메뉴 건너뛰기




Volumn 65, Issue , 2013, Pages 1-11

Synthesis of pyrazolo[1,5-a][1,3,5]triazine derivatives as inhibitors of thymidine phosphorylase

Author keywords

Enzyme inhibitor; Pyrazolo 1,5 a 1,3,5 triazines; Thymidine phosphorylase

Indexed keywords

1,3 DIHYDRO 7 (4 BROMOPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 7 (4 CHLOROPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 7 (4 FLUOROPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 7 (4 METHOXYPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 7 (4 METHYLPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 7 (4 TERT BUTYLPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 7 (4 TRIFLUOROMETHYLPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 7 METHYLPYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 7 PHENYLPYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 7 TERT BUTYLPYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 7 TRIFLUOROMETHYLPYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 (4 BROMOPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 (4 CHLOROPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 (4 ETHOXYPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 (4 FLUOROPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 (4 METHOXYPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 (4 METHYLPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 (4 TERT BUTYLPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 (4 TRIFLUOROMETHYLPHENYL)PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 BROMOPYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 CHLOROPYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 IODOPYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 METHYLPYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO 8 PHENYLPYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; 1,3 DIHYDRO PYRAZOLO[1,5 A][1,3,5]TRIAZIN 2 THIOXO 4 ONE; GLYCOSYLTRANSFERASE INHIBITOR; PYRAZOLONE DERIVATIVE; THYMIDINE PHOSPHORYLASE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84884223080     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.03.063     Document Type: Article
Times cited : (53)

References (35)
  • 1
    • 0035427998 scopus 로고    scopus 로고
    • Thymidine phosphorylase: A two-face janus in anticancer chemotherapy
    • F. Focher, S. Spadari, Thymidine phosphorylase: a two-face janus in anticancer chemotherapy, Curr. Cancer Drug Targets 1 (2001) 141-153. (Pubitemid 33772392)
    • (2001) Current Cancer Drug Targets , vol.1 , Issue.2 , pp. 141-153
    • Pocher, F.1    Spadari, S.2
  • 2
    • 0021019292 scopus 로고
    • Phosphorolysis of (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) and other 5-substituted-2'-deoxyuridines by purified human thymidine phosphorylase and intact blood platelets
    • DOI 10.1016/0006-2952(83)90307-6
    • C. Desgranges, G. Razaka, M. Rabaud, H. Bricaud, J. Balzarini, E. de Clercq, Phosphorolysis of (E)-5-(2-bromovinyl)-2′-deoxyuridine (BVDU) and other 5-substituted-2′-deoxyuridines by purified human thymidine phosphorylase and intact blood platelets, Biochem. Pharmacol. 32 (1983) 3583-3590. (Pubitemid 14205368)
    • (1983) Biochemical Pharmacology , vol.32 , Issue.23 , pp. 3583-3590
    • Desgranges, C.1    Razaka, G.2    Rabaud, M.3
  • 3
    • 84965916832 scopus 로고
    • The rarity of liver toxicity in patients treated with coumarin (1,2-benzopyrone)
    • D. Cox, R. O'Kennedy, R.D. Thornes, The rarity of liver toxicity in patients treated with coumarin (1,2-benzopyrone), Hum. Exp. Toxicol. 8 (1989) 501-506. (Pubitemid 19271831)
    • (1989) Human Toxicology , vol.8 , Issue.6 , pp. 501-506
    • Cox, D.1    O'Kennedy, R.2    Thornes, R.D.3
  • 7
    • 0034657004 scopus 로고    scopus 로고
    • Structure and activity of specific inhibitors of thymidine phosphorylase to potentiate the function of antitumor 2'-deoxyribonucleosides
    • DOI 10.1016/S0006-2952(00)00253-7, PII S0006295200002537
    • M. Fukushima, N. Suzuki, T. Emura, S. Yano, H. Kazuno, Y. Tada, Y. Yamada, T. Asao, Structure and activity of specific inhibitors of thymidine phosphorylase to potentiate the function of antitumor 2′- deoxyribonucleosides, Biochem. Pharmacol. 59 (2000) 1227-1236. (Pubitemid 30157885)
    • (2000) Biochemical Pharmacology , vol.59 , Issue.10 , pp. 1227-1236
    • Fukushima, M.1    Suzuki, N.2    Emura, T.3    Yano, S.4    Kazuno, H.5    Tada, Y.6    Yamada, Y.7    Asao, T.8
  • 8
    • 2942608177 scopus 로고    scopus 로고
    • Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 2: Optimization of inhibitors of human thymidine phosphorylase and their selectivity with uridine phosphorylase
    • DOI 10.1016/j.bmc.2004.04.046, PII S0968089604003396
    • S. Yano, H. Kazuno, T. Sato, N. Suzuki, T. Emura, K. Wierzba, J.-i. Yamashita, Y. Tada, Y. Yamada, M. Fukushima, T. Asao, Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 2: optimization of inhibitors of human thymidine phosphorylase and their selectivity with uridine phosphorylase, Bioorg. Med. Chem. Lett. 12 (2004) 3443-3450. (Pubitemid 38746848)
    • (2004) Bioorganic and Medicinal Chemistry , vol.12 , Issue.13 , pp. 3443-3450
    • Yano, S.1    Kazuno, H.2    Sato, T.3    Suzuki, N.4    Emura, T.5    Wierzba, K.6    Yamashita, J.-I.7    Tada, Y.8    Yamada, Y.9    Fukushima, M.10    Asao, T.11
  • 10
    • 0034624754 scopus 로고    scopus 로고
    • Design, synthesis, and enzymatic evaluation of multisubstrate analogue inhibitors of Escherichia coli thymidine phosphorylase
    • DOI 10.1021/jm9911377
    • A. Esteban-Gamboa, J. Balzarini, R. Esnouf, E. De Clercq, M.-J. Camarasa, M.-J. Pérez-Pérez, Design, synthesis, and enzymatic evaluation of multi-substrate analogue inhibitors of Escherichia coli thymidine phosphorylase, J. Med. Chem. 43 (2000) 971-983. (Pubitemid 30152302)
    • (2000) Journal of Medicinal Chemistry , vol.43 , Issue.5 , pp. 971-983
    • Esteban-Gamboa, A.1    Balzarini, J.2    Esnouf, R.3    De Clercq, E.4    Camarasa, M.-J.5    Perez-Perez, M.-J.6
  • 12
    • 84858742379 scopus 로고    scopus 로고
    • Fluorophosphonylated nucleoside derivatives as new series of thymidine phosphorylase multi-substrate inhibitors
    • S.A. Diab, S.C. De, M. Muzard, R. Plantier-Royon, E. Pfund, T. Lequeux, Fluorophosphonylated nucleoside derivatives as new series of thymidine phosphorylase multi-substrate inhibitors, J. Med. Chem. 55 (2012) 2758-2768.
    • (2012) J. Med. Chem. , vol.55 , pp. 2758-2768
    • Diab, S.A.1    De, S.C.2    Muzard, M.3    Plantier-Royon, R.4    Pfund, E.5    Lequeux, T.6
  • 13
    • 51349150681 scopus 로고    scopus 로고
    • Pyrazolo[1,5-a][1,3,5]triazines(5-aza-9-deazapurines): Synthesis and biological activity
    • A.V. Dolzhenko, A.V. Dolzhenko, W.-K. Chui, Pyrazolo[1,5-a][1,3,5] triazines(5-aza-9-deazapurines): synthesis and biological activity, Heterocycles 75 (2008) 1575-1622.
    • (2008) Heterocycles , vol.75 , pp. 1575-1622
    • Dolzhenko, A.V.1    Dolzhenko, A.V.2    Chui, W.-K.3
  • 14
    • 0022178771 scopus 로고
    • Purine analog inhibitors of xanthine oxidase - Structure activity relationships and proposed binding of the molybdenum cofactor
    • R.K. Robins, G.R. Revankar, D.E. O'Brien, R.H. Springer, T. Novinson, A. Albert, K. Senga, J.P. Miller, D.G. Streeter, Purine analog inhibitors of xanthine oxidase - structure activity relationships and proposed binding of the molybdenum cofactor, J. Heterocycl. 22 (1985) 601-634. (Pubitemid 16249683)
    • (1985) Journal of Heterocyclic Chemistry , vol.22 , Issue.3 , pp. 601-634
    • Robins, R.K.1    Revankar, G.R.2    O'Brien, D.E.3
  • 15
    • 34347388601 scopus 로고    scopus 로고
    • Structure-based design, synthesis, and study of pyrazolo[1,5-a][1,3,5] triazine derivatives as potent inhibitors of protein kinase CK2
    • DOI 10.1016/j.bmcl.2007.05.041, PII S0960894X07006075
    • Z. Nie, C. Perretta, P. Erickson, S. Margosiak, R. Almassy, J. Lu, A. Averill, K.M. Yager, S. Chu, Structure-based design, synthesis, and study of pyrazolo [1,5-a][1,3,5]triazine derivatives as potent inhibitors of protein kinase CK2, Bioorg. Med. Chem. Lett. 17 (2007) 4191-4195. (Pubitemid 47021399)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.15 , pp. 4191-4195
    • Nie, Z.1    Perretta, C.2    Erickson, P.3    Margosiak, S.4    Almassy, R.5    Lu, J.6    Averill, A.7    Yager, K.M.8    Chu, S.9
  • 18
    • 0020069536 scopus 로고
    • Synthesis and enzymic activity of various substituted pyrazolo[1,5-a]-1,3,5-triazines as adenosine cyclic 3',5'-phosphate phosphodiesterase inhibitors
    • K. Senga, D.E. O'Brien, M.B. Scholten, T. Novinson, J.P. Miller, R.K. Robins, Synthesis and enzymic activity of various substituted pyrazolo[1,5-a]-1,3,5-triazines as adenosine cyclic 3′,5′-phosphate phosphodiesterase inhibitors, J. Med. Chem. 25 (1982) 243-249. (Pubitemid 12158024)
    • (1982) Journal of Medicinal Chemistry , vol.25 , Issue.3 , pp. 243-249
    • Senga, K.1    O'Brien, D.E.2    Scholten, M.B.3
  • 22
    • 0342313482 scopus 로고    scopus 로고
    • Design, synthesis, and structure - Activity relationship studies of ATP analogues as DNA gyrase inhibitors
    • DOI 10.1016/S0960-894X(00)00109-8, PII S0960894X00001098
    • T. Lübbers, P. Angehrn, H. Gmünder, S. Herzig, J. Kulhanek, Design, synthesis, and structure-eactivity relationship studies of ATP analogues as DNA gyrase inhibitors, Bioorg. Med. Chem. Lett. 10 (2000) 821-826. (Pubitemid 30215892)
    • (2000) Bioorganic and Medicinal Chemistry Letters , vol.10 , Issue.8 , pp. 821-826
    • Lubbers, T.1    Angehrn, P.2    Gmunder, H.3    Herzig, S.4    Kulhanek, J.5
  • 25
    • 40949153952 scopus 로고    scopus 로고
    • Studies with enaminonitriles: Synthesis and chemical reactivity of 2-phenyl-3-piperidin-1-yl acrylonitrile under microwave heating
    • A.M. Salaheldin, M.K. Alphy, Studies with enaminonitriles: synthesis and chemical reactivity of 2-phenyl-3-piperidin-1-yl acrylonitrile under microwave heating, J. Heterocycl. Chem. 45 (2008) 307-310. (Pubitemid 351415370)
    • (2008) Journal of Heterocyclic Chemistry , vol.45 , Issue.2 , pp. 307-310
    • Salaheldin, A.M.1    Alphy, M.K.2
  • 26
    • 0008767331 scopus 로고
    • Synthesis of some new fluorine-containing 5-amino-1,3-disubstituted pyrazoles and 1H-pyrazolo[3,4-b]pyridines
    • K.C. Joshi, V.N. Pathak, U. Garg, Synthesis of some new fluorine-containing 5-amino-1,3-disubstituted pyrazoles and 1H-pyrazolo[3,4-b] pyridines, J. Heterocycl. Chem. 16 (1979) 1141-1145.
    • (1979) J. Heterocycl. Chem. , vol.16 , pp. 1141-1145
    • Joshi, K.C.1    Pathak, V.N.2    Garg, U.3
  • 27
    • 84980230200 scopus 로고
    • Heterocyclizations. IX. Preparation of pyrazolo-, triazolo-, oxazolo-, and thiazolo-s-triazines with a bridgehead nitrogen and of an isopurine N-carboxylic ester
    • L. Capuano, H.J. Schrepfer, Heterocyclizations. IX. Preparation of pyrazolo-, triazolo-, oxazolo-, and thiazolo-s-triazines with a bridgehead nitrogen and of an isopurine N-carboxylic ester, Chem. Ber. 104 (1971) 3039-3047.
    • (1971) Chem. Ber. , vol.104 , pp. 3039-3047
    • Capuano, L.1    Schrepfer, H.J.2
  • 28
    • 0034808462 scopus 로고    scopus 로고
    • Reactions of chlorocarbonyl isocyanate with 5-aminopyrazoles and active methylene nitriles: A novel synthesis of pyrazolo[1,5-a]-1,3,5-triazines and barbiturates
    • DOI 10.1081/SCC-100106205
    • G.H. Elgemeie, S.R. El-Ezbawy, H.A. Ali, Reactions of chlorocarbonyl isocyanate with 5-aminopyrazoles and active methylene nitriles: a novel synthesis of pyrazolo[1,5-a]-1,3,5-triazines and barbiturates, Synth. Commun. 31 (2001) 3459-3467. (Pubitemid 32916774)
    • (2001) Synthetic Communications , vol.31 , Issue.22 , pp. 3459-3467
    • Eigemeie, G.H.1    El-Ezbawy, S.R.2    Ali, H.A.3
  • 29
    • 84980300474 scopus 로고
    • Synthesis of 1,3-dialkylpyrazolo [1,5-a]-1,3,5-triazine-2,4-diones. Isomers of 1,3-dialkylxanthines
    • K. Senga, J. Kobe, R.K. Robins, D.E. O'Brien, Synthesis of 1,3-dialkylpyrazolo [1,5-a]-1,3,5-triazine-2,4-diones. Isomers of 1,3-dialkylxanthines, J. Hetero cycl. Chem. 12 (1975) 893-898.
    • (1975) J. Hetero Cycl. Chem. , vol.12 , pp. 893-898
    • Senga, K.1    Kobe, J.2    Robins, R.K.3    O'Brien, D.E.4
  • 32
    • 0035504659 scopus 로고    scopus 로고
    • Novel 6-substituted uracil analogs as inhibitors of the angiogenic actions of thymidine phosphorylase
    • DOI 10.1016/S0006-2952(01)00783-3, PII S0006295201007833
    • R.S. Klein, M. Lenzi, T.H. Lim, K.A. Hotchkiss, P. Wilson, E.L. Schwartz, Novel 6-substituted uracil analogs as inhibitors of the angiogenic actions of thymidine phosphorylase, Biochem. Pharmacol. 62 (2001) 1257-1263. (Pubitemid 33055630)
    • (2001) Biochemical Pharmacology , vol.62 , Issue.9 , pp. 1257-1263
    • Klein, R.S.1    Lenzi, M.2    Lim, T.H.3    Hotchkiss, K.A.4    Wilson, P.5    Schwartz, E.L.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.