Advances in the stereoselective synthesis of antifungal agents and ...

More documents

Recommendations

Info

Chapter 9 213References chapter 1:1) Ariens, E., J. Clin. Pharmacal. Ther. 1987, 42,361-3632) Ariens, E. J.;Wuis, E.W.; Veringa,E. J. Biochem. Pharmacol.1988,37, 9-18.3) Lehmann,F.P.A.; Rodriguez de Miranda, J.F.;Ariens, E. J. in:Progress Research, Jucker, E.,(ed) Vol20 Birkhauser Verlag,Basel 1976, 101-142.4) Lehmann,F.P.A. in : Receptor and recognition. Cuatrecasas, P.;Greaves, M.F. (ed) Vol.5 Series A Chapman and Hall, London1987, 1-77.5) Stinson, S. C. C.& En. News 1992,28 46-79.6) Nebert, D.W.; Nelson, D. R.; Coon, M. J.; Estabrook, R. W.;Feyereisen, R.; Fujii-Kuriyama, Y.; Gonzales, F. J.; Guengerich, F.P.; Gunsalus, I. C.; Johnson, E.R.; Loper, J. C.; Sato, R.;Waterman, M. R. and Waxman, D.J. DNA Cell. Biol.1991,10,1-4.7) Nebert, D.W.; Nelson, D. R.; Adesnik, M.; Coon, M. J.; Estabrook,R. W.; Kemper, B.; Levin. W.; Philips, I. R.; Sato. R andWaterman, M. R. DNA 1989,8,1-14.8) Nebert, D.W.; Adesnik, M.; Coon, M. J.; Estabrook, R. W.;Gonzales, F. J.; Guengerich, F. P.; Gunsalus, I. C.; Johnson, E.R.;Kemper, B.; Levin. W.; Philips, I. R.; Sato. R and Waterman,M. R. DNA 1987,6,1-11.9) Cytochrome P-450: Structure, Mechanism and Biochemisty; Ortizde Montellano, P.R. ED. Plenum Press: New York and London1986; and references cited therein.10) Vanden Bossche, H.; in: Sterol Biosynthesis Inhibitors.Pharmaceutical and Agrochemical Aspects Berg, D., Plentel, M.ed; Ellis Horwood; Chichester, England, 1988; 79-119.11) Siegel, M. R. Plant Disease 1981, 65,986-989.12) Kato, T. J. Pestic. Sci. 1982, 7 427-437.13) Mitrapoulus, K. A.; Gibboson, G. F. ; Connel, C. M.; Woods, R. A.Biochem. Biophys. Res. Commun. 1976,71, 892-900.14) Gadher, P.; Mercer, E. I.; Baldwin, B.C.; Wiggins, T.E. ;Pest.Biochem. and Phys. 1983, 19, 1-10.
Chapter 9 21415) Gibboson, G. F.; Pulliger, C.R. ; Mitropoulos, K.A. Biochem.1979,183,309.16) Adams, J. L.; Metcalf, B. W. Therapeutic consequences of theinhibition of sterol metabolism in Comprehensive MedicinalChemistry, Vol. 2; Monsch, C.; Sammes, P. G.; Taylor, J. B.; Eds.Pergamon Press: Oxford, England, 1990, pp. 333-364.17) Hitchcock, C. A.; Dickinson, K.; Brown, S. B.; Evans, E. G. V.;Adams, D. J. Biochem. J. 1990, 266, 475-480.18) Yeagle, P. L.; Martin, R. B.; Lala, A. K.; Lin, H. K.; Block, K.Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 4942-4926.19) Yoshida, Y.; Aoyama, Y. Biochem. Pharmacol. 1987, 36, 229 -235.20) Goldman, R. C.; Klein, L. L. Problems and progress inOpportunistic Infections in Annual Reports in Medicinal ChemistryV. 29; Bristol, A. J.; Ed.; Academic Press, Inc.: San Diego, CA,1994; pp. 155-164.21) Odds, F. C.; Schimd, J.; Soll, D. R. Epidemiology of CandidaInfections in AIDS. In Mycoses in AIDS Patients; Vanden Bossche,H., Ed.; Plenum Press: New York, 1990; pp. 67 - 74.22) Heeres, J.; Backx,L. J. J.; Mostmans, J. H. and Van Cutsem, J.J. Med. Chem. 1979, 22, 1003-1005.23) Thienpont, D.; Van Cutsem, J.; Van Gerven, F.; Heeres, J. andJanssen, P. A. J. Experientia, 1979, 35, 606-607.24) Thienpont, D.; Van Cutsem, J. and Borgers, M. Rev. Infect. Dis.1980, 2, 570-576.25) Thienpont, D.; Van Cutsem, J. and Borgers, M. Review ofInfection Diseases 1980, 2(4),519-699.26) The American Journal of Medecine 1983, 74, 1-90.27) Dismukes, W. E.; Stamm, A. M.; Graybill, J. R.; Craven, P. C.;Stevens, D. A.; Stiller, R. L. et al. Ann. Intern. Med. 1983, 98, 13- 20.28) Hume, A. L. and Kerkering, T. M. Drug Intell Clin Pharm 1983,17, 169-173.29) Koch, H. Pharm Intl 1983, 4, 151-152.30) Beggs, W. H. and Sarosi, G. A. Antimicrob Agents Chemother1982, 21, 355-357.
Page 1 and 2:
Advances in the stereoselectivesynt
Page 3:
ACKNOWLEDGMENT:I would like to than
Page 6 and 7:
Summary:Numerous drugs are chiral,
Page 8 and 9:
IndexII2.2 Synthesis of enantiopure
Page 10 and 11:
IndexIV4.4. Stereochemical Assignme
Page 12 and 13:
IndexVImethyl amine 69 1446.6. Stud
Page 14 and 15:
IndexVIII8.23.3.1 Desilylation usin
Page 16 and 17:
Chapter 1 11.Introduction1.1. Chira
Page 18 and 19:
Chapter 1 3The concept of stereoche
Page 20 and 21:
Chapter 1 5switches is in the area
Page 22 and 23:
Chapter 1 7-bonds 9 . It is now wid
Page 24 and 25:
Chapter 1 914CH 3Cyt P-450 DMOH3O 2
Page 26 and 27:
Chapter 1 11piperazine) is also the
Page 28 and 29:
Chapter 1 13The four stereoisomers
Page 30 and 31:
Chapter 1 15single enantiomers and
Page 32 and 33:
Chapter 1 17was synthesized by the
Page 34 and 35:
Chapter 1 19HOHODesmolaseHOCholeste
Page 36 and 37:
Chapter 1 21formic acid results in
Page 38 and 39:
Chapter 1 23inactivation. 113 . Bec
Page 40 and 41:
Chapter 1 25Two newer compounds whi
Page 42 and 43:
Chapter 1 2715 is an advanced repre
Page 44 and 45:
Chapter 1 29transformation of the a
Page 46 and 47:
Chapter 1 31Enantioselective synthe
Page 48 and 49:
Chapter 1 33+R,S DRUG ANCHOR R MOLE
Page 50 and 51:
Chapter 1 35solubilized in hot etha
Page 52 and 53:
Chapter 2 37RsORmRmRsRLRL RRRLH - A
Page 54 and 55:
Chapter 2 39The stereochemistry and
Page 56 and 57:
Chapter 2 41An asymmetric reducing
Page 58 and 59:
Chapter 2 43This approach clearly e
Page 60 and 61:
Chapter 2 45PhaxeqP 1MP 2axeqPhP 2M
Page 62 and 63:
Chapter 2 47pyrrolidine ] 20 , LAH-
Page 64 and 65:
Chapter 2 49Enzymatic reactions are
Page 66 and 67:
Chapter 2 51As [ES] in equation 4 c
Page 68 and 69:
Chapter 2 53E+AK 1AK -1AEAK 2AE+PE+
Page 70 and 71:
Chapter 2 552.2.4 Lipases.Most lipa
Page 72 and 73:
Chapter 2 57enzyme intermediate can
Page 74 and 75:
Chapter 2 59projecting above the pl
Page 76 and 77:
Chapter 2 612.3.1.1. Step 1: Adduct
Page 78 and 79:
Chapter 2 63A -+ ROHRO - + AH'RO 2
Page 80 and 81:
Chapter 2 65There are various effec
Page 82 and 83:
Chapter 2 67The reactions were foun
Page 84 and 85:
Chapter 2 69Yamanaka and coworkers
Page 86 and 87:
Chapter 2 71sodium or potassium car
Page 88 and 89:
Chapter 3 73The reaction is quite s
Page 90 and 91:
Chapter 3 75literature as the best
Page 92 and 93:
Chapter 3 77dry solvents and, is ch
Page 94 and 95:
Chapter 3 79XXOH+ H 2 NDry K 2 CO 3
Page 96 and 97:
Chapter 3 81substituents are the mo
Page 98 and 99:
Chapter 3 83induces a rotation of t
Page 100 and 101:
Chapter 3 85very sharp and it was p
Page 102 and 103:
Chapter 3 87Raney NickelOH Br MeOH;
Page 104 and 105:
Chapter 4 8933a-m were hydrolysed t
Page 106 and 107:
Chapter 4 91benzo[b]furane (entries
Page 108 and 109:
Chapter 4 93hydroxy or amine groups
Page 110 and 111:
Chapter 4 95the products with ethyl
Page 112 and 113:
Chapter 4 97NCO 2 HNCO 2 H(±)34c(-
Page 114 and 115:
Chapter 4 99NNH37CO2EtOH(±)-27a(+)
Page 116 and 117:
Chapter 4 101As already outlined ab
Page 118 and 119:
Chapter 4 103(+)-(S)-2-octylimidazo
Page 120 and 121:
Chapter 4 105CNNH N2 NCN nC 6 H 13N
Page 122 and 123:
Chapter 4 107key step is the conver
Page 124 and 125:
Chapter 4 109reverse addition in th
Page 126 and 127:
Chapter 4 111which was eliminated e
Page 128 and 129:
Chapter 4 113separate (±)-57a and
Page 130 and 131:
Chapter 5 115to avoid this side rea
Page 132 and 133:
Chapter 5 117Complete degradation o
Page 134 and 135:
Chapter 5 119Entry R T °C Product
Page 136 and 137:
Chapter 5 1212:1:3 in weight. All t
Page 138 and 139:
Chapter 5 123reaction conditions we
Page 140 and 141:
Chapter 5 125Entry Substrate R Time
Page 142 and 143:
Chapter 5 127experiments. But it wa
Page 144 and 145:
Chapter 5 129OClOSAM IIPH=7; R.T.OH
Page 146 and 147:
Chapter 5 131OHOXHOHRHK 2 CO 3 ; Me
Page 148 and 149:
Chapter 6 133HCuSO 4 .5H 2 O,NH 4 O
Page 150 and 151:
Chapter 6 1356.2.1 Heteroannullatio
Page 152 and 153:
Chapter 6 137This discovery allowed
Page 154 and 155:
Chapter 6 139OH(±)-62OHFigure 6.1
Page 156 and 157:
Chapter 6 141Entry Substrate R Time
Page 158 and 159:
Chapter 6 143HOH58-a-c,e,h-lRPdCl 2
Page 160 and 161:
Chapter 6 145afforded the benzo[b]f
Page 162 and 163:
Chapter 6 147RR[P(Ph) 3 ]Pd°OHOPh
Page 164 and 165:
Chapter 6 149H2-IodophenolOHOH(±)-
Page 166 and 167:
Chapter 6 151presence of base as de
Page 168 and 169:
Chapter 7 153A chiral lithium alumi
Page 170 and 171:
Chapter 7 155derivatives were tried
Page 172 and 173:
Chapter 7 157Finally an hypothesis
Page 174 and 175:
Chapter 8 159were washed with a sat
Page 176 and 177:
Chapter 8 16145 min, the mixture wa
Page 178 and 179: Chapter 8 1638.9 Decarboxylation of
Page 180 and 181: Chapter 8 165Alcohol 27a (0.2 mmol)
Page 182 and 183: Chapter 8 167for 48 h. After coolin
Page 184 and 185: Chapter 8 169room temperature for t
Page 186 and 187: Chapter 8 171in CH 2 Cl 2 and washe
Page 188 and 189: Chapter 8 1738.26 Screening of lipa
Page 190 and 191: Chapter 8 175Na 2 SO 4 . After remo
Page 192 and 193: Chapter 8 177NMR and MS analysis we
Page 194 and 195: Chapter 8 179Argon was bubbled thru
Page 196 and 197: Chapter 8 181IR (CHCl 3 ): ν cm-1=
Page 198 and 199: Chapter 8 183GC-MS: 305 M + (68%),
Page 200 and 201: Chapter 8 185[α] 20 D -5.7 (c 1.75
Page 202 and 203: Chapter 8 187Synthetic method 7.7.1
Page 204 and 205: Chapter 8 189(R,S)-(±)-1-(2-Octyl)
Page 206 and 207: Chapter 8 191M.P. = oil.Elementary
Page 208 and 209: Chapter 8 193Synthetic method 7.11.
Page 210 and 211: Chapter 8 195(±)-N-1-(2-Octyl)-2-t
Page 212 and 213: Chapter 8 197IR (CHCl 3 ) ν cm-1 =
Page 214 and 215: Chapter 8 199(±)-1-(4-Fluorophenyl
Page 216 and 217: Chapter 8 201Physical and spectral
Page 218 and 219: Chapter 8 203(±)-1-(Phenyl)-2-prop
Page 220 and 221: Chapter 8 205128.61, 128.87, 130.39
Page 222 and 223: Chapter 8 207min.Physical and spect
Page 224 and 225: Chapter 8 20913C J MOD NMR (CDCl 3
Page 226 and 227: Chapter 8 211(±)-2'-Methylphenyl-2
Page 230 and 231: Chapter 9 21531) De Felice, R.; Joh
Page 232 and 233: Chapter 9 21768) Brodie, A.M.H. in
Page 234 and 235: Chapter 9 219112) Brodie, A. M. H.;
Page 236 and 237: Chapter 9 2214) Karabatsos, M.C. J.
Page 238 and 239: Chapter 9 22334c) Blow D. Nature 19
Page 240 and 241: Chapter 9 22567a) Kundu, N.G.; Pal,
Page 242: Chapter 9 22712) Thompson,A.S.; Hum
show all

Advances in the stereoselective synthesis of antifungal agents and ...

Create successful ePaper yourself

Delete template?

Save as template?