메뉴 건너뛰기




Volumn 50, Issue 2, 2007, Pages 254-263

Optimization of monocarboxylate transporter 1 blockers through analysis and modulation of atropisomer interconversion properties

Author keywords

[No Author keywords available]

Indexed keywords

6 [(3,5 DIMETHYL 1H PYRAZOL 4 YL)METHYL] 5 [(4 HYDROXYISOXAZOLIDIN 2 YL)CARBONYL] 1 ISOBUTYL 3 METHYLTHIENO[2,3 D]PYRIMIDINE 2,4(1H,3H) DIONE; AMIDE; IMMUNOSUPPRESSIVE AGENT; IONOMYCIN; MONOCARBOXYLATE TRANSPORTER 1; MONOCARBOXYLATE TRANSPORTER 1 BLOCKER; PHORBOL 13 ACETATE 12 MYRISTATE; UNCLASSIFIED DRUG;

EID: 33846404916     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060995h     Document Type: Article
Times cited : (57)

References (34)
  • 3
    • 0034678033 scopus 로고    scopus 로고
    • Target-oriented and diversity-oriented organic synthesis in drug discovery
    • Schreiber, S. L. Target-oriented and diversity-oriented organic synthesis in drug discovery. Science 2000, 287, 1964-1969.
    • (2000) Science , vol.287 , pp. 1964-1969
    • Schreiber, S.L.1
  • 4
    • 33644790739 scopus 로고    scopus 로고
    • Murray, C. M.; Hutchinson, R.; Bantick, J. R.; Belfield, G. P.; Benjamin, A. D.; Brazma, D.; Bundick, R. V.; Cook, I. D.; Craggs, R. I.; Edwards, S.; Evans, L. R.; Harrison, R.; Holness, E.; Jackson, A. P.; Jackson, C. G.; Kingston, L. P.; Perry, M. W. D.; Ross, A. R. J.: Rugman, P. A.; Sidhu, S. S.; Sullivan, M.; Taylor-Fishwick, D. A.; Walker, P. C.; Whitehead, Y. M.; Wilkinson, D. J.; Wright, A.; Donald, D. K. Monocarboxylate transporter MCT1 is a target for immunosuppression. Nat. Chem. Biol. 2005, 1, 371-376.
    • Murray, C. M.; Hutchinson, R.; Bantick, J. R.; Belfield, G. P.; Benjamin, A. D.; Brazma, D.; Bundick, R. V.; Cook, I. D.; Craggs, R. I.; Edwards, S.; Evans, L. R.; Harrison, R.; Holness, E.; Jackson, A. P.; Jackson, C. G.; Kingston, L. P.; Perry, M. W. D.; Ross, A. R. J.: Rugman, P. A.; Sidhu, S. S.; Sullivan, M.; Taylor-Fishwick, D. A.; Walker, P. C.; Whitehead, Y. M.; Wilkinson, D. J.; Wright, A.; Donald, D. K. Monocarboxylate transporter MCT1 is a target for immunosuppression. Nat. Chem. Biol. 2005, 1, 371-376.
  • 5
    • 0033569442 scopus 로고    scopus 로고
    • The proton-linked monocarboxylate transporter (MCT) family: Structure, function and regulation
    • Halestrap, A. P.; Price, N. T. The proton-linked monocarboxylate transporter (MCT) family: structure, function and regulation. Biochem. J. 1999, 343, 281-299.
    • (1999) Biochem. J , vol.343 , pp. 281-299
    • Halestrap, A.P.1    Price, N.T.2
  • 6
    • 0002999412 scopus 로고
    • Recent advances in atropisomerism
    • Oki, M. Recent advances in atropisomerism. Top. Stereochem. 1983, 14, 1-81.
    • (1983) Top. Stereochem , vol.14 , pp. 1-81
    • Oki, M.1
  • 7
    • 0028883544 scopus 로고
    • Racemization, Enantiomerization, Diastereomerization and Epimerization: Their meaning and Pharmacological Significance
    • Reist, M.; Testa, B.; Carrupt, P.-A.; Jung, M.; Schurig, V. Racemization, Enantiomerization, Diastereomerization and Epimerization: Their meaning and Pharmacological Significance. Chirality 1995, 7, 396-400.
    • (1995) Chirality , vol.7 , pp. 396-400
    • Reist, M.1    Testa, B.2    Carrupt, P.-A.3    Jung, M.4    Schurig, V.5
  • 10
    • 0037294907 scopus 로고    scopus 로고
    • Oximino-piperidino- piperidine-based CCR5 antagonists. Part 2: Synthesis, SAR and biological evaluation of symmetrical heteroaryl carboxamides
    • (b) Palani, A.; Shapiro, S.; Clader, J. W.; Greenlee, W. J.; Vice, S.; McCombie, S.; Cox, K.; Strizki, J.; Baroudy, B. M. Oximino-piperidino- piperidine-based CCR5 antagonists. Part 2: synthesis, SAR and biological evaluation of symmetrical heteroaryl carboxamides. Bioorg. Med. Chem. Lett. 2003, 13, 709-712.
    • (2003) Bioorg. Med. Chem. Lett , vol.13 , pp. 709-712
    • Palani, A.1    Shapiro, S.2    Clader, J.W.3    Greenlee, W.J.4    Vice, S.5    McCombie, S.6    Cox, K.7    Strizki, J.8    Baroudy, B.M.9
  • 11
    • 5644229648 scopus 로고    scopus 로고
    • Seto, S. Convenient synthesis of 7-aryl-3,4,5,6-tetrahydro-2H- pyrido[4,3-b]- and [2,3-b]-1,5-oxazocine-6-ones. Tetrahedron Lett. 2004, 45, 8475-8478.
    • (a) Seto, S. Convenient synthesis of 7-aryl-3,4,5,6-tetrahydro-2H- pyrido[4,3-b]- and [2,3-b]-1,5-oxazocine-6-ones. Tetrahedron Lett. 2004, 45, 8475-8478.
  • 12
    • 13944275182 scopus 로고    scopus 로고
    • Seto, S.; Tanioka, A.; Ikeda, M.; Izawa, S. Design and synthesis of novel 9-substituted-7-aryl-3,4,5,6-tetrahydro-2H-pyrido[4,3-b]- and [2,3-b]-1,5-oxazocin-6-ones as NK1 antagonists. Bioorg. Med. Chem. Lett. 2005, 15, 1479-1484.
    • (b) Seto, S.; Tanioka, A.; Ikeda, M.; Izawa, S. Design and synthesis of novel 9-substituted-7-aryl-3,4,5,6-tetrahydro-2H-pyrido[4,3-b]- and [2,3-b]-1,5-oxazocin-6-ones as NK1 antagonists. Bioorg. Med. Chem. Lett. 2005, 15, 1479-1484.
  • 13
    • 13944271836 scopus 로고    scopus 로고
    • Seto, S.; Tanioka, A.; Ikeda, M.; Izawa, S. 2-Substituted-4-aryl-6,7. 8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one as a structurally new NK1 antagonist. Bioorg. Med. Chem. Lett. 2005, 15, 1485-1488.
    • (c) Seto, S.; Tanioka, A.; Ikeda, M.; Izawa, S. 2-Substituted-4-aryl-6,7. 8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one as a structurally new NK1 antagonist. Bioorg. Med. Chem. Lett. 2005, 15, 1485-1488.
  • 14
    • 15644372975 scopus 로고    scopus 로고
    • Axially Chiral N-Benzyl-N,7-dimethyl-5-phenyl-1,7-naphthyridine-6-carboxamide Derivatives as Tachykinin NK1 Receptor Antagonists: Determination of the Absolute Stereochemical Requirements
    • (a) Ikeura, Y.; Ishichi, Y.; Tanaka, T.; Fujishima, A.; Murabayashi, M.; Kawada, M.; Ishimaru, T.; Kamo, I.; Doi, T.; Natsugari, H. Axially Chiral N-Benzyl-N,7-dimethyl-5-phenyl-1,7-naphthyridine-6-carboxamide Derivatives as Tachykinin NK1 Receptor Antagonists: Determination of the Absolute Stereochemical Requirements. J. Med. Chem. 1998, 41, 4232-4239.
    • (1998) J. Med. Chem , vol.41 , pp. 4232-4239
    • Ikeura, Y.1    Ishichi, Y.2    Tanaka, T.3    Fujishima, A.4    Murabayashi, M.5    Kawada, M.6    Ishimaru, T.7    Kamo, I.8    Doi, T.9    Natsugari, H.10
  • 15
    • 0033598446 scopus 로고    scopus 로고
    • Axially chiral 1,7-naphthyridine-6-carboxamide derivatives as orally active tachykinin NK1 receptor antagonists: Synthesis, antagonistic activity, and effects on bladder functions
    • (b) Natsugari, H.; Ikeura, Y.; Kamo, I.; Ishimaru, T.; Ishichi, Y.; Fujishima, A.; Tanaka, T.; Kasahara, F.; Kawada, M.; Doi, T. Axially chiral 1,7-naphthyridine-6-carboxamide derivatives as orally active tachykinin NK1 receptor antagonists: synthesis, antagonistic activity, and effects on bladder functions. J. Med. Chem. 1999, 42, 3982-3993.
    • (1999) J. Med. Chem , vol.42 , pp. 3982-3993
    • Natsugari, H.1    Ikeura, Y.2    Kamo, I.3    Ishimaru, T.4    Ishichi, Y.5    Fujishima, A.6    Tanaka, T.7    Kasahara, F.8    Kawada, M.9    Doi, T.10
  • 16
    • 1942468807 scopus 로고    scopus 로고
    • Ishichi, Y.; Ikeura, Y.; Natsugari, H. Amide-based atropisomers in tachykinin NK1-receptor antagonists: synthesis and antagonistic activity of axially chiral N-benzylcarboxamide derivatives of 2,3,4,5-tetrahydro-6H- pyrido[2,3-b][1,5]oxazocin-6-one. Tetrahedron 2004, 60, 4481-4490.
    • (c) Ishichi, Y.; Ikeura, Y.; Natsugari, H. Amide-based atropisomers in tachykinin NK1-receptor antagonists: synthesis and antagonistic activity of axially chiral N-benzylcarboxamide derivatives of 2,3,4,5-tetrahydro-6H- pyrido[2,3-b][1,5]oxazocin-6-one. Tetrahedron 2004, 60, 4481-4490.
  • 21
    • 27344459800 scopus 로고    scopus 로고
    • Atropisomeric property of 1-(2,6-difluorobenzyl)-3-[(2R)-amino-2-phenethyl]-5-(2-fluoro-3- methoxyphenyl)-6-methyluracil
    • and references cited therein
    • Tucci, F. C.; Hu, T.; Mesleh, M. F.; Bokser, A.; Allsopp, E.; Gross, T. D.; Guo, Z.; Zhu, Y.-F.; Struthers, R. S.; Ling, N.; Chen, C. Atropisomeric property of 1-(2,6-difluorobenzyl)-3-[(2R)-amino-2-phenethyl]-5-(2-fluoro-3- methoxyphenyl)-6-methyluracil. Chirality 2005, 17, 559-564. and references cited therein.
    • (2005) Chirality , vol.17 , pp. 559-564
    • Tucci, F.C.1    Hu, T.2    Mesleh, M.F.3    Bokser, A.4    Allsopp, E.5    Gross, T.D.6    Guo, Z.7    Zhu, Y.-F.8    Struthers, R.S.9    Ling, N.10    Chen, C.11
  • 22
    • 0038012572 scopus 로고    scopus 로고
    • LC - NMR - MS in drug discovery
    • (a) Corcoran, O.; Spraul, M. LC - NMR - MS in drug discovery. Drug Discovery Today 2003, 8, 624-631.
    • (2003) Drug Discovery Today , vol.8 , pp. 624-631
    • Corcoran, O.1    Spraul, M.2
  • 23
    • 0142138604 scopus 로고    scopus 로고
    • Advantages and disadvantages of nuclear magnetic resonance spectroscopy as a hyphenated technique
    • (b) Silva Elipe, M. V. Advantages and disadvantages of nuclear magnetic resonance spectroscopy as a hyphenated technique. Anal. Chim. Acta 2003, 497, 1-25.
    • (2003) Anal. Chim. Acta , vol.497 , pp. 1-25
    • Silva Elipe, M.V.1
  • 24
    • 0037236115 scopus 로고    scopus 로고
    • 1H chemical shifts in NMR: Part 19. Carbonyl anisotropies and steric effects in aromatic aldehydes and ketones
    • 1H chemical shifts in NMR: part 19. Carbonyl anisotropies and steric effects in aromatic aldehydes and ketones. Magn. Reson. Chem. 2003, 41, 26-36.
    • (2003) Magn. Reson. Chem , vol.41 , pp. 26-36
    • Abraham, R.J.1    Mobli, M.2    Smith, R.J.3
  • 25
    • 37049138113 scopus 로고
    • Correlation of interproton spin-spin coupling constants with structure
    • Sternhell, S. Correlation of interproton spin-spin coupling constants with structure. Q. Rev. Chem. Soc. 1969, 236-270.
    • (1969) Q. Rev. Chem. Soc , pp. 236-270
    • Sternhell, S.1
  • 26
    • 0034311851 scopus 로고    scopus 로고
    • Correlated rotation in a conformationally restricted amide
    • Johnston, E. R.; Fortt, R.; Barborak, J. C. Correlated rotation in a conformationally restricted amide. Magn. Reson. Chem. 2000, 38, 932-936.
    • (2000) Magn. Reson. Chem , vol.38 , pp. 932-936
    • Johnston, E.R.1    Fortt, R.2    Barborak, J.C.3
  • 27
    • 0032479733 scopus 로고    scopus 로고
    • Concerted rotation in a tertiary aromatic amide: Towards a simple molecular gear
    • Clayden, J.; Pink, J. H. Concerted rotation in a tertiary aromatic amide: towards a simple molecular gear. Angew. Chem., Int. Ed. 1998, 37, 1937-1939.
    • (1998) Angew. Chem., Int. Ed , vol.37 , pp. 1937-1939
    • Clayden, J.1    Pink, J.H.2
  • 28
    • 0037087637 scopus 로고    scopus 로고
    • Stereodynamics of bond rotation in tertiary aromatic amides
    • Bragg, R. A.; Clayden, J.; Morris, G. A.; Pink, J. H. Stereodynamics of bond rotation in tertiary aromatic amides. Chem. Eur. J. 2002, 8, 1279-1289.
    • (2002) Chem. Eur. J , vol.8 , pp. 1279-1289
    • Bragg, R.A.1    Clayden, J.2    Morris, G.A.3    Pink, J.H.4
  • 29
    • 33846425663 scopus 로고    scopus 로고
    • is available from ModelKinetix, Wallingford, United Kingdom
    • Modelmaker is available from ModelKinetix, Wallingford, United Kingdom, http://www.modelkinetix.com.
    • Modelmaker
  • 31
    • 27844466269 scopus 로고
    • N-Methoxy-N-methylamides as effective acylating agents
    • Nahm, S.; Weinreb, S. M. N-Methoxy-N-methylamides as effective acylating agents. Tetrahedron Lett. 1981, 22, 3815-18.
    • (1981) Tetrahedron Lett , vol.22 , pp. 3815-3818
    • Nahm, S.1    Weinreb, S.M.2
  • 32
    • 58149365344 scopus 로고
    • WET solvent suppression and its applications to LC NMR and high-resolution NMR spectroscopy
    • Smallcombe, S. H.; Patt, S. L.; Keifer, P. A. WET solvent suppression and its applications to LC NMR and high-resolution NMR spectroscopy. J. Magn. Reson. (Series A) 1995, 117 295-303.
    • (1995) J. Magn. Reson. (Series A , vol.117 , pp. 295-303
    • Smallcombe, S.H.1    Patt, S.L.2    Keifer, P.A.3
  • 33
    • 84987577413 scopus 로고
    • Synthesis of aminoerythrose and of aminoerythritol derivatives via Diels-Alder cycloadditions of 1-tert-butyldimethylsiloxybutadiene with acylnitrose dienophiles
    • Defoin, A.; Pires, J.; Streith, J. Synthesis of aminoerythrose and of aminoerythritol derivatives via Diels-Alder cycloadditions of 1-tert-butyldimethylsiloxybutadiene with acylnitrose dienophiles. Synlett 1990, 2, 111-13.
    • (1990) Synlett , vol.2 , pp. 111-113
    • Defoin, A.1    Pires, J.2    Streith, J.3
  • 34
    • 33748906068 scopus 로고    scopus 로고
    • A simple and efficient synthesis of optically pure 4-alkylisoxazolidin-4-ols from chiral epoxides
    • Martin, B. P.; Guile, S. D.; Donald, D. K.; Cooper, M. E. A simple and efficient synthesis of optically pure 4-alkylisoxazolidin-4-ols from chiral epoxides. Tetrahedron Lett. 2006, 47, 7635-7639.
    • (2006) Tetrahedron Lett , vol.47 , pp. 7635-7639
    • Martin, B.P.1    Guile, S.D.2    Donald, D.K.3    Cooper, M.E.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.