C-Furyl glycosides, I: Synthesis and antimicrobial evaluation of C-furyl glycosides and chalcones derived therefrom

Abstract

New C-furyl glycosides were synthesized in order to increase the number of compounds screened for antimicrobial activity. The antimicrobial activity showed that the bromo as well as the nitro derivatives were the most active compounds.

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References

  1. Y Du RJ Linhardt (1998) Tetrahedron 54 9913 Occurrence Handle10.1016/S0040-4020(98)00405-0 Occurrence Handle1:CAS:528:DyaK1cXltFOitro%3D

    Article  CAS  Google Scholar 

  2. JM Beau T Gallagher (1997) Top Curr Chem 187 1 Occurrence Handle10.1007/BFb0119252 Occurrence Handle1:CAS:528:DyaK2sXjs1Cqu7g%3D

    Article  CAS  Google Scholar 

  3. J Xie (1999) Recent Res Dev Org Chem 3 505 Occurrence Handle1:CAS:528:DC%2BD3cXovF2itb0%3D

    CAS  Google Scholar 

  4. U Hacksell GD Daves SuffixJr (1985) Progress Med Chem 22 1 Occurrence Handle10.1016/S0079-6468(08)70228-5 Occurrence Handle1:STN:280:DyaL283mtVOisg%3D%3D

    Article  CAS  Google Scholar 

  5. F Nicotra (1997) Top Curr Chem 187 55 Occurrence Handle10.1007/BFb0119253 Occurrence Handle1:CAS:528:DyaK2sXjs1Cqu7k%3D

    Article  CAS  Google Scholar 

  6. S Hanessian (1983) Total synthesis of natural products: the Chiron approach Pregamon Oxford

    Google Scholar 

  7. JN BeMiller MP Yadav VN Kalabokis RW Myers (1990) Carbohydr Res 200 111 Occurrence Handle10.1016/0008-6215(90)84186-X Occurrence Handle1:CAS:528:DyaK3cXlslamt7Y%3D

    Article  CAS  Google Scholar 

  8. RR Schmidt H Dietrich (1991) Angew Chem Int Ed 30 1328 Occurrence Handle10.1002/anie.199113281

    Article  Google Scholar 

  9. M Jay MR Viricel JF Gonnet (2006) NoChapterTitle OM Andersen KR Markham (Eds) Flavonoids: Chemistry, Biochemistry and Applications CRC Press Boca Raton 857

    Google Scholar 

  10. MR Hansen LH Hurley (1996) Acc Chem Res 29 249 Occurrence Handle10.1021/ar950167a Occurrence Handle1:CAS:528:DyaK28XisVymsrk%3D

    Article  CAS  Google Scholar 

  11. J Qian-Cutrone JM Kolb K McBrien S Huang D Gustavson SE Lowe SP Manly (1998) J Nat Prod 61 1379 Occurrence Handle10.1021/np980234k Occurrence Handle1:CAS:528:DyaK1cXmtV2ksrY%3D

    Article  CAS  Google Scholar 

  12. PW Ford M Gadepalli BS Davidson (1998) J Nat Prod 61 1232 Occurrence Handle10.1021/np980126y Occurrence Handle1:CAS:528:DyaK1cXkvF2mtb8%3D

    Article  CAS  Google Scholar 

  13. T Bililign BR Griffth JS Thorson (2005) Nat Prod Pep 22 742 Occurrence Handle1:CAS:528:DC%2BD28XjslCrtw%3D%3D

    CAS  Google Scholar 

  14. TC Wu PG Goekjian Y Kishi (1987) J Org Chem 52 4819 Occurrence Handle10.1021/jo00230a038 Occurrence Handle1:CAS:528:DyaL2sXlvFyku7o%3D

    Article  CAS  Google Scholar 

  15. A Wei A Haudrechy C Audin HS Jun N Haudrechy-Bretel Y Kishi (1995) J Org Chem 60 2160 Occurrence Handle10.1021/jo00112a040 Occurrence Handle1:CAS:528:DyaK2MXks1Kitbc%3D

    Article  CAS  Google Scholar 

  16. Jaramillo C, Knapp S (1993) Synthesis:1

  17. DE Levy C Tang (1995) NoChapterTitle The Chemistry of C-Glycosides Elsevier Science Tarrytown, NY

    Google Scholar 

  18. MHD Postema (1995) NoChapterTitle CW Rees (Eds) C-Glycoside Synthesis CRC Press Boca Raton, FL

    Google Scholar 

  19. MHD Postema (1992) Tetrahedron 48 8545 Occurrence Handle10.1016/S0040-4020(01)89435-7 Occurrence Handle1:CAS:528:DyaK3sXnt1Gg

    Article  CAS  Google Scholar 

  20. Schmidt RR, Effenberger G (1998) Liebigs Ann Chem 825

  21. I Maeba K Iwata F Usami H Furukawa (1983) J Org Chem 48 2998 Occurrence Handle10.1021/jo00166a012 Occurrence Handle1:CAS:528:DyaL3sXltVGlsb4%3D

    Article  CAS  Google Scholar 

  22. G Grynkiewcz JN BeMiller (1984) Carbohydr Res 131 273 Occurrence Handle10.1016/0008-6215(84)85249-0

    Article  Google Scholar 

  23. BH Lipshutz (1986) Chem Rev 86 795 Occurrence Handle10.1021/cr00075a005 Occurrence Handle1:CAS:528:DyaL28XlsFartrw%3D

    Article  CAS  Google Scholar 

  24. TK Chakraborty S Ghosh S Jayaprakash JARP Sharma V Ravikanth PV Diwan R Nagaraj AC Kunwar (2000) J Org Chem 65 6441 Occurrence Handle10.1021/jo000408e Occurrence Handle1:CAS:528:DC%2BD3cXmtFaqtL8%3D

    Article  CAS  Google Scholar 

  25. DD Long MD Smith A Martin JR Wheatley DG Watkin M Muller GWJ Fleet (2002) J Chem Soc Perkin Trans 1 1982 Occurrence Handle10.1039/b111258a Occurrence Handle1:CAS:528:DC%2BD38XmsVWnsLo%3D

    Article  CAS  Google Scholar 

  26. NL Hungerford TDW Claridge MP Watterson RT Aplin A Moreno GWJ Fleet (2000) J Chem Soc Perkin Trans 1 3666 Occurrence Handle10.1039/b002996n

    Article  Google Scholar 

  27. AK Misra G Agnihotri (2004) Carbohydr Res 339 1381 Occurrence Handle10.1016/j.carres.2004.02.011 Occurrence Handle1:CAS:528:DC%2BD2cXjsVKgsbc%3D

    Article  CAS  Google Scholar 

  28. NL Hungerford GWJ Fleet (2000) J Chem Soc Perkin Trans 1 3680 Occurrence Handle10.1039/b002997l

    Article  Google Scholar 

  29. MD Smith GWJ Fleet (1999) J Peptide Sci 5 425 Occurrence Handle10.1002/(SICI)1099-1387(199910)5:10<425::AID-PSC222>3.0.CO;2-O Occurrence Handle1:CAS:528:DyaK1MXntVaqt7o%3D

    Article  CAS  Google Scholar 

  30. DM Poeta WA Schell C Christine SK Jones R Tidwell A Kumar DW Baykin JR Perfect (1998) Antimicrob Agents Chemother 42 2503

    Google Scholar 

  31. H Lercetto DR Maio M Gonzalez M Rissao S Gabriel G Seoane A Denicola G Feluffo C Quijano AOM Stoppani (2000) Eur J Med Chem 35 343 Occurrence Handle10.1016/S0223-5234(00)00131-8

    Article  Google Scholar 

  32. S Setsuyo H Obase S Ichikawa T Kitazawa H Nonaka R Yoshizaki A Ishii K Shuto (1993) J Med Chem 36 572 Occurrence Handle10.1021/jm00057a007

    Article  Google Scholar 

  33. JA Daniel J Dave K Douglas S Gerry J Larsen D Ganiel E Hongding J Cohen J Lee R Warner (1999) Bioorg Med Chem Lett 9 1069 Occurrence Handle10.1016/S0960-894X(99)00144-4

    Article  Google Scholar 

  34. Y Han A Giroux C Lepine F Laliberte Z Haung H Perrier CI Bayly RN Young (1999) Tetrahedron 55 11669 Occurrence Handle10.1016/S0040-4020(99)00686-9 Occurrence Handle1:CAS:528:DyaK1MXmt1Gmtr4%3D

    Article  CAS  Google Scholar 

  35. AJ Moreno-Vargas J Jimenez-Barbiro I Robina (2003) J Org Chem 68 4128

    Google Scholar 

  36. AJ Moreno-Vargas R Demange J Fuentes I Robina P Vogel (2002) Biorg Med Chem Lett 12 2335 Occurrence Handle10.1016/S0960-894X(02)00397-9 Occurrence Handle1:CAS:528:DC%2BD38XlvVGjtLs%3D

    Article  CAS  Google Scholar 

  37. AJ Moreno-Vargas JG Fernandez-Bolanos J Fuentes I Robina (2001) Tetraheron Lett 42 1283 Occurrence Handle10.1016/S0040-4039(00)02266-8 Occurrence Handle1:CAS:528:DC%2BD3MXhtVahsr0%3D

    Article  CAS  Google Scholar 

  38. JS Yadav BVS Reddy M Sreenivas G Satheesh (2007) Synthesis 11 1712 Occurrence Handle10.1055/s-2007-966056 Occurrence Handle1:CAS:528:DC%2BD2sXnsVOrsL4%3D

    Article  CAS  Google Scholar 

  39. JG Schmidt (1880) Ber Dtsch Chem Ges 13 2342 Occurrence Handle10.1002/cber.188001302266

    Article  Google Scholar 

  40. L Claisen A Claparede (1981) Ber Dtsch Chem Ges 14 349 Occurrence Handle10.1002/cber.18810140182

    Article  Google Scholar 

  41. EP Kohler HM Chadwell (1922) Org Synth 2 1

    Google Scholar 

  42. LVG Nargund V Hariprasad GRN Reddy (1992) J Pharm Sci 81 892 Occurrence Handle10.1002/jps.2600810910 Occurrence Handle1:CAS:528:DyaK38Xmtleqs7g%3D

    Article  CAS  Google Scholar 

  43. AAH Abdel-Rahman AES Abdel-Megied MAM Hawata ER Kasem MT Shabaan (2007) Monatsh Chem 138 889 Occurrence Handle10.1007/s00706-007-0700-8 Occurrence Handle1:CAS:528:DC%2BD2sXpvFWhsrw%3D

    Article  CAS  Google Scholar 

  44. BS Holla PM Akberali MK Shivananda (2001) I Farmaco 56 919 Occurrence Handle10.1016/S0014-827X(01)01124-7 Occurrence Handle1:CAS:528:DC%2BD3MXpt1artLo%3D

    Article  CAS  Google Scholar 

  45. BA Bhat KL Dhar SC Puri AK Saxena M Shanmugavel GN Qazib (2005) Bioorg Med Chem Lett 15 3177 Occurrence Handle10.1016/j.bmcl.2005.03.121 Occurrence Handle1:CAS:528:DC%2BD2MXltFWgu7c%3D

    Article  CAS  Google Scholar 

  46. Janssen AM, Scheffer JJ, Svendsen AB (1986) Planta Medica:395

  47. MT Shaaban ME El-Sharif (2001) Afr J Mycol Biotechnol 9 IssueID2 15

    Google Scholar 

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Correspondence to Adel A.-H. Abdel-Rahman.

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Correspondence: Adel A.-H. Abdel-Rahman, Faculty of Science, Department of Chemistry, Menoufia University, Shebin El-Koam, Egypt.

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El-Sayed, W., Ramiz, M. & Abdel-Rahman, AH. C-Furyl glycosides, I: Synthesis and antimicrobial evaluation of C-furyl glycosides and chalcones derived therefrom. Monatsh Chem 139, 1499 (2008). https://doi.org/10.1007/s00706-008-0941-1

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Keywords

  • C-Furyl glycosides; N-Glycosides; Chalcones; Antimicrobial activity.