메뉴 건너뛰기




Volumn 24, Issue 10, 2012, Pages 789-795

Cis-diastereoselectivity in pictet-spengler reactions of L-tryptophan and electronic circular dichroism studies

Author keywords

chiral synthesis; electronic circular dichroism; solid state CD; stereoselective synthesis; TDDFT; tetrahydro b carbolines

Indexed keywords

TRYPTOLINE DERIVATIVE; TRYPTOPHAN;

EID: 84867057758     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22070     Document Type: Article
Times cited : (16)

References (59)
  • 2
    • 0033382636 scopus 로고    scopus 로고
    • Fumitremorgin C analogs that reverse mitoxantrone resistance in human colon carcinoma cells
    • He HY, Rabindran SG, Greenberger LM, Carter GT,. Fumitremorgin C analogs that reverse mitoxantrone resistance in human colon carcinoma cells. Med Chem Res 1999; 9: 424-437.
    • (1999) Med Chem Res , vol.9 , pp. 424-437
    • He, H.Y.1    Rabindran, S.G.2    Greenberger, L.M.3    Carter, G.T.4
  • 4
    • 44249085638 scopus 로고    scopus 로고
    • Synthesis of 2-[3-(7-Chloro-quinolin-4-ylamino)-alkyl]-1-(substituted phenyl)-2,3,4,9-tetrahydro-1H-beta-carbolines as a new class of antimalarial agents
    • Gupta L, Srivastava K, Singh S, Puri SK, Chauhan PMS,. Synthesis of 2-[3-(7-Chloro-quinolin-4-ylamino)-alkyl]-1-(substituted phenyl)-2,3,4,9- tetrahydro-1H-beta-carbolines as a new class of antimalarial agents. Bioorg Med Chem Lett 2008; 18: 3306-3309.
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 3306-3309
    • Gupta, L.1    Srivastava, K.2    Singh, S.3    Puri, S.K.4    Chauhan, P.M.S.5
  • 5
    • 34548863361 scopus 로고    scopus 로고
    • Design, synthesis and cardioprotective effect of a new class of dual-acting agents: Phenolic tetrahydro-beta-carboline RGD peptidomimetic conjugates
    • Bi W, Cai J, Liu S, Baudy-Floc'h M, Bi LR,. Design, synthesis and cardioprotective effect of a new class of dual-acting agents: Phenolic tetrahydro-beta-carboline RGD peptidomimetic conjugates. Bioorg Med Chem 2007; 15: 6909-6919.
    • (2007) Bioorg Med Chem , vol.15 , pp. 6909-6919
    • Bi, W.1    Cai, J.2    Liu, S.3    Baudy-Floc'H, M.4    Bi, L.R.5
  • 6
    • 61349112113 scopus 로고    scopus 로고
    • Comparative study of the trypanocidal activity of the methyl 1-nitrophenyl-1,2,3,4-9H-tetrahydro-beta-carboline-3-carboxylate derivatives and benznidazole using theoretical calculations and cyclic voltammetry
    • Tonin LTD, Barbosa VA, Bocca CC, Ramos ERF, Nakamura CV, da Costa WF, Basso EA, Nakamura TU, Sarragiotto MH,. Comparative study of the trypanocidal activity of the methyl 1-nitrophenyl-1,2,3,4-9H-tetrahydro-beta-carboline-3- carboxylate derivatives and benznidazole using theoretical calculations and cyclic voltammetry. Eur J Med Chem 2009; 44: 1745-1750.
    • (2009) Eur J Med Chem , vol.44 , pp. 1745-1750
    • Tonin, L.T.D.1    Barbosa, V.A.2    Bocca, C.C.3    Ramos, E.R.F.4    Nakamura, C.V.5    Da Costa, W.F.6    Basso, E.A.7    Nakamura, T.U.8    Sarragiotto, M.H.9
  • 9
    • 0037012733 scopus 로고    scopus 로고
    • Biochemical and pharmacological characterization of 1-trichloromethyl-1, 2,3,4-tetrahydro-beta-carboline: A biologically relevant neurotoxin?
    • Riederer P, Foley P, Bringmann G, Feineis D, Bruckner R, Gerlach M,. Biochemical and pharmacological characterization of 1-trichloromethyl-1, 2,3,4-tetrahydro-beta-carboline: a biologically relevant neurotoxin? Eur J Pharmacol 2002; 442: 1-16.
    • (2002) Eur J Pharmacol , vol.442 , pp. 1-16
    • Riederer, P.1    Foley, P.2    Bringmann, G.3    Feineis, D.4    Bruckner, R.5    Gerlach, M.6
  • 11
    • 0141992796 scopus 로고    scopus 로고
    • The discovery of tadalafil: A novel and highly selective PDE5 inhibitor. 2: 2,3,6,7,12,12a-hexahydropyrazino[1',2': 1,6]pyrido[3,4-b]indole-1,4-dione analogues
    • Daugan A, Grondin P, Ruault C, Le Monier de Gourville AC, Coste H, Linget JM, Kirilovsky J, Hyafil F, Labaudinière R,. The discovery of tadalafil: A novel and highly selective PDE5 inhibitor. 2: 2,3,6,7,12,12a- hexahydropyrazino[1',2': 1,6]pyrido[3,4-b]indole-1,4-dione analogues. J Med Chem 2003; 46: 4533-4542.
    • (2003) J Med Chem , vol.46 , pp. 4533-4542
    • Daugan, A.1    Grondin, P.2    Ruault, C.3    Le Monier De Gourville, A.C.4    Coste, H.5    Linget, J.M.6    Kirilovsky, J.7    Hyafil, F.8    Labaudinière, R.9
  • 12
    • 0037451871 scopus 로고    scopus 로고
    • Design, synthesis and biological activity of beta-carboline-based type-5 phosphodiesterase inhibitors
    • Maw GN, Allerton CMN, Gbekor E, Million WA,. Design, synthesis and biological activity of beta-carboline-based type-5 phosphodiesterase inhibitors. Bioorg Med Chem Lett 2003; 13: 1425-1428.
    • (2003) Bioorg Med Chem Lett , vol.13 , pp. 1425-1428
    • Maw, G.N.1    Allerton, C.M.N.2    Gbekor, E.3    Million, W.A.4
  • 13
    • 2442421847 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel beta-carboline derivatives as Tat-TAR interaction inhibitors
    • Yu X, Lin W, Li J, Yang M,. Synthesis and biological evaluation of novel beta-carboline derivatives as Tat-TAR interaction inhibitors. Bioorg Med Chem Lett 2004; 14: 3127-3130.
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 3127-3130
    • Yu, X.1    Lin, W.2    Li, J.3    Yang, M.4
  • 15
    • 29244491409 scopus 로고    scopus 로고
    • Simple indole alkaloids and those with a nonrearranged monoterpenoid unit
    • Kawasaki T, Higuchi K,. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat Prod Rep 2005; 22: 761-793.
    • (2005) Nat Prod Rep , vol.22 , pp. 761-793
    • Kawasaki, T.1    Higuchi, K.2
  • 16
    • 0000656873 scopus 로고    scopus 로고
    • General approach to the synthesis of sarpagine and ajmaline alkaloids. Enantiospecific total synthesis of (+)-ajmaline and alkaloid G via the asymmetric Pictet-Spengler reaction
    • Li J, Cook JM,. General approach to the synthesis of sarpagine and ajmaline alkaloids. Enantiospecific total synthesis of (+)-ajmaline and alkaloid G via the asymmetric Pictet-Spengler reaction. J Org Chem 1998; 63: 4166-4167.
    • (1998) J Org Chem , vol.63 , pp. 4166-4167
    • Li, J.1    Cook, J.M.2
  • 17
    • 0033523248 scopus 로고    scopus 로고
    • General approach for the synthesis of ajmaline/sarpagine indole alkaloids: Enantiospecific total synthesis of (+)-ajmaline, alkaloid G, and norsuaveoline via the asymmetric Pictet-Spengler reaction
    • Li J, Wang T, Yu P, Peterson A, Weber R, Soerens D, Grubisha D, Bennett D, Cook JM,. General approach for the synthesis of ajmaline/sarpagine indole alkaloids: Enantiospecific total synthesis of (+)-ajmaline, alkaloid G, and norsuaveoline via the asymmetric Pictet-Spengler reaction. J Am Chem Soc 1999; 121: 6998-7010.
    • (1999) J Am Chem Soc , vol.121 , pp. 6998-7010
    • Li, J.1    Wang, T.2    Yu, P.3    Peterson, A.4    Weber, R.5    Soerens, D.6    Grubisha, D.7    Bennett, D.8    Cook, J.M.9
  • 19
    • 0001690298 scopus 로고    scopus 로고
    • Total synthesis of fumitremorgins and verruculogens
    • Hino T, Nakagawa M,. Total synthesis of fumitremorgins and verruculogens. Heterocycles 1997; 46: 673-704.
    • (1997) Heterocycles , vol.46 , pp. 673-704
    • Hino, T.1    Nakagawa, M.2
  • 20
    • 84937424396 scopus 로고
    • Über die Bildung von Isochinolin-derivaten durch Einwirkung von Methylal auf Phenyl-äthylamin, Phenyl-alanin und Tyrosin
    • Pictet A, Spengler T,. Über die Bildung von Isochinolin-derivaten durch Einwirkung von Methylal auf Phenyl-äthylamin, Phenyl-alanin und Tyrosin. Ber Dtsch Chem Ges 1911; 44: 2030-2036.
    • (1911) Ber Dtsch Chem Ges , vol.44 , pp. 2030-2036
    • Pictet, A.1    Spengler, T.2
  • 21
    • 2942574530 scopus 로고    scopus 로고
    • Chiral heterocycles by iminium ion cyclization
    • Royer J, Bonin M, Micouin L,. Chiral heterocycles by iminium ion cyclization. Chem Rev 2004; 104: 2311-2352.
    • (2004) Chem Rev , vol.104 , pp. 2311-2352
    • Royer, J.1    Bonin, M.2    Micouin, L.3
  • 22
    • 4243241249 scopus 로고
    • The Pictet-Spengler Condensation: A New Direction for an Old Reaction
    • Cox ED, Cook JM,. The Pictet-Spengler Condensation: A New Direction for an Old Reaction. Chem Rev 1995; 95: 1797.
    • (1995) Chem Rev , vol.95 , pp. 1797
    • Cox, E.D.1    Cook, J.M.2
  • 24
    • 50949132675 scopus 로고    scopus 로고
    • Rigorous biogenetic network for a group of indole alkaloids derived from strictosidine
    • Szabó LF,. Rigorous biogenetic network for a group of indole alkaloids derived from strictosidine. Molecules 2008; 13: 1875-1896.
    • (2008) Molecules , vol.13 , pp. 1875-1896
    • Szabó, L.F.1
  • 25
    • 37049108698 scopus 로고
    • Strictosidine (Isovincoside) - Key Intermediate in Biosynthesis of Monoterpenoid Indole Alkaloids
    • Stöckigt J, Zenk MH,. Strictosidine (Isovincoside)-Key Intermediate in Biosynthesis of Monoterpenoid Indole Alkaloids. J Chem Soc Chem Commun 1977; 18: 646-648.
    • (1977) J Chem Soc Chem Commun , vol.18 , pp. 646-648
    • Stöckigt, J.1    Zenk, M.H.2
  • 28
    • 63249130548 scopus 로고    scopus 로고
    • Syntheses of chiral 1,3-disubstituted tetrahydro-beta-carbolines via CIAT process: Highly stereoselective Pictet-Spengler reaction of D-tryptophan ester hydrochlorides with various aldehydes
    • Xiao S, Lu X, Shi XX, Sun Y, Liang LL, Yu XH, Dong J,. Syntheses of chiral 1,3-disubstituted tetrahydro-beta-carbolines via CIAT process: highly stereoselective Pictet-Spengler reaction of D-tryptophan ester hydrochlorides with various aldehydes. Tetrahedron: Asymmetry 2009; 20: 430-439.
    • (2009) Tetrahedron: Asymmetry , vol.20 , pp. 430-439
    • Xiao, S.1    Lu, X.2    Shi, X.X.3    Sun, Y.4    Liang, L.L.5    Yu, X.H.6    Dong, J.7
  • 31
    • 65549117573 scopus 로고    scopus 로고
    • Unexpected cis selectivity in the Pictet-Spengler reaction
    • Bailey PD, Beard MA, Phillips TR,. Unexpected cis selectivity in the Pictet-Spengler reaction. Tetrahedron Lett 2009; 50: 3645-3647.
    • (2009) Tetrahedron Lett , vol.50 , pp. 3645-3647
    • Bailey, P.D.1    Beard, M.A.2    Phillips, T.R.3
  • 32
    • 33846382303 scopus 로고    scopus 로고
    • Water as an efficient medium for the synthesis of tetrahydro-beta- carbolines via Pictet-Spengler reactions
    • Saha B, Sharma S, Sawant D, Kundu B,. Water as an efficient medium for the synthesis of tetrahydro-beta-carbolines via Pictet-Spengler reactions. Tetrahedron Lett 2007; 48: 1379-1383.
    • (2007) Tetrahedron Lett , vol.48 , pp. 1379-1383
    • Saha, B.1    Sharma, S.2    Sawant, D.3    Kundu, B.4
  • 33
    • 4744372596 scopus 로고    scopus 로고
    • Synthesis of tetrahydro-beta-carbolinediketopiperazines in [bdmim][PF6] ionic liquid accelerated by controlled microwave heating
    • Yen YH, Chu YH,. Synthesis of tetrahydro-beta-carbolinediketopiperazines in [bdmim][PF6] ionic liquid accelerated by controlled microwave heating. Tetrahedron Lett 2004; 45: 8137-8140.
    • (2004) Tetrahedron Lett , vol.45 , pp. 8137-8140
    • Yen, Y.H.1    Chu, Y.H.2
  • 34
    • 9644275534 scopus 로고    scopus 로고
    • Microwave accelerated Pictet-Spengler reactions of tryptophan with ketones directed toward the preparation of 1,1-disubstituted indole alkaloids
    • Kuo FM, Tseng MC, Yen YH, Chu YH,. Microwave accelerated Pictet-Spengler reactions of tryptophan with ketones directed toward the preparation of 1,1-disubstituted indole alkaloids. Tetrahedron 2004; 60: 12075-12084.
    • (2004) Tetrahedron , vol.60 , pp. 12075-12084
    • Kuo, F.M.1    Tseng, M.C.2    Yen, Y.H.3    Chu, Y.H.4
  • 35
    • 84986680760 scopus 로고
    • Synthesis of Enantiomerically Pure Tetrahydro-2-Methylharman
    • Peng SQ, Guo M, Winterfeldt E,. Synthesis of Enantiomerically Pure Tetrahydro-2-Methylharman. Liebigs Ann Chem 1993; 137-140.
    • (1993) Liebigs Ann Chem , pp. 137-140
    • Peng, S.Q.1    Guo, M.2    Winterfeldt, E.3
  • 36
    • 33847086491 scopus 로고
    • General-method for the assignment of stereochemistry of 1,3-disubstituted 1,2,3,4-tetrahydro-beta-carbolines by C-13 spectroscopy
    • Ungemach F, Soerens D, Weber R, Dipierro M, Campos O, Mokry P, Cook JM, Silverton JV,. General-method for the assignment of stereochemistry of 1,3-disubstituted 1,2,3,4-tetrahydro-beta-carbolines by C-13 spectroscopy. J Am Chem Soc 1980; 102: 6976-6984.
    • (1980) J Am Chem Soc , vol.102 , pp. 6976-6984
    • Ungemach, F.1    Soerens, D.2    Weber, R.3    Dipierro, M.4    Campos, O.5    Mokry, P.6    Cook, J.M.7    Silverton, J.V.8
  • 37
    • 0037344394 scopus 로고    scopus 로고
    • Synthesis and CD measurement of chiral 1-ethyl-3-carboxy-1,2,3,4- tetrahydro-beta-carbolines: C1 configuration and second sphere chirality
    • Yokoya M, Masubuchi K, Kitajima M, Takayama H, Aimi N,. Synthesis and CD measurement of chiral 1-ethyl-3-carboxy-1,2,3,4-tetrahydro-beta-carbolines: C1 configuration and second sphere chirality. Heterocycles 2003; 59: 521-526.
    • (2003) Heterocycles , vol.59 , pp. 521-526
    • Yokoya, M.1    Masubuchi, K.2    Kitajima, M.3    Takayama, H.4    Aimi, N.5
  • 38
    • 4143122496 scopus 로고    scopus 로고
    • Resolution and chiroptical properties of the neurotoxin 1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline (TaClo) and related compounds: Quantum chemical CD calculations and X-ray diffraction analysis
    • Bringmann G, Feineis D, God R, Maksimenka K, Mühlbach J, Messer K, Münchbach M, Gulden KP, Peters EM, Peters K,. Resolution and chiroptical properties of the neurotoxin 1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline (TaClo) and related compounds: quantum chemical CD calculations and X-ray diffraction analysis. Tetrahedron 2004; 60: 8143-8151.
    • (2004) Tetrahedron , vol.60 , pp. 8143-8151
    • Bringmann, G.1    Feineis, D.2    God, R.3    Maksimenka, K.4    Mühlbach, J.5    Messer, K.6    Münchbach, M.7    Gulden, K.P.8    Peters, E.M.9    Peters, K.10
  • 40
    • 0015611087 scopus 로고
    • Alkaloids in mammalian tissues. 3. Condensation of L-tryptophan and L-5-hydroxytryptophan with formaldehyde and acetaldehyde
    • Brossi A, Focella A, Teitel S,. Alkaloids in mammalian tissues. 3. Condensation of L-tryptophan and L-5-hydroxytryptophan with formaldehyde and acetaldehyde. J Med Chem 1973; 16: 418.
    • (1973) J Med Chem , vol.16 , pp. 418
    • Brossi, A.1    Focella, A.2    Teitel, S.3
  • 41
    • 0009750706 scopus 로고
    • The ergot alkaloid VIII. the Synthesis of 4-carboline carbonic acids
    • Jacobs WA, Craig LC,. The ergot alkaloid VIII. The Synthesis of 4-carboline carbonic acids. J Biol Chem 1936; 113: 759.
    • (1936) J Biol Chem , vol.113 , pp. 759
    • Jacobs, W.A.1    Craig, L.C.2
  • 44
    • 79951815559 scopus 로고    scopus 로고
    • Time-dependent density functional response theory for electronic chiroptical properties of chiral molecules
    • Autschbach J, Nitsch-Velasquez L, Rudolph M,. Time-dependent density functional response theory for electronic chiroptical properties of chiral molecules. Top Curr Chem 2011; 298: 1-98.
    • (2011) Top Curr Chem , vol.298 , pp. 1-98
    • Autschbach, J.1    Nitsch-Velasquez, L.2    Rudolph, M.3
  • 45
    • 77952975205 scopus 로고    scopus 로고
    • Absolute structural elucidation of natural products-a focus on quantum-mechanical calculations of solid-state CD spectra
    • Pescitelli G, Kurtán T, Flörke U, Krohn K,. Absolute structural elucidation of natural products-a focus on quantum-mechanical calculations of solid-state CD spectra. Chirality 2009; 21: E181-E201.
    • (2009) Chirality , vol.21
    • Pescitelli, G.1    Kurtán, T.2    Flörke, U.3    Krohn, K.4
  • 46
    • 84865638056 scopus 로고    scopus 로고
    • Assignment of the absolute configurations of natural products by means of solid-state electronic circular dichroism and quantum mechanical calculations
    • Berova N. Polavarapu P.L. Nakanishi K. Woody R.W. editors. John Wiley & Sons, Inc.: Hoboken, NJ, USA;. DOI: 10.1002/9781118120392.ch6
    • Pescitelli G, Kurtán T, Krohn K,. Assignment of the absolute configurations of natural products by means of solid-state electronic circular dichroism and quantum mechanical calculations. In:, Berova N, Polavarapu PL, Nakanishi K, Woody RW, editors. Comprehensive chiroptical spectroscopy: applications in stereochemical analysis of synthetic compounds, natural products, and biomolecules, Vol. 2. John Wiley & Sons, Inc.,: Hoboken, NJ, USA; 2012. DOI: 10.1002/9781118120392.ch6.
    • (2012) Comprehensive Chiroptical Spectroscopy: Applications in Stereochemical Analysis of Synthetic Compounds, Natural Products, and Biomolecules , vol.2
    • Pescitelli, G.1    Kurtán, T.2    Krohn, K.3
  • 47
    • 80051549579 scopus 로고    scopus 로고
    • Solid-state circular dichroism and hydrogen bonding: Absolute configuration of massarigenin A from microsphaeropsis sp
    • Hussain H, Ahmed I, Schulz B, Draeger S, Flörke U, Pescitelli G, Krohn K,. Solid-state circular dichroism and hydrogen bonding: Absolute configuration of massarigenin A from microsphaeropsis sp. Chirality 2011; 23: 617-623.
    • (2011) Chirality , vol.23 , pp. 617-623
    • Hussain, H.1    Ahmed, I.2    Schulz, B.3    Draeger, S.4    Flörke, U.5    Pescitelli, G.6    Krohn, K.7
  • 48
    • 84865656123 scopus 로고    scopus 로고
    • Solid-state circular dichroism and hydrogen bonding, part 2: The case of hypothemycin reinvestigated
    • accepted for publication
    • Pescitelli G,. Solid-state circular dichroism and hydrogen bonding, part 2: the case of hypothemycin reinvestigated. Chirality 2012, accepted for publication.
    • (2012) Chirality
    • Pescitelli, G.1
  • 51
    • 0018466586 scopus 로고
    • Circular dichroism and absolute conformation: Application of qualitative MO theory to chiroptical phenomena
    • Snatzke G., Circular dichroism and absolute conformation: application of qualitative MO theory to chiroptical phenomena. Angew Chem Int Ed Engl 1979; 18: 363-377.
    • (1979) Angew Chem Int Ed Engl , vol.18 , pp. 363-377
    • Snatzke, G.1
  • 52
    • 16244418450 scopus 로고    scopus 로고
    • Conformation and chiroptical properties of dienes and polyenes in the chemistry of dienes and polyenes
    • In Rappoport Z. editor. Chichester: Wiley;. p
    • Salvadori P, Rosini C, Di Bari L,. Conformation and chiroptical properties of dienes and polyenes in the chemistry of dienes and polyenes. In, Rappoport Z, editor. The chemistry of dienes and polyenes, Vol. 1. Chichester: Wiley; 1997. p 111.
    • (1997) The Chemistry of Dienes and Polyenes , vol.1 , pp. 111
    • Salvadori, P.1    Rosini, C.2    Di Bari, L.3
  • 53
    • 0002704505 scopus 로고
    • Conformational analysis. LXXVIII. the conformation of phenylcyclohexane, and related molecules
    • Allinger NL, Tribble MT,. Conformational analysis. LXXVIII. The conformation of phenylcyclohexane, and related molecules. Tetrahedron Lett 1971; 12: 3259-3262.
    • (1971) Tetrahedron Lett , vol.12 , pp. 3259-3262
    • Allinger, N.L.1    Tribble, M.T.2
  • 55
    • 3142771297 scopus 로고    scopus 로고
    • A new hybrid exchange-correlation functional using the Coulombattenuating method (CAM-B3LYP)
    • Yanai T, Tew DP, Handy NC,. A new hybrid exchange-correlation functional using the Coulombattenuating method (CAM-B3LYP). Chem Phys Lett 2004; 393: 51.
    • (2004) Chem Phys Lett , vol.393 , pp. 51
    • Yanai, T.1    Tew, D.P.2    Handy, N.C.3
  • 56
    • 0039209924 scopus 로고
    • Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr
    • Schäfer A, Huber C, Ahlrichs R,. Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr. J Chem Phys 1994; 100: 5829.
    • (1994) J Chem Phys , vol.100 , pp. 5829
    • Schäfer, A.1    Huber, C.2    Ahlrichs, R.3
  • 57
    • 33748124815 scopus 로고    scopus 로고
    • Synthesis and cytotoxic activities of beta-carboline amino acid ester conjugates
    • Zhao M, Bi L, Wang W, Wang C, Baudy-Floc'h M, Ju J, Peng S,. Synthesis and cytotoxic activities of beta-carboline amino acid ester conjugates. Bioorg Med Chem 2006; 14: 6998-7010.
    • (2006) Bioorg Med Chem , vol.14 , pp. 6998-7010
    • Zhao, M.1    Bi, L.2    Wang, W.3    Wang, C.4    Baudy-Floc'H, M.5    Ju, J.6    Peng, S.7
  • 58
    • 0028200750 scopus 로고
    • Enhancing the yield and diastereoselectivity of the pictet-spengler reaction - A highly efficient route to cis-1,3-disubstituted tetrahydro-beta-carbolines
    • Bailey PD, Moore MH, Morgan KM, Smith DI, Vernon JM,. Enhancing the yield and diastereoselectivity of the pictet-spengler reaction-a highly efficient route to cis-1,3-disubstituted tetrahydro-beta-carbolines. Tetrahedron Lett 1994; 35: 3587-3588.
    • (1994) Tetrahedron Lett , vol.35 , pp. 3587-3588
    • Bailey, P.D.1    Moore, M.H.2    Morgan, K.M.3    Smith, D.I.4    Vernon, J.M.5
  • 59
    • 0023605494 scopus 로고
    • Synthesis of 1,2,3,4-tetrahydro-beta-carboline derivatives as hepatoprotective agents.4. Positional isomers of 1,2,3,4-tetrahydro-2- methylthiothiocarbonyl-beta-carboline-3-carboxylic acid and its 1-alkylated derivatives
    • Saiga Y, Iijima I, Ishida A, Miyagishima T, Takamura N, Oh-ishi T, Matsumoto M, Matsuoka Y,. Synthesis of 1,2,3,4-tetrahydro-beta-carboline derivatives as hepatoprotective agents.4. Positional isomers of 1,2,3,4-tetrahydro-2-methylthiothiocarbonyl-beta-carboline-3-carboxylic acid and its 1-alkylated derivatives. Chem Pharm Bull 1987; 35: 3705-3712.
    • (1987) Chem Pharm Bull , vol.35 , pp. 3705-3712
    • Saiga, Y.1    Iijima, I.2    Ishida, A.3    Miyagishima, T.4    Takamura, N.5    Oh-Ishi, T.6    Matsumoto, M.7    Matsuoka, Y.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.