Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives and studies of the reaction mechanism

Tetrahedron Asymmetry

Volumn 20, Issue 4, 2009, Pages 399-410

  Han, Dong ^b   Meng, Xiang Bao ^a,b   Wang, Lin Na ^b   Liu, Hong ^b   Yao, Yun ^b   Wang, Zhuo ^a   Yang, Zhen Jun ^a   Liu, Zhen Min ^a   Li, Zhong Jun ^a,b  

^a PEKING UNIVERSITY   (China)

^b PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 BUTYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 ETHYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 HEPTADECYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 HEPTYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 HEXYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 METHYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 NONYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 OCTYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 PENTADECYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 PENTYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 PROPYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); 3 ACETYL 2',2',2'',2'' TETRAMETHYL 5 UNDECYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE 2 SPIRO 7' [1',3' DIOXOLANO[4,5 C]PYRANO] 6' SPIRO 4'' (1'',3'' DIAOXOLANE); ACETIC ACID; ANTINEOPLASTIC AGENT; CYTOTOXIC AGENT; FRUCTOSE; HYDRAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; CYCLIZATION; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; HEATING; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; ISOMER; MICROWAVE IRRADIATION; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TUMOR CELL LINE;

EID: 63249122359     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.12.033     Document Type: Article

References (31)

1. Brown P., Best D.J., Broom N.J.P., Cassels R., Hanlon P.J.O., Mitchell T.J., Osborne N.F., and Wilson J.M. J. Med. Chem. 40 (1997) 2563-2570
2. Morton H.M., Heuser D.J., Joyner C.T., Batchelor J.F., and White H.L. J. Med. Chem. 39 (1996) 1857-1863
3. Chen C., Senanayake C.H., Bill T.J., Larsen R.D., Verhoeven T.R., and Reider P.J. J. Org. Chem. 59 (1994) 3738-3741
4. Amir M., and Shikha K. Eur. J. Med. Chem. 39 (2004) 535-545
5. Vardan S., Mookherjee S., and Eich R. Clin. Pharm. Ther. 34 (1983) 290-296
6. Yale H.L., and Losee K. J. Med. Chem. 9 (1966) 478-483
7. Guimaraes C.R.W., Boger D.L., and Jorgensen W.L. J. Am. Chem. Soc. 127 (2005) 17377-17384 and references cited therein
8. Dolman S.J., Gosselin F., O'Shea P.D., and Davies I.W. J. Org. Chem. 71 (2006) 9548-9551
9. Polshettiwar V., and Varma R.S. Tetrahedron Lett. 49 (2008) 879-883
10. Brown B.J., Clemens I.R., and Neesom J.K. Synlett (2000) 131-133
11. Hassan E., Al-Ashmawi M.I., and Abdel-Fattah B. Pharmazie 38 (1983) 833-835
12. Khalil M.A., El-Sayed O.A., and El-Shamny H.A. Arch. Pharm. 326 (1993) 489-492
13. Jin L.H., Chen J., Song B.A., Chen Z., Yang S., Li Q.Z., Hu D.Y., and Xu R.Q. Bioorg. Med. Chem. Lett. 16 (2006) 5036-5040
14. Yu J.X., Zhang S.N., Li Z.J., Lu W.J., Zhang L.J., Zhou R., Liu Y.T., and Cai M.S. J. Carbohydr. Chem. 20 (2001) 877-884
15. Li, Z. J.; Zhang, S. N.; Cui, J. R.; Yu, J. X.; Cai, M. S. ZL 03119612.8, 2004.
16. Pan Y., Song Q.L., Lin Y.H., Lu N., Yu H.M., and Li X.J. Acta Pharmacol. Sinica 26 (2005) 881-886
17. Abdel Rahman M.A., El Ashry E.S.H., Abdallah A.A., and Rashed N. Carbohydr. Res. 73 (1979) 103-111
18. Somogyi L. Carbohydr. Res. 75 (1979) 325-330
19. El Ashry E.S.H., El Kilany Y., Abdallah A.A., and Mackawy K. Carbohydr. Res. 113 (1983) 273-279
20. El Ashry E.S.H., Abdel Rahman M.A., El Kilany Y., and Rashed N. Carbohydr. Res. 163 (1987) 123-126
21. Somogyi L. Carbohydr. Res. 182 (1988) 19-29
22. Martins Alho M.A., and D'Accorso N.B. J. Heterocycl. Chem. 44 (2007) 901-907
23. Somogyi L. Tetrahedron 41 (1985) 5187-5190
24. Armesto D., Gallego M.G., Horspool W.M., and Ramos A. Tetrahedron Lett. 29 (1988) 3581-3584
25. Somogyi L. Bull. Chem. Soc. Jpn. 74 (2001) 873-881
26. Hearn M.J., and Chanyaputhipong P.Y. J. Heterocycl. Chem. 32 (1995) 1647-1649
27. Somogyi L., Czugler M., and Sohár P. Tetrahedron 48 (1992) 9355-9362
28. Lidström P., Tierney J., Wathey B., and Westman J. Tetrahedron 57 (2001) 9225-9283
29. Kappe C.O., and Stadler A. Microwave Org. Synth. (2002) 405
30. Molteni V., and Ellis D.A. Curr. Org. Synth. 2 (2005) 333-375
31. Complete crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 634,353 2a and 668,704 4a. Copies of this information may be obtained free of charge from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB21EZ, UK. (fax: +44-1223-336033, e-mail: deposit @ccdc.cam.ac.uk or via: www.ccdc.cam.ac.uk).