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Volumn 40, Issue 16, 1997, Pages 2502-2524

Protein structure-based design, synthesis, and biological evaluation of 5-thia-2,6-diamino-4(3H)-oxopyrimidines: Potent inhibitors of glycinamide ribonucleotide transformylase with potent cell growth inhibition

Author keywords

[No Author keywords available]

Indexed keywords

5 BROMO 2,6 DIAMINO 4(3H) PYRIMIDINONE; 5 THIAPYRIMIDINONE; ANTINEOPLASTIC AGENT; FOLATE BINDING PROTEIN; PHOSPHORIBOSYLGLYCINAMIDE FORMYLTRANSFERASE; UNCLASSIFIED DRUG;

EID: 15144340856     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9607459     Document Type: Article
Times cited : (41)

References (76)
  • 1
    • 0025970198 scopus 로고
    • The Renewed Potential for Folate Antagonists in Contemporary Cancer Chemotherapy
    • (a) Berman, E. M.; Werbel, L. M. The Renewed Potential for Folate Antagonists in Contemporary Cancer Chemotherapy. J. Med. Chem. 1991, 34, 479-485.
    • (1991) J. Med. Chem. , vol.34 , pp. 479-485
    • Berman, E.M.1    Werbel, L.M.2
  • 2
    • 0027043115 scopus 로고
    • Recent Advances in Antifolates as Anticancer Agents
    • and references cited therein
    • (b) Varney, M. D.; Romines, W. H. Recent Advances in Antifolates as Anticancer Agents. Curr. Opin. Ther. Pat. 1992, 2, 1979-1992 and references cited therein.
    • (1992) Curr. Opin. Ther. Pat. , vol.2 , pp. 1979-1992
    • Varney, M.D.1    Romines, W.H.2
  • 3
    • 0004053615 scopus 로고
    • Worth Publishers, Inc.: New York
    • (a) Lehninger, A. L. Biochemistry, 2nd ed.; Worth Publishers, Inc.: New York, 1975; pp 729-732.
    • (1975) Biochemistry, 2nd Ed. , pp. 729-732
    • Lehninger, A.L.1
  • 4
    • 0017905124 scopus 로고
    • N10-Formyltetrahydrofolate is the Formyl Donor for Glycinamide Ribotide Transformylase in Escherichia coli
    • (b) Dev, I. K.; Harvey, R. J. N10-Formyltetrahydrofolate is the Formyl Donor for Glycinamide Ribotide Transformylase in Escherichia coli. J. Biol. Chem. 1978, 253, 4242-4244.
    • (1978) J. Biol. Chem. , vol.253 , pp. 4242-4244
    • Dev, I.K.1    Harvey, R.J.2
  • 5
    • 0020477484 scopus 로고
    • Direct Transfer of One-Carbon Units in the Transformylations of de novo Purine Biosynthesis
    • (c) Smith, G. K.; Mueller, W. T.; Slieker, W. T.; DeBrosse, C. W.; Benkovic, S. J. Direct Transfer of One-Carbon Units in the Transformylations of de novo Purine Biosynthesis. Biochemistry 1982, 21, 2870-2874.
    • (1982) Biochemistry , vol.21 , pp. 2870-2874
    • Smith, G.K.1    Mueller, W.T.2    Slieker, W.T.3    DeBrosse, C.W.4    Benkovic, S.J.5
  • 6
    • 0021813844 scopus 로고
    • Synthesis of the Antileukemic Agents 5,10-Dideazaaminopterin and 5,10-Dideaza-5,6,7,8-tetrahydroaminopterin
    • (a) Taylor. E. C.; Harrington, P. J.; Fletcher, S. R.; Beardsley, G. P.; Moran, R. G. Synthesis of the Antileukemic Agents 5,10-Dideazaaminopterin and 5,10-Dideaza-5,6,7,8-tetrahydroaminopterin. J. Med. Chem. 1985, 28, 914-921.
    • (1985) J. Med. Chem. , vol.28 , pp. 914-921
    • Taylor, E.C.1    Harrington, P.J.2    Fletcher, S.R.3    Beardsley, G.P.4    Moran, R.G.5
  • 7
    • 0024499104 scopus 로고
    • A New Folate Antimetabolite, 5,10-Dideaza-5,6,7,8-tetrahydrofolate Is a Potent Inhibitor of de novo Purine Synthesis
    • (b) Beardsley, G. P.; Moroson, B. A.; Taylor, E. C.; Moran, R. G. A New Folate Antimetabolite, 5,10-Dideaza-5,6,7,8-tetrahydrofolate Is a Potent Inhibitor of de novo Purine Synthesis. J. Biol. Chem. 1989, 264, 328-333.
    • (1989) J. Biol. Chem. , vol.264 , pp. 328-333
    • Beardsley, G.P.1    Moroson, B.A.2    Taylor, E.C.3    Moran, R.G.4
  • 8
    • 0024802389 scopus 로고
    • The 6S-and 6R-Diastereomers of 5,10-Dideaza-5,6,7,8-tetrahydrofolate Are Equiactive Inhibitors of de novo Purine Synthesis
    • Moran, R. G.; Baldwin, S. W.; Taylor, E. C.; Shih, C. The 6S-and 6R-Diastereomers of 5,10-Dideaza-5,6,7,8-tetrahydrofolate Are Equiactive Inhibitors of de novo Purine Synthesis. J. Biol. Chem. 1989, 264, 21047-21051.
    • (1989) J. Biol. Chem. , vol.264 , pp. 21047-21051
    • Moran, R.G.1    Baldwin, S.W.2    Taylor, E.C.3    Shih, C.4
  • 9
    • 0027179429 scopus 로고
    • Phase I Study of (6R)-5,10-Dideazatetrahydrofolate: A Folate Antimetabolite Inhibitory to de Novo Purine Synthesis
    • (a) Ray, M. S.; Muggia, F. M.; Leichman, G.; Grunberg, S. M.; Nelson, R. L.; Dyke, R. W.; Moran, R. G. Phase I Study of (6R)-5,10-Dideazatetrahydrofolate: a Folate Antimetabolite Inhibitory to De Novo Purine Synthesis. J. Natl. Cancer Inst. 1993, 85, 1154-1159.
    • (1993) J. Natl. Cancer Inst. , vol.85 , pp. 1154-1159
    • Ray, M.S.1    Muggia, F.M.2    Leichman, G.3    Grunberg, S.M.4    Nelson, R.L.5    Dyke, R.W.6    Moran, R.G.7
  • 10
    • 0008945744 scopus 로고
    • Lometrexol (DDATHF): Phase I Trial of a Weekly Schedule of This New Antifolate
    • (b) Cole, J. T.; Gralla, R. J.; Kardinal, C. G.; Rivera, N. P. Lometrexol (DDATHF): Phase I Trial of a Weekly Schedule of This New Antifolate. Proc. Am. Assoc. Cancer Res. 1992, 33, 2468.
    • (1992) Proc. Am. Assoc. Cancer Res. , vol.33 , pp. 2468
    • Cole, J.T.1    Gralla, R.J.2    Kardinal, C.G.3    Rivera, N.P.4
  • 12
    • 0009488236 scopus 로고
    • Synthesis of 5,10-Dideazatetrahydrofolic Acid (DDATHF) and Analogues
    • Cooper, B. A., Whitehead, V. M., Eds.; de Gruyter: Berlin
    • (a) Taylor, E. C.; Wong, G. S. K.; Fletcher, S. R.; Harrington, P. J.; Beardsley, G. P.; Shih, C. Synthesis of 5,10-Dideazatetrahydrofolic Acid (DDATHF) and Analogues. In Chemistry and Biology of Pteridines, 1986; Cooper, B. A., Whitehead, V. M., Eds.; de Gruyter: Berlin, 1986; pp 61-64.
    • (1986) Chemistry and Biology of Pteridines , vol.1986 , pp. 61-64
    • Taylor, E.C.1    Wong, G.S.K.2    Fletcher, S.R.3    Harrington, P.J.4    Beardsley, G.P.5    Shih, C.6
  • 13
    • 0028114968 scopus 로고
    • Synthesis of 10-(Hydroxymethyl)-5,10-dideaza-5,6,7,8-tetrahydrofolic Acid, a Potent New Analogue of DDATHF (Lometrexol)
    • (b) Taylor, E. C.; Yoon, C. Synthesis of 10-(Hydroxymethyl)-5,10-dideaza-5,6,7,8-tetrahydrofolic Acid, a Potent New Analogue of DDATHF (Lometrexol). J. Org. Chem. 1994, 59, 7096-7098.
    • (1994) J. Org. Chem. , vol.59 , pp. 7096-7098
    • Taylor, E.C.1    Yoon, C.2
  • 14
    • 0025752884 scopus 로고
    • Structural Features of 5,10-Dideaza-5,6,7,8-tetrahydrofolate That Determine Inhibition of Mammalian Glycinamide Ribonucleotide Formyltransferase
    • (c) Baldwin, S. W.; Tse, A.; Gossett, L. S.; Taylor, E. C.; Rosowsky, A.; Shih, C.; Moran, R. G. Structural Features of 5,10-Dideaza-5,6,7,8-tetrahydrofolate That Determine Inhibition of Mammalian Glycinamide Ribonucleotide Formyltransferase. Biochemistry 1991, 30, 1997-2006.
    • (1991) Biochemistry , vol.30 , pp. 1997-2006
    • Baldwin, S.W.1    Tse, A.2    Gossett, L.S.3    Taylor, E.C.4    Rosowsky, A.5    Shih, C.6    Moran, R.G.7
  • 16
    • 84909648141 scopus 로고
    • Synthesis and Structure-Activity Relationship Studies of 5,10-Dideazatetrahydrofolic Acid
    • Curtius, H.-C., Ghisla, S., Blau, N., Eds.; de Gruyter: Berlin
    • (b) Shih, C.; Grindey, G. B.; Gossett, L. S.; Moran, R. G. Synthesis and Structure-Activity Relationship Studies of 5,10-Dideazatetrahydrofolic Acid. In Chemistry and Biology of Pteridines, 1989; Curtius, H.-C., Ghisla, S., Blau, N., Eds.; de Gruyter: Berlin, 1990; pp 1035-1038.
    • (1990) Chemistry and Biology of Pteridines , vol.1989 , pp. 1035-1038
    • Shih, C.1    Grindey, G.B.2    Gossett, L.S.3    Moran, R.G.4
  • 17
    • 0000291015 scopus 로고
    • A Facile Route to "Open Chain" Analogues of DDATHF
    • (a) Taylor, E. C.; Harrington, P. M.; Shih, C. A Facile Route to "Open Chain" Analogues of DDATHF. Heterocycles 1989, 28, 1169-1178.
    • (1989) Heterocycles , vol.28 , pp. 1169-1178
    • Taylor, E.C.1    Harrington, P.M.2    Shih, C.3
  • 18
    • 0025128663 scopus 로고
    • Synthesis and Biological Activity of an Acyclic Analogue of 5,6,7,8-Tetrahydrofolic Acid, N-[4-[[3-(2,4-Diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propyl]amino]-benzoyl]-L- glutamic Acid
    • (b) Kelley, J. L.; McLean, E. W.; Cohn, N. K.; Edelstein, M. P.; Duch, D. S.; Smith, G. K.; Hanlon, M. H.; Ferone, R. Synthesis and Biological Activity of an Acyclic Analogue of 5,6,7,8-Tetrahydrofolic Acid, N-[4-[[3-(2,4-Diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propyl]amino]-benzoyl]-L- glutamic Acid. J. Med. Chem. 1990, 33, 561-567.
    • (1990) J. Med. Chem. , vol.33 , pp. 561-567
    • Kelley, J.L.1    McLean, E.W.2    Cohn, N.K.3    Edelstein, M.P.4    Duch, D.S.5    Smith, G.K.6    Hanlon, M.H.7    Ferone, R.8
  • 20
    • 0026632377 scopus 로고
    • Synthesis and Biological Activity of Open-Chain Analogues of 5,6,7,8-Tetrahydrofolic Acid-Potential Antitumor Agents
    • (d) Bigham, E. C.; Hodson, S. J.; Mallory, R.; Wilson, D.; Duch, D. S.; Smith, G. K.; Ferone, R. Synthesis and Biological Activity of Open-Chain Analogues of 5,6,7,8-Tetrahydrofolic Acid-Potential Antitumor Agents. J. Med. Chem. 1992, 35, 1399-1410.
    • (1992) J. Med. Chem. , vol.35 , pp. 1399-1410
    • Bigham, E.C.1    Hodson, S.J.2    Mallory, R.3    Wilson, D.4    Duch, D.S.5    Smith, G.K.6    Ferone, R.7
  • 21
    • 0026598854 scopus 로고
    • Synthesis of 10-Substituted "Open-Chain" Analogues of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid (DDATHF, Lometrexol)
    • (e) Taylor, E. C.; Schrader, T. H.; Walensky, L. D. Synthesis of 10-Substituted "Open-Chain" Analogues of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid (DDATHF, Lometrexol). Tetrahedron 1992, 48, 19-32.
    • (1992) Tetrahedron , vol.48 , pp. 19-32
    • Taylor, E.C.1    Schrader, T.H.2    Walensky, L.D.3
  • 22
    • 0027932250 scopus 로고
    • Thienyl and Thiazolyl Acyclic Analogues of 5-Deazatetrahydrofolic Acid
    • (f) Hodson, S. J.; Bigham, E. C.; Duch D. S.; Smith, G. K.; Ferone, R. Thienyl and Thiazolyl Acyclic Analogues of 5-Deazatetrahydrofolic Acid. J. Med. Chem. 1994, 37, 2112-2115.
    • (1994) J. Med. Chem. , vol.37 , pp. 2112-2115
    • Hodson, S.J.1    Bigham, E.C.2    Duch, D.S.3    Smith, G.K.4    Ferone, R.5
  • 23
    • 0026306992 scopus 로고
    • Folate Antimetabolites Inhibitory to de novo Purine Synthesis
    • Muggia, F. M., Ed.; Kluwer Academic Publications: Boston
    • (a) Moran, R. G. Folate Antimetabolites Inhibitory to de novo Purine Synthesis. In New Drugs, Concepts and Results in Cancer Chemotherapy; Muggia, F. M., Ed.; Kluwer Academic Publications: Boston, 1992; pp 65-87.
    • (1992) New Drugs, Concepts and Results in Cancer Chemotherapy , pp. 65-87
    • Moran, R.G.1
  • 24
    • 0025328890 scopus 로고
    • In vivo and in Vitro Metabolism of 5-Deacaacyclotetrahydrofolate, an Acyclic Tetrahydrofolate Analogue
    • (b) Hanlon, M. H.; Ferone, R.; Mullin, R. J.; Keith, B. R. In vivo and in Vitro Metabolism of 5-Deacaacyclotetrahydrofolate, an Acyclic Tetrahydrofolate Analogue. Cancer Res. 1990, 50, 3207-3211.
    • (1990) Cancer Res. , vol.50 , pp. 3207-3211
    • Hanlon, M.H.1    Ferone, R.2    Mullin, R.J.3    Keith, B.R.4
  • 25
    • 0026668340 scopus 로고
    • Structures of Apo and Complexed Escherichia coli Glycinamide Ribonucleotide Transformylase
    • (a) Almassy, R. J.; Janson, C. C.; Kan, C. C.; Hostomska, Z. Structures of Apo and Complexed Escherichia coli Glycinamide Ribonucleotide Transformylase. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 6114-6118.
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 6114-6118
    • Almassy, R.J.1    Janson, C.C.2    Kan, C.C.3    Hostomska, Z.4
  • 26
    • 0026758035 scopus 로고
    • Crystal Structure of Glycinamide Ribonucleotide Transformylase from Escherichia coli at 3.0 A Resolution A Target Enzyme for Chemotherapy
    • (b) Chen, P.; Schulze-Gahmen, U.; Stura, E. A.; Inglese, J.; Johnson, D. L.; Marolewski, A.; Benkovic, S. J.; Wilson, I. A. Crystal Structure of Glycinamide Ribonucleotide Transformylase from Escherichia coli at 3.0 A Resolution A Target Enzyme for Chemotherapy. J. Mol. Biol. 1992, 227, 283-292.
    • (1992) J. Mol. Biol. , vol.227 , pp. 283-292
    • Chen, P.1    Schulze-Gahmen, U.2    Stura, E.A.3    Inglese, J.4    Johnson, D.L.5    Marolewski, A.6    Benkovic, S.J.7    Wilson, I.A.8
  • 27
    • 0029025769 scopus 로고
    • Towards Structure-based Drug Design: Crystal Structure of a Multisubstrate Adduct Complex of Glycinamide Ribonucleotide Transformylase at 1.96 Å Resolution
    • (c) Klein, C.; Chen, P.; Arevalo, J. H.; Stura, E. A.; Marolewski, Warren M. S.; Benkovic, S. J.; Wilson, I. A. Towards Structure-based Drug Design: Crystal Structure of a Multisubstrate Adduct Complex of Glycinamide Ribonucleotide Transformylase at 1.96 Å Resolution. J. Mol. Biol. 1995, 249, 153-175.
    • (1995) J. Mol. Biol. , vol.249 , pp. 153-175
    • Klein, C.1    Chen, P.2    Arevalo, J.H.3    Stura, E.A.4    Marolewski, W.M.S.5    Benkovic, S.J.6    Wilson, I.A.7
  • 28
    • 0026494632 scopus 로고
    • Heterologous Expression and Purification of Active Human Phosphoribosylglycinamide Formyltransferase as a Single Domain
    • Kan, C. C.; Gehring, M. R.; Nodes, B. R.; Janson, C. A.; Almassy, R. J.; Hostomska, Z. Heterologous Expression and Purification of Active Human Phosphoribosylglycinamide Formyltransferase as a Single Domain. J. Protein Chem. 1992, 11, 467-473.
    • (1992) J. Protein Chem. , vol.11 , pp. 467-473
    • Kan, C.C.1    Gehring, M.R.2    Nodes, B.R.3    Janson, C.A.4    Almassy, R.J.5    Hostomska, Z.6
  • 29
    • 0028297495 scopus 로고
    • New and Facile Synthesis of 5,6,7,8-Tetrahydro-5-deaza-5-thiapterins via the Aliphatic S-N Type Smiles Rearrangement
    • Subsequent to the completion of this work, a set of reports appeared describing the synthesis and in vitro cell culture activity of the 5-thia analogue of 5dTHF. GART inhibition data were not reported. (a) Sako, M.; Totani, R.; Hirota, K.; Maki, Y. New and Facile Synthesis of 5,6,7,8-Tetrahydro-5-deaza-5-thiapterins via the Aliphatic S-N Type Smiles Rearrangement. Chem. Pharm. Bull. 1994, 42, 806-810. (b) Totani, R.; Sako, M.; Hirota, K.; Maki, Y. Synthesis of a Novel 5-Deaza-5-thia Analogue of Tetrahydrofolic Acid, N-(p-{[(2-Amino-6,7-dihydro-4-oxo-3H,8H-pyrimido[5,4-b][1,4]thiazin-6-yl)methyl] amino}-benzoy)glutamic Acid. J. Chem. Soc., Perkin Trans. 1 1994, 833-836.
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 806-810
    • Sako, M.1    Totani, R.2    Hirota, K.3    Maki, Y.4
  • 30
    • 37049084396 scopus 로고
    • Synthesis of a Novel 5-Deaza-5-thia Analogue of Tetrahydrofolic Acid, N-(p-{[(2-Amino-6,7-dihydro-4-oxo-3H,8H-pyrimido[5,4-b][1,4]thiazin-6-yl)methyl] amino}-benzoy)glutamic Acid
    • Subsequent to the completion of this work, a set of reports appeared describing the synthesis and in vitro cell culture activity of the 5-thia analogue of 5dTHF. GART inhibition data were not reported. (a) Sako, M.; Totani, R.; Hirota, K.; Maki, Y. New and Facile Synthesis of 5,6,7,8-Tetrahydro-5-deaza-5-thiapterins via the Aliphatic S-N Type Smiles Rearrangement. Chem. Pharm. Bull. 1994, 42, 806-810. (b) Totani, R.; Sako, M.; Hirota, K.; Maki, Y. Synthesis of a Novel 5-Deaza-5-thia Analogue of Tetrahydrofolic Acid, N-(p-{[(2-Amino-6,7-dihydro-4-oxo-3H,8H-pyrimido[5,4-b][1,4]thiazin-6-yl)methyl] amino}-benzoy)glutamic Acid. J. Chem. Soc., Perkin Trans. 1 1994, 833-836.
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 833-836
    • Totani, R.1    Sako, M.2    Hirota, K.3    Maki, Y.4
  • 31
    • 0028885828 scopus 로고
    • Synthesis and Biological Evaluation of N-[4-(2-trans-[([2,6-Diamino-4(3H)-oxopyrimidin-5-yl]methyl)-thio]cyclobutyl) benzoyl]-L-glutamic acid a Novel 5-Thiapyrimidinone Inhibitor of Dihydrofolate Reductase
    • Varney, M. D.; Romines, W. H.; Boritzki, T.; Margosiak, S. A.; Bartlett, C.; Howland, E. J. Synthesis and Biological Evaluation of N-[4-(2-trans-[([2,6-Diamino-4(3H)-oxopyrimidin-5-yl]methyl)-thio]cyclobutyl) benzoyl]-L-glutamic acid a Novel 5-Thiapyrimidinone Inhibitor of Dihydrofolate Reductase. J. Heterocycl. Chem. 1995, 32, 1493-1498.
    • (1995) J. Heterocycl. Chem. , vol.32 , pp. 1493-1498
    • Varney, M.D.1    Romines, W.H.2    Boritzki, T.3    Margosiak, S.A.4    Bartlett, C.5    Howland, E.J.6
  • 32
    • 84967852329 scopus 로고
    • MERLOT, an Integrated Package of Computer Programs for the Determination of Crystal Structures by Molecular Replacement
    • (a) Fitzgerald, P. M. D. MERLOT, an Integrated Package of Computer Programs for the Determination of Crystal Structures by Molecular Replacement. J. Appl. Crystallogr. 1988, 21, 273-278.
    • (1988) J. Appl. Crystallogr. , vol.21 , pp. 273-278
    • Fitzgerald, P.M.D.1
  • 33
    • 0000144850 scopus 로고
    • The Fast Rotation Function
    • Rossmann, M. G., Ed.; Gordon and Breach: New York
    • (b) Crowther, R. A. The Fast Rotation Function. In The Molecular Replacement Method, 1972; Rossmann, M. G., Ed.; Gordon and Breach: New York, 1972.
    • (1972) The Molecular Replacement Method , vol.1972
    • Crowther, R.A.1
  • 34
    • 0001247138 scopus 로고
    • A Method of Positioning a Known Molecule in an Unknown Crystal Structure
    • (c) Crowther, R. A.; Blow, D. M. A Method of Positioning a Known Molecule in an Unknown Crystal Structure. Acta Crystallogr. 1967, 23, 544-548.
    • (1967) Acta Crystallogr. , vol.23 , pp. 544-548
    • Crowther, R.A.1    Blow, D.M.2
  • 35
    • 37049130452 scopus 로고
    • Synthesis of Derivatives of Thiazolo-[4,5-d]pyrimidine
    • Baker, J. A.; Chatfield, P. V. Synthesis of Derivatives of Thiazolo-[4,5-d]pyrimidine. Part I. J. Chem. Soc. 1969, 603-606.
    • (1969) J. Chem. Soc. , Issue.1 PART , pp. 603-606
    • Baker, J.A.1    Chatfield, P.V.2
  • 36
    • 84970556295 scopus 로고
    • A New Synthesis of 2,5-Diamino-7-hydroxythiazolo-[4,5-d]pyrimidine and a New Aspect on the Reactivity of 5-Bromopyrimidines
    • Horiuchi, M. A New Synthesis of 2,5-Diamino-7-hydroxythiazolo-[4,5-d]pyrimidine and a New Aspect on the Reactivity of 5-Bromopyrimidines. Chem. Pharm. Bull. 1959, 7, 393-394.
    • (1959) Chem. Pharm. Bull. , vol.7 , pp. 393-394
    • Horiuchi, M.1
  • 37
    • 0000595912 scopus 로고
    • A New, Highly Efficient Method for the Conversion of Alcohols to Thioesters and Thiols
    • Volante, R. P. A New, Highly Efficient Method for the Conversion of Alcohols to Thioesters and Thiols. Tetrahedron Lett. 1981, 22, 3119-3122.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3119-3122
    • Volante, R.P.1
  • 38
    • 0345385805 scopus 로고
    • Synthesis of 7-Substituted Benzo[b]thiophene Derivatives
    • (a) MacDowell, D. W. H.; Greenwood, T. D. A Synthesis of 7-Substituted Benzo[b]thiophene Derivatives. J. Hetercycl. Chem. 1965, 2, 44-48.
    • (1965) J. Hetercycl. Chem. , vol.2 , pp. 44-48
    • MacDowell, D.W.H.1    Greenwood, T.D.A.2
  • 39
    • 0024345742 scopus 로고
    • Synthesis and Thromboxane Synthetase Inhibitory Activity of Di- or Tetrahydrobenzo[b]thiophenecarboxylic Acid Derivatives
    • (b) Amemiya, Y.; Terada, A.; Wachi, K.; Miyazawa, H.; Hatakeyama, N.; Matsuda, K.; Oshima, T. Synthesis and Thromboxane Synthetase Inhibitory Activity of Di- or Tetrahydrobenzo[b]thiophenecarboxylic Acid Derivatives. J. Med. Chem. 1989, 32, 1265-1272.
    • (1989) J. Med. Chem. , vol.32 , pp. 1265-1272
    • Amemiya, Y.1    Terada, A.2    Wachi, K.3    Miyazawa, H.4    Hatakeyama, N.5    Matsuda, K.6    Oshima, T.7
  • 40
    • 15144359202 scopus 로고    scopus 로고
    • note
    • Compound 15 was prepared in an analogous fashion to compound 14 via Scheme 4 using methyl 3-iodobenzoate as the starting material.
  • 41
    • 85004704152 scopus 로고
    • New Method for Removing the S-p-Methoxybenzyl and S-tert-Butyl Groups of Cystein Residues with Mercuric Trifluoroacetate
    • Nishimura, O.; Kitada, C.; Fujino, M. New Method for Removing the S-p-Methoxybenzyl and S-tert-Butyl Groups of Cystein Residues with Mercuric Trifluoroacetate. Chem. Pharm. Bull. 1978, 26, 1576-1585.
    • (1978) Chem. Pharm. Bull. , vol.26 , pp. 1576-1585
    • Nishimura, O.1    Kitada, C.2    Fujino, M.3
  • 43
    • 0020658352 scopus 로고
    • Preparation of 2-Amino-4(3H)-oxopyrimido[5,4-b][1,4]thiazines(5-Thiapterins) and Their Evaluation as Cofactors for Phenylalanine Hydroxylase
    • Henrie, R. N.; Lazarus, R. A.; Benkovic, S. J. Preparation of 2-Amino-4(3H)-oxopyrimido[5,4-b][1,4]thiazines(5-Thiapterins) and Their Evaluation as Cofactors for Phenylalanine Hydroxylase. J. Med. Chem. 1983, 26, 559-563.
    • (1983) J. Med. Chem. , vol.26 , pp. 559-563
    • Henrie, R.N.1    Lazarus, R.A.2    Benkovic, S.J.3
  • 44
    • 0024444842 scopus 로고
    • Studies on the Molybdenum Cofactor. Determination of the Structure and Absolute Configuration of Form A
    • Taylor, E. C.; Ray, P. S.; Darwish, I. S.; Johnson, J. L.; Rajagopalan, K. V. Studies on the Molybdenum Cofactor. Determination of the Structure and Absolute Configuration of Form A. J. Am. Chem. Soc. 1989, 111, 7664-7665.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 7664-7665
    • Taylor, E.C.1    Ray, P.S.2    Darwish, I.S.3    Johnson, J.L.4    Rajagopalan, K.V.5
  • 45
    • 0002591784 scopus 로고
    • D-(R)-Glyceraldehyde Acetonide
    • Schmid, C. R.; Bryant, J. D. D-(R)-Glyceraldehyde Acetonide. Org. Synth. 1993, 72, 6-13.
    • (1993) Org. Synth. , vol.72 , pp. 6-13
    • Schmid, C.R.1    Bryant, J.D.2
  • 47
    • 0025030574 scopus 로고
    • Efficient Metal Salt Catalyzed Azidolysis of Epoxides with Sodium Azide in Acetonitrile
    • Chini, M.; Crotti, P.; Macchia, F. Efficient Metal Salt Catalyzed Azidolysis of Epoxides with Sodium Azide in Acetonitrile. Tetrahedron Lett. 1990, 31, 5641-5644.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5641-5644
    • Chini, M.1    Crotti, P.2    Macchia, F.3
  • 48
    • 37049146428 scopus 로고
    • Dithiols. Part IV. The Reaction of Toluene-p-sulphonates and Methanesulphonates with Potassium Thiolacetate: A New Method for the Preparation of Thiols
    • Chapman, J. H.; Owen, L. N. Dithiols. Part IV. The Reaction of Toluene-p-sulphonates and Methanesulphonates with Potassium Thiolacetate: A New Method for the Preparation of Thiols. J. Chem. Soc. 1950, 579-585.
    • (1950) J. Chem. Soc. , pp. 579-585
    • Chapman, J.H.1    Owen, L.N.2
  • 49
    • 0021762396 scopus 로고
    • An Antibody Probe to Determine the Native Species of Glycinamide Ribonucleotide Transformylase in Chicken Liver
    • Young, M., Sammons, R. D., Mueller, W. T., and Benkovic, S. J. An Antibody Probe to Determine the Native Species of Glycinamide Ribonucleotide Transformylase in Chicken Liver. Biochemistry 1984, 23, 3979-3986.
    • (1984) Biochemistry , vol.23 , pp. 3979-3986
    • Young, M.1    Sammons, R.D.2    Mueller, W.T.3    Benkovic, S.J.4
  • 50
    • 0014454095 scopus 로고
    • Kinetics of the Reversible Inhibition of Enzyme-catalyzed Reactions by Tight-binding Inhibitors
    • Morrison, J. F. Kinetics of the Reversible Inhibition of Enzyme-catalyzed Reactions by Tight-binding Inhibitors. Biochem. Biophys. Acta 1969, 185, 269-286.
    • (1969) Biochem. Biophys. Acta , vol.185 , pp. 269-286
    • Morrison, J.F.1
  • 51
    • 15144343419 scopus 로고    scopus 로고
    • Obtained from the American Type Culture Collection
    • Obtained from the American Type Culture Collection.
  • 52
    • 0021174011 scopus 로고
    • Transport of the Antitumor Antibiotic CI-920 into L1210 Leukemia Cells by the Reduced Folate Carrier System
    • Fry, D. W.; Besserer, J. A.; Boritzki, T. J. Transport of the Antitumor Antibiotic CI-920 into L1210 Leukemia Cells by the Reduced Folate Carrier System. Cancer Res. 1984, 44, 3366-3370.
    • (1984) Cancer Res. , vol.44 , pp. 3366-3370
    • Fry, D.W.1    Besserer, J.A.2    Boritzki, T.J.3
  • 53
    • 15144340018 scopus 로고    scopus 로고
    • Obtained from Mediatech, Washington, D.C.
    • Obtained from Mediatech, Washington, D.C.
  • 54
    • 15144338883 scopus 로고    scopus 로고
    • Obtained from Hyclone Laboratories Inc., Logan, UT
    • Obtained from Hyclone Laboratories Inc., Logan, UT.
  • 55
    • 0021061819 scopus 로고
    • Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays
    • Mosmann, T. J. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol. Methods 1983, 65, 55.
    • (1983) J. Immunol. Methods , vol.65 , pp. 55
    • Mosmann, T.J.1
  • 56
    • 0021141123 scopus 로고
    • Measurement of Folylpolyglutamate Synthetase in Mammalian Tissues
    • Moran, R. G.; Colman, P. D. Measurement of Folylpolyglutamate Synthetase in Mammalian Tissues. Anal. Biochem. 1984, 140, 326-342.
    • (1984) Anal. Biochem. , vol.140 , pp. 326-342
    • Moran, R.G.1    Colman, P.D.2
  • 57
    • 0017184389 scopus 로고
    • A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding
    • Bradford, M. M. A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding. Anal. Biochem. 1976, 72, 248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 58
    • 0021770912 scopus 로고
    • Mammalian Folyl Polyglutamate Synthetase: Partial Purification and Properties of the Mouse Liver Enzyme
    • Moran, R. G.; Colman, P. D. Mammalian Folyl Polyglutamate Synthetase: Partial Purification and Properties of the Mouse Liver Enzyme. Biochemistry 1984, 23, 4580-4589.
    • (1984) Biochemistry , vol.23 , pp. 4580-4589
    • Moran, R.G.1    Colman, P.D.2
  • 59
    • 0022979473 scopus 로고
    • The Isolation, Characterization, and Comparison of the Membrane-associated and Soluble Folate-binding Proteins from KB Cells
    • Elwood, P. C.; Kane, M. A.; Portillo, R. M.; Kolhouse, J. F. The Isolation, Characterization, and Comparison of the Membrane-associated and Soluble Folate-binding Proteins From KB Cells. J. Biol. Chem. 1986, 261, 5416-5423.
    • (1986) J. Biol. Chem. , vol.261 , pp. 5416-5423
    • Elwood, P.C.1    Kane, M.A.2    Portillo, R.M.3    Kolhouse, J.F.4
  • 60
    • 0011137678 scopus 로고
    • Mechanisms of Receptor-Mediated Folate and Antifolate Membrane Transport in Cancer Chemotherapy
    • Matherly, L. H. Mechanisms of Receptor-Mediated Folate and Antifolate Membrane Transport in Cancer Chemotherapy. Infect. Dis. Ther. 1995, 17, 453-524.
    • (1995) Infect. Dis. Ther. , vol.17 , pp. 453-524
    • Matherly, L.H.1
  • 61
    • 0025890055 scopus 로고
    • Growth-inhibitory Effects of 5,10-Dideazatetrahydrofolic Acid on Variant murine L1210 and Human CCRF-CEM Leukemia Cells with Different Membrane-Transport Characteristics for (Anti)Folate Compounds
    • (a) Jansen, G.; Westerhof, G. R.; Kathmann, I.; Rijksen, G.; Schomagel, J. H. Growth-inhibitory Effects of 5,10-Dideazatetrahydrofolic Acid on Variant murine L1210 and Human CCRF-CEM Leukemia Cells with Different Membrane-Transport Characteristics for (Anti)Folate Compounds. Cancer Chemother. Pharmacol. 1991, 28, 115-117.
    • (1991) Cancer Chemother. Pharmacol. , vol.28 , pp. 115-117
    • Jansen, G.1    Westerhof, G.R.2    Kathmann, I.3    Rijksen, G.4    Schomagel, J.H.5
  • 63
    • 3142546829 scopus 로고
    • Evaluation of the Mechanism(s) of Inhibition of the Toxicity, but not the Antitumor Activity of Lometrexol (DDATHF) by folic acid
    • Abstract 2432
    • (a) Alati, T.; Shih, C.; Pohland, R. C.; Lantz, R. J.; Grindey, G. B. Evaluation of the Mechanism(s) of Inhibition of the Toxicity, but not the Antitumor Activity of Lometrexol (DDATHF) by folic acid. Proc. Am. Assoc. Cancer Res. 1992, 33, Abstract 2432.
    • (1992) Proc. Am. Assoc. Cancer Res. , vol.33
    • Alati, T.1    Shih, C.2    Pohland, R.C.3    Lantz, R.J.4    Grindey, G.B.5
  • 64
    • 0028267011 scopus 로고
    • A Novel Class of Monoglutamated Antifolates Exhibits Tight-binding Inhibition of Human Glycinamide Ribonucleatide Formyltransferase and Potent Activity against Solid Tumors
    • (b) Leitner, T. A.; Shackelford, K. A.; Gossett, L. S.; Schultz, R. M.; Andis, S. L.; Shih, C.; Grindey, G. B.; Mendelsohn, L. G. A Novel Class of Monoglutamated Antifolates Exhibits Tight-binding Inhibition of Human Glycinamide Ribonucleatide Formyltransferase and Potent Activity against Solid Tumors. Cancer Res. 1994, 54, 1021-1026.
    • (1994) Cancer Res. , vol.54 , pp. 1021-1026
    • Leitner, T.A.1    Shackelford, K.A.2    Gossett, L.S.3    Schultz, R.M.4    Andis, S.L.5    Shih, C.6    Grindey, G.B.7    Mendelsohn, L.G.8
  • 65
    • 15144341419 scopus 로고    scopus 로고
    • note
    • The relationship between mFBP binding affinity and the in vivo toxicity and antitumor activity of compound 19 is currently being studied and will be reported in due course.
  • 70
    • 84986492477 scopus 로고
    • Atomic Charges Derived from Semiempirical Methods
    • (b) Besler, B. H.; Merz, K. M.; Kollman, P. A. Atomic Charges Derived from Semiempirical Methods. J. Comput. Chem. 1990, 11, 431-439.
    • (1990) J. Comput. Chem. , vol.11 , pp. 431-439
    • Besler, B.H.1    Merz, K.M.2    Kollman, P.A.3
  • 72
    • 84988053694 scopus 로고
    • An All Atom Force Field for Simulations of Proteins and Nucleic Acids
    • (b) Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. An All Atom Force Field for Simulations of Proteins and Nucleic Acids. J. Comput. Chem. 1986, 7, 230-252
    • (1986) J. Comput. Chem. , vol.7 , pp. 230-252
    • Weiner, S.J.1    Kollman, P.A.2    Nguyen, D.T.3    Case, D.A.4
  • 73
    • 0344778061 scopus 로고
    • Semianalytical Treatment of Solvation for Molecular Mechanics and Dynamics
    • Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. Semianalytical Treatment of Solvation for Molecular Mechanics and Dynamics. J. Am. Chem. Soc. 1990, 112, 6127-6129.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.C.3    Hendrickson, T.4
  • 74
    • 37049117297 scopus 로고
    • Application of the Hammett Relationship to a Series of Tetrasubstituted Thiophens. Kinetics of Piperidino-debromination of Some 2-Bromo-3-nitro-5-X-thiophens and 2-Bromo-4-methyl-3-nitro-5-X-thiophens in Methanol
    • D. Spinelli, D.; Consiglio, G.; Corrao, A. Application of the Hammett Relationship to a Series of Tetrasubstituted Thiophens. Kinetics of Piperidino-debromination of Some 2-Bromo-3-nitro-5-X-thiophens and 2-Bromo-4-methyl-3-nitro-5-X-thiophens in Methanol. J. Chem. Soc., Perkin Trans. 2 1972, 1866-1869.
    • (1972) J. Chem. Soc., Perkin Trans. 2 , pp. 1866-1869
    • D. Spinelli, D.1    Consiglio, G.2    Corrao, A.3
  • 76
    • 15144353215 scopus 로고    scopus 로고
    • note
    • The coordinates for these three structures will be placed in the PDB as part of a full account of the details of the structure determination which will be submitted for publication elsewhere.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.