European Journal of Chemistry 2010, 1(4), 297-301 | doi: https://doi.org/10.5155/eurjchem.1.4.297-301.20 | Get rights and content






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Synthesis and bioactivity of phosphorylated derivatives of stavudine


Alahari Janardhan Rao (1) , Valasani Koteswara Rao (2) , Pasupuleti Visweswara Rao (3) , Chamarthi Naga Raju (4,*) , Sunil Kumar Ghosh (5)

(1) Department of Chemistry, Sri Venkateswara University, Tirupati, IN-517502, India
(2) Department of Chemistry, Sri Venkateswara University, Tirupati, IN-517502, India
(3) Department of Biotechnology, Sri Venkateswara University, Tirupati, IN-517502, India
(4) Department of Chemistry, Sri Venkateswara University, Tirupati, IN-517502, India
(5) Bio-organic Division, Bhabha Atomic Research Centre, Mumbai, IN-400085, India
(*) Corresponding Author

Received: 28 Mar 2010 | Revised: 25 Jul 2010 | Accepted: 20 Sep 2010 | Published: 22 Dec 2010 | Issue Date: December 2010

Abstract


Novel phosphorylated derivatives of stavudine were synthesized by the reaction of bis(2-chloroethyl)phosphoramidic dichloride/4-nitrophenyl phosphorodichloridate with various cyclic amines and amino acid esters in the presence of triethylamine in dry tetrahydrofuran through the corresponding monochloride intermediates 2a-l. Further reaction of the intermediates 2a-l with stavudine in tetrahydrofuran and pyridine in the presence of triethylamine formed the title compounds 4a-l. Their structures were characterized by IR,   1H-, 13C-, 31P-NMR and mass spectral data analyses. They exhibited good antibacterial and antioxidant activities. Their bioactivity was greatly influenced by the different groups present at the phosphorus.

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Keywords


Phosphorylated derivatives of stavudine; Gram-positive bacteria; Gram-negative bacteria; Antibacterial activity; Antioxidant activity

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DOI: 10.5155/eurjchem.1.4.297-301.20

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[1]. Syed Rasheed, Golla Madhava, Shaik Thaslim Basha, Gemmalamadugu Fareeda, Chamarthi Naga Raju
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DOI: 10.1080/10426507.2015.1119138
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[2]. Subba Rao Devineni, Madhava Golla, Thaslim Basha Shaik, Janardhan Avilala, Madhu Sudhana Saddala, Narasimha Golla, Naga Raju Chamarthi
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[3]. E. Veerashekhar Goud, Akella Sivaramakrishna, Kari Vijayakrishna
Aminophosphine Oxides: A Platform for Diversified Functions
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How to cite


Rao, A.; Rao, V.; Rao, P.; Raju, C.; Ghosh, S. Eur. J. Chem. 2010, 1(4), 297-301. doi:10.5155/eurjchem.1.4.297-301.20
Rao, A.; Rao, V.; Rao, P.; Raju, C.; Ghosh, S. Synthesis and bioactivity of phosphorylated derivatives of stavudine. Eur. J. Chem. 2010, 1(4), 297-301. doi:10.5155/eurjchem.1.4.297-301.20
Rao, A., Rao, V., Rao, P., Raju, C., & Ghosh, S. (2010). Synthesis and bioactivity of phosphorylated derivatives of stavudine. European Journal of Chemistry, 1(4), 297-301. doi:10.5155/eurjchem.1.4.297-301.20
Rao, Alahari, Valasani Koteswara Rao, Pasupuleti Visweswara Rao, Chamarthi Naga Raju, & Sunil Kumar Ghosh. "Synthesis and bioactivity of phosphorylated derivatives of stavudine." European Journal of Chemistry [Online], 1.4 (2010): 297-301. Web. 25 May. 2020
Rao, Alahari, Rao, Valasani, Rao, Pasupuleti, Raju, Chamarthi, AND Ghosh, Sunil. "Synthesis and bioactivity of phosphorylated derivatives of stavudine" European Journal of Chemistry [Online], Volume 1 Number 4 (22 December 2010)

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DOI Link: https://doi.org/10.5155/eurjchem.1.4.297-301.20

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