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Abstract
The synthesis of β-lactams as azapseudopeptides was carried out in three stages affording reasonable yields. The Schiff base [ethyl 2-{2- (benzylidene)hydrazinyl}acetate] (2) has been prepared from ethyl hydrazinylacetate and benzaldehydes derivatives. Schiff bases led to novel azapseudopeptide derivatives 3 on treatment with chloro acetyl chloride in the presence of triethylamine. Identification of final compounds were confirmed by FT-IR, 1H NMR and 13C NMR data.
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References
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References
A.F. Spatola, Peptide Backbone Modifications: A Structure-Activity Analysis of Peptides Containing Amide Bond Surrogates, Conformational Constraints and Related Backbone Replacements, Marcel Dekker, Inc.: New York and Basel (1983).
J. Gante, Angew. Chem. Int. Ed. Engl., 33, 1699 (1994); http://dx.doi.org/10.1002/anie.199416991.
M. Goodman and S. Roin eds. M.E. Wolff, Principles and Practice, Wiley: New York, edn 5, vol. 1, pp. 803-861 (1995).
W.-J. Zhang, A. Berglund, J.L.-F. Kao, J.-P. Couty, M.C. Gershengorn and G.R. Marshall, J. Am. Chem. Soc., 125, 1221 (2003); http://dx.doi.org/10.1021/ja020994o.
A. Zega and U. Urleb, Acta Chim. Slov., 49, 649 (2002).
K. Bouget, S. Aubin, J.-G. Delcros, Y. Arlot-Bonnemains and M. Baudy-Floc’h, Bioorg. Med. Chem., 11, 4881 (2003); http://dx.doi.org/10.1016/j.bmc.2003.09.018.
S. Aubin, B. Martin, J.-G. Delcros, Y. Arlot-Bonnemains and M. Baudy-Floc’h, J. Med. Chem., 48, 330 (2005); http://dx.doi.org/10.1021/jm049455f.
J. Gante, Synthesis, 405 (1989); http://dx.doi.org/10.1055/s-1989-27269.
H.-J. Hess, W.T. Moreland and G.D. Laubach, J. Am. Chem. Soc., 85, 4040 (1963); http://dx.doi.org/10.1021/ja00907a036.
C. Abbas, G. Pickaert, C. Didierjean, B.J. Grégoire and R. Vanderesse, Tetrahedron Lett., 50, 4158 (2009); http://dx.doi.org/10.1016/j.tetlet.2009.04.131.
R. Xing and R.P. Hanzlik, J. Med. Chem., 41, 1344 (1998); http://dx.doi.org/10.1021/jm970802d.
F.G. Hutchinson and B.J.A. Furr, Trends Biotechnol., 5, 102 (1987); http://dx.doi.org/10.1016/0167-7799(87)90028-X.
J.C. Powers, R. Boone, D.L. Carroll, B.F. Gupton, C.M. Kam, N. Nishino, M. Sakamoto and P.M. Tuhy, J. Biol. Chem., 259, 4288 (1984).
J.C. Powers and B. Frank Gupton, Methods Enzymol., 46, 208 (1977); http://dx.doi.org/10.1016/S0076-6879(77)46021-X.
B.F. Gupton, D.L. Carroll, P.M. Tuhy and C.M. Kam, J. Biol. Chem., 259, 4279 (1984).
M. Nardini, M. Pesce, M. Rizzi, E. Casale, R. Ferraccioli, G. Balliano, P. Milla, P. Ascenzi and M. Bolognesi, J. Mol. Biol., 258, 851 (1996); http://dx.doi.org/10.1006/jmbi.1996.0292.
J.E. Semple, D.C. Rowley, T.K. Brunck and W.C. Ripka, Bioorg. Med. Chem. Lett., 7, 315 (1997); http://dx.doi.org/10.1016/S0960-894X(97)00005-X.
T.L. Graybill, M.J. Ross, B.R. Gauvin, J.S. Gregory, A.L. Harris, M.A. Ator, J.M. Rinker and R.E. Dolle, Bioorg. Med. Chem. Lett., 2, 1375 (1992); http://dx.doi.org/10.1016/S0960-894X(00)80516-8.
Y. Mehellou and E. De Clercq, J. Med. Chem., 53, 521 (2010); http://dx.doi.org/10.1021/jm900492g.
A.F. Santos and M.A. Soares, Viruses, 2, 503 (2010); http://dx.doi.org/10.3390/v2020503.
D. Kato, S.H.L. Verhelst, K.B. Sexton and M. Bogyo, Org. Lett., 7, 5649 (2005); http://dx.doi.org/10.1021/ol052275v.
A. Fässler, G. Bold, H.-G. Capraro, R. Cozens, J. Mestan, B. Poncioni, J. Rösel, M. Tintelnot-Blomley and M. Lang, J. Med. Chem., 39, 3203 (1996); http://dx.doi.org/10.1021/jm960022p.
F. Lebon and M. Ledecq, Curr. Med. Chem., 7, 455 (2000); http://dx.doi.org/10.2174/0929867003375146.
A. Mastrolorenzo, S. Rusconi, A. Scozzafava, G. Barbaro and C.T. Supuran, Curr. Med. Chem., 14, 2734 (2007); http://dx.doi.org/10.2174/092986707782360141.
J. Marchandbrynaert, P. Mougenot, Y. Combret, D. Belotti, N. Guillot and L. Ghosez, Farmaco, 50, 455 (1995).
A. Zega, G. Mlinsek, P. Sepic, S. Golie-Grdadolnik, T. Solmajer, T.B. Tschopp, B. Steiner, D. Kikelj and U. Urleb, Bioorg. Med. Chem., 9, 2745 (2001); http://dx.doi.org/10.1016/S0968-0896(01)00202-4.
A. Zega, A. Trampus-Bakija, M. Fortuna, M. Stegnar, T.B. Tschopp, B. Steiner and U. Urleb, Pharmazie, 56, 683 (2001).
S.V. Andurkar, C. Béguin, J.P. Stables and H. Kohn, J. Med. Chem., 44, 1475 (2001); http://dx.doi.org/10.1021/jm000517l.
S.G. Shingade, S.B. Bari and U.B. Waghmare, Med. Chem. Res., 21, 1302 (2012); http://dx.doi.org/10.1007/s00044-011-9644-y.
S. Rollas and S.G. Kücükgüzel, Molecules, 12, 1910 (2007); http://dx.doi.org/10.3390/12081910.
M. Noolvi, S. Agrawal, H. Patel, A. Badiger, M. Gaba and A. Zambre, Arabian J. Chem., 7, 219 (2014); http://dx.doi.org/10.1016/j.arabjc.2011.02.011.
G.S. Singh, M. Elbert and P. Tshepo, ARKIVOC, 80 (2007). http://dx.doi.org/10.3998/ark.5550190.0008.910.
R. Ahmad, M. Zia-ul-Haq and R. Jabeen, Turk. J. Chem., 20, 186 (1996).
S. Jubie, B. Gowramma and K. Nitin, Int. J. ChemTech Res., 1, 153 (2009).
K.S. Gawande and E.R. Khadsan, Der Pharma Chemica, 6, 70 (2014).
T.M. Patel and A.M. Patel, Der Pharm. Lett., 4, 579 (2012).
A. Bhalla, S.S. Bari, S. Berry, J. Bhalla, S. Vats, S. Mandal and S. Khullar, ARKIVOC, 10 (2015). http://dx.doi.org/10.3998/ark.5550190.p009.172.
M. Gopal, B. Padmashali, Y.N. Manohara and B.M. Gurupadayya, Indian J. Pharm. Sci., 70, 572 (2008); http://dx.doi.org/10.4103/0250-474X.45393.
40 E.J. Kantorowski and M.J. Kurth, Tetrahedron, 56, 4317 (2000); http://dx.doi.org/10.1016/S0040-4020(00)00218-0.
F. Abdulaziz Al-Omary, Ph.D. Thesis: Studies on Monocyclic b-Lactams, College of Pharmacy, King Saud University, p. 32 (2000).
C. Palomo, J.M. Aizpurua, I. Ganboa and M. Oiarbide, Eur. J. Org. Chem., 3223 (1999); http://dx.doi.org/10.1002/(SICI)1099-0690(199912)1999:12<3223::AID-EJOC3223>3.0.CO;2-1.