메뉴 건너뛰기




Volumn 8, Issue 4, 2004, Pages 427-430

A new efficient synthetic methodology for tetrahydroisoquinoline and tetrahydro-β-carboline derivatives using the Pictet-Spengler reaction

Author keywords

combinatorial chemistry; microwave methodology; Pictet Spengler reaction; tetrahydro carboline; tetrahydro isoquinoline

Indexed keywords

1 (4' CHLOROPHENYL) 3 METHOXYCARBONYL 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (4' CHLOROPHENYL) 6,7 DIHYDROXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 1 (4' CHLOROPHENYL) 6,7 DIHYDROXY 3 METHOXYCARBONYL 1,2,3,4 TETRAHYDROISOQUINOLINE; CARBOLINE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 8544269346     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000047505.29920.35     Document Type: Article
Times cited : (13)

References (26)
  • 1
    • 0036558479 scopus 로고    scopus 로고
    • Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics
    • (a) Scott, J.D. and Williams, R.M., Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics, Chem. Rev., 102 (2002) 1669-1730.
    • (2002) Chem. Rev. , vol.102 , pp. 1669-1730
    • Scott, J.D.1    Williams, R.M.2
  • 2
    • 0031687689 scopus 로고    scopus 로고
    • Effects of trypostatin derivatives on microtubule assembly in vitro and in situ, 7
    • (b) Kondoh, M., Usui, T., Mayumi, T. and Osada, H. J., Effects of trypostatin derivatives on microtubule assembly in vitro and in situ, 7. Antibiot., 51 (1998) 801-804.
    • (1998) Antibiot. , vol.51 , pp. 801-804
    • Kondoh, M.1    Usui, T.2    Mayumi, T.3    Osada, H.J.4
  • 3
    • 0034692166 scopus 로고    scopus 로고
    • Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues
    • (c) Wang, H., Usui, T., Osada, H. and Ganesan, A., Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues, J. Med. Chem., 43 (2000) 1557-1585.
    • (2000) J. Med. Chem. , vol.43 , pp. 1557-1585
    • Wang, H.1    Usui, T.2    Osada, H.3    Ganesan, A.4
  • 4
    • 0020660276 scopus 로고
    • A benzodiazepine receptor antagonist decreases sleep and reverse the hypnotic actions of flurazepam
    • (a) Medelson, W.B., Cain, M., Cook, J.M., Paul, S.M. and Skolnick, P., A benzodiazepine receptor antagonist decreases sleep and reverse the hypnotic actions of flurazepam, Science, 219 (1983) 414-416.
    • (1983) Science , vol.219 , pp. 414-416
    • Medelson, W.B.1    Cain, M.2    Cook, J.M.3    Paul, S.M.4    Skolnick, P.5
  • 6
    • 0014943286 scopus 로고
    • Alcohol, amines and alkaloids: A possible biochemical basis for alcohol addictions
    • (c) Davis, V.E. and Walsh, M.J., Alcohol, amines and alkaloids: A possible biochemical basis for alcohol addictions, Science, 167 (1970) 1005-1007.
    • (1970) Science , vol.167 , pp. 1005-1007
    • Davis, V.E.1    Walsh, M.J.2
  • 7
    • 0034704888 scopus 로고    scopus 로고
    • Mapping the melatonine receptor: Melatonine agonists and antagonists derived from 6H-isoindolo[2,1-a]indoles, 5,6-dihydroindolo[2,1-a]isoquinolines, and 6,7-dihydro-5H-benzo[c]azepino[2,1-a]indoles
    • (d) Faust, R., Garratt, P.J., Jones, R. and Yeh, L.-K.J., Mapping the melatonine receptor: Melatonine agonists and antagonists derived from 6H-isoindolo[2,1-a]indoles, 5,6-dihydroindolo[2,1-a]isoquinolines, and 6,7-dihydro-5H-benzo[c]azepino[2,1-a]indoles, J. Med. Chem., 43 (2000) 1050-1061.
    • (2000) J. Med. Chem. , vol.43 , pp. 1050-1061
    • Faust, R.1    Garratt, P.J.2    Jones, R.3    Yeh, L.-K.J.4
  • 8
    • 0026737677 scopus 로고
    • Substituted 1-(Aminomethyl)-2-(arylacetyl)-1,2,3,4- tetrahydroisoquinolines: A novel class of very potent antinociceptive agents with varying degrees of selectivity for κ and μ opioid receptors
    • (e) Vecchietti, V., Clarke, G.D., Colle, R., Giardina, G., Petrone, G. and Sbacchi, M., Substituted 1-(Aminomethyl)-2-(arylacetyl)-1,2,3,4- tetrahydroisoquinolines: A novel class of very potent antinociceptive agents with varying degrees of selectivity for κ and μ opioid receptors, J. Med. Chem., 35 (1992) 2970-2978.
    • (1992) J. Med. Chem. , vol.35 , pp. 2970-2978
    • Vecchietti, V.1    Clarke, G.D.2    Colle, R.3    Giardina, G.4    Petrone, G.5    Sbacchi, M.6
  • 10
    • 0036213472 scopus 로고    scopus 로고
    • Solid-phase and solution-phase parallel synthesis of tetrahydro- isoquinolines via Pictet-Spengler reaction
    • (b) Sun, Q. and Kyle, D., Solid-phase and solution-phase parallel synthesis of tetrahydro-isoquinolines via Pictet-Spengler reaction, Com. Chem. (High Throughput Screening), 5 (2002) 75-81.
    • (2002) Com. Chem. (High Throughput Screening) , vol.5 , pp. 75-81
    • Sun, Q.1    Kyle, D.2
  • 11
    • 0029891295 scopus 로고    scopus 로고
    • Pictet-Spengler reaction on solid support: Synthesis of 1,2,3,4-tetrahydro-β-carbolines libraries
    • (c) Mohan, R., Chou, Y.-L. and Morrissey, M.M., Pictet-Spengler reaction on solid support: Synthesis of 1,2,3,4-tetrahydro-β-carbolines libraries, Tetrahedron Lett., 37 (1996) 3963-3966.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3963-3966
    • Mohan, R.1    Chou, Y.-L.2    Morrissey, M.M.3
  • 12
    • 0028784613 scopus 로고
    • The solid phase synthesis of dihydro- and tetrahydroisoquinolines
    • (d) Meutermans, W.D.F. and Alewood, P.F., The solid phase synthesis of dihydro- and tetrahydroisoquinolines, Tetrahedron Lett., 36 (1995) 7709-7712.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7709-7712
    • Meutermans, W.D.F.1    Alewood, P.F.2
  • 13
    • 0035843415 scopus 로고    scopus 로고
    • Asymmetric synthesis of quaternary tetrahydroisoquinoline-3-carboxylic acid derivatives
    • (e) Alezra, V., Bonin, M., Micouin, L. and Husson, H.P., Asymmetric synthesis of quaternary tetrahydroisoquinoline-3-carboxylic acid derivatives, Tetrahedron Lett., 42 (2001) 2111-2113.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2111-2113
    • Alezra, V.1    Bonin, M.2    Micouin, L.3    Husson, H.P.4
  • 14
    • 4243241249 scopus 로고
    • The Pictet-Spengler condensation
    • Cox, E.D. and Cook, J.M., The Pictet-Spengler condensation. Chem. Rev., 95 (1995) 1797-1842.
    • (1995) Chem. Rev. , vol.95 , pp. 1797-1842
    • Cox, E.D.1    Cook, J.M.2
  • 16
    • 0041461964 scopus 로고    scopus 로고
    • Increasing rates of reaction: Microwave-assisted organic synthesis for combinatorial chemistry
    • (b) Lew, A., Krutzik, P.O., Hart, M.E. and Chamberlin, A.R., Increasing rates of reaction: Microwave-assisted organic synthesis for combinatorial chemistry, J. Comb. Chem., 4 (2002) 95-105.
    • (2002) J. Comb. Chem. , vol.4 , pp. 95-105
    • Lew, A.1    Krutzik, P.O.2    Hart, M.E.3    Chamberlin, A.R.4
  • 17
    • 0035813244 scopus 로고    scopus 로고
    • Microwave assisted organic synthesis: A review
    • (c) Lidstrom, P., Tierney, J., Wathey, B. and Westman, J., Microwave assisted organic synthesis: A review, Tetrahedron, 57 (2001) 9225-9283.
    • (2001) Tetrahedron , vol.57 , pp. 9225-9283
    • Lidstrom, P.1    Tierney, J.2    Wathey, B.3    Westman, J.4
  • 18
    • 0035341584 scopus 로고    scopus 로고
    • Microwave-assisted high-speed chemistry: A new technique in drug discovery
    • (d) Larhed, M. and Hallberg, A., Microwave-assisted high-speed chemistry: A new technique in drug discovery, Drug. Discov. Today, 6 (2001) 406-416.
    • (2001) Drug. Discov. Today , vol.6 , pp. 406-416
    • Larhed, M.1    Hallberg, A.2
  • 19
    • 0037677097 scopus 로고    scopus 로고
    • Microwave Assisted Pictet-Spengler and Bischler-Napieralski Reactions
    • (a) Bikash, P., Parasuraman, J. and Venkatachalam, S., Microwave Assisted Pictet-Spengler and Bischler-Napieralski Reactions, Synthetic Commun., 33 (2003) 2339-2348.
    • (2003) Synthetic Commun. , vol.33 , pp. 2339-2348
    • Bikash, P.1    Parasuraman, J.2    Venkatachalam, S.3
  • 20
    • 0036400027 scopus 로고    scopus 로고
    • Parallel synthesis of 1,2,3,4-Tetrahydro-β-carbolines using microwave irradiation
    • (b) Wu, C.Y., Sun and C.M., Parallel synthesis of 1,2,3,4-Tetrahydro- β-carbolines using microwave irradiation, Synlett., 10 (2002) 1709-1711.
    • (2002) Synlett. , vol.10 , pp. 1709-1711
    • Wu, C.Y.1    Sun, C.M.2
  • 21
    • 0037425327 scopus 로고    scopus 로고
    • Highly efficient Lewis acid-catalysed Pictet-Spengler reactions discovered by parallel screening
    • (c) Srinivasan, N. and Ganesan, A., Highly efficient Lewis acid-catalysed Pictet-Spengler reactions discovered by parallel screening, Chem. Comm., 7 (2003) 916-917.
    • (2003) Chem. Comm. , vol.7 , pp. 916-917
    • Srinivasan, N.1    Ganesan, A.2
  • 22
    • 0001259682 scopus 로고    scopus 로고
    • Side reactions in the preparation of 1,2,3,4-Tetrahydro-β- carbolines-3-carboxylic acid
    • Iterbeke, K., Laus, G., Verheyden, P. and Tourwé, D., Side reactions in the preparation of 1,2,3,4-Tetrahydro-β-carbolines-3- carboxylic acid, Lett. Pept. Sci., 5 (1998) 121-123.
    • (1998) Lett. Pept. Sci. , vol.5 , pp. 121-123
    • Iterbeke, K.1    Laus, G.2    Verheyden, P.3    Tourwé, D.4
  • 24
    • 0019510099 scopus 로고
    • Improved synthesis and characterization of Pictet-Spengler adducts of Phenylpyruvic acid and biogenic amines
    • (b) Hudlicky, T., Kutchan, T.M., Shen, G., Sutliff, V.E. and Coscia, C.J., Improved synthesis and characterization of Pictet-Spengler adducts of Phenylpyruvic acid and biogenic amines, J. Org. Chem., 46 (1981) 1738-1741.
    • (1981) J. Org. Chem. , vol.46 , pp. 1738-1741
    • Hudlicky, T.1    Kutchan, T.M.2    Shen, G.3    Sutliff, V.E.4    Coscia, C.J.5
  • 26
    • 0035958484 scopus 로고    scopus 로고
    • An unusual decarboxylative Maillard reaction between L-dopa annd D-glucose under biomimetic conditions: Factors governing competition with Pictet-Spengler condensation
    • (d) Manini, P., d'Ischia, M. and Prota, G., An unusual decarboxylative Maillard reaction between L-dopa annd D-glucose under biomimetic conditions: Factors governing competition with Pictet-Spengler condensation. J. Org. Chem., 66 (2001) 5048-5053.
    • (2001) J. Org. Chem. , vol.66 , pp. 5048-5053
    • Manini, P.1    D'Ischia, M.2    Prota, G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.