메뉴 건너뛰기




Volumn 46, Issue 9, 2003, Pages 1706-1715

Synthesis and biological evaluation of N-heterocyclic indolyl glyoxylamides as orally active anticancer agents

Author keywords

[No Author keywords available]

Indexed keywords

(3 METHYL 5 ISOTHIAZOLYL) 1 [(3 METHYL 5 ISOXAZOLYL)METHYL] 1H 3 INDOLYL 2 OXOACETAMIDE; (3 METHYL 5 ISOTHIAZOLYL)[1 (4 CYANOBENZYL) 1H 3 INDOLYL] 2 OXOACETAMIDE; ANTINEOPLASTIC AGENT; DNA FRAGMENT; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; INDOLYLGLYOXYLAMIDE; UNCLASSIFIED DRUG;

EID: 0037464479     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020471r     Document Type: Article
Times cited : (175)

References (33)
  • 1
    • 0033554845 scopus 로고    scopus 로고
    • Crystal structure of wild-type tryptophan synthase complexed with the natural substrate indole-3-glycerol phosphate
    • Weyand, M.; Schlichting, I. Crystal structure of wild-type tryptophan synthase complexed with the natural substrate indole-3-glycerol phosphate. Biochemistry 1999, 38, 16469-16480.
    • (1999) Biochemistry , vol.38 , pp. 16469-16480
    • Weyand, M.1    Schlichting, I.2
  • 2
    • 0031733197 scopus 로고    scopus 로고
    • Isolation of a nitrile-containing indole alkaloid from the terrestrial blue-green alga hapalosiphon delicatulus
    • Huber, U.; Moore, R. E.; Patterson, G. M. L. Isolation of a nitrile-containing indole alkaloid from the terrestrial blue-green alga hapalosiphon delicatulus. J. Nat. Prod. 1998, 61, 1304-1306.
    • (1998) J. Nat. Prod. , vol.61 , pp. 1304-1306
    • Huber, U.1    Moore, R.E.2    Patterson, G.M.L.3
  • 3
    • 0035950137 scopus 로고    scopus 로고
    • Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: Structure-activity relationships for cytotoxicity and antitumor activity
    • Skibo, E. B.; Xing, C.; Dorr, R. T. Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: structure-activity relationships for cytotoxicity and antitumor activity. J. Med. Chem. 2001, 44, 3545-3562.
    • (2001) J. Med. Chem. , vol.44 , pp. 3545-3562
    • Skibo, E.B.1    Xing, C.2    Dorr, R.T.3
  • 4
    • 0033519655 scopus 로고    scopus 로고
    • New generation dopaminergic agents. 6. Structure-activity relationship studies of a series of 4-(aminoethoxy)indole and 4-(aminoethoxy)indolone derivatives based on the newly discovered 3-hydroxyphenoxyethylamine D2 template
    • Mewshaw, R. E.; Webb, M. B.; Marquis, K. L.; McGaughey, G. B.; Shi, X.; Wasik, T.; Scerni, R.; Brennan, J. A.; Andree, T. H. New generation dopaminergic agents. 6. Structure-activity relationship studies of a series of 4-(aminoethoxy)indole and 4-(aminoethoxy)indolone derivatives based on the newly discovered 3-hydroxyphenoxyethylamine D2 template. J. Med. Chem. 1999, 42, 2007-2020.
    • (1999) J. Med. Chem. , vol.42 , pp. 2007-2020
    • Mewshaw, R.E.1    Webb, M.B.2    Marquis, K.L.3    McGaughey, G.B.4    Shi, X.5    Wasik, T.6    Scerni, R.7    Brennan, J.A.8    Andree, T.H.9
  • 6
    • 0034721194 scopus 로고    scopus 로고
    • Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors
    • Kalgutkar, A. S.; Marnett, A. B.; Crews, B. C.; Remmel, R. P.; Marnett, L. J. Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2000, 43, 2860-2870.
    • (2000) J. Med. Chem. , vol.43 , pp. 2860-2870
    • Kalgutkar, A.S.1    Marnett, A.B.2    Crews, B.C.3    Remmel, R.P.4    Marnett, L.J.5
  • 7
    • 0030913442 scopus 로고    scopus 로고
    • Pharmacological options in the treatment of benign prostatic hyperplasia
    • Kenny, B.; Ballard, S.; Blagg, J.; Fox, D. Pharmacological options in the treatment of benign prostatic hyperplasia. J. Med. Chem. 1997, 40, 1293-1315.
    • (1997) J. Med. Chem. , vol.40 , pp. 1293-1315
    • Kenny, B.1    Ballard, S.2    Blagg, J.3    Fox, D.4
  • 8
    • 0037059917 scopus 로고    scopus 로고
    • Studies toward the discovery of the next generation of antidepressants. Part 2: Incorporating a 5-HT(1A) antagonist component into a class of serotonin reuptake inhibitors
    • Mewshaw, R. E.; Meagher, K. L.; Zhou, P.; Zhou, D.; Shi, X.; Scerni, R.; Smith, D.; Schechter, L. E.; Andree, T. H. Studies toward the discovery of the next generation of antidepressants. Part 2: incorporating a 5-HT(1A) antagonist component into a class of serotonin reuptake inhibitors. Bioorg. Med. Chem. Lett. 2002, 12, 307-310.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 307-310
    • Mewshaw, R.E.1    Meagher, K.L.2    Zhou, P.3    Zhou, D.4    Shi, X.5    Scerni, R.6    Smith, D.7    Schechter, L.E.8    Andree, T.H.9
  • 9
    • 0035133804 scopus 로고    scopus 로고
    • D-24851, a novel synthetic microtubule inhibitor, exerts curative antitumoral activity in vivo, shows efficacy toward multidrug-resistant tumor cells, and lacks neurotoxicity
    • Bacher, G.; Nickel, B.; Emig, P.; Vanhoefer, U.; Seeber, S.; Shandra, A.; Klenner, T. B.; Beckers, T. D-24851, a novel synthetic microtubule inhibitor, exerts curative antitumoral activity in vivo, shows efficacy toward multidrug-resistant tumor cells, and lacks neurotoxicity. Cancer Res. 2001, 61, 392-399.
    • (2001) Cancer Res. , vol.61 , pp. 392-399
    • Bacher, G.1    Nickel, B.2    Emig, P.3    Vanhoefer, U.4    Seeber, S.5    Shandra, A.6    Klenner, T.B.7    Beckers, T.8
  • 10
    • 0034752731 scopus 로고    scopus 로고
    • Differential roles of p21(Waf1) and p27(Kip1) in modulating chemosensitivity and their possible application in drug discovery studies
    • Schmidt, M.; Lu, Y.; Parant, J.; Lozano, G.; Bacher, G.; Beckers, T.; Fan, Z. Differential roles of p21(Waf1) and p27(Kip1) in modulating chemosensitivity and their possible application in drug discovery studies. Mol. Pharmacol. 2001, 60, 900-906.
    • (2001) Mol. Pharmacol. , vol.60 , pp. 900-906
    • Schmidt, M.1    Lu, Y.2    Parant, J.3    Lozano, G.4    Bacher, G.5    Beckers, T.6    Fan, Z.7
  • 13
    • 0027419562 scopus 로고
    • Pharmacokinetics of gyrase inhibitors, Part 1: Basic chemistry and gastrointestinal disposition
    • Sorgel, F.; Kinzig, M. Pharmacokinetics of gyrase inhibitors, Part 1: Basic chemistry and gastrointestinal disposition. Am. J. Med. 1993, 94, 44S-55S.
    • (1993) Am. J. Med. , vol.94
    • Sorgel, F.1    Kinzig, M.2
  • 15
    • 0037122756 scopus 로고    scopus 로고
    • Orally effective, long-acting sorbitol dehydrogenase inhibitors: Synthesis, structure-activity relationships, and in vivo evaluations of novel heterocycle-substituted piperazinopyrimidines
    • Chu-Moyer, M. Y.; Ballinger, W. E.; Beebe, D. A.; Berger, R. Coutcher, J. B.; Day, W. W.; Li, J.; Mylari, B. L.; Oates, P. J.; Weekly, R. M. Orally effective, long-acting sorbitol dehydrogenase inhibitors: synthesis, structure-activity relationships, and in vivo evaluations of novel heterocycle-substituted piperazinopyrimidines. J. Med. Chem. 2002, 45, 511-528.
    • (2002) J. Med. Chem. , vol.45 , pp. 511-528
    • Chu-Moyer, M.Y.1    Ballinger, W.E.2    Beebe, D.A.3    Berger, R.4    Coutcher, J.B.5    Day, W.W.6    Li, J.7    Mylari, B.L.8    Oates, P.J.9    Weekly, R.M.10
  • 16
    • 33845553875 scopus 로고
    • Generation and reactions of 3-lithio-1-(phenylsulfonyl)indole
    • Sauliner, M. G.; Gribble, G. W. Generation and reactions of 3-lithio-1-(phenylsulfonyl)indole. J. Org. Chem. 1982, 47, 757-761.
    • (1982) J. Org. Chem. , vol.47 , pp. 757-761
    • Sauliner, M.G.1    Gribble, G.W.2
  • 17
    • 0001606083 scopus 로고    scopus 로고
    • Regiospecific bromination of 3-methylindoles with NBS and its application to the concise synthesis of optically active unusual Tryptophans present in marine cyclic peptides
    • Liu, R.; Zhang, P.; Gan, T.; Cook, J. M. Regiospecific bromination of 3-methylindoles with NBS and its application to the concise synthesis of optically active unusual Tryptophans present in marine cyclic peptides. J. Org. Chem. 1997, 62, 7447-7456.
    • (1997) J. Org. Chem. , vol.62 , pp. 7447-7456
    • Liu, R.1    Zhang, P.2    Gan, T.3    Cook, J.M.4
  • 18
    • 0345575639 scopus 로고
    • Transmission of substituent effects in heterocyclic systems. Rates of solvolysis of substituted 1-(4-thiazolyl)ethyl chlorides
    • Noyce, D. S.; Fike, S. A. Transmission of substituent effects in heterocyclic systems. Rates of solvolysis of substituted 1-(4-thiazolyl)ethyl chlorides. J. Org. Chem. 1973, 38, 3321-3324.
    • (1973) J. Org. Chem. , vol.38 , pp. 3321-3324
    • Noyce, D.S.1    Fike, S.A.2
  • 19
    • 0001389269 scopus 로고
    • Acylation of the zinc salt of indole
    • Bergman, J.; Venemalm, L. Acylation of the zinc salt of indole. Tetrahedron 1990, 46, 6061-6066.
    • (1990) Tetrahedron , vol.46 , pp. 6061-6066
    • Bergman, J.1    Venemalm, L.2
  • 20
    • 0030918989 scopus 로고    scopus 로고
    • The use of Lewis acid in the reaction of zinc salts of indoles and acyl chloride
    • Yang, C. X.; Patel, H. H.; Ku, Y.-Y.; Shah, R.; Sawick, D. The use of Lewis acid in the reaction of zinc salts of indoles and acyl chloride. Synth. Commun. 1997, 27, 2125-2132.
    • (1997) Synth. Commun. , vol.27 , pp. 2125-2132
    • Yang, C.X.1    Patel, H.H.2    Ku, Y.-Y.3    Shah, R.4    Sawick, D.5
  • 21
    • 0001444269 scopus 로고    scopus 로고
    • An expedient route for the stereoselective construction of bridged polyheterocyclic ring systems using the tandem "pincer" Diels-Alder reaction
    • Lautens, M.; Fillion, E. An expedient route for the stereoselective construction of bridged polyheterocyclic ring systems using the tandem "pincer" Diels-Alder reaction. J. Org. Chem. 1997, 62, 4418-4427.
    • (1997) J. Org. Chem. , vol.62 , pp. 4418-4427
    • Lautens, M.1    Fillion, E.2
  • 22
    • 0032704105 scopus 로고    scopus 로고
    • Thionyl chloride-benzotriazole in methylene chloride: A convenient solution for conversion of alcohols and carboxylic acids expeditiously into alkyl chlorides and acid chlorides by simple titration
    • Chaudhari, S. S.; Akamanchi, K. G. Thionyl chloride-benzotriazole in methylene chloride: A convenient solution for conversion of alcohols and carboxylic acids expeditiously into alkyl chlorides and acid chlorides by simple titration. Synlett. 1999, 11, 1763-1765.
    • (1999) Synlett. , vol.11 , pp. 1763-1765
    • Chaudhari, S.S.1    Akamanchi, K.G.2
  • 23
    • 33749093333 scopus 로고    scopus 로고
    • 5-Nitrofuran-2-ylmethyl group as a potential bioreductively activated pro-drug system
    • Berry, J. M.; Watson, C. Y.; Whish, J. D.; Threadgill, D. 5-Nitrofuran-2-ylmethyl group as a potential bioreductively activated pro-drug system. J. Chem. Soc., Perkin Trans. 1 1997, 8, 1147-1156.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , vol.8 , pp. 1147-1156
    • Berry, J.M.1    Watson, C.Y.2    Whish, J.D.3    Threadgill, D.4
  • 24
    • 0000699576 scopus 로고
    • Simplified synthesis of unsaturated nitrogen-heterocycles using nitrile betaines
    • Lee, G. A. simplified synthesis of unsaturated nitrogen- heterocycles using nitrile betaines. Synthesis 1982, 508-509.
    • (1982) Synthesis , pp. 508-509
    • Lee, G.A.1
  • 25
    • 0034682140 scopus 로고    scopus 로고
    • A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminium chloride
    • Okauchi, T.; Itonaga, M.; Minami, T.; Owa, T.; Kitoh, K.; Yoshino, H. A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminium chloride. Org. Lett. 2000, 10, 1485-1487.
    • (2000) Org. Lett. , vol.10 , pp. 1485-1487
    • Okauchi, T.1    Itonaga, M.2    Minami, T.3    Owa, T.4    Kitoh, K.5    Yoshino, H.6
  • 26
    • 0035810401 scopus 로고    scopus 로고
    • Acylation of indole under Friedel-Crafts conditions - An improved method to obtain 3-acylindoles regioselectively
    • Ottoni, O.; Neder, A. de V. F.; Dias, A. K. B.; Cruz, R. P. A.; Aquino, L. B. Acylation of indole under Friedel-Crafts conditions - an improved method to obtain 3-acylindoles regioselectively. Org. Lett. 2001, 3, 1005-1008.
    • (2001) Org. Lett. , vol.3 , pp. 1005-1008
    • Ottoni, O.1    Neder, A.D.V.F.2    Dias, A.K.B.3    Cruz, R.P.A.4    Aquino, L.B.5
  • 27
    • 0028873979 scopus 로고
    • Microculture tetrazolium assays: A comparison between two new tetrazolium salts, XTT and MTS
    • Goodwin, C. J.; Holt, S. J.; Downes, S.; Marshall, N. J. Microculture tetrazolium assays: a comparison between two new tetrazolium salts, XTT and MTS. J. Immunol. Methods 1995, 179, 95-103.
    • (1995) J. Immunol. Methods , vol.179 , pp. 95-103
    • Goodwin, C.J.1    Holt, S.J.2    Downes, S.3    Marshall, N.J.4
  • 28
    • 0032578406 scopus 로고    scopus 로고
    • Norepinephrine stimulates apoptosis in adult rat ventricular myocytes by activation of the beta-adrenergic pathway
    • Communal, C.; Singh, K.; Pimentel, D. R.; Colucci, W. S. Norepinephrine stimulates apoptosis in adult rat ventricular myocytes by activation of the beta-adrenergic pathway. Circulation 1998, 98, 1329-1334.
    • (1998) Circulation , vol.98 , pp. 1329-1334
    • Communal, C.1    Singh, K.2    Pimentel, D.R.3    Colucci, W.S.4
  • 30
    • 0000381930 scopus 로고    scopus 로고
    • Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: An analysis of ALOGP and CLOGP methods
    • Ghose, A. K.; Viswanadhan, V. N.; Wendoloski, J. J. Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: An analysis of ALOGP and CLOGP methods. J. Phys. Chem. A 1998, 102, 3762-3772.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 3762-3772
    • Ghose, A.K.1    Viswanadhan, V.N.2    Wendoloski, J.J.3
  • 32
    • 0036202208 scopus 로고    scopus 로고
    • P-glycoprotein inhibition by the multidrug resistance-reversing agent MS-209 enhances bioavailability and antitumor efficacy of orally administered paclitaxel
    • Kimura, Y.; Aoki, J.; Kohno, M.; Ooka, H.; Tsuruo, T.; Nakanishi, O. P-glycoprotein inhibition by the multidrug resistance-reversing agent MS-209 enhances bioavailability and antitumor efficacy of orally administered paclitaxel. Cancer Chemother. Pharmacol. 2002, 49, 322-328.
    • (2002) Cancer Chemother. Pharmacol. , vol.49 , pp. 322-328
    • Kimura, Y.1    Aoki, J.2    Kohno, M.3    Ooka, H.4    Tsuruo, T.5    Nakanishi, O.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.