

Synthesis and bioactivity of phosphorylated derivatives of stavudine
Alahari Janardhan Rao (1)





(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

References
[1]. Browne, M. J.; Mayer, K. H.; Chafee, S. B. D.; Dudley, M. N.; Posner, M. R.; Steinberg, S. M.; Graham, K. K.; Geletko, S. M.; Zinner, S. H.; Denamn, S. L.; Dunkle, L. M.; Kaul, S.; McLaren, C.; Skowron, G.; Kouttab, N. M.; Kennedy, T. A.; Weitberg, A. B.; Curt, G. A. J. Infect. Dis. 1993, 167, 21–29.
[2]. Murray, H. W.; Squires, K. E.; Weiss, W.; Sledz, S.; Sacks, H. S.; Hassett, J.; Cross, A.; Anderson, R. E.; Dunkle, L. M. J. Infect. Dis. 1995, 171(2), 123–130.
[3]. Balzarini, J.; Herdewijn, P.; Clercq, E. D. J. Biol. Chem. 1989, 264, 6127–6133.
[4]. Ho, H.-T.; Hitchcock, M. J. M. Antimicrob. Agents Chemother. 1989, 33, 844–849.
PMid:2764535 PMCid:284243
[5]. Mansuri, M. M.; Starrett, J. E.; Ghazzouli, I.; Hitchcock, M. J. M.; Sterzycki, R. Z.; Brankovan, V.; Lin, T.-S.; August, E. M.; Prussoff, W. H.; Sommadossi, J.-P.; Martin, J. C. J. Med. Chem. 1989, 32, 461–466.
doi:10.1021/jm00122a029
PMid:2536441
[6]. Siddiqui, A. Q.; McGuigan, C.; Ballatore, C.; Zuccotto, F.; Gilbert, I. H.; De Clercq, E.; Balzarini, J. J. Med. Chem. 1999, 42, 4122-4128.
doi:10.1021/jm9807104
PMid:10514282
[7]. Wagner, C.R.; Iyer, V. V.; McIntee, E. J. Med. Res. Rev 2000, 20, 417-451.
doi:10.1002/1098-1128(200011)20:6<417::AID-MED1>3.0.CO;2-Z
[8]. Mavromoustakos, T.; Calogeropoulou, T.; Koufaki, M.; Kolocouris, A.; Daliani, I.; Demetzos, C.; Meng, Z.; Makriyannis, A.; Balzarini, J.; De Clercq, E. J. Med. Chem. 2001, 44, 1702-1709.
doi:10.1021/jm001121c
PMid:11356105
[9]. Balzarini, J.; Aquaro, S.; Knispel, T.; Rampazzo, C.; Bianchi, V.; Perno, C. F.; De Clercq, E.; Meier, C. Mol. Pharmacol. 2000, 58, 928-35.
PMid:11040039
[10]. Cardona, V. M.; Ayi, A. I.; Aubertin, A. M.; Guedj, R. Antiviral Res. 1999, 42,189-196.
doi:10.1016/S0166-3542(99)00021-2
[11]. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th ed., Butterworth, Heinemann, Oxford, OX2 8DP 1997.
[12]. Murray, P. R.; Baron, E. J.; Pfaller, M. A.; Tenover, F. C.; Yolken, H. R. Manual of Clinical microbiology, 6th Ed. ASM Press, Washington DC, pp. 15-18, 1995.
[13]. Burits, M.; Bucar, F. Phytother. Res. 2000, 14, 323–328.
doi:10.1002/1099-1573(200008)14:5<323::AID-PTR621>3.0.CO;2-Q
[14]. Kishore, K. R,; Anil, K. M.; Narayana, R. M. V.; Devendranath, R.C.; Suresh, R. C. Tetrahedron Lett. 2008, 49, 6337-6340.
doi:10.1016/j.tetlet.2008.08.069
[15]. Shirokova, E. A.; Jasko, M. V.; Khandazhinskaya, A. L.; Ivanov, A. V.; Yanvarev, D. V.; Skoblov, Y. S.; Mitkevich, V. A.; Bocharov, E. V.; Pronyaeva, T. R.; Fedyuk, N. V.; Kukhanova, M. K.; Pokrovsky, A. G. J. Med. Chem. 2004, 47, 3606–3614.
doi:10.1021/jm0310176
PMid:15214788
[16]. Kim, J.; Chou, T. F.; Griesgraber, G. W.; Wagner, C. R. Mol. Pharmaceutics 2004, 1, 102-111.
doi:10.1021/mp0340338
PMid:15832506
[17]. McGuigan, C.; Cahard, D.; Sheeka, H.M.; Clercq, E.D.; Balzarini, J. J. Med. Chem. 1996, 39, 1748-1753.
doi:10.1021/jm950605j
PMid:8648614
[18]. Koteswara Rao, V.; Janardhan Rao, A.; Subba Reddy, S.; Naga Raju, C.; Visweswara Rao, P.; Ghosh. S. K. Eur. J. Med. Chem. 2010, 45, 203–209.
doi:10.1016/j.ejmech.2009.09.045
PMid:19853328
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