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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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DOI: 10.5155/eurjchem.1.4.297-301.20
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Citations
[1]. Syed Rasheed, Golla Madhava, Shaik Thaslim Basha, Gemmalamadugu Fareeda, Chamarthi Naga Raju
Synthesis, spectral characterization, and pro- and antioxidant activity of phosphorylated derivatives of cis-tramadol
Phosphorus, Sulfur, and Silicon and the Related Elements 192(12), 1247, 2017
DOI: 10.1080/10426507.2015.1119138
[2]. Subba Rao Devineni, Madhava Golla, Thaslim Basha Shaik, Janardhan Avilala, Madhu Sudhana Saddala, Narasimha Golla, Naga Raju Chamarthi
Ethyl phosphoramidates of acyclovir: design, synthesis, molecular docking (HN Protein), and evaluation of antiviral and antioxidant activities
Medicinal Chemistry Research 26(5), 999, 2017
DOI: 10.1007/s00044-017-1819-8
[3]. E. Veerashekhar Goud, Akella Sivaramakrishna, Kari Vijayakrishna
Aminophosphine Oxides: A Platform for Diversified Functions
Topics in Current Chemistry 375(1), , 2017
DOI: 10.1007/s41061-016-0090-7
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DOI Link: https://doi.org/10.5155/eurjchem.1.4.297-301.20
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