메뉴 건너뛰기




Volumn 40, Issue 12, 2007, Pages 1377-1384

Construction of a chiral central nervous system (CNS)-active aminotetralin drug compound based on a synthesis strategy using multitasking properties of (s)-1-phenylethylamine

Author keywords

[No Author keywords available]

Indexed keywords


EID: 38049049180     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar700102c     Document Type: Review
Times cited : (37)

References (31)
  • 4
    • 38049062013 scopus 로고
    • Enantiomeric enrichment and stereoselective synthesis of chiral amines
    • U.S. Patent 4,950,606
    • Stirling, D. I.; Zeitlin, A. L.; Matcham, G. W. Enantiomeric enrichment and stereoselective synthesis of chiral amines. U.S. Patent 4,950,606, 1990.
    • (1990)
    • Stirling, D.I.1    Zeitlin, A.L.2    Matcham, G.W.3
  • 5
    • 0034666574 scopus 로고    scopus 로고
    • 1B/D receptors in psychiatric disorders and their potential as target for therapy
    • 1B/D receptors in psychiatric disorders and their potential as target for therapy. Eur. J. Pharmacol. 2000, 404, 1-12.
    • (2000) Eur. J. Pharmacol , vol.404 , pp. 1-12
    • Moret, C.1    Briley, M.2
  • 7
    • 7444254932 scopus 로고    scopus 로고
    • 1B receptors: From protein to physiological function and behavior
    • 1B receptors: From protein to physiological function and behavior. Neurosci. Biobehav. Rev. 2004, 28, 565-582.
    • (2004) Neurosci. Biobehav. Rev , vol.28 , pp. 565-582
    • Sari, Y.1
  • 8
    • 0042067947 scopus 로고    scopus 로고
    • Logistics of process R&D: Transforming laboratory methods to manufacturing scale
    • Federsel, H.-J. Logistics of process R&D: Transforming laboratory methods to manufacturing scale. Nat. Rev. Drug Discovery 2003, 2, 654-664.
    • (2003) Nat. Rev. Drug Discovery , vol.2 , pp. 654-664
    • Federsel, H.-J.1
  • 9
    • 38049055164 scopus 로고    scopus 로고
    • Celgene Corp., P.O. Box 4914, 7 Powder Horn Drive, Warren, NJ 07059. The company name has now changed to Chiragene.
    • Celgene Corp., P.O. Box 4914, 7 Powder Horn Drive, Warren, NJ 07059. The company name has now changed to Chiragene.
  • 10
    • 38049067479 scopus 로고    scopus 로고
    • Berg, S.; Linderberg, M.; Ross, S.; Thorberg, S.-O.; Ulff, B. Preparation of 1,2,3,4-tetrahydronaphthalenes as h5-HT1B antagonists. PCT Int. Appl. WO 9,905,134, 1999.
    • Berg, S.; Linderberg, M.; Ross, S.; Thorberg, S.-O.; Ulff, B. Preparation of 1,2,3,4-tetrahydronaphthalenes as h5-HT1B antagonists. PCT Int. Appl. WO 9,905,134, 1999.
  • 11
    • 0017720339 scopus 로고
    • Fluorinated tricyclic neuroleptics with prolonged effects; some new 8-chloro-3-fluoro-10- piperazino-10,11-dihydrodibenzo[b, f]thiepins
    • Rajšner, M.; Svátek, E.; Metyšová, J.; Bartošová, M.; Mikšík, F.; Protiva, M. Fluorinated tricyclic neuroleptics with prolonged effects; some new 8-chloro-3-fluoro-10- piperazino-10,11-dihydrodibenzo[b, f]thiepins. Collect. Czech. Chem. Commun. 1977, 42, 3079-3093.
    • (1977) Collect. Czech. Chem. Commun , vol.42 , pp. 3079-3093
    • Rajšner, M.1    Svátek, E.2    Metyšová, J.3    Bartošová, M.4    Mikšík, F.5    Protiva, M.6
  • 12
    • 33947438923 scopus 로고
    • 3,5-Dimethyl-, 2-ethyl-5-methyl-, and 3-ethyl-5-methyl-phenantrene. A contribution to the abnormal selenium dehydrogenation of strophanthidin
    • Lewis, E. E.; Elderfield, R. C. 3,5-Dimethyl-, 2-ethyl-5-methyl-, and 3-ethyl-5-methyl-phenantrene. A contribution to the abnormal selenium dehydrogenation of strophanthidin. J. Org. Chem. 1940, 5, 290-299.
    • (1940) J. Org. Chem , vol.5 , pp. 290-299
    • Lewis, E.E.1    Elderfield, R.C.2
  • 14
    • 38049000699 scopus 로고
    • An improved synthesis of β-tetralone
    • (b) Hunden, D.C. An improved synthesis of β-tetralone. Org. Prep. Proc. Int. 1984, 16, 294-297.
    • (1984) Org. Prep. Proc. Int , vol.16 , pp. 294-297
    • Hunden, D.C.1
  • 15
    • 0000844109 scopus 로고    scopus 로고
    • Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
    • Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures. J. Org. Chem. 1996, 61, 3849-3862.
    • (1996) J. Org. Chem , vol.61 , pp. 3849-3862
    • Abdel-Magid, A.F.1    Carson, K.G.2    Harris, B.D.3    Maryanoff, C.A.4    Shah, R.D.5
  • 16
    • 33745079610 scopus 로고    scopus 로고
    • Analysis of the reactions used for the preparation of drug candidate molecules
    • Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Analysis of the reactions used for the preparation of drug candidate molecules. Org. Biomol. Chem. 2006, 4, 2337-2347.
    • (2006) Org. Biomol. Chem , vol.4 , pp. 2337-2347
    • Carey, J.S.1    Laffan, D.2    Thomson, C.3    Williams, M.T.4
  • 17
    • 0032560932 scopus 로고    scopus 로고
    • A highly active catalyst for palladium-catalyzed cross-coupling reactions: Room-temperature Suzuki couplings and amination of unactivated aryl chlorides
    • (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. A highly active catalyst for palladium-catalyzed cross-coupling reactions: Room-temperature Suzuki couplings and amination of unactivated aryl chlorides. J. Am. Chem. Soc. 1998, 120, 9722-9723.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 9722-9723
    • Old, D.W.1    Wolfe, J.P.2    Buchwald, S.L.3
  • 18
    • 0033597748 scopus 로고    scopus 로고
    • Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand
    • (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand. J. Org. Chem. 1999, 64, 5575-5580.
    • (1999) J. Org. Chem , vol.64 , pp. 5575-5580
    • Hartwig, J.F.1    Kawatsura, M.2    Hauck, S.I.3    Shaughnessy, K.H.4    Alcazar-Roman, L.M.5
  • 19
    • 0034712161 scopus 로고    scopus 로고
    • Scope and limitations of the Pd/BINAP-catalyzed amination of aryl bromides
    • (c) Wolfe, J. P.; Buchwald, S. L. Scope and limitations of the Pd/BINAP-catalyzed amination of aryl bromides. J. Org. Chem. 2000, 65, 1144-1157.
    • (2000) J. Org. Chem , vol.65 , pp. 1144-1157
    • Wolfe, J.P.1    Buchwald, S.L.2
  • 20
    • 0035917354 scopus 로고    scopus 로고
    • An improved method for the palladium-catalyzed amination of aryl iodides
    • (d) Mayssam, H. A.; Buchwald, S. L. An improved method for the palladium-catalyzed amination of aryl iodides. J. Org. Chem. 2001, 66, 2560-2565.
    • (2001) J. Org. Chem , vol.66 , pp. 2560-2565
    • Mayssam, H.A.1    Buchwald, S.L.2
  • 21
    • 24144441333 scopus 로고    scopus 로고
    • Palladium-catalyzed aromatic carbon-nitrogen bond formation
    • de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim, Germany, Chapter 13, pp
    • (e) Jiang, L.; Buchwald, S. L. Palladium-catalyzed aromatic carbon-nitrogen bond formation. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, Chapter 13, pp 699-760.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.2 , pp. 699-760
    • Jiang, L.1    Buchwald, S.L.2
  • 22
    • 33645387715 scopus 로고    scopus 로고
    • Re-evaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes
    • For an authoritative reassessment of mechanistic aspects of the Buchwald-Hartwig reaction, see f
    • For an authoritative reassessment of mechanistic aspects of the Buchwald-Hartwig reaction, see (f) Shekhar, S.; Ryberg, P.; Hartwig, J. F.; Mathew, J. S.; Blackmond, D. G.; Strieter, E. R.; Buchwald, S. L. Re-evaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes. J. Am. Chem. Soc. 2006, 128, 3584-3591.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 3584-3591
    • Shekhar, S.1    Ryberg, P.2    Hartwig, J.F.3    Mathew, J.S.4    Blackmond, D.G.5    Strieter, E.R.6    Buchwald, S.L.7
  • 24
    • 0035902397 scopus 로고    scopus 로고
    • An extension of this approach into ene carbamates has been reported, albeit with only moderate enantiomeric excess ee's, ≤77, being achieved: Dupau, P, Hay, A.-E, Bruneau, C, Dixneuf, P. H. Synthesis of optically active 2-aminotetralin derivatives via enantioselective ruthenium-catalyzed hydrogenation of ene carbamates. Tetrahedron: Asymmetry 2001, 12, 863-867
    • (b) An extension of this approach into ene carbamates has been reported, albeit with only moderate enantiomeric excess (ee's) (≤77%) being achieved: Dupau, P.; Hay, A.-E.; Bruneau, C.; Dixneuf, P. H. Synthesis of optically active 2-aminotetralin derivatives via enantioselective ruthenium-catalyzed hydrogenation of ene carbamates. Tetrahedron: Asymmetry 2001, 12, 863-867.
  • 25
    • 38049004002 scopus 로고    scopus 로고
    • Preparation of optically active primary amine by reduction of imine
    • Kanai, Y.; Saitou, K.; Koki, U. Preparation of optically active primary amine by reduction of imine. Japan Kokai Koho 10,072,411, 1998.
    • (1998) Japan Kokai Koho , vol.10 , pp. 072-411
    • Kanai, Y.1    Saitou, K.2    Koki, U.3
  • 28
    • 38049077304 scopus 로고    scopus 로고
    • Product code used by the producer Johnson Matthey, Orchard Road, Royston, Hertfordshire SG8 5HE, U.K. Homepage address: www.jmcatalysts.com/pct.
    • Product code used by the producer Johnson Matthey, Orchard Road, Royston, Hertfordshire SG8 5HE, U.K. Homepage address: www.jmcatalysts.com/pct.
  • 29
    • 38049034270 scopus 로고    scopus 로고
    • A new process for the synthesis of morpholinylbenzenes
    • WO 01/87865
    • Tian, W. A new process for the synthesis of morpholinylbenzenes. WO 01/87865, 2001.
    • (2001)
    • Tian, W.1
  • 30
    • 85018200009 scopus 로고    scopus 로고
    • Stereoselective synthesis of drugs - An industrial perspective
    • Francotte, E, Lindner, W, Eds, Wiley-VCH: Weinheim, Germany, Chapter 2, pp
    • (a) Federsel, H.-J. Stereoselective synthesis of drugs - An industrial perspective. In Chirality in Drug Research; Francotte, E., Lindner, W., Eds.; Wiley-VCH: Weinheim, Germany, 2006; Vol. 33, Chapter 2, pp 29-65.
    • (2006) Chirality in Drug Research , vol.33 , pp. 29-65
    • Federsel, H.-J.1
  • 31
    • 38049056138 scopus 로고    scopus 로고
    • Chiral drug discovery and development - From concept stage to market launch
    • Taylor, J. B, Triggle, D. J, Eds, Elsevier: Oxford, U.K
    • (b) Federsel, H.-J. Chiral drug discovery and development - From concept stage to market launch. In Comprehensive Medicinal Chemistry II; Taylor, J. B., Triggle, D. J., Eds.; Elsevier: Oxford, U.K., 2007; Vol. 2, pp 713-736.
    • (2007) Comprehensive Medicinal Chemistry II , vol.2 , pp. 713-736
    • Federsel, H.-J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.