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Synthesis and Antimicrobial Activities of 2-S-Hepta-O-benzoyl lactosyl-1-aryl-5-hepta-O-benzoyl-b-lactosyl-2-isothiobiurets
Corresponding Author(s) : Shirish P. Deshmukh
Asian Journal of Chemistry,
Vol. 27 No. 9 (2015): Vol 27 Issue 9
Abstract
A series of novel 2-S-hepta-O-benzoyl lactosyl-1-aryl-5-hepta-O-benzoyl-b-lactosyl-2-isothiobiurets have been synthesized by the interaction of S-hepta-O-benzoyl lactosyl-1-arylisothiocarbamides and hepta-O-benzoyl-b-D-lactosyl isocyanate. These compounds were screened for their antibacterial and antifungal activities against Escherichia coli, Proteus vulgaris, Salmonella typhimurium, Staphylococcus aureus, Pseudomonas aeruginosa and Aspergillus niger. The newly synthesized compounds have been characterized by analytical and IR, 1H NMR and mass spectral studies.
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- (a) Z. Kazimierczuk, M. Chalimoniuk, A.E. Laudy, R. Moo-Puc, R. Cedillo-Rivera, B.J. Starosciak and S.J. Chrapusta, Arch. Pharm. Res., 33, 821 (2010); doi:10.1007/s12272-010-0604-8; (b) E.G. Chalina and L. Chakarova, Eur. J. Med. Chem., 33, 975 (1998); doi:10.1016/S0223-5234(99)80022-1; (c) H. Stark, K. Purand, X. Ligneau, A. Rouleau, J.-M. Arrang, M. Garbarg, J.-C. Schwartz and W. Schunack, J. Med. Chem., 39, 1157 (1996); doi:10.1021/jm9507688.
- C. Walpole, S.Y. Ko, M. Brown, D. Beattie, E. Campbell, F. Dickenson, S. Ewan, G.A. Hughes, M. Lemaire, J. Lerpiniere, S. Patel and L. Urban, J. Med. Chem., 41, 3159 (1998); doi:10.1021/jm970499g.
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- R. Roy, in eds.: G.J. Booms, The Chemistry of Neoglycoconjugates, In: Carbohydrate Chemistry, Blackie Academic & Professional: London, pp. 243-320 (1998).
- C.M. Reichert, C.E. Hayes and I. Goldstein, J. Methods Enzymol., 242, 108 (1994); doi:10.1016/0076-6879(94)42012-2.
- (a) T.K. Lindhorst and C. Kieburg, Angew. Chem. Int. Ed. Engl., 35, 1953 (1996); doi:10.1002/anie.199619531; (b) S. Arvind and R. Roy, Chem. Commun., 1913 (1996); (c) D. Page and R. Roy, Bioconjugate Chem., 8, 714 (1997); doi:10.1021/bc970126u.
- C. Ortiz-Mellet, J.M. Benito, J.M.G. Fernandez, H. Law, K. Chmurski, J. Defaye, M.L. O'Sullivan and H.N. Caro, Chem. Eur. J., 4, 2523 (1998); doi:10.1002/(SICI)1521-3765(19981204)4:12<2523::AID-CHEM2523>3.0.CO;2-2.
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- S.N. Pandeya, A. Kumar and B.N. Singh and D.N. Mishra, Pharmaceut. Res., 4, 321 (1987); doi:10.1023/A:1016449321049.
- a) E. Karanov and G.N. Vosilev, Chem. Abstr., 73, 119454Y (1970); (b) A.B.Borkovec, J.E. Oliver, S.C. Chang and R.T. Brown, J. Med. Chem., 14, 772 (1971); doi:10.1021/jm00290a025.
- J.E. Oliver, R.T. Brown, R.L. Fye and A.B. Borkovec, J. Agric. Food Chem., 21, 753 (1973); doi:10.1021/jf60189a043.
- J. Zielinsk and N.J. Kenilworth, US Patent, US3818104A (1974).
- N. Siddiqui and A. Husain, Indian J. Pharmacol., 33, 382 (2001).
- N. Felföldi, M. Tóth, E.D. Chrysina, M.-D. Charavgi, K.-M. Alexacou and L. Somsák, Carbohydr. Res., 345, 208 (2010); doi:10.1016/j.carres.2009.10.016.
- D.V. Mangte and S.P. Deshmukhet al., Indian J. Pharm. Sci., 69, 395 (2007).
- Ó. López, S. Maza, I. Maya, J. Fuentes and J.G. Fernández-Bolaños, Tetrahedron, 61, 9058 (2005); doi:10.1016/j.tet.2005.07.041.
- R.M. Silverstein and G.C. Bassler, Spectrometric Identification of Organic Compounds, John Wiley & Sons, INC, New York, edn 5, p. 108, 119, 120, 123 (2003).
- N.B. Colthup, L.H. Daly and S.E. Wiberley, Introduction to Infrared and Raman Spectroscopy, Academic Press, New York, p. 279 (2003).
- D.H. Williams and I. Flemming, Spectroscopic Methods in Organic Chemistry, Tata McGraw-Hill Publication, New Delhi, edn 4, p. 40, 41, 47, 53 (2003).
References
(a) Z. Kazimierczuk, M. Chalimoniuk, A.E. Laudy, R. Moo-Puc, R. Cedillo-Rivera, B.J. Starosciak and S.J. Chrapusta, Arch. Pharm. Res., 33, 821 (2010); doi:10.1007/s12272-010-0604-8; (b) E.G. Chalina and L. Chakarova, Eur. J. Med. Chem., 33, 975 (1998); doi:10.1016/S0223-5234(99)80022-1; (c) H. Stark, K. Purand, X. Ligneau, A. Rouleau, J.-M. Arrang, M. Garbarg, J.-C. Schwartz and W. Schunack, J. Med. Chem., 39, 1157 (1996); doi:10.1021/jm9507688.
C. Walpole, S.Y. Ko, M. Brown, D. Beattie, E. Campbell, F. Dickenson, S. Ewan, G.A. Hughes, M. Lemaire, J. Lerpiniere, S. Patel and L. Urban, J. Med. Chem., 41, 3159 (1998); doi:10.1021/jm970499g.
(a) J.M.G. Fernandez and C. Ortiz-Mellet, Sulfur reports, 19, 61 (1996); doi:10.1080/01961779608047905; (b) J.M.G. Fernandez and C. Ortiz-Mellet, Adv. Carbohydr. Chem. Biochem., 55, 35 (2000); doi:10.1016/S0065-2318(00)55004-5.
R. Roy, in eds.: G.J. Booms, The Chemistry of Neoglycoconjugates, In: Carbohydrate Chemistry, Blackie Academic & Professional: London, pp. 243-320 (1998).
C.M. Reichert, C.E. Hayes and I. Goldstein, J. Methods Enzymol., 242, 108 (1994); doi:10.1016/0076-6879(94)42012-2.
(a) T.K. Lindhorst and C. Kieburg, Angew. Chem. Int. Ed. Engl., 35, 1953 (1996); doi:10.1002/anie.199619531; (b) S. Arvind and R. Roy, Chem. Commun., 1913 (1996); (c) D. Page and R. Roy, Bioconjugate Chem., 8, 714 (1997); doi:10.1021/bc970126u.
C. Ortiz-Mellet, J.M. Benito, J.M.G. Fernandez, H. Law, K. Chmurski, J. Defaye, M.L. O'Sullivan and H.N. Caro, Chem. Eur. J., 4, 2523 (1998); doi:10.1002/(SICI)1521-3765(19981204)4:12<2523::AID-CHEM2523>3.0.CO;2-2.
J.M.G. Fernandez, C. Ortiz-Mellet, V.M. Diaz Perez, J.L. Jiménez-Blanco and J. Fuentes, Tetrahedron, 52, 12947 (1996); doi:10.1016/0040-4020(96)00673-4.
S.N. Pandeya, A. Kumar and B.N. Singh and D.N. Mishra, Pharmaceut. Res., 4, 321 (1987); doi:10.1023/A:1016449321049.
a) E. Karanov and G.N. Vosilev, Chem. Abstr., 73, 119454Y (1970); (b) A.B.Borkovec, J.E. Oliver, S.C. Chang and R.T. Brown, J. Med. Chem., 14, 772 (1971); doi:10.1021/jm00290a025.
J.E. Oliver, R.T. Brown, R.L. Fye and A.B. Borkovec, J. Agric. Food Chem., 21, 753 (1973); doi:10.1021/jf60189a043.
J. Zielinsk and N.J. Kenilworth, US Patent, US3818104A (1974).
N. Siddiqui and A. Husain, Indian J. Pharmacol., 33, 382 (2001).
N. Felföldi, M. Tóth, E.D. Chrysina, M.-D. Charavgi, K.-M. Alexacou and L. Somsák, Carbohydr. Res., 345, 208 (2010); doi:10.1016/j.carres.2009.10.016.
D.V. Mangte and S.P. Deshmukhet al., Indian J. Pharm. Sci., 69, 395 (2007).
Ó. López, S. Maza, I. Maya, J. Fuentes and J.G. Fernández-Bolaños, Tetrahedron, 61, 9058 (2005); doi:10.1016/j.tet.2005.07.041.
R.M. Silverstein and G.C. Bassler, Spectrometric Identification of Organic Compounds, John Wiley & Sons, INC, New York, edn 5, p. 108, 119, 120, 123 (2003).
N.B. Colthup, L.H. Daly and S.E. Wiberley, Introduction to Infrared and Raman Spectroscopy, Academic Press, New York, p. 279 (2003).
D.H. Williams and I. Flemming, Spectroscopic Methods in Organic Chemistry, Tata McGraw-Hill Publication, New Delhi, edn 4, p. 40, 41, 47, 53 (2003).