Synthesis and pharmacological activities of amine-boranes

Current Medicinal Chemistry

Volumn 12, Issue 17, 2005, Pages 1995-2010

  Burnham, Bruce S ^a  

^a RIDER UNIVERSITY   (United States)

Author keywords

Amine borane; Anti inflammatory; Anticancer; BNCT; Borane; Boron; Hypolipidemia; Osteoporosis

Indexed keywords

2' DEOXYNUCLEOSIDE; ACETYL COENZYME A CARBOXYLASE; ACETYL COENZYME A SYNTHETASE; ALIPHATIC AMINE; ALPHA AMINO ACID; AMIDOPHOSPHORIBOSYLTRANSFERASE; AMINE; AROMATIC AMINE; BORANE DERIVATIVE; CARBOXY(TRIMETHYLAMINO)BORANE; CHOLESTEROL; DIHYDROFOLATE REDUCTASE; DOPAMINE RECEPTOR BLOCKING AGENT; HETEROCYCLIC AMINE; HIGH DENSITY LIPOPROTEIN CHOLESTEROL; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE; INOSINATE DEHYDROGENASE; LIPID; LOW DENSITY LIPOPROTEIN CHOLESTEROL; LYASE; METHYLAMINE; MORPHOLINE DERIVATIVE; N METHYLMORPHOLINE CYANOBORANE; NUCLEOSIDE; PHOSPHATASE; PIPERIDINE DERIVATIVE; PURINE; TETRAKIS MU (TRIMETHYLAMINE BORANECARBOXYLATO) BIS(TRIMETHYLAMINE CARBOXYBORANE)DICOPPER; TRIMETHYLAMINE CYANOBORANE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANALGESIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; CHOLESTEROL SYNTHESIS; CONCENTRATION RESPONSE; CYTOTOXICITY; DNA SYNTHESIS INHIBITION; DRUG ACTIVITY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; IN VITRO STUDY; IN VIVO STUDY; LIPOGENESIS; NONHUMAN; PURINE SYNTHESIS; REVIEW;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTILIPEMIC AGENTS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; BORANES; DOPAMINE ANTAGONISTS; HUMANS; MOLECULAR STRUCTURE; OSTEOPOROSIS; RECEPTORS, PURINERGIC P2; TIME FACTORS;

EID: 22544480302     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867054546573     Document Type: Review

References (77)

1. Bloomfield, S.F.; Sizer, T.J. The Pharmaceutical J. 1985, 235, 153.
2. Martindale, The Extra Pharmacopeia. J.E.F. Reynolds, Ed.; The Pharmaceutical Press, London, 1982, 28th ed.
3. Linden, C.H.; Hall, A.H.; Kuli K.W.; Rumack, B.H. Clin. Toxicol. 1986, 24, 269.
4. Locher, G.L. Am. J. Roentgenol. 1936, 36, 1.
5. Soloway, A. H. In Progress in Boron Chemistry, H. Steinberg and A.L. McCloskey, Eds.; Macmillan Company, New York, 1964, Vol. 1, pp. 203-231.
6. Perks, C.A.; Mill, A.J.; Constantine, G.; Harrison, K.G.; Gibson J.A.B. Br. J. Radiol. 1988, 61, 1115.
7. Fairchild, R.G.; Bond, V.P. Strahlenther. 1984, 160, 764.
8. Wisian-Neilson, P.; Das, M.K.; Spielvogel, B.F. Inorg. Chem. 1978, 17, 2327.
9. Sood, C.K.; Sood, A.; Spielvogel, B.F.; Yousef, J.A.; Burnham, B.; Hall, I.H. J. Pharm. Sci. 1991, 80, 1133.
10. Spielvogel, B.F.; Wojnowich, L.; Das, M.K.; McPhail, A.T.; Hargrave, K.D. J. Am. Chem. Soc. 1976, 98, 5702.
11. Spielvogel, B.F.; Ahmed, F.U.; Silvey, G.L.; Wisian-Neilson, P.; McPhail, A.T. Inorg. Chem. 1984, 23, 4322.
12. Spielvogel, B.F.; Ahmed, F.U.; Morse, K.W.; McPhail, A.T. Inorg. Chem. 1984, 23, 1776.
13. Miller, M.C.; Sood, A.; Spielvogel, B.F.; Hall, I.H. Anticancer Res. 1997, 17, 3299.
14. Hall, I.H.; Starnes, C.O.; Spielvogel, B.F.; Wisian-Nielson, P.; Das, M.K.; Wojnowick, L. J. Pharm. Sci. 1979, 68, 685.
15. Spielvogel, B.F. In Advances in Boron and the Boranes, J.F. Liebman and A. Greenberg, Eds.; VCH Publishers, New York, 1988, pp. 329-342.
16. Hall, I.H.; Spielvogel, B.F.; Sood, A. Anti-Cancer Drugs 1990, 1, 133.
17. Hall, I.H.; Reynolds, D.J.; Chang, J.; Spielvogel, B.F.; Griffin, T.S.; Docks, E.L. Arch. Pharm. (Weinheim) 1991, 324, 573.
18. Chen, S.Y.; Burnham, B.S.; Spielvogel, B.F.; Sood, A.; Wyrick, S.D.; Hall, I.H. Appl. Organometal. Chem. 1996, 10, 279.
19. Miller, M.C.; Woods, C.M,; Murthy, M.E.; Elkins, A.; Spielvogel, B.F.; Hall, I.H. Biomed. Pharmacother. 1998, 52, 169.
20. Hall, M.E.; Shrewsbury, R.; Chen, S.Y.; Elkins, A.L.; Burnham, B.S.; Spielvogel, B.F.; Hall, I.H. Pharmaceut. Sci. 1997, 3, 473.
21. Hall, I.H.; Spielvogel, B.F.; McPhail, A.T. J. Pharm. Sci. 1984, 73, 222.
22. Hall, I.H.; Morse, K.W.; Spielvogel, B.F.; Sood, A. Anti-Cancer Drugs 1991, 2, 389.
23. Hall, I.H.; Gilbert, C.J.; McPhail, A.T.; Morse, K.W.; Hassett, K.; Spielvogel, B.F. J. Pharm. Sci. 1985, 74, 755.
24. Miller, M.C.; Sood, A.; Spielvogel, B.F.; Hall, I.H. Appl. Organometal. Chem. 1998, 12, 87.
25. Miller, M.C.; Sood, A.; Spielvogel, B.F.; Hall, I.H. Res. Comm. Pharmacol. Toxicol. 1996, 1, 245.
26. Sood, A.; Sood, C.K.; Spielvogel, B.F.; Hall, I.H. Eur. J. Med. Chem. 1990, 25, 301.
27. Spielvogel, B.F.; Sood, A.; Tomasz, J.; Shaw, B.R.; Karthikeyan, S.; Powel, W.; Laster, B.; Brugger, B.M.; Coderre, J. In Advances in Neutron Capture Therapy, A.H. Soloway, R.F. Barth and D.E. Carpenter, Eds.; Plenum Press, New York, 1993, pp. 361-365.
28. Sood, A.; Sood, C.K.; Spielvogel, B.F.; Hall, I.H.; Wong, O.T. J. Pharm. Sci. 1992, 81, 458.
29. Das, M.K; Maiti, P.D.; Roy, S.; Mittakanti, M.; Morse, K.W.; Hall, I.H. Arch. Pharm. (Weinheim) 1992, 325, 267.
30. Burnham, B.S.; Chen, S.Y.; Sood, A.; Spielvogel, B.F.; Hall, I.H. Pharmazie 1995, 50, 779.
31. Sood, A.; Sood, C.K.; Hall, I.H.; Spielvogel, B.F. Tetrahedron 1991, 47, 6915.
32. Sood, C.K.; Sood, A.; Spielvogel, B.F.; Yousef, J.A.; Burnham, B.; Hall, I.H. J. Pharm. Sci. 1991, 80, 1133.
33. Miller, M.C.; Sood, A.; Spielvogel, B.F.; Bastow, K.; Hall, I.H. Metal-Based Drugs 1997, 4, 229.
34. Sood, A.; Spielvogel, B.F.; Shaw, B.R.; Carlton, L.D.; Burnham, B.S.; Hall, E.S.; Hall, I.H. Anticancer Res. 1992, 12, 335.
35. Hall, I.H.; Elkins, A.; Sood, A; Tomasz, J; Spielvogel, B.F. Anticancer Res. 1996, 16, 3709.
36. Spielvogel, B.F.; Sood, A.; Shaw, B.R.; Hall, I.H.; Fairchild, R.G.; Laster, B.H.; Gordon, C. In Progress in Neutron Capture Therapy for Cancer, B.J. Allen, et. al., Eds.; Plenum Press, New York, 1992, pp. 211-213.
37. Burnham, B.S.; Hall, I.H.; Shrewsbury, R.P.; Hall, E.S.; Sood, A.; Spielvogel, B.F. Drug Invest. 1993, 6, 75.
38. Hall, I.H.; Burnham, B.S.; Rajendran, K.G.; Chang, J.-J.; Sood, A.; Spielvogel, B.F. Metal-Based Drugs 1993, 1, 19.
39. Sood, A.; Spielvogel, B.F.; Powell, W.J.; Bastow, K.F.; Miller, M.C.; Hall, I.H. Anticancer Res. 1994, 14, 1483.
40. Scarlett, T.C.; Durham, R.; Hall, I.H.; Crosswicks, R.J.; Berkowitz, J.D.; Burnham, B.S. Metal Based Drugs 2002, 9, 19.
41. Burnham, B.S.; Chen, S.Y.; Sood, A.; Spielvogel, B.F.; Miller, M.C.; Hall, I.H. Anticancer Res. 1995, 15, 951.
42. Sood, A.; Spielvogel, B.F.; Shaw, B.R.; Hall, E.S.; Chi, L.K.; Hall, I.H. Pharmazie 1992, 47, 833.
43. Hall, I.H.; Hall, E.S.; Chi, L.K.; Shaw, B.R.; Sood, A.; Spielvogel, B.F. Anticancer Res. 1992, 12, 1091.
44. Spielvogel, B.F.; Sood, A.; Shaw, B.R.; Hall, I.H.; Fairchild, R.G.; Laster, B.H.; Gordon, C. Pure Appl. Chem. 1991, 63, 415.
45. Sarfati, S.; Guerreiro, C.; Canard, B.; Dereuddre-Bosquet, N.; Clayette, P.; Dormont, D. Nucleosides Nucleotides 1999, 18, 1023.
46. Baraniak, J.; Kaczmarek, R.; Wasilewska, E. Tet. Lett. 2004, 45, 671.
47. Hall, I.H.; Das, M.K.; Harchelroad Jr., F.; Wisian-Nielson, P.; McPhail, A.T.; Spielvogel, B.F. J. Pharm. Sci. 1981, 70, 339.
48. Hall, I.H.; Spielvogel, B.F.; Sood, A.; Ahmed, F.; Jafri, S. J. Pharm. Sci. 1987, 76, 359.
49. Eisen, E.J.; Jones, E.E.; Rajendran, K.G.; Hall, I.H. Growth Devel. Aging 1996, 60, 7.
50. Hall, I.H.; Reynolds, D.J.; Chang, J.; Spielvogel, B.F.; Griffin, T.S.; Docks, E.L. Arch. Pharm. (Weinheim) 1991, 324, 573.
51. Sood, A.; Sood, C.K.; Spielvogel, B.F. Arch. Pharm. (Weinheim) 1991, 324, 423.
52. Griffin, T.S.; Docks, E.L.; Brotherton, R.J.; Hall, I.H. Eur. J. Med. Chem. 1991, 26, 517.
53. Hall, I.H.; Spielvogel, B.F.; Griffin, T.S.; Docks, E.L.; Brotherton, R.J. Res. Commun. Chem. Path. Pharm. 1989, 65, 297.
54. Burnham, B.S.; Chen, S.Y.; Sood, A.; Spielvogel, B.F.; Hall, I.H. Metal-Based Drugs 1995, 2, 221.
55. Hall, I.H.; Williams Jr., W.L.; Gilbert C.J.; McPhail, A.T.; Spielvogel B.F. J. Pharm. Sci. 1984, 73, 973.
56. Hall, I.H.; Brotherton, R.J.; Docks, E.L.; Griffin, T.S.; Sood, A.; Spielvogel, B.F. Biomed. Biochim. Acta 1991, 50, 1007.
57. Sood, A.; Sood, C.K.; Spielvogel, B.F.; Hall, I.H. Eur. J. Med. Chem. 1990, 25, 301.
58. Sood, A.; Sood, C.K.; Spielvogel, B.F.; Hall, I.H.; Wong, O.T. J. Pharm. Sci. 1992, 81, 458.
59. Das, M.K; Maiti, P.D.; Roy, S.; Mittakanti, M.; Morse, K.W.; Hall, I.H. Arch. Pharm. (Weinheim) 1992, 325, 267.
60. Hall, I. H.; Sood, A.; Spielvogel, B.F. Biomed. Pharmacother. 1991, 45, 333.
61. Hall, I. H.; Burnham, B.S.; Rajendran, K.G.; Chen, S.Y.; Sood, A.; Spielvogel, B.F.; Shaw, B.R. Biomed. Pharmacother. 1993, 47, 79.
62. Burnham, B.S.; Sood, A.; Tomasz, J.; Powell, W.J.; Spielvogel, B.F.; Chen, S.Y.; Hall, I.H. Metal-Based Drugs 1996, 3, 173.
63. Kaneko I.; Hazama-Shimda y, Endo A. Eur. J. Biochem, 1978, 87, 313.
64. Hall, I.H.; Hall, E.S.; Wong, O.T. Anti-Cancer Drugs, 1992, 3, 55.
65. Hall, I.H.; Lee, K.H.; Starnes, C.O.; Muraoka, O.; Sumida, Y.; Waddell, T.G. J. Pharm. Sci. 1980, 69, 694.
66. Simlot, R.; Izydore, R.A.; Wong, O.T.; Hall, I.H. J. Pharm. Sci. 1993, 82, 408-415.
67. Holub, J.M.; O'Toole-Colin, K.; Getzel, A.; Argenti, A.; Evans, M.A.; Smith, D.C.; Dalglish, G.A.; Rifat, S.; Wilson, D.L.; Taylor, B.M.; Miott, U.; Glersaye, J.; Lam, S.K.; McCranor, B.J.; Berkowitz, J.D.; Miller, R.B.; Lukens, J.R.; Krumpe, K.; Gupton, J.T.; Burnham, B.S. Molecules 2004, 9, 134.
68. Hall, I.H.; Starnes, C.O.; McPhail, A.T.; Wisian-Neilson, P.; Das, M.K.; Harchelroad Jr., F.; Spielvogel, B.F. J. Pharm. Sci. 1980, 69, 1025.
69. Hall, I.H.; Rajendran, K.G.; Chen, S.Y.; Wong, O.T.; Sood, A.; Spielvogel, B.F. Arch. Pharm. (Weinheim) 1995, 328, 39.
70. Hall, I.H.; Gilbert, C.J.; McPhail, A.T.; Morse, K.W.; Hassett, K.; Spielvogel, B.F. J. Pharm. Sci. 1985, 74, 755.
71. Zimmer, H.; Andrews, E.R.; Sill, A.D. Arzneimittelforschung 1967, 17, 607.
72. Rajendran, K.G.; Sood, A.; Spielvogel, B.F.; Hall, I.H.; Norwood, V.M.; Morse, K.W. Appl. Organometal. Chem. 1995, 9, 111.
73. Rajendran, K.G.; Chen, S.Y.; Sood, A.; Spielvogel, B.F.; Hall, I.H. Biomed. Pharmacother. 1995, 49, 131.
74. Murphy, M.E.; Elkins, A.L.; Shrewsbury, R.P.; Sood, A.; Spielvogel, B.F.; Hall, I.H. Metal Based Drugs 1996, 3, 31.
75. Shah, J.H.; Izenwasser, S.; Geter-Douglas, B.; Witkin, J.M.; Newman, A.H. J. Med. Chem. 1995, 38, 4284.
76. Nahum, V.; Zundorf, G.; Levesque, S.A.; Beaudoin, A.R.; Reiser, G.; Fischer, B. J. Med. Chem. 2002, 45, 5384.
77. Gyori, B.; Berente, Z. Inorg. Chem. 2001, 40, 1770.