested microbes when compared to standard antimicrobial drugs streptomycin and ketoconazole. These synthesized compounds exhibited significant minimum inhibitory concentration (MIC) values against Gram positive and Gram negative bacteria. Amongst compound 4b, 4c, 4d, 4e, 5a, and 5e exhibited very high potent MIC values against tested twelve bacteria and three fungi when compared to control. When subjected to molecular docking, in silico studies revealed significant binding energies ranging from -7.06 to -8.90kcal/mol for all obtained compounds towards target receptor DNA topoisomerase IV and amongst compounds 4b and 4d have shown maximum binding energies 8.70 and 8.90kcal/mol, respectively. © 2015.


Chennakesava Rao K.,CSIR - Central Leather Research Institute | Chennakesava Rao K.,Malladi Drugs and Pharmaceuticals Ltd | Easwaramoorthi K.,Malladi Drugs and Pharmaceuticals Ltd | Arun Y.,CSIR - Central Leather Research Institute | And 6 more authors.
Bioorganic and Medicinal Chemistry Letters | Year: 2015

Antimicrobial agents 4a-g and 5a-g with very good potency were synthesized with 100% ee from phenylpropanolamine (norephedrine) by BF3 catalyzed three components one pot Mannich reaction in good yields. Obtained compounds were characterized using spectral techniques. Antimicrobial study of these compounds revealed a good to very high potential activity against tested microbes when compared to standard antimicrobial drugs streptomycin and ketoconazole. These synthesized compounds exhibited significant minimum inhibitory concentration (MIC) values against Gram positive and Gram negative bacteria. Amongst compound 4b, 4c, 4d, 4e, 5a, and 5e exhibited very high potent MIC values against tested twelve bacteria and three fungi when compared to control. When subjected to molecular docking, in silico studies revealed significant binding energies ranging from -7.06 to -8.90 kcal/mol for all obtained compounds towards target receptor DNA topoisomerase IV and amongst compounds 4b and 4d have shown maximum binding energies 8.70 and 8.90 kcal/mol, respectively. © 2015 Elsevier Ltd. All rights reserved.


Balachandran C.,Aichi University | Chennakesava Rao K.,Malladi Drugs and Pharmaceuticals Ltd. | Chennakesava Rao K.,CSIR - Central Leather Research Institute | Arun Y.,CSIR - Central Leather Research Institute | And 6 more authors.
RSC Advances | Year: 2016

A novel series of Mannich derivatives of 3a-g and 3a′-g′ were designed and synthesized from pseudophenylpropanolamine (Ψ-PPA). The stereo chemical aspects of the synthesized compounds were studied and all compounds were well characterized with respect to spectral techniques. All Mannich derivatives, 3a-g and 3a′-g′ were evaluated for their anti-proliferative activity against A549 and HepG-2 cells. Among the tested compounds, 3a showed significant anti-proliferative activity against HepG-2 cells at 25 μM when compared to other compounds. The treatment of 3a exhibited morphological changes, nuclear condensation, colony formatting ability, apoptosis and cell cycle arrest at G2/M phase in HepG-2 cells. Besides, 3a triggered mitochondrial mediated apoptotic pathway as indicated by down regulation of Bcl-2, up-regulation of Bax, and release of cytochrome c and caspases-3. Furthermore, 3a effectively suppressed the cell proliferation and cell growth via JAK2/STAT3 signaling pathway in a time and dose dependent manner. In vivo administration of 3a inhibited tumor growth without significant change in body weight in HepG-2 xenograft mice model. Molecular docking studies revealed that good binding energies of compound 3a against JAK2 (-6.10 kcal mol-1) and Bcl-2 (-6.04 kcal mol-1) receptors. Taken together, 3a possessed potent antitumor activity; it could be a promising lead candidate for the potential treatment of human hepatocellular carcinoma. © 2016 The Royal Society of Chemistry.


Rangan S.,Presidency College at Chennai | Rangan S.,Malladi Drugs and Pharmaceuticals Ltd. | Arul Antony S.,Presidency College at Chennai | Kandhaswamy A.,Malladi Drugs and Pharmaceuticals Ltd. | And 2 more authors.
International Journal of ChemTech Research | Year: 2016

The crystal structure of the potential active (2S, 3S) -2-morpholino-3-phenylpentan- 3-ol hydrochloride and (2S, 3R) -2-morpholino-3-phenylpentan-3-ol hydrochloride has been determined from single crystal X-ray diffraction data. The both compound are structurally diastereomers, but it adopts different crystal system. In compound I crystallizes in the monoclinic system space group C121 with unit cell dimension a=12. 9486 (15) Å, b=6. 0083 (5) Å and c= 19. 670 (18) Å [α=90°, β= 95. 484 (5) ° and γ= 90°] and for the compound II crystallizes in the orthoromic system space group P212121 with unit cell dimension a= 5. 8923 (9) Å, b=11. 413 (2) Å and c= 22. 659 (4) Å [α=90°, β= 90° and γ= 90°] In both the compound morpholino ring adopts chair conformation. The crystal packing is stabilized by intermolecular C-H… O hydrogen bond interaction. © 2016, Sphinx Knowledge House. All rights reserved.


Chennakesava Rao K.,Malladi Drugs and Pharmaceuticals Ltd | Chennakesava Rao K.,CSIR - Central Leather Research Institute | Chennakesava Rao K.,Entomology Research Institute | Arun Y.,CSIR - Central Leather Research Institute | And 5 more authors.
Bioorganic and Medicinal Chemistry Letters | Year: 2014

Enantiomerically pure N-alkylated β-amino alcohols 1a, 1a′, 1c, 1c′, 1d, 1d′, 1e and 1e′, with ee 100% have been synthesized from phenylpropanolamines 2. Effect of the neighboring chiral environment on the newly formed chiral center has been studied experimentally and concluded that the newly formed chiral center's absolute configuration is opposite to the adjacent (α- or β-) chiral environment. The antimicrobial activity of the synthesized β-amino alcohols were screened using in vitro disc diffusion method and variable antimicrobial activities were shown for 1a, 1a′, 1c, 1c′, 1d, 1d′, 1e & 1e′ and amongst them 1d & 1d′ exhibited significant activity against bacteria and fungi. In silico studies revealed all the synthesized β-amino alcohols 1a-e and 1a′-e′ have shown good binding energies ranging from -7.38 to -6.09 kJ/mol towards the target receptor DNA topoisomerase IV and 1d′ has shown maximum binding energy -7.38 kJ/mol. © 2014 Elsevier Ltd. All rights reserved.

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