The concept of chiral conformers and its significance in molecular pharmacology

Advances in Drug Research

Volumn 30, Issue , 1997, Pages 73-110

  Simonyi, M ^a  

^a CTRL RES INSTITUTE FOR CHEMISTRY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYRIDINE; 4 AMINOBUTYRIC ACID; ANTIBIOTIC AGENT; BENZODIAZEPINE DERIVATIVE; DNA; HUMAN SERUM ALBUMIN; ION CHANNEL; PEPTIDE; RACHELMYCIN; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ALLOSTERISM; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DNA STRUCTURE; DRUG CONFORMATION; DRUG DESIGN; DRUG STRUCTURE; MOLECULAR BIOLOGY; PHARMACOLOGY; PRIORITY JOURNAL;

EID: 0030863196     PISSN: 00652490     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0065-2490(97)80005-6     Document Type: Article

References (134)

1. Aki H. Yamamoto M. J. Pharm. Pharmacol. 41 1989 674 679
2. Alebić-Kolbah T. Kajfeż F. Rendić S. Sunjić V. Konowal A. Snatzke G. Biochem. Pharmacol. 28 1979 2457 2465
3. Allan R.D. Johnston G.A.R. Med. Res. Rev. 3 1983 91 118
4. Allan R.D. Dickenson H.W. Fong J. Eur. J. Pharmacol. 122 1986 339 348
5. Allinger N.L. Grev R.S. Yates B.F. Schaefer H.F. III J. Am. Chem. Soc. 112 1990 114 118
6. Altona C. Sundaralingam M. J. Am. Chem. Soc. 94 1972 8205 8212
7. Altona C. Sundaralingam M. J. Am. Chem. Soc. 95 1973 2333 2344
8. Ando T. Ota M. Kashiwagi T. Nagashima N. Ariyoshi Y. Chadha R.K. Yamazaki T. Goodman M. J. Am. Chem. Soc. 115 1993 397 402
9. Ariyoshi Y. Agr. Biol. Chem. 40 1976 983 992
10. Baldwin J.J. Claremon D.A. Lumma P.K. McClure D.E. Rosenthal S.A. Winquist R.J. Faison E.P. Kaczorowski G.J. Trumble M.J. Smith G.M. J. Med. Chem. 30 1987 690 695
11. Barnard E. Trends Pharmacol. Sci. 17 1996 305 309
12. Beard H. McKie R. Sailing: A Sailors Dictionary 1981 Workman New York
13. Blauer G. Harmatz D. Snir J. Biochim. Biophys. Acta 278 1972 68 88
14. Blount J.F. Fryer R.J. Gilman N.W. Todaro L.J. Mol. Pharmacol. 24 1983 425 428
15. Boger D.L. Bergman J. van der Plas H.C. Simonyi M. Heterocycles in Bio-organic Chemistry 1991 The Royal Society of Chemistry Cambridge 103 129
16. Boger D.L. Acc. Chem. Res. 28 1995 20 29
17. Boger D.L. Ishizaki T. Tetrahedron Lett. 31 1990 793 796
18. Boger D.L. Mésini P. J. Am. Chem. Soc. 117 1995 11647 11655
19. Boger D.L. Zhou J. J. Org. Chem. 58 1993 3018 3024
20. Boger D.L. Ishizaki T. Wysocki R.J. Jr Munk S.A. Kitos P.A. Suntornwat O. J. Am. Chem. Soc. 111 1989 6461 6463
21. Boger D.L. Coleman R.S. Invergo B.J. Sakya S.M. Ishizaki T. Munk S.A. Zarrinmayeh H. Kitos P.A. Collins Thompson S. J. Am. Chem. Soc. 113 1990 4623 4632
22. Boger D.L. Zarrinmayeh H. Munk S.A. Kitos P.A. Suntornwat O. Proc. Natl. Acad. Sci. USA 88 1991 1431 1435
23. Boger D.L. Nishi T. Teegarden B.R. J. Org. Chem. 59 1994 4943 4949
24. Böhringer M. Roth H.J. Hunziker J. Göbel M. Krishnan R. Giger A. Schweizer B. Schreiber J. Leumann C. Eschenmoser A. Helv. Chim. Acta 75 1992 1416 1477
25. Borea P.A. Dalpiaz A. Gessi S. Gilli G. Eur. J. Pharmacol. 298 1996 329 334
26. Bos O.J.M. Fischer M.J.E. Wilting J. Janssen L.H.M. Biochem. Pharmacol. 38 1989 1979 1984
27. Brée F. Urien S. Nguyen P. Tillement J.P. Steiner A. Vallat-Molliet C. Testa B. Visy J. Simonyi M. J. Pharm. Pharmacol 45 1993 1050 1053
28. Brodersen R. Crit. Rev. Clin. Lab. Sci. 11 1980 305 399
29. Cheng C.C. Zee-Cheng R.K.Y. Heterocycles 15 1981 1275 1283
30. Chidester C.G. Krueger W.C. Mizsak S.A. Duchamp D.J. Martin D.G. J. Am. Chem. Soc. 103 1981 7629 7635
31. Collet A. Simonyi M. Problems and Wonders of Chiral Molecule's 1990 Akadémiai Kiadó Budapest 91 109
32. Crick F.H.C. Watson J.D. Proc. Roy. Soc. A 223 1954 80 96
33. Curotto G. Donati D. Pentasuglia G. Ursini A. Bioorg. Med. Chem. Lett. 5 1995 3011 3016
34. De Clercq E. Medical Virology 6 1996 97 117
35. Dröge J.H. Janssen L.H. Wilting J. Biochim. Biophys. Acta 827 1985 396 402
36. Doucet J.-P. Weber J. Computer-Aided Molecular Design: Theory and Applications 1996 Academic Press London
37. Eliel E.L. Wilen S.H. Mander L.N. Stereochemistry of Organic Compounds 1994 Wiley New York
38. Eltze M. Eur. J. Pharmacol. 180 1990 161 168
39. Eltze M. Gonne S. Riedel R. Schlotke B. Schudt C. Simon W.A. Eur. J. Pharmacol. 112 1985 211 224
40. Eschenmoser A. Chatgilialoglu C. Snieckus U. Chemical Synthesis 1996 Kluwer Academic Publishers Dordrecht 293 340
41. Eschenmoser A. Dobler M. Helv. Chim. Acta 75 1992 218 259
42. Eschenmoser A. Loewenthal E. Chem. Soc. Rev. 1992 1 16
43. Eveleigh P. Hulme E.C. Schudt C. Birdsall N.J.M. Mol. Pharamcol. 35 1989 477 483
44. Fahey R.C. Hunt J.S. Windham G.C. J. Mol. Evol. 10 1977 155 160
45. Falch E. Hedegaard A. Nielsen L. Jensen B.R. Hjeds H. Krogsgaard-Larsen P. J. Neurochem. 47 1986 898 903
46. Feigenspan A. Wassle H. Bormann J. Nature 361 1993 159 161
47. Fitos I. Simonyi M. Tegyey Zs. Kajtár M. Ötvös L. Arch. Pharm. 319 1986 744 749
48. Fitos I. Tegyey Zs. Simonyi M. Sjöholm I. Larsson T. Lagercrantz C. Biochem. Pharmacol. 35 1986 263 269
49. Fitos I. Visy J. Magyar A. Kajtár J. Simonyi M. Chirality 2 1990 161 166
50. Foot M. Wallace J. Epilepsy Res. Suppl. 3 1991 109 114
51. Fossheim R. Svarteng K. Mostad A. Römming C. Shefter E. Triggle D.J. J. Med. Chem. 25 1982 126 131
52. Fujino M. Wakimasu M. Tanaka K. Aoki H. Nakaima N. Naturwissenschaften 60 1973 351
53. Gilman N.W. Rosen P. Earley J.V. Cook Ch. Todaro L.J. J. Am. Chem. Soc. 112 1990 3969 3978
54. Goldmann S. Stoltefuss J. Angew. Chem. Int. Ed. Engl. 30 1991 1559 1578
55. Goldmann S. Born L. Kazda S. Pittel B. Schramm M. J. Med. Chem. 33 1990 1413 1418
56. Golik J. Clardy J. Dubay G. Groenewold G. Kawaguchi H. Konishi M. Krishnan B. Ohkuma H. Sithoh K. Doyle T.W. J. Am. Chem. Soc. 109 1987 3461 3462
57. Golik J. Clardy J. Dubay G. Groenewold G. Kawaguchi H. Konishi M. Krishnan B. Ohkuma H. Sithoh K. Doyle T.W. J. Am. Chem. Soc. 109 1987 3462 3464
58. Goodman M. Coddington J. Mierke D.F. J. Am. Chem. Soc. 109 1987 4712 4714
59. Hammer R. Berrie C.P. Birdsall N.J.M. Burgen A.S.V. Hulme E.C. Nature 283 1980 90 92
60. Hawley R.C. Kiessling L.L. Schreiber S.L. Proc. Natl. Acad. Sci. USA 86 1989 1105 1109
61. He X.M. Carter D.C. Nature 358 1992 209 215
62. Hibert M.F. Wermuth C.G. The Practice of Medicinal Chemistry 1996 Academic Press London 523 546
63. Hill D.R. Bowery N.G. Nature 290 1981 149 152
64. Hunziker J. Roth H.J. Böhringer M. Giger A. Diederichsen U. Göbel M. Krishnan R. Jaun B.J. Leumann C. Eschenmoser A. Helv. Chim. Acta 76 1993 259 352
65. Hurley L.H. Needham-Van Devanter D.R. Acc. Chem. Res. 19 1986 230 237
66. Hurley L.H. Needham-Van Devanter D.R. Lee C.S. Proc. Natl. Acad. Sci. USA 84 1987 6412 6416
67. Jenkins B.G. Lauffer R.B. Mol. Pharmacol. 37 1990 111 118
68. Kawai M. Nyfeler R. Bermann J.M. Goodman M. J. Med. Chem. 25 1982 397 402
69. Kier L.B. J. Pharm. Sci. 61 1972 1394 1397
70. Kilpatrick J.E. Pitzer K.S. Spitzer R. J. Am. Chem. Soc. 69 1947 2483 2488
71. Klyne W. Prelog V. Experientia 16 1960 521 523
72. Krogsgaard-Larsen P. Nielsen L. Falch E. Curtis D.R. J. Med. Chem. 28 1985 1612 1617
73. Krogsgaard-Larsen P. Hjeds H. Falch E. Jørgensen F.S. Nielsen L. Testa B. Advances in Drug Research 1988 Academic Press London 381 456
74. Lee M.D. Dunne T.S. Siegel M.M. Chang C.C. Morton G.O. Borders D.B. J. Am. Chem. Soc. 109 1987 3464 3466
75. Lee M.D. Dunne T.S. Chang C.C. Ellestad G.A. Siegel M.M. Morton G.O. McGahren W.J. Borders D.B. J. Am. Chem. Soc. 109 1987 3466 3468
76. Lightner D.A. Reisinger M. Landen G.L. J. Biol. Chem. 261 1986 6034 6038
77. Linscheid F. Lehn J.-M. Bull. Soc. Chim. France 1967 992 997
78. Lockhart T.P. Bergman R.G. J. Am. Chem. Soc. 103 1981 4091 4096
79. Macor J.E. Blake J.F. Desai K. Post R.J. Schmidt A.W. Bioorg. Med. Chem. Lett. 5 1995 2397 2402
80. Maksay G. Mol. Pharmacol. 46 1994 386 390
81. Maksay G. Neurochem. Int. 29 1996 361 370
82. Maksay G. J. Neurochem. 67 1996 407 411
83. Maksay G. Simonyi M. Eur. J. Pharmacol. 117 1985 275 278
84. Maksay G. Simonyi M. Mol. Pharmacol. 30 1986 321 328
85. Maksay G. van Rijn C.M. J. Neurochem. 61 1993 2081 2088
86. Maksay G. Tegyey Zs. Simonyi M. Mol. Pharmacol. 39 1991 725 732
87. Maksay G. Molnár P. Simonyi M. Naunyn-Schmiedeberg's Arch. Pharmacol. 353 1996 306 313
88. Manfredi K.P. Blunt J.W. Cardellina J.H. McMahon J.B. Pannell L.L. Cragg G.M. Boyd M.R. J. Med. Chem. 34 1991 3402 3405
89. Martin D.G. Biles C. Gerpheide S.A. Hanka L.J. Krueger W.C. McGovren J.P. Mizska S.A. Neil G.L. Stewart J.C. Visser J. J. Antibiot. 34 1981 1119 1125
90. Mazur R.H. Schlatter J.M. Goldcamp A.H. J. Am. Chem. Soc. 91 1969 2684 2691
91. Minghetti P.P. Ruffner D.E. Kuang W.J. Dennison O.E. Hawkins J.W. Beattie W.G. Dugaiczyk A. J. Biol. Chem. 261 1986 6747 6757
92. Nicolaou K.C. Angew. Chem. Int. Ed. Engl. 32 1993 1377 1385
93. Nicolaou K.C. Ebata T. Stylianides N.A. Groneberg R.D. Carrol P.J. Angew. Chem. Int. Ed. Engl. 27 1988 1097 1099
94. Nicolaou K.C. Tsay S.C. Suzuki T. Joyce G.F. J. Am. Chem. Soc. 114 1992 7555 7557
95. Nicolaou K.C. Smith A.L. Yue E.W. Proc. Natl Acad. Sci. USA 90 1993 5881 5888
96. Nicolaou K.C. Li T. Nakada M. Hummel C.W. Hiatt A. Wrasidlo W. Angew. Chem. Int. Ed. Engl. 33 1994 183 186
97. Oida T. J. Biochem. (Tokyo) 100 1986 99 113
98. Oki M. Top. Stereochem. 14 1983 1 81
99. Oki M. Acc. Chem. Res. 17 1984 154 159
100. Otting G. Billeter M. Wüthrich K. Roth H.J.J. Leumann C. Eschenmoser A. Helv. Chim. Acta 76 1993 2701 2756
101. Peters T. Jr. All about Albumin 1996 Academic Press San Diego
102. Peters T. Jr. Reed R.G. Blauer G. Sund H. Transport by Proteins 1978 de Gruyter Berlin 57 73
103. Pitsch S. Wendeborn S. Jaun B. Eschenmoser A. Helv. Chim. Acta 76 1993 2161 2183
104. Plavec J. Tong W. Chattopadhyaya J. J. Am. Chem. Soc. 115 1993 9734 9746
105. Plavec J. Thibaudeau C. Viswanadham G. Sund C. Chattopadhyaya J. J. Chem. Soc. Chem. Commun. 1994 781 783
106. Plavec J. Thibaudeau C. Viswanadham G. Sund C. Sandström A. Chattopadhyaya J. Tetrahedron 51 1995 11775 11792
107. Qian H. Dowling J.E. Nature 361 1993 162 164
108. Ren J. Esnouf R. Garman E. Stammers D. Kirby I. Keeling J. Jones Y. Darby G. Somers D. Nature Structural Biol. 2 1995 293 302
109. Ruiz-Gomez A. Garcia-Calvo M. Vázquez J. Marvizon J.C.G. Valdivieso F. Mayor F. J. Neurochem. 52 1989 1775 1780
110. Schallenberger R.S. Acree T.E. Nature 216 1967 480 482
111. Schmieden V. Betz H. Mol. Pharmacol. 48 1995 919 927
112. Simonyi M. Med. Res. Rev. 4 1984 359 413
113. Simonyi M. Chem. Brit. 31 1995 942
114. Simonyi M. Enantiomer 1 1996 403 414
115. Simonyi M. Fitos I. Biochem. Pharmacol. 32 1983 1917 1920
116. Simonyi M. Maksay G. Kovács I. Tegyey Zs. Párkányi L. Kálmán A. ötvös L. Bioorg. Chem. 12 1990 1 12
117. Sjöholm I. Ekman B. Kober A. Ljungstedt-Phlman I. Seiving B. Sjödin T. Mol. Pharmacol. 16 1979 767 777
118. Stephenson F.A. Biochem. J. 310 1995 1 9
119. Sudlow G. Birkett D.J. Wade D.N. Mol. Pharmacol. 12 1976 1052 1061
120. Sunjić V. Kajfeż F. Stromar I. Blazevic N. Kolbah D. J. Heterocycl. Chem. 10 1973 591 599
121. Taylor C.P. Neurology 44 Suppl. 5 1994 10 15
122. Testa B. Kier L.B. Med. Res. Rev 11 1991 35 48
123. Testa B. Jenner P. Kilpatrick G.J. El Tayar N. Van De Waterbeemd H. Marsden C.D. Biochem. Pharmacol. 36 1987 4041 4046
124. Thibaudeau C. Plavec J. Chattopadhyaya J. J. Am. Chem. Soc. 116 1994 8033 8037
125. Triggle D.J. Chirality 6 1994 58 62
126. Triggle D.J. Langs D.A. Janis R.A. Med. Res. Rev 9 1989 123 180
127. Trummlitz G. Schmidt G. Wagner H.W. Luger P. Arzneim. Forsch/Drug Res. 34 1984 849 859
128. Unwin N. Nature 373 1995 37 43
129. Visy J. Simonyi M. Chirality 1 1989 271 275
130. Walker S. Valentine K.G. Kahne D. J. Am. Chem. Soc. 112 1990 6428 6429
131. Wiberg K.B. Murcko M.A. J. Am. Chem. Soc. 110 1988 8029 8038
132. Yamazaki T. Zhu Y.F. Probstl A. Chadha R.K. Goodman M. J. Org. Chem. 56 1991 6644 6655
133. Yamazaki T. Benedetti E. Kent D. Goodman M. Angew. Chem. Int. Ed. Engl. 33 1994 1437 1451
134. Zein N. Poncin M. Nilakantan R. Ellestad G.A. Science 244 1989 697 699