Novel glycosylated carboranylquinazolines for boron neutron capture therapy of tumors: Synthesis, characterization, and in vitro toxicity studies

Applied Organometallic Chemistry

Volumn 22, Issue 4, 2008, Pages 227-232

  Genady, Afaf R ^b   El Zaria, Mohamed E ^a  

^a TANTA UNIVERSITY   (Egypt)

^b Tanta University   (Egypt)

Author keywords

Antitumor agents; BNCT; Carboranes; N glycosides; Quinazolines

Indexed keywords

ACIDS; BORON; BORON COMPOUNDS; SODIUM;

ANTITUMOR AGENTS; BNCT; CARBORANES; N-GLYCOSIDES; QUINAZOLINES;

CONDENSATION REACTIONS;

EID: 51349123565     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1376     Document Type: Article

References (47)

1. Gielen M. Appl. Organomet. Chem. 2002; 16: 481.
2. DiMeo C, Panza L, Capitani D, Mannina L, Banzato A, Rondina M, Renier D, Rosato A, Crescenzi V. Biomacromolecules 2007; 8: 552.
3. Soloway AH, Tjarks W, Barnum BA, Rong F-G, Barth RF, Codogni IM, Wilson JG. Chem. Rev. 1998; 98: 1515.
4. Salt C, Lennox AJ, Takagaki M, Maguire JA, Hosmane NS. Russian Chem. Bull. 2005; 53: 1871.
5. Rana G, Vyakaranam K, Maguire JA, Hosmane NS, sB boron compounds as therapeutic drugs, in Metallotherapeutic Drugs and Metal-based Diagnostic Agents the Use of Metal in Medicine (Eds.: Gielen M, Tiekink E,), Wiley: Chichester, 2005; pp. 19-46.
6. Hosmane NS, Adams L, Wang J, Vyakaranam K, Rana G, Hosmane SN, Spielvogel BF, Eklund JE, in Research and Development in Neutron Capture Therapy (Eds.: Sauerwein W, Moss R, Wittig A,), Monduzzi Editore: Bologna, 2002; pp. 99-105.
7. Yinghuai Z, Yan KC, Maguire JA, Hosmane NS. Curr. Chem. Biol. 2007; 1: 141.
8. Szarics E, Nyikos L, Barabas P, Kovacs I, Skuban N, Temesvarine-Major E, Egyed O, Nagy PI, Kokosi J, Takacs-Novak K, Kardos J. Mol. Pharm. 2001; 59: 920.
9. Sielecki TM, Johnson TL, Liu J, Muckelbauer JK, Grafstrom RH, Cox S, Boylan J, Burton CR, Chen HY, Smallwood A, Chang CH, Boisclair M, Benfield PA, Trainor GL, Seitz SP. Bioorg. Med. Chem. Lett. 2001 ; 11 : 1157.
10. El-Hiti GA, Abdel-Megeed MF. Heterocycles 2005; 65: 3007.
11. Bartroli J, Turmo E, Alguero M, Boncompte E, Vericat ML, Conte L, Ramis J, Merlos M, Garcia-Rafanell J, Forn J. J. Med. Chem. 1998; 41 : 1869.
12. Shiba SA, El-Khamry AA, Shaban MF, Atia KS. Pharmazie 1997; 52: 189.
13. Abdel-Hamid SG. J. Ind. Chem. Soc. 1997; 74: 613.
14. Barker AJ, Eur. Patent 635498, 1995; Chem. Abstr. 122, 214099.
15. Kurogi Y, Inoue Y, Tsutsumi K, Nakamura S, Nagao K, Yoshitsugu H, Tsuda Y. J. Med. Chem. 1996; 39: 143.
16. El-Brollosy NR, Abdel-Megeed MF, Genady AR. Monatsh. Chem. 2001; 132: 1063.
17. Ager IR, Harrison DR, Kennewell PD, Taylor JB. J. Med. Chem., 1977; 20: 379.
18. Zhuo J-C, Soloway AH, Beeson JC, Weihua J, Barnum BA, Rong F-G, Tjarks W, IV Jordan GT, Liu J, Shore SG. J. Org. Chem. 1999; 64: 9566.
19. Bandyopadhyaya AK, Narayanasamy S, Barth RF, Tjarks W. Tetrahedron Lett. 2007; 48: 4467.
20. Naeslund C, Ghirmai S, Sjöberg S. Tetrahedron 2005; 61: 1181.
21. Ohta K, Yamazaki H, Pichierri F, Kawahata M, Yamaguchi K, Endo Y. Tetrahedron 2007; 63: 12160.
22. Chen Y-Q, Wang J-Q, Jin G-X. J. Orgonomet al.Chem. 2007; 692; 5190.
23. Bandyopadhyaya AK, Tiwari R, Tjarks W. Bioorg. Med. Chem. 2006; 14: 6924.
24. Vyakaranam K, Rana G, Ratanasuwan A, Hosmane SN, Maguire JA, and Hosmane NS. Organometallics 2002; 21: 3905.
25. Lee J-D, Lee C-H, Nakamura H, Lee S-H, Lee C-H, Jun B, Ko J, Kang S--O, in Research and Development in Neutron Capture Therapy (Eds.: Sauerwein W, Moss R, and Wittig A,), Monduzzi Editore: Bologna, 2002; pp31-35.
26. Compostella F, Monti D, Panza L, Poltti L, Prosperi D, in Research and Development in Neutron Capture Therapy (Eds.: Sauerwein W, Moss R, and Wittig A,), Monduzzi Editore: Bologna, 2002; pp. 81-84.
27. Vyakaranam K, Hosmane NS. Bioinorg. Chem. Applic. 2004; 2: 31.
28. Yinghuai Z, Peng AT, Carpenter K, Maguire JA, Hosmane NS, Takagaki M. J. Am. Chem. Soc. 2005; 127: 9875.
29. Nakahara T, Nishimura S-I, Shirai T. Curr. Chem. Biol. 2007; 1: 265.
30. Tietze LF, Bothe U. Chem. Eur. J1998; 4: 1179.
31. Tietze LF, Bothe U, Schuberth I. Chem. Eur. J 2000; 6: 836.
32. Tietze LF, Bothe U, Griesbach U, Nakaichi M, Hasegawa T, Nakamura H, Yamamoto Y. Bioorg. Med. Chem. 2001 ; 9: 1747.
33. Tietze LF, Bothe U, Griesbach U, Nakaichi M, Hasegawa T, Nakamura H, Yamamoto Y. ChemBioChem. 2001 ; 2: 326.
34. Tietze LF, Griebach U, Schuberth I, Bothe U, Marra A, Dondoni A. Chem. Eur. J 2003; 9: 1296.
35. Basak P, Lowary TL. Can. J. Chem. 2002; 80: 943.
36. Orlova AV, Zinin Al, Malysheva NN, Kononov LO, Sivaev IB, Bregadze VI. Russ. Chem. Bull., Int. Edn 2003; 52: 2766.
37. Kononov LO, Orlova AV, Zinin Al, Kimel BG, Sivaev IB, Bregadze VI. J. Organomet. Chem. 2005; 690: 2769.
38. Orlova AV, Kononov LO, Kimel BG, Sivaev IB, Bregadze VI. Appl. Organomet. Chem. 2006; 20: 416.
39. Orlova AV, Kondakov NN, Zinin Al, Kimel BG, Kononov LO, Sivaev IB, Bregadze VI. Russ. Chem. Bull., Int. Edn 2005; 54: 1352.
40. Orlova AV, Kondakov NN, Zinin Al, Kimel BG, Kononov LO, Sivaev IB, Bregadze Vl. Russ. J. Bioorg. Chem. 2006; 32: 568.
41. Ronchi S, Prosperi D, Thimon C, Morin C, Panza L. Tetrahedron Asym. 2005; 16: 39.
42. Yoshihisa Y. Chem. Pharm. Bull. 1983; 31 (4): 1158.
43. Wilson JG, Anisuzzaman AKM, Alam F, Soloway AH. Inorg. Chem. 1992; 31: 1955.
44. Maurer JL, Serino AJ, Hawthorne MF. Organometallics 1988; 7: 2519.
45. El-Brollosy NR, Abdel-Megeed MF, El-Hiti GA, Genady AR. Afinidad 2003; 504: 199.
46. Tjarks W, Anisuzzaman AKM, Liu L, Soloway AH, Barth RF, Perkins DJ, Adams DM. J. Med. Chem. 1992; 35: 1628.
47. Bergeron RJ, Neims AH, McManis JS, Hawthorne TR, Vinson JRT, Bortell R, Ingeno MJ. J. Med. Chem. 1988; 31: 183.