Abstract
New C-furyl glycosides bearing pyrazolines, isoxazolines, and dihydropyrimidine-2(1H)-thiones were synthesized in order to increase the number of tested compounds screened for antimicrobial activity. The antimicrobial activity screening showed that the pyrazoline derivatives were the most active compounds.
Graphical abstract

This is a preview of subscription content, access via your institution.

References
- 1.
Sturgeon RJ (2003) Advances in macromolecular carbohydrate research, vol 2. JAI, Stamford, CT
- 2.
Osborn HMI, Harwood LM (2003) In: Best synthetic methods: carbohydrates. Academic, San Diego, CA
- 3.
Stick RV (2003) In: Carbohydrates: the sweet molecules of life. Academic, San Diego, CA
- 4.
Ferrier RJ (2003) Carbohydrate chemistry, vol 34. Royal Society of Chemistry, Cambridge, UK
- 5.
Hricovini M (2004) Curr Med Chem 11:2565
- 6.
Ali A, Gowda DC, Vishwakarma RA (2005) Chem Commun 1224
- 7.
Gabius HJ, Gabius S (1997) Glycosciences: status and perspectives. Chapman & Hall, Weinheim
- 8.
Paulson JC (1989) Trends Biochem Sci 14:272
- 9.
Dwek RA (1996) Chem Rev 96:683
- 10.
Du Y, Linhardt RJ (1998) Tetrahedron 54:9913
- 11.
Beau JM, Gallagher T (1997) Top Curr Chem 187:1
- 12.
Xie J (1999) Recent Res Dev Org Chem 3:505
- 13.
Hacksell U, Daves GD Jr (1985) Progr Med Chem 22:1
- 14.
Rohr J, Thiericke R (1992) Nat Prod Rep 9:103
- 15.
Nicotra F (1997) Top Curr Chem 187:55
- 16.
Weymouth-Wilson AC (1997) Nat Prod Rep 14:99
- 17.
Jay M, Viricel MR, Gonnet JF (2006) In: Andersen OM, Markham KR (eds) Flavonoids: chemistry, biochemistry and applications. CRC Press, Boca Raton, FL, pp 857–915
- 18.
Hansen MR, Hurley LH (1996) Acc Chem Res 29:249
- 19.
Qian-Cutrone J, Kolb JM, McBrien K, Huang S, Gustavson D, Lowe SE, Manly SP (1998) J Nat Prod 61:1379
- 20.
Ford PW, Gadepalli M, Davidson BS (1998) J Nat Prod 61:1232
- 21.
Bililign T, Griffth BR, Thorson JS (2005) Nat Prod Pep 22:742
- 22.
Hanessian S (1983) Total synthesis of natural products: the Chiron approach. Pergamon, Oxford
- 23.
BeMiller JN, Yadav MP, Kalabokis VN, Myers RW (1990) Carbohydr Res 200:111
- 24.
Schmidt RR, Dietrich H (1991) Angew Chem Int Ed 30:1328
- 25.
Postema MHD (1992) Tetrahedron 48:8545
- 26.
Schmidt RR, Effenberger G (1998) Liebigs Ann Chem 825
- 27.
Maeba I, Iwata K, Usami F, Furukawa H (1983) J Org Chem 48:2998
- 28.
Grynkiewcz G, BeMiller JN (1984) Carbohydr Res 131:273
- 29.
Maeba I, Usami F, Ishikawa T, Furukawa H (1985) Carbohydr Res 141:1
- 30.
Lipshutz BH (1986) Chem Rev 86:795
- 31.
Chakraborty TK, Ghosh S, Jayaprakash S, Sharma JARP, Ravikanth V, Diwan PV, Nagaraj R, Kunwar AC (2000) J Org Chem 65:6441
- 32.
Elguero J (1984) In: Katrizky A (ed) Comprehensive heterocyclic chemistry. Pergamon, Oxford, 5:277
- 33.
Elguero J (1996) In: Shinkai I (ed) Comprehensive heterocyclic chemistry II. Elsevier, Oxford, 3:3
- 34.
Wagner E, Becan L, Nowakowska E (2004) Bioorg Med Chem 12:265
- 35.
Pastor J, Alca′zar J, Alvarez RM, Andre’s JI, Cid JM, De Lucas AI, Di′az A (2004) Bioorg Med Chem Lett 14:2917
- 36.
Sadashiva BPS, Nanjunda SS, Mahendra M, Shashidhara PJ, Viswanath BS, Rangappa KS (2004) Bioorg Med Chem Lett 14:3679
- 37.
Bashiardes G, Safir I, Barbot F, Laduranty J (2003) Tetrahedron Lett 44:8417
- 38.
Sadashiva BPS, Mantelingu K, Nanjunda SS, Rangappa KS (2003) Bioorg Med Chem 11:4539
- 39.
Ulgheri F, Bacsa J, Nassimbeni L, Spanu P (2003) Tetrahedron Lett 44:671
- 40.
Cocco MT, Congiu C, Onnis V, Piras R (2001) Farmaco 56:741
- 41.
Cocco MT, Congiu C, Onnis V (1995) Farmaco 50:73
- 42.
El-Essawy FA, Khattab AF, Abdel-Rahman AA-H (2007) Monatsh Chem 138:777
- 43.
Abdel-Rahman AA-H, Abdel-Megied AE-S, Hawata MAM, Kasem ER, Shabaan (2007) Monatsh Chem 138:889
- 44.
El-Sayed WA, Hegab MI, Tolan HEM, Abdel-Rahman AA-H (2008) Monatsh Chem (in press)
- 45.
Kamel MM, Gadalla KZ, El-Hamouly WS, El-Wassimi MT (1985) Z Naturforsch 40B:661
- 46.
Kamel MM, Nabih I, Gadalla KZ, Ashour MM (1986) Pharmazie 1:56
- 47.
Janssen AM, Scheffer JJ, Svendsen AB (1986) Planta Medica 395
- 48.
Shaaban MT, El-Sharif ME (2001) Afr J Mycol Biotechnol 9(2):15
- 49.
El-Sayed WA, Ramiz MMM, Abdel-Rahman AA-H (2008) Monatsh Chem (in press)
Author information
Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
El-Sayed, W.A., Nassar, I.F. & Abdel-Rahman, A.AH. C-Furyl glycosides, II: synthesis and antimicrobial evaluation of C-furyl glycosides bearing pyrazolines, isoxazolines, and 5,6-dihydropyrimidine-2(1H)-thiones. Monatsh Chem 140, 365–370 (2009). https://doi.org/10.1007/s00706-008-0033-2
Received:
Accepted:
Published:
Issue Date:
Keywords
- C-Furyl glycosides
- Pyrazolines
- Isoxazolines
- Antimicrobial activity