메뉴 건너뛰기




Volumn 13, Issue 6, 2010, Pages 669-684

Pictet-Spengler reactions for the synthesis of pharmaceutically relevant heterocycles

Author keywords

nucleophile; Alkaloid; heterocycle; Pictet Spengler reaction; tetrahydro carboline; tetrahydroisoquinoline

Indexed keywords

7 DEOXYFRENOLICINE B; 7 DEOXYKALAFUNGIN; ALKALOID DERIVATIVE; ALLO ELEUTHERIN; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; CRIBROSTATIN 4; ELEUTHERIN; EUDISTOMIN B; EUDISTOMIN C; EUDISTOMIN DERIVATIVE; EUDISTOMIN E; HETEROCYCLIC COMPOUND; LEMONOMYCIN; QUINOCARCIN; QUINOCARMYCIN CITRATE; RENIERAMYCIN G; SCHULZEINE A; SCHULZEINE B; SCHULZEINE C; TADALAFIL; TETRAHYDROISOQUINOLINE; TRABECTEDIN; TRYPTOLINE; TUROFEXORATE ISOPROPYL; UNCLASSIFIED DRUG;

EID: 78650166294     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review
Times cited : (51)

References (95)
  • 1
    • 84937424396 scopus 로고
    • Formation of isoquinoline derivatives by the action of methylal on phenylethylamine, phenylalanine and tyrosine
    • Pictet A, Spengler T: Formation of isoquinoline derivatives by the action of methylal on phenylethylamine, phenylalanine and tyrosine. Ber Dtsch Chem Ges (1911) 44:2030-2036.
    • (1911) Ber Dtsch Chem Ges , vol.44 , pp. 2030-2036
    • Pictet, A.1    Spengler, T.2
  • 2
    • 33847026560 scopus 로고
    • Synthesis of carboline derivatives
    • Tatsui G: Synthesis of carboline derivatives. Yakugaku Zasshi (1928) 48:453-459.
    • (1928) Yakugaku Zasshi , vol.48 , pp. 453-459
    • Tatsui, G.1
  • 3
    • 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(6):1797-1842.
    • (1995) Chem Rev , vol.95 , Issue.6 , pp. 1797-1842
    • Cox, E.D.1    Cook, J.M.2
  • 4
    • 27544485773 scopus 로고    scopus 로고
    • The intermolecular Pictet-Spengler condensation with chiral carbonyl derivatives in the stereoselective syntheses of optically-active isoquinoline and indole alkaloids
    • Larghi EL, Amongero M, Bracca ABJ, Kaufman TS: The intermolecular Pictet-Spengler condensation with chiral carbonyl derivatives in the stereoselective syntheses of optically-active isoquinoline and indole alkaloids. ARKIVOC (2005) (12):98-153.
    • (2005) ARKIVOC , vol.12 , pp. 98-153
    • Larghi, E.L.1    Amongero, M.2    Abj, B.3    Kaufman, T.S.4
  • 5
    • 37649019603 scopus 로고    scopus 로고
    • Diastereoselective Pictet-Spengler condensation of tryptophan with α-amino aldehydes as chiral carbonyl components
    • Pulka K, Kulis P, Tymecka D, Frankiewicz L, Wilczek M, Kozminski W, Misicka A: Diastereoselective Pictet-Spengler condensation of tryptophan with α-amino aldehydes as chiral carbonyl components. Tetrahedron (2008) 64(7):1506-1514.
    • (2008) Tetrahedron , vol.64 , Issue.7 , pp. 1506-1514
    • Pulka, K.1    Kulis, P.2    Tymecka, D.3    Frankiewicz, L.4    Wilczek, M.5    Kozminski, W.6    Misicka, A.7
  • 7
    • 70349783579 scopus 로고    scopus 로고
    • Highly enantioselective Pictet-Spengler reactions with α-ketoamide-derived ketimines: Access to an unusual class of quaternary α-amino amides
    • Bou-Hamdan FR, Leighton JL: Highly enantioselective Pictet-Spengler reactions with α-ketoamide-derived ketimines: Access to an unusual class of quaternary α-amino amides. Angew Chem Int Ed Engl (2009) 48(13):2403-2406.
    • (2009) Angew Chem Int Ed Engl , vol.48 , Issue.13 , pp. 2403-2406
    • Bou-Hamdan, F.R.1    Leighton, J.L.2
  • 8
    • 62749185586 scopus 로고    scopus 로고
    • Weak Brønsted acid-thiourea co-catalysis: Enantioselective, catalytic protio-Pictet-Spengler reactions
    • Klausen RS, Jacobsen EN: Weak Brønsted acid-thiourea co-catalysis: Enantioselective, catalytic protio-Pictet-Spengler reactions. Org Lett (2009) 11(4):887-890.
    • (2009) Org Lett , vol.11 , Issue.4 , pp. 887-890
    • Klausen, R.S.1    Jacobsen, E.N.2
  • 9
    • 77950463160 scopus 로고    scopus 로고
    • Organocatalyzed enantioselective one-pot three-component access to indoloquinolizidines by a Michael addition-Pictet-Spengler sequence
    • Wu X, Dai X, Nie L, Fang H, Chen J, Ren Z, Cao W, Zhao G: Organocatalyzed enantioselective one-pot three-component access to indoloquinolizidines by a Michael addition-Pictet-Spengler sequence. Chem Commun (2010) 46(16):2733-2735.
    • (2010) Chem Commun , vol.46 , Issue.16 , pp. 2733-2735
    • Wu, X.1    Dai, X.2    Nie, L.3    Fang, H.4    Chen, J.5    Ren, Z.6    Cao, W.7    Zhao, G.8
  • 10
    • 0347089132 scopus 로고    scopus 로고
    • The Pictet-Spengler reaction in solid-phase combinatorial chemistry
    • Nielsen TE, Diness F, Meldal M: The Pictet-Spengler reaction in solid-phase combinatorial chemistry. Curr Opin Drug Discov Devel (2003) 6(6):801-814.
    • (2003) Curr Opin Drug Discov Devel , vol.6 , Issue.6 , pp. 801-814
    • Nielsen, T.E.1    Diness, F.2    Meldal, M.3
  • 11
    • 70350749437 scopus 로고    scopus 로고
    • Solid-phase synthesis of complex and pharmacologically interesting heterocycles
    • Nielsen TE, Meldal M: Solid-phase synthesis of complex and pharmacologically interesting heterocycles. Curr Opin Drug Discov Devel (2009) 12(6):798-810.
    • (2009) Curr Opin Drug Discov Devel , vol.12 , Issue.6 , pp. 798-810
    • Nielsen, T.E.1    Meldal, M.2
  • 13
    • 59049083621 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of tetracyclic 2,5-diketopiperazines on a soluble polymer support: A structural analogue of tadalafl
    • Chang W-J, Chanda K, Sun C-M: Microwave-assisted synthesis of tetracyclic 2,5-diketopiperazines on a soluble polymer support: A structural analogue of tadalafl. Aust J Chem (2009) 62(1):42-50.
    • (2009) Aust J Chem , vol.62 , Issue.1 , pp. 42-50
    • Chang, W.-J.1    Chanda, K.2    Sun, C.-M.3
  • 14
    • 70350686744 scopus 로고    scopus 로고
    • Traceless synthesis of hydantoin fused tetrahydro-β-carboline on ionic liquid support in green media
    • Maiti B, Chanda K, Sun CM: Traceless synthesis of hydantoin fused tetrahydro-β-carboline on ionic liquid support in green media. Org Lett (2009) 11(21):4826-4829.
    • (2009) Org Lett , vol.11 , Issue.21 , pp. 4826-4829
    • Maiti, B.1    Chanda, K.2    Sun, C.M.3
  • 15
    • 69549101621 scopus 로고    scopus 로고
    • Effcient and diverse synthesis of indole derivatives
    • Liu H, Dömling A: Effcient and diverse synthesis of indole derivatives. J Org Chem (2009) 74(17):6895-6898.
    • (2009) J Org Chem , vol.74 , Issue.17 , pp. 6895-6898
    • Liu, H.1    Dömling, A.2
  • 16
    • 74549143940 scopus 로고    scopus 로고
    • Polycyclic indole alkaloid-type compounds by MCR
    • Wang W, Herdtweck E, Dömling A: Polycyclic indole alkaloid-type compounds by MCR. Chem Commun (2010) 46(5):770-772.
    • (2010) Chem Commun , vol.46 , Issue.5 , pp. 770-772
    • Wang, W.1    Herdtweck, E.2    Dömling, A.3
  • 17
    • 61349200089 scopus 로고    scopus 로고
    • Calcium-catalyzed Pictet-Spengler reactions
    • Vanden Eynden MJ, Stambuli JP: Calcium-catalyzed Pictet-Spengler reactions. Org Lett (2008) 10(22):5289-5291.
    • (2008) Org Lett , vol.10 , Issue.22 , pp. 5289-5291
    • Vanden Eynden, M.J.1    Stambuli, J.P.2
  • 18
    • 34548400252 scopus 로고    scopus 로고
    • The synthesis of 1,1-disubstituted tetrahydro-β-carbolines induced by iodine
    • Lingam Y, Rao DM, Bhowmik DR, Santu PS, Rao KR, Islam A: The synthesis of 1,1-disubstituted tetrahydro-β-carbolines induced by iodine. Tetrahedron Lett (2007) 48(40):7243-7245.
    • (2007) Tetrahedron Lett , vol.48 , Issue.40 , pp. 7243-7245
    • Lingam, Y.1    Rao, D.M.2    Bhowmik, D.R.3    Santu, P.S.4    Rao, K.R.5    Islam, A.6
  • 19
    • 72149126855 scopus 로고    scopus 로고
    • Novel synthesis of tetrahydro-β-carbolines and tetrahydro- isoquinolines via three-component reaction using hexagonally ordered mesoporous AlSBA-15 catalysts
    • Vinu A, Kalita P, Samie L, Chari MA, Pal R, Reddy BVS: Novel synthesis of tetrahydro-β-carbolines and tetrahydro-isoquinolines via three-component reaction using hexagonally ordered mesoporous AlSBA-15 catalysts. Tetrahedron Lett (2010) 51(4):702-706.
    • (2010) Tetrahedron Lett , vol.51 , Issue.4 , pp. 702-706
    • Vinu, A.1    Kalita, P.2    Samie, L.3    Chari, M.A.4    Pal, R.5    Bvs, R.6
  • 20
    • 33845912130 scopus 로고    scopus 로고
    • Pictet-Spengler reactions catalyzed by Brønsted acid-surfactant-combined catalyst in water or aqueous media
    • Saito A, Numaguchi J, Hanzawa Y: Pictet-Spengler reactions catalyzed by Brønsted acid-surfactant-combined catalyst in water or aqueous media. Tetrahedron Lett (2007) 48(5):835-839.
    • (2007) Tetrahedron Lett , vol.48 , Issue.5 , pp. 835-839
    • Saito, A.1    Numaguchi, J.2    Hanzawa, Y.3
  • 21
    • 44949127129 scopus 로고    scopus 로고
    • Alkaloid biosynthesis: Metabolism and traffcking
    • Ziegler J, Facchini PJ: Alkaloid biosynthesis: Metabolism and traffcking. Annu Rev Plant Biol (2008) 59:735-769.
    • (2008) Annu Rev Plant Biol , vol.59 , pp. 735-769
    • Ziegler, J.1    Facchini, P.J.2
  • 24
    • 0036558479 scopus 로고    scopus 로고
    • Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics
    • Scott JD, Williams RM: Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics. Chem Rev (2002) 102(5):1669-1730.
    • (2002) Chem Rev , vol.102 , Issue.5 , pp. 1669-1730
    • Scott, J.D.1    Williams, R.M.2
  • 25
    • 3543059896 scopus 로고    scopus 로고
    • Asymmetric synthesis of isoquinoline alkaloids
    • Chrzanowska M, Rozwadowska MD: Asymmetric synthesis of isoquinoline alkaloids. Chem Rev (2004) 104(7):3341-3370.
    • (2004) Chem Rev , vol.104 , Issue.7 , pp. 3341-3370
    • Chrzanowska, M.1    Rozwadowska, M.D.2
  • 26
    • 56549110286 scopus 로고    scopus 로고
    • Recent progress in the total synthesis of naphthyridinomycin and lemonomycin tetrahydroisoquinoline antitumor antibiotics (TAAs)
    • Siengalewicz P, Rinner U, Mulzer J: Recent progress in the total synthesis of naphthyridinomycin and lemonomycin tetrahydroisoquinoline antitumor antibiotics (TAAs). Chem Soc Rev (2008) 37(12):2676-2690.
    • (2008) Chem Soc Rev , vol.37 , Issue.12 , pp. 2676-2690
    • Siengalewicz, P.1    Rinner, U.2    Mulzer, J.3
  • 29
    • 0029805757 scopus 로고    scopus 로고
    • Enantioselective total synthesis of ecteinascidin 743
    • Corey EJ, Gin DY, Kania RS: Enantioselective total synthesis of ecteinascidin 743. J Am Chem Soc (1996) 118(38):9202-9203.
    • (1996) J Am Chem Soc , vol.118 , Issue.38 , pp. 9202-9203
    • Corey, E.J.1    Gin, D.Y.2    Kania, R.S.3
  • 30
    • 0034611483 scopus 로고    scopus 로고
    • A new, more effcient, and effective process for the synthesis of a key pentacyclic intermediate for production of ecteinascidin and phthalascidin antitumor agents
    • Martinez EJ, Corey EJ: A new, more effcient, and effective process for the synthesis of a key pentacyclic intermediate for production of ecteinascidin and phthalascidin antitumor agents. Org Lett (2000) 2(7):993-996.
    • (2000) Org Lett , vol.2 , Issue.7 , pp. 993-996
    • Martinez, E.J.1    Corey, E.J.2
  • 33
    • 58049204535 scopus 로고    scopus 로고
    • Synthetic studies on ET-743. Assembly of the pentacyclic core and a formal total synthesis
    • Fishlock D, Williams RM: Synthetic studies on ET-743. Assembly of the pentacyclic core and a formal total synthesis. J Org Chem (2008) 73(24):9594-9600.
    • (2008) J Org Chem , vol.73 , Issue.24 , pp. 9594-9600
    • Fishlock, D.1    Williams, R.M.2
  • 34
    • 34247264233 scopus 로고    scopus 로고
    • Asymmetric total synthesis of (-) -cribrostatin 4 (renieramycin H)
    • Vincent G, Williams RM: Asymmetric total synthesis of (-)-cribrostatin 4 (renieramycin H). Angew Chem Int Ed Engl (2007) 46(9):1517-1520.
    • (2007) Angew Chem Int Ed Engl , vol.46 , Issue.9 , pp. 1517-1520
    • Vincent, G.1    Williams, R.M.2
  • 35
    • 0141519496 scopus 로고    scopus 로고
    • Synthetic studies on ecteinascidin-743: Constructing a versatile pentacyclic intermediate for the synthesis of ecteinascidins and saframycins
    • Jin W, Metobo S, Williams RM: Synthetic studies on ecteinascidin-743: Constructing a versatile pentacyclic intermediate for the synthesis of ecteinascidins and saframycins. Org Lett (2003) 5(12):2095-2098.
    • (2003) Org Lett , vol.5 , Issue.12 , pp. 2095-2098
    • Jin, W.1    Metobo, S.2    Williams, R.M.3
  • 36
    • 24744469211 scopus 로고    scopus 로고
    • Asymmetric total syntheses of (-)-jorumycin, (-)-renieramycin G, 3-epi-jorumycin, and 3-epi-renieramycin G
    • Lane JW, Chen Y, Williams RM: Asymmetric total syntheses of (-)-jorumycin, (-)-renieramycin G, 3-epi-jorumycin, and 3-epi-renieramycin G. J Am Chem Soc (2005) 127(36): 12684-12690.
    • (2005) J Am Chem Soc , vol.127 , Issue.36 , pp. 12684-12690
    • Lane, J.W.1    Chen, Y.2    Williams, R.M.3
  • 37
    • 34247205246 scopus 로고    scopus 로고
    • Regioselectivity of Pictet-Spengler cyclization reactions to construct the pentacyclic frameworks of the ecteinascidin-saframycin class of tetrahydroisoquinoline antitumor antibiotics
    • Vincent G, Lane JW, Williams RM: Regioselectivity of Pictet-Spengler cyclization reactions to construct the pentacyclic frameworks of the ecteinascidin-saframycin class of tetrahydroisoquinoline antitumor antibiotics. Tetrahedron Lett (2007) 48(21):3719-3722.
    • (2007) Tetrahedron Lett , vol.48 , Issue.21 , pp. 3719-3722
    • Vincent, G.1    Lane, J.W.2    Williams, R.M.3
  • 39
    • 0028797864 scopus 로고
    • Effcacy of the quinocarmycins KW2152 and DX-52-1 against human melanoma lines growing in culture and in mice
    • Plowman J, Dykes DJ, Narayanan VL, Abbott BJ, Saito H, Hirata T, Grever MR: Effcacy of the quinocarmycins KW2152 and DX-52-1 against human melanoma lines growing in culture and in mice. Cancer Res (1995) 55(4):862-867.
    • (1995) Cancer Res , vol.55 , Issue.4 , pp. 862-867
    • Plowman, J.1    Dykes, D.J.2    Narayanan, V.L.3    Abbott, B.J.4    Saito, H.5    Hirata, T.6    Grever, M.R.7
  • 40
    • 44449121406 scopus 로고    scopus 로고
    • Asymmetric total synthesis of (-)-quinocarcin
    • Wu YC, Liron M, Zhu J: Asymmetric total synthesis of (-)-quinocarcin. J Am Chem Soc (2008) 130(22):7148-7152.
    • (2008) J Am Chem Soc , vol.130 , Issue.22 , pp. 7148-7152
    • Wu, Y.C.1    Liron, M.2    Zhu, J.3
  • 41
    • 64249142616 scopus 로고    scopus 로고
    • Synthetic studies on (-)-lemonomycin: An effcient asymmetric synthesis of lemonomycinone amide
    • Wu YC, Bernadat G, Masson G, Couturier C, Schlama T, Zhu J: Synthetic studies on (-)-lemonomycin: An effcient asymmetric synthesis of lemonomycinone amide. J Org Chem (2009) 74(5):2046-2052.
    • (2009) J Org Chem , vol.74 , Issue.5 , pp. 2046-2052
    • Wu, Y.C.1    Bernadat, G.2    Masson, G.3    Couturier, C.4    Schlama, T.5    Zhu, J.6
  • 42
    • 0345868513 scopus 로고    scopus 로고
    • Schulzeines A-C, new α-glucosidase inhibitors from the marine sponge Penares schulzei
    • Takada K, Uehara T, Nakao Y, Matsunaga S, van Soest RW, Fusetani N: Schulzeines A-C, new α-glucosidase inhibitors from the marine sponge Penares schulzei. J Am Chem Soc (2004) 126(1):187-193.
    • (2004) J Am Chem Soc , vol.126 , Issue.1 , pp. 187-193
    • Takada, K.1    Uehara, T.2    Nakao, Y.3    Matsunaga, S.4    Van Soest, R.W.5    Fusetani, N.6
  • 43
    • 64349084679 scopus 로고    scopus 로고
    • Enantioselective synthesis of schulzeines B and C via a β-lactone-derived surrogate for bishomoserine aldehyde
    • Liu G, Romo D: Enantioselective synthesis of schulzeines B and C via a β-lactone-derived surrogate for bishomoserine aldehyde. Org Lett (2009) 11(5):1143-1146.
    • (2009) Org Lett , vol.11 , Issue.5 , pp. 1143-1146
    • Liu, G.1    Romo, D.2
  • 44
    • 70149103104 scopus 로고    scopus 로고
    • Total synthesis of the α-glucosidase inhibitors schulzeine A, B, and C and a structural revision of schulzeine A
    • Bowen EG, Wardrop DJ: Total synthesis of the α-glucosidase inhibitors schulzeine A, B, and C and a structural revision of schulzeine A. J Am Chem Soc (2009) 131(17):6062-6063.
    • (2009) J Am Chem Soc , vol.131 , Issue.17 , pp. 6062-6063
    • Bowen, E.G.1    Wardrop, D.J.2
  • 45
    • 33845470171 scopus 로고
    • Eudistomins C, E, K and L, potent antiviral compounds containing a novel oxathiazepine ring from the Caribbean tunicate Eudistoma olivaceum
    • Rinehart KL, Kobayashi J, Harbour GC, Hughes Jr RG, Mizsak SA, Scahill TA: Eudistomins C, E, K and L, potent antiviral compounds containing a novel oxathiazepine ring from the Caribbean tunicate Eudistoma olivaceum. J Am Chem Soc (1984) 106(5):1524-1526.
    • (1984) J Am Chem Soc , vol.106 , Issue.5 , pp. 1524-1526
    • Rinehart, K.L.1    Kobayashi, J.2    Harbour, G.C.3    Hughes Jr., R.G.4    Mizsak, S.A.5    Scahill, T.A.6
  • 48
    • 37049074537 scopus 로고
    • Diastereoselective Pictet-Spengler reactions of l-(Boc)phenylalaninal and l-(Boc)prolinal: Biomimetic syntheses of eudistomin T and (-)-woodinine
    • McNulty J, Still IWJ: Diastereoselective Pictet-Spengler reactions of l-(Boc)phenylalaninal and l-(Boc)prolinal: Biomimetic syntheses of eudistomin T and (-)-woodinine. J Chem Soc Perkin Trans I (1994):1329-1337.
    • (1994) J Chem Soc Perkin Trans i , pp. 1329-1337
    • McNulty, J.1    Iwj, S.2
  • 49
    • 0001537922 scopus 로고
    • Synthesis of 2-hydroxy-3-(ethoxycarbonyl)-1, 2, 3,4-tetrahydro-β- carbolines from N-hydroxytryptophans. An approach to the eudistomin series
    • Plate R, van Hout RHM, Behm H, Ottenheijm HCJ: Synthesis of 2-hydroxy-3-(ethoxycarbonyl)-1,2,3,4-tetrahydro-β-carbolines from N-hydroxytryptophans. An approach to the eudistomin series. J Org Chem (1987) 52(4):555-560.
    • (1987) J Org Chem , vol.52 , Issue.4 , pp. 555-560
    • Plate, R.1    Van Hout Rhm2    Behm, H.3    Hcj, O.4
  • 51
    • 66949158373 scopus 로고    scopus 로고
    • Asymmetric total synthesis of reported structure of eudistomidin B, an indole alkaloid isolated from a marine tunicate
    • Ito T, Kitajima M, Takayama H: Asymmetric total synthesis of reported structure of eudistomidin B, an indole alkaloid isolated from a marine tunicate. Tetrahedron Lett (2009) 50(31):4506-4508.
    • (2009) Tetrahedron Lett , vol.50 , Issue.31 , pp. 4506-4508
    • Ito, T.1    Kitajima, M.2    Takayama, H.3
  • 52
    • 0025128157 scopus 로고
    • Eudistomidins B, C, and D: Novel antileukemic alkaloids from the Okinawan marine tunicate Eudistoma glaucus
    • DOI 10.1021/jo00298a056
    • Kobayashi J, Cheng J-F, Ohta T, Nozoe S, Ohizumi Y, Sasaki T: Eudistomidins B, C, and D: Novel antileukemic alkaloids from the Okinawan marine tunicate Eudistoma glaucus. J Org Chem (1990) 55(11):3666-3670. (Pubitemid 20282034)
    • (1990) Journal of Organic Chemistry , vol.55 , Issue.11 , pp. 3666-3670
    • Kobayashi, J.1    Cheng, J.-F.2    Ohta, T.3    Nozoe, S.4    Ohizumi, Y.5    Sasaki, T.6
  • 53
    • 78650115358 scopus 로고    scopus 로고
    • Tetracyclic derivatives; Process of preparation and use
    • ICOS Corp (Daugan AC-M)
    • ICOS Corp (Daugan AC-M): Tetracyclic derivatives; process of preparation and use. US-05859006 (1999).
    • (1999) US-05859006
  • 57
    • 39949084132 scopus 로고    scopus 로고
    • Highly stereoselective Pictet-Spengler reaction of d-tryptophan methyl ester with piperonal: Convenient syntheses of Cialis (Tadalafl), 12a-epi-Cialis, and their deuterated analogues
    • Shi X-X, Liu S-L, Xu W, Xu Y-L: Highly stereoselective Pictet-Spengler reaction of d-tryptophan methyl ester with piperonal: Convenient syntheses of Cialis (Tadalafl), 12a-epi-Cialis, and their deuterated analogues. Tetrahedron Asymmetry (2008) 19(4):435-442.
    • (2008) Tetrahedron Asymmetry , vol.19 , Issue.4 , pp. 435-442
    • Shi, X.-X.1    Liu, S.-L.2    Xu, W.3    Xu, Y.-L.4
  • 59
    • 73349135641 scopus 로고    scopus 로고
    • Tadalafl, a long-acting inhibitor of PDE5, improves pulmonary hemodynamics and survival rate of monocrotaline-induced pulmonary artery hypertension in rats
    • Sawamura F, Kato M, Fujita K, Nakazawa T, Beardsworth A: Tadalafl, a long-acting inhibitor of PDE5, improves pulmonary hemodynamics and survival rate of monocrotaline-induced pulmonary artery hypertension in rats. J Pharmacol Sci (2009) 111(3):235-243.
    • (2009) J Pharmacol Sci , vol.111 , Issue.3 , pp. 235-243
    • Sawamura, F.1    Kato, M.2    Fujita, K.3    Nakazawa, T.4    Beardsworth, A.5
  • 60
    • 63249130548 scopus 로고    scopus 로고
    • Syntheses of chiral 13-disubstituted tetrahydro-β-carbolines via CIAT process: Highly stereoselective Pictet-Spengler reaction of d-tryptophan ester hydrochlorides with various aldehydes
    • Xiao S, Lu X, Shi X-X, Sun Y, Liang L-L, Yu X-H, Dong J: Syntheses of chiral 1,3-disubstituted tetrahydro-β-carbolines via CIAT process: Highly stereoselective Pictet-Spengler reaction of d-tryptophan ester hydrochlorides with various aldehydes. Tetrahedron Asymmetry (2009) 20(4):430-439.
    • (2009) Tetrahedron Asymmetry , vol.20 , Issue.4 , 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
  • 61
    • 77949311532 scopus 로고    scopus 로고
    • An effcient and general method for the stereodivergent syntheses of tadalafl-like tetracyclic compounds
    • Xiao S, Shi X-X, Ni F, Xing J, Yan J-J, Liu S-L: An effcient and general method for the stereodivergent syntheses of tadalafl-like tetracyclic compounds. Eur J Org Chem (2010) 2010(9):1711-1716.
    • (2010) Eur J Org Chem , vol.2010 , Issue.9 , pp. 1711-1716
    • Xiao, S.1    Shi, X.-X.2    Ni, F.3    Xing, J.4    Yan, J.-J.5    Liu, S.-L.6
  • 62
    • 77949541280 scopus 로고    scopus 로고
    • The frst highly stereoselective approach to the mitotic kinesis EQ5 inhibitor HR22C16 and its analogues
    • Xiao S, Shi X-X: The frst highly stereoselective approach to the mitotic kinesis EQ5 inhibitor HR22C16 and its analogues. Tetrahedron Asymmetry (2010) 21(2):226-231.
    • (2010) Tetrahedron Asymmetry , vol.21 , Issue.2 , pp. 226-231
    • Xiao, S.1    Shi, X.-X.2
  • 63
    • 77349119224 scopus 로고    scopus 로고
    • Synthesis, molecular modeling and biological evaluation of novel tadalafl analogues as phosphodiesterase 5 and colon tumor cell growth inhibitors, new stereochemical perspective
    • Abadi AH, Gary BD, Tinsley HN, Piazza GA, Abdel-Halim M: Synthesis, molecular modeling and biological evaluation of novel tadalafl analogues as phosphodiesterase 5 and colon tumor cell growth inhibitors, new stereochemical perspective. Eur J Med Chem (2010) 45(4):1278-1286.
    • (2010) Eur J Med Chem , vol.45 , Issue.4 , pp. 1278-1286
    • Abadi, A.H.1    Gary, B.D.2    Tinsley, H.N.3    Piazza, G.A.4    Abdel-Halim, M.5
  • 64
    • 33646818277 scopus 로고    scopus 로고
    • Synthesis of new class dipeptide analogues with improved permeability and antithrombotic activity
    • Zhao M, Bi L, Bi W, Wang C, Yang Z, Ju J, Peng S: Synthesis of new class dipeptide analogues with improved permeability and antithrombotic activity. Bioorg Med Chem (2006) 14(14): 4761-4774.
    • (2006) Bioorg Med Chem , vol.14 , Issue.14 , pp. 4761-4774
    • Zhao, M.1    Bi, L.2    Bi, W.3    Wang, C.4    Yang, Z.5    Ju, J.6    Peng, S.7
  • 65
    • 77951143986 scopus 로고    scopus 로고
    • A class of 3S-2-aminoacyltetrahydro-β-carboline-3-carboxylic acids: Their facile syn thesis, inhibition for platelet activation, and high in vivo anti-thrombotic potency
    • Liu J, Jiang X, Zhao M, Zhang X, Zheng M, Peng L, Peng S: A class of 3S-2-aminoacyltetrahydro-β-carboline-3-carboxylic acids: Their facile synthesis, inhibition for platelet activation, and high in vivo anti-thrombotic potency. J Med Chem (2010) 53(8):3106-3116.
    • (2010) J Med Chem , vol.53 , Issue.8 , pp. 3106-3116
    • Liu, J.1    Jiang, X.2    Zhao, M.3    Zhang, X.4    Zheng, M.5    Peng, L.6    Peng, S.7
  • 66
    • 61349112113 scopus 로고    scopus 로고
    • Comparative study of the trypanocidal activity of the methyl 1-nitrophenyl-1, 2, 3,4-9H-tetrahydro-β-carboline-3-carboxylate derivatives and benznidazole using theoretical calculations and cyclic voltammetry
    • Tonin LT, Barbosa VA, Bocca CC, Ramos ER, 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-β-carboline-3- carboxylate derivatives and benznidazole using theoretical calculations and cyclic voltammetry. Eur J Med Chem (2009) 44(4):1745-1750.
    • (2009) Eur J Med Chem , vol.44 , Issue.4 , pp. 1745-1750
    • Tonin, L.T.1    Barbosa, V.A.2    Bocca, C.C.3    Ramos, E.R.4    Nakamura, C.V.5    Da Costa, W.F.6    Basso, E.A.7    Nakamura, T.U.8    Sarragiotto, M.H.9
  • 69
    • 67651149490 scopus 로고    scopus 로고
    • Facile synthesis and in vitro properties of 1-alkyl- and 1-alkyl-N-propargyl-1, 2, 3,4-tetrahydroisoquinoline derivatives on PC12 cells
    • Kitabatake M, Nagai J, Abe K, Tsuchiya Y, Ogawa K, Yokoyama T, Mohri K, Taguchi K, Horiguchi Y: Facile synthesis and in vitro properties of 1-alkyl- and 1-alkyl-N-propargyl-1,2,3,4-tetrahydroisoquinoline derivatives on PC12 cells. Eur J Med Chem (2009) 44(10):4034-4043.
    • (2009) Eur J Med Chem , vol.44 , Issue.10 , pp. 4034-4043
    • Kitabatake, M.1    Nagai, J.2    Abe, K.3    Tsuchiya, Y.4    Ogawa, K.5    Yokoyama, T.6    Mohri, K.7    Taguchi, K.8    Horiguchi, Y.9
  • 70
    • 77949869987 scopus 로고    scopus 로고
    • Identification of 3,4-dihydroisoquinoline-2(1H)-sulfonamides as potent carbonic anhydrase inhibitors: Syn thesis, biological evaluation, and enzyme-ligand X-ray studies
    • Gitto R, Agnello S, Ferro S, De Luca L, Vullo D, Brynda J, Mader P, Supuran CT, Chimirri A: Identification of 3,4-dihydroisoquinoline-2(1H)- sulfonamides as potent carbonic anhydrase inhibitors: Synthesis, biological evaluation, and enzyme-ligand X-ray studies. J Med Chem (2010) 53(6): 2401-2408.
    • (2010) J Med Chem , vol.53 , Issue.6 , pp. 2401-2408
    • Gitto, R.1    Agnello, S.2    Ferro, S.3    De Luca, L.4    Vullo, D.5    Brynda, J.6    Mader, P.7    Supuran, C.T.8    Chimirri, A.9
  • 71
    • 17144384747 scopus 로고    scopus 로고
    • A modifed strategy for Pictet-Spengler reaction leading to the synthesis of imidazoquinoxalines on solid phase
    • Kundu B, Sawant D, Chhabra R: A modifed strategy for Pictet-Spengler reaction leading to the synthesis of imidazoquinoxalines on solid phase. J Comb Chem (2005) 7(2):317-321.
    • (2005) J Comb Chem , vol.7 , Issue.2 , pp. 317-321
    • Kundu, B.1    Sawant, D.2    Chhabra, R.3
  • 72
    • 20344383734 scopus 로고    scopus 로고
    • New application of Pictet-Spengler reaction leading to the synthesis of an unusual seven-membered heterocyclic ring system
    • Kundu B, Sawant D, Partani P, Kesarwani AP: New application of Pictet-Spengler reaction leading to the synthesis of an unusual seven-membered heterocyclic ring system. J Org Chem (2005) 70(12):4889-4892.
    • (2005) J Org Chem , vol.70 , Issue.12 , pp. 4889-4892
    • Kundu, B.1    Sawant, D.2    Partani, P.3    Kesarwani, A.P.4
  • 73
    • 33644914455 scopus 로고    scopus 로고
    • Application of modifed Pictet-Spengler reaction for the synthesis of thiazolo- and pyrazolo-quinolines
    • Duggineni S, Sawant D, Saha B, Kundu B: Application of modifed Pictet-Spengler reaction for the synthesis of thiazolo- and pyrazolo-quinolines. Tetrahedron (2006) 62(14):3228-3241.
    • (2006) Tetrahedron , vol.62 , Issue.14 , pp. 3228-3241
    • Duggineni, S.1    Sawant, D.2    Saha, B.3    Kundu, B.4
  • 74
    • 34948840010 scopus 로고    scopus 로고
    • Synthesis of novel N-rich polycyclic skeletons based on azoles and pyridines
    • Sharma S, Saha B, Sawant D, Kundu B: Synthesis of novel N-rich polycyclic skeletons based on azoles and pyridines. J Comb Chem (2007) 9(5):783-792.
    • (2007) J Comb Chem , vol.9 , Issue.5 , pp. 783-792
    • Sharma, S.1    Saha, B.2    Sawant, D.3    Kundu, B.4
  • 75
    • 48049111168 scopus 로고    scopus 로고
    • Application of the Pictet-Spengler reaction to aryl amine substrates linked to deactivated aromatic heterosystems
    • Saha B, Sharma S, Sawant D, Kundu B: Application of the Pictet-Spengler reaction to aryl amine substrates linked to deactivated aromatic heterosystems. Tetrahedron (2008) 64(37):8676-8684.
    • (2008) Tetrahedron , vol.64 , Issue.37 , pp. 8676-8684
    • Saha, B.1    Sharma, S.2    Sawant, D.3    Kundu, B.4
  • 76
    • 58149170443 scopus 로고    scopus 로고
    • Application of the Pictet-Spengler reaction to aryl amine-based substrates having pyrimidine as a π-nucleophile: Synthesis of pyrimidoquinolines with structural analogy to benzonaphthyridines present in alkaloids
    • Agarwal PK, Sharma SK, Sawant D, Kundu B: Application of the Pictet-Spengler reaction to aryl amine-based substrates having pyrimidine as a π-nucleophile: Synthesis of pyrimidoquinolines with structural analogy to benzonaphthyridines present in alkaloids. Tetrahedron (2009) 65(6):1153-1161.
    • (2009) Tetrahedron , vol.65 , Issue.6 , pp. 1153-1161
    • Agarwal, P.K.1    Sharma, S.K.2    Sawant, D.3    Kundu, B.4
  • 77
    • 63449115780 scopus 로고    scopus 로고
    • Application of 7-endo-trig Pictet-Spengler cyclization to the formation of the benzazepine ring: Synthesis of benzazepinoindoles
    • Sharma SK, Sharma S, Agarwal PK, Kundu B: Application of 7-endo-trig Pictet-Spengler cyclization to the formation of the benzazepine ring: Synthesis of benzazepinoindoles. Eur J Org Chem (2009) (9):1309-1312.
    • (2009) Eur J Org Chem , vol.9 , pp. 1309-1312
    • Sharma, S.K.1    Sharma, S.2    Agarwal, P.K.3    Kundu, B.4
  • 79
    • 77952350796 scopus 로고    scopus 로고
    • Multistep microwave-assisted divergent synthesis of indolo-fused pyrazino-/ diazepinoquinoxalinones on PEG support
    • Lai J-J, Salunke DB, Sun CM: Multistep microwave-assisted divergent synthesis of indolo-fused pyrazino-/ diazepinoquinoxalinones on PEG support. Org Lett (2010) 12(10):2174-2177.
    • (2010) Org Lett , vol.12 , Issue.10 , pp. 2174-2177
    • Lai, J.-J.1    Salunke, D.B.2    Sun, C.M.3
  • 80
    • 58649119073 scopus 로고    scopus 로고
    • New route to the synthesis of the isocryptolepine alkaloid and its related skeletons using a modifed Pictet-Spengler reaction
    • Agarwal PK, Sawant D, Sharma S, Kundu B: New route to the synthesis of the isocryptolepine alkaloid and its related skeletons using a modifed Pictet-Spengler reaction. Eur J Org Chem (2009) 292-303.
    • (2009) Eur J Org Chem , pp. 292-303
    • Agarwal, P.K.1    Sawant, D.2    Sharma, S.3    Kundu, B.4
  • 81
    • 72149120610 scopus 로고    scopus 로고
    • Regioselective intramolecular electrophilic substitution reactions involving π-defcient pyridine substrates: A new entry to pyrido-quinazolines and benzo[h][1,6]naphthyridines
    • Agarwal PK, Saifuddin M, Kundu B: Regioselective intramolecular electrophilic substitution reactions involving π-defcient pyridine substrates: A new entry to pyrido-quinazolines and benzo[h][1,6]naphthyridines. Tetrahedron (2010) 66(4):862-870.
    • (2010) Tetrahedron , vol.66 , Issue.4 , pp. 862-870
    • Agarwal, P.K.1    Saifuddin, M.2    Kundu, B.3
  • 82
    • 67549112170 scopus 로고    scopus 로고
    • A new entry to phenanthridine ring systems via sequential application of Suzuki and the modifed Pictet-Spengler reactions
    • Mandadapu AK, Saifuddin M, Agarwal PK, Kundu B: A new entry to phenanthridine ring systems via sequential application of Suzuki and the modifed Pictet-Spengler reactions. Org Biomol Chem (2009) 7(13):2796-2803.
    • (2009) Org Biomol Chem , vol.7 , Issue.13 , pp. 2796-2803
    • Mandadapu, A.K.1    Saifuddin, M.2    Agarwal, P.K.3    Kundu, B.4
  • 83
    • 67650692766 scopus 로고    scopus 로고
    • Application of the modifed Pictet-Spengler cyclization reaction for the preparation of an imidazopyrazine ring: Synthesis of new pyrido- and pyrimido-imidazopyrazines
    • Sharma S, Kundu B: Application of the modifed Pictet-Spengler cyclization reaction for the preparation of an imidazopyrazine ring: Synthesis of new pyrido- and pyrimido-imidazopyrazines. J Comb Chem (2009) 11(4):720-731.
    • (2009) J Comb Chem , vol.11 , Issue.4 , pp. 720-731
    • Sharma, S.1    Kundu, B.2
  • 84
    • 38849090728 scopus 로고    scopus 로고
    • Synthesis of novel pyrimidine fused 8-membered heterocycles via iminium ion cyclization reactions
    • Che X, Zheng L, Dang Q, Bai X: Synthesis of novel pyrimidine fused 8-membered heterocycles via iminium ion cyclization reactions. J Org Chem (2008) 73(3):1147-1149.
    • (2008) J Org Chem , vol.73 , Issue.3 , pp. 1147-1149
    • Che, X.1    Zheng, L.2    Dang, Q.3    Bai, X.4
  • 85
    • 51649087976 scopus 로고    scopus 로고
    • Diastereoselective Pictet-Spengler approach for the synthesis of pyrrolo[3,2-e][1,4]diazepin-2-one peptide turn mimics
    • Deaudelin P, Lubell WD: Diastereoselective Pictet-Spengler approach for the synthesis of pyrrolo[3,2-e][1,4]diazepin-2-one peptide turn mimics. Org Lett (2008) 10(13):2841-2844.
    • (2008) Org Lett , vol.10 , Issue.13 , pp. 2841-2844
    • Deaudelin, P.1    Lubell, W.D.2
  • 86
    • 44449107794 scopus 로고    scopus 로고
    • Regio- and enantioselective catalytic cyclization of pyrroles onto N-acyliminium ions
    • Raheem IT, Thiara PS, Jacobsen EN: Regio- and enantioselective catalytic cyclization of pyrroles onto N-acyliminium ions. Org Lett (2008) 10(8):1577-1580.
    • (2008) Org Lett , vol.10 , Issue.8 , pp. 1577-1580
    • Raheem, I.T.1    Thiara, P.S.2    Jacobsen, E.N.3
  • 87
    • 43549092132 scopus 로고    scopus 로고
    • 2-Vinylpyrroles and pyrrolo[3,2-d] pyrimidines from direct addition of aldehydes to 4-amino-pyrrole-2-carboxylate derivatives
    • Fridkin G, Lubell WD: 2-Vinylpyrroles and pyrrolo[3,2-d] pyrimidines from direct addition of aldehydes to 4-amino-pyrrole-2-carboxylate derivatives. Org Lett (2008) 10(5):849-852.
    • (2008) Org Lett , vol.10 , Issue.5 , pp. 849-852
    • Fridkin, G.1    Lubell, W.D.2
  • 88
    • 45149116915 scopus 로고    scopus 로고
    • Solid-phase synthesis of aryl-substituted thienoindolizines: Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes
    • Le Quement ST, Nielsen TE, Meldal M: Solid-phase synthesis of aryl-substituted thienoindolizines: Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes. J Comb Chem (2008) 10(3):447-455.
    • (2008) J Comb Chem , vol.10 , Issue.3 , pp. 447-455
    • Le Quement, S.T.1    Nielsen, T.E.2    Meldal, M.3
  • 90
    • 51549108264 scopus 로고    scopus 로고
    • A short enantioselective synthesis of (+)-eleutherin, (+) -allo-eleutherin and a formal synthesis of (+)-nocardione B
    • Fernandes RA, Chavan VP, Ingle AB: A short enantioselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and a formal synthesis of (+)-nocardione B. Tetrahedron Lett (2008) 49(44):6341-6343.
    • (2008) Tetrahedron Lett , vol.49 , Issue.44 , pp. 6341-6343
    • Fernandes, R.A.1    Chavan, V.P.2    Ingle, A.B.3
  • 92
    • 58149305978 scopus 로고    scopus 로고
    • Direct oxa-Pictet-Spengler cyclization to the natural (3a,5)-trans-stereochemistry in the syntheses of (+)-7-deoxyfrenolicin B and (+)-7-deoxykalafungin
    • Eid CN, Shim J, Bikker J, Lin M: Direct oxa-Pictet-Spengler cyclization to the natural (3a,5)-trans-stereochemistry in the syntheses of (+)-7-deoxyfrenolicin B and (+)-7-deoxykalafungin. J Org Chem (2009) 74(1):423-426.
    • (2009) J Org Chem , vol.74 , Issue.1 , pp. 423-426
    • Eid, C.N.1    Shim, J.2    Bikker, J.3    Lin, M.4
  • 93
    • 48549085895 scopus 로고    scopus 로고
    • Bismuth trifate-catalyzed oxa- and thia-Pictet-Spengler reactions: Access to iso- and isothio-chroman compounds
    • Lherbet C, Soupaya D, Baudoin-Dehoux C, André C, Blonski C, Hoffmann P: Bismuth trifate-catalyzed oxa- and thia-Pictet-Spengler reactions: Access to iso- and isothio-chroman compounds. Tetrahedron Lett (2008) 49(38):5449-5451.
    • (2008) Tetrahedron Lett , vol.49 , Issue.38 , pp. 5449-5451
    • Lherbet, C.1    Soupaya, D.2    Baudoin-Dehoux, C.3    André, C.4    Blonski, C.5    Hoffmann, P.6
  • 94
    • 85044700435 scopus 로고    scopus 로고
    • The effect of histochrome on the lipid peroxidation indices during the surgical treatment of patients with ischemic heart disease of different functional classes
    • Afanas'ev SA, Lasukova TV, Cherniavski AM, Vecherski IuIu, Ponomarenko IV: [The effect of histochrome on the lipid peroxidation indices during the surgical treatment of patients with ischemic heart disease of different functional classes]. Eksp Klin Farmakol (1999) 62(6):32-34.
    • (1999) Eksp Klin Farmakol , vol.62 , Issue.6 , pp. 32-34
    • Afanas'Ev, S.A.1    Lasukova, T.V.2    Cherniavski, A.M.3    Iui, V.4    Ponomarenko, I.V.5
  • 95
    • 43049173714 scopus 로고    scopus 로고
    • Isoeleutherin and eleutherinol, naturally occurring selective modulators of Th cell-mediated immune responses
    • Hong JH, Yu ES, Han AR, Nam JW, Seo EK, Hwang ES: Isoeleutherin and eleutherinol, naturally occurring selective modulators of Th cell-mediated immune responses. Biochem Biophys Res Commun (2008) 371(2):278-282.
    • (2008) Biochem Biophys Res Commun , vol.371 , Issue.2 , pp. 278-282
    • Hong, J.H.1    Yu, E.S.2    Han, A.R.3    Nam, J.W.4    Seo, E.K.5    Hwang, E.S.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.