메뉴 건너뛰기




Volumn 47, Issue 4, 2004, Pages 1044-1050

Inhibition of Adenosine Deaminase by Novel 5:7 Fused Heterocycles Containing the Imidazo[4,5-e][1,2,4]triazepine Ring System: A Structure-Activity Relationship Study

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROIMIDAZOLE; 7,8 DIHYDRO 1 (4 METHOXYBENZYL) 8 (2 METHOXYETHOXY) 6H 6,7 DIMETHYLIMIDAZO[4,5 E][1,2,4]TRIAZEPINE; 7,8 DIHYDRO 1 (4 METHOXYBENZYL) 8 (3 METHYLBENZYLOXY) 6H 6,7 DIMETHYLIMIDAZO[4,5 E][1,2,4]TRIAZEPINE; 7,8 DIHYDRO 1 (4 METHOXYBENZYL) 8 (4 METHOXYBENZYLOXY) 6H 6,7 DIMETHYLIMIDAZO[4,5 E][1,2,4]TRIAZEPINE; 7,8 DIHYDRO 1 [4 METHOXYBENZYL] 6H 6,7 DIMETHYL 8 PROPOXYIMIDAZO[4,5 E][1,2,4]TRIAZEPINE; 7,8 DIHYDRO 8 ETHOXY 1 (4 METHOXYBENZYL) 6H 6,7 DIMETHYLIMIDAZO[4,5 E][1,2,4]TRIAZEPINE; 7,8 DIHYDRO 8 ISOPROPOXY 1 (4 METHOXYBENZYL) 6H 6,7 DIMETHYLIMIDAZO[4,5 E][1,2,4]TRIAZEPINE; 7,8 DIHYDRO 8 METHOXY 1 (4 METHOXYBENZYL) 6H 6,7 DIMETHYLIMIDAZO[4,5 E][1,2,4]TRIAZEPINE; 8 BUTOXY 7,8 DIHYDRO 1 (4 METHOXYBENZYL) 6H 6,7 DIMETHYLIMIDAZO[4,5 E][1,2,4]TRIAZEPINE; ADENOSINE DEAMINASE; ADENOSINE DEAMINASE INHIBITOR; ALCOHOL; COFORMYCIN; IMIDAZO[4,5 E][1,2,4]TRIAZEPINE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0842282711     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0304257     Document Type: Article
Times cited : (26)

References (48)
  • 2
    • 0036819746 scopus 로고    scopus 로고
    • Advances in gene therapy for ADA-deficient SCID
    • Aiuti, A. Advances in gene therapy for ADA-deficient SCID. Curr. Opin. Mol. Therapeut. 2002, 4, 515-522.
    • (2002) Curr. Opin. Mol. Therapeut. , vol.4 , pp. 515-522
    • Aiuti, A.1
  • 9
    • 0016177627 scopus 로고
    • A novel adenosine and ara-A deaminase Inhibitor, (R)-3-(2-deoxy-β -D-erythropentofuranosyl)-3,6,7,8-tetrahydroimidazo-[4,5-d]diazepin-8-ol
    • Woo, P. W. K.; Dion, H. W.; Lange, S. M.; Dahl, L. F.; Durham, L. J. A novel adenosine and ara-A deaminase Inhibitor, (R)-3-(2-deoxy-β -D-erythropentofuranosyl)-3,6,7,8-tetrahydroimidazo-[4,5-d]diazepin-8-ol. J. Heterocycl. Chem. 1974, 11, 641-643.
    • (1974) J. Heterocycl. Chem. , vol.11 , pp. 641-643
    • Woo, P.W.K.1    Dion, H.W.2    Lange, S.M.3    Dahl, L.F.4    Durham, L.J.5
  • 10
    • 0018616744 scopus 로고
    • A total synthesis of pentostatin, the potent inhibitor of adenosine deaminase
    • Baker, D. C.; Putt, S. R. A total synthesis of pentostatin, the potent inhibitor of adenosine deaminase. J. Am. Chem. Soc. 1979, 101, 6127-6128.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 6127-6128
    • Baker, D.C.1    Putt, S.R.2
  • 11
    • 0020549522 scopus 로고
    • Studies related to the total synthesis of pentostatin. Approaches to the synthesis of (8R)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol and N-3 alkyl congeners
    • Baker, D. C.; Putt, S. R.; Showalter, H. D. H. Studies related to the total synthesis of pentostatin. Approaches to the synthesis of (8R)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol and N-3 alkyl congeners. J. Heterocycl. Chem. 1983, 20, 629-634.
    • (1983) J. Heterocycl. Chem. , vol.20 , pp. 629-634
    • Baker, D.C.1    Putt, S.R.2    Showalter, H.D.H.3
  • 12
    • 0020413594 scopus 로고
    • Total synthesis of (8R)-3-(2-deoxy-β -D-erythropentofuranosyl-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (pentostatin), the potent inhibitor of adenosine deaminase
    • Chan, E.; Putt, S. R.; Showalter, H. D. H.; Baker, D. C. Total synthesis of (8R)-3-(2-deoxy-β -D-erythropentofuranosyl-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (pentostatin), the potent inhibitor of adenosine deaminase. J. Org. Chem. 1982, 47, 3457-3464.
    • (1982) J. Org. Chem. , vol.47 , pp. 3457-3464
    • Chan, E.1    Putt, S.R.2    Showalter, H.D.H.3    Baker, D.C.4
  • 13
    • 0021354862 scopus 로고
    • Evidence for the conversion of adenosine to 2′-deoxycoformycin by streptomyces antibiotics
    • Hanvey, J. C.; Hardman, J. K.; Suhadolnik, R. J.; Baker, D. C. Evidence for the conversion of adenosine to 2′-deoxycoformycin by streptomyces antibiotics. Biochemistry 1984, 23, 904-907.
    • (1984) Biochemistry , vol.23 , pp. 904-907
    • Hanvey, J.C.1    Hardman, J.K.2    Suhadolnik, R.J.3    Baker, D.C.4
  • 14
    • 0023191216 scopus 로고
    • Biosynthesis of 2′-deoxycoformycin: Evidence for ring-expansion of the adenine moiety of adenosine to a tetrahydroimidazo[4,5-d][1,3]diazepine system
    • Hanvey, J. C.; Hawkins, E. S.; Tunac, J. B.; Dechter, J. J.; Baker, D. C.; Suhadolnik, R. J. Biosynthesis of 2′-deoxycoformycin: Evidence for ring-expansion of the adenine moiety of adenosine to a tetrahydroimidazo[4,5-d][1,3]diazepine system. Biochemistry 1987, 26, 5636-5641.
    • (1987) Biochemistry , vol.26 , pp. 5636-5641
    • Hanvey, J.C.1    Hawkins, E.S.2    Tunac, J.B.3    Dechter, J.J.4    Baker, D.C.5    Suhadolnik, R.J.6
  • 16
    • 0017662542 scopus 로고
    • Influence of substituent ribose on transition state affinity in reactions catalyzed by adenosine deaminase
    • Wolfenden, R.; Wentworth, D. F.; Mitchell, G. N. Influence of substituent ribose on transition state affinity in reactions catalyzed by adenosine deaminase. Biochemistry 1977, 16, 5071-5077.
    • (1977) Biochemistry , vol.16 , pp. 5071-5077
    • Wolfenden, R.1    Wentworth, D.F.2    Mitchell, G.N.3
  • 17
    • 0022497287 scopus 로고
    • Transition-state stabilization by adenosine deaminase: Structural studies of its inhibitory complex with deoxycoformycin
    • Frick, L.; Wolfenden, R.; Smal, E.; Baker, D. C. Transition-state stabilization by adenosine deaminase: Structural studies of its inhibitory complex with deoxycoformycin. Biochemistry 1986, 25, 1616-1621.
    • (1986) Biochemistry , vol.25 , pp. 1616-1621
    • Frick, L.1    Wolfenden, R.2    Smal, E.3    Baker, D.C.4
  • 18
    • 0024974086 scopus 로고
    • Contribution of a single hydroxyl group to transition-state discrimination by adenosine deaminase: Evidence for an "entropy trap" mechanism
    • Kati, W. M.; Wolfenden, R. Contribution of a single hydroxyl group to transition-state discrimination by adenosine deaminase: Evidence for an "entropy trap" mechanism. Biochemistry 1989, 28, 7919-7927.
    • (1989) Biochemistry , vol.28 , pp. 7919-7927
    • Kati, W.M.1    Wolfenden, R.2
  • 19
    • 0026499905 scopus 로고
    • The rate of formation of transition-state analogues in the active site of adenosine deaminase is encounter-controlled: Implications for the mechanism
    • Kurz, L. C.; Moix, L.; Riley, M. C.; Frieden, C. The rate of formation of transition-state analogues in the active site of adenosine deaminase is encounter-controlled: Implications for the mechanism. Biochemistry 1992, 31, 39-48.
    • (1992) Biochemistry , vol.31 , pp. 39-48
    • Kurz, L.C.1    Moix, L.2    Riley, M.C.3    Frieden, C.4
  • 20
    • 0017360775 scopus 로고
    • Tight-binding inhibitors. IV. Inhibition of adenosine deaminases by various inhibitors
    • Agarwal, R. P.; Spector, T.; Parks, R. E., Jr. Tight-binding inhibitors. IV. Inhibition of adenosine deaminases by various inhibitors. Biochem. Pharmacol. 1977, 26, 359-367.
    • (1977) Biochem. Pharmacol. , vol.26 , pp. 359-367
    • Agarwal, R.P.1    Spector, T.2    Parks Jr., R.E.3
  • 21
    • 0016733786 scopus 로고
    • Adenosine deaminase activity in leukemia
    • Smyth, J. F.; Harrap, K. R. Adenosine deaminase activity in leukemia. Br. J. Cancer 1975, 31, 544-549.
    • (1975) Br. J. Cancer , vol.31 , pp. 544-549
    • Smyth, J.F.1    Harrap, K.R.2
  • 22
    • 0018088826 scopus 로고
    • Correlation of adenosine deaminase activity with cell surface markers in acute lymphoblastic leukemia
    • Smyth, J. F.; Poplack, D. G.; Holiman, B. J.; Leventhal, B. G.; Yarbro, G. Correlation of adenosine deaminase activity with cell surface markers in acute lymphoblastic leukemia. J. Clin. Invest. 1978, 62, 710-712.
    • (1978) J. Clin. Invest. , vol.62 , pp. 710-712
    • Smyth, J.F.1    Poplack, D.G.2    Holiman, B.J.3    Leventhal, B.G.4    Yarbro, G.5
  • 24
    • 0017282589 scopus 로고
    • Enhancement of the antitumor activity of arabinofuranosyladenine by 2′-deoxycoformycin
    • LePage, G. A.; Worth, L. S.; Kimball, A. P. Enhancement of the antitumor activity of arabinofuranosyladenine by 2′-deoxycoformycin. Cancer Res. 1976, 36, 1481-1485.
    • (1976) Cancer Res. , vol.36 , pp. 1481-1485
    • LePage, G.A.1    Worth, L.S.2    Kimball, A.P.3
  • 26
    • 0017155480 scopus 로고
    • Enhancement of the biological activity of cordycepin (3′ -deoxyadenosine) by the adenosine deaminase inhibitor 2′-deoxycoformycin
    • Johns, D. G.; Adamson, R. H. Enhancement of the biological activity of cordycepin (3′-deoxyadenosine) by the adenosine deaminase inhibitor 2′-deoxycoformycin. Biochem. Pharmacol. 1976, 25, 1441-1444.
    • (1976) Biochem. Pharmacol. , vol.25 , pp. 1441-1444
    • Johns, D.G.1    Adamson, R.H.2
  • 28
    • 0019521591 scopus 로고
    • Clinical pharmacology of deoxycoformycin
    • Major, P. P.; Agarwal, R. P.; Kufe, D. W. Clinical pharmacology of deoxycoformycin. Blood 1981, 58, 91-96.
    • (1981) Blood , vol.58 , pp. 91-96
    • Major, P.P.1    Agarwal, R.P.2    Kufe, D.W.3
  • 29
    • 0019512909 scopus 로고
    • The biochemical and clinical consequences of 2′-deoxycoformycin in refractory lymphoproliferative malignancy
    • Grever, M. R.; Siaw, M. F.; Jacob, W. F.; Niedhart, J. A.; Miser, J. S.; Coleman, M. S.; Hutton, J. J.; Balcerzak, S. P. The biochemical and clinical consequences of 2′-deoxycoformycin in refractory lymphoproliferative malignancy. Blood 1981, 57, 406-417.
    • (1981) Blood , vol.57 , pp. 406-417
    • Grever, M.R.1    Siaw, M.F.2    Jacob, W.F.3    Niedhart, J.A.4    Miser, J.S.5    Coleman, M.S.6    Hutton, J.J.7    Balcerzak, S.P.8
  • 31
    • 0020605742 scopus 로고
    • A novel approach towards the synthesis of the 3,4,5-trihydro-1,3-diazepin-5-ol ring structure
    • Acevedo, O. L.; Krawczyk, S. H.; Townsend, L. B. A novel approach towards the synthesis of the 3,4,5-trihydro-1,3-diazepin-5-ol ring structure. Tetrahederon Lett. 1983, 24, 4789-4792.
    • (1983) Tetrahederon Lett. , vol.24 , pp. 4789-4792
    • Acevedo, O.L.1    Krawczyk, S.H.2    Townsend, L.B.3
  • 32
    • 84986533259 scopus 로고
    • Synthesis of the new ring system, pyrazolo[3,4-d][1,3]diazepines
    • Acevedo, O. L.; Krawczyk, S. H.; Townsend, L. B. Synthesis of the new ring system, pyrazolo[3,4-d][1,3]diazepines. J. Heterocycl. Chem. 1985, 22, 349-352.
    • (1985) J. Heterocycl. Chem. , vol.22 , pp. 349-352
    • Acevedo, O.L.1    Krawczyk, S.H.2    Townsend, L.B.3
  • 33
    • 0022579422 scopus 로고
    • Total synthesis of (4R)- and (4S)-5,6-dihydro-1-β -D-ribofuranosyl-4H-pyrazolo-[3,4-d][1,3]diazepin-4-ol and (8R)- and (8S)-7,8-dihydro-3-β-D-ribofuranosyl-6H-v-triazolo[4,5-d][1,3] diazepin-8-ol: Two heterocyclic analogues of the nucleoside antibiotic coformycin
    • Acevedo, O. L.; Krawczyk, S. H.; Townsend, L. B. Total synthesis of (4R)- and (4S)-5,6-dihydro-1-β -D-ribofuranosyl-4H-pyrazolo-[3,4-d][1,3]diazepin-4-ol and (8R)- and (8S)-7,8-dihydro-3-β-D-ribofuranosyl-6H-v-triazolo[4,5-d][1,3] diazepin-8-ol: Two heterocyclic analogues of the nucleoside antibiotic coformycin. J. Org. Chem. 1986, 51, 1050-1058.
    • (1986) J. Org. Chem. , vol.51 , pp. 1050-1058
    • Acevedo, O.L.1    Krawczyk, S.H.2    Townsend, L.B.3
  • 34
    • 0030867033 scopus 로고    scopus 로고
    • Irreversible, tight-binding inhibition of adenosine deaminase by coformycins: Inhibitor structural features that contribute to the mode of inhibition
    • Hong, M.; Hosmane, R. S. Irreversible, tight-binding inhibition of adenosine deaminase by coformycins: Inhibitor structural features that contribute to the mode of inhibition. Nucleosides Nucleotides 1997, 16, 1053-1057.
    • (1997) Nucleosides Nucleotides. , vol.16 , pp. 1053-1057
    • Hong, M.1    Hosmane, R.S.2
  • 35
    • 0031561116 scopus 로고    scopus 로고
    • How important is the N-3 sugar moiety in the tight-binding interaction of coformycin with adenosine deaminase?
    • Hosmane, R. S.; Hong, M. How important is the N-3 sugar moiety in the tight-binding interaction of coformycin with adenosine deaminase? Biochem. Biophys. Res. Commun. 1997, 236, 88-93.
    • (1997) Biochem. Biophys. Res. Commun. , vol.236 , pp. 88-93
    • Hosmane, R.S.1    Hong, M.2
  • 36
    • 0032499630 scopus 로고    scopus 로고
    • Complexes of adenosine deaminase with two potent inhibitors: X-ray structures in four Independent molecules at pH of maximum activity
    • Wang, Z.; Quiocho, F. A. Complexes of adenosine deaminase with two potent inhibitors: X-ray structures in four Independent molecules at pH of maximum activity. Biochemistry 1998, 37, 8314-8324.
    • (1998) Biochemistry , vol.37 , pp. 8314-8324
    • Wang, Z.1    Quiocho, F.A.2
  • 37
    • 0030020948 scopus 로고    scopus 로고
    • Theoretical study of inhibition of adenosine deaminase by (8R) -coformycin and (8R)-deoxycoformycin
    • Marrone, T. J.; Straatsma, T. P.; Briggs, J. M.; Wilson, D. K.; Quiocho, F. A.; McCammon, J. A. Theoretical study of inhibition of adenosine deaminase by (8R)-coformycin and (8R)-deoxycoformycin. J. Med. Chem. 1996, 39, 277-284.
    • (1996) J. Med. Chem. , vol.39 , pp. 277-284
    • Marrone, T.J.1    Straatsma, T.P.2    Briggs, J.M.3    Wilson, D.K.4    Quiocho, F.A.5    McCammon, J.A.6
  • 38
    • 0030061575 scopus 로고    scopus 로고
    • Inhibition of adenosine deaminase activity of aortic endothelial cells by selected flavonoids
    • Melzig, M. F. Inhibition of adenosine deaminase activity of aortic endothelial cells by selected flavonoids. Planta Medica 1996, 62, 20-21.
    • (1996) Planta Medica , vol.62 , pp. 20-21
    • Melzig, M.F.1
  • 39
    • 0026465456 scopus 로고
    • In vitro inhibition of adenosine deaminase by flavonoids and related compounds. New insight into the mechanism of action of plant phenolics
    • Koch, H. P.; Jager, W.; Groh, U.; Plank, G. In vitro inhibition of adenosine deaminase by flavonoids and related compounds. New insight into the mechanism of action of plant phenolics. Methods Find. Exp. Clin. Pharmacol. 1992, 14, 413-417.
    • (1992) Methods Find. Exp. Clin. Pharmacol. , vol.14 , pp. 413-417
    • Koch, H.P.1    Jager, W.2    Groh, U.3    Plank, G.4
  • 40
    • 0028265942 scopus 로고
    • In vitro inhibition of adenosine deaminase by a group of steroid and triterpenoid compounds
    • Koch, H. P.; Aichinger, A.; Bohne, B.; Plank, G. In vitro inhibition of adenosine deaminase by a group of steroid and triterpenoid compounds. Phytother. Res. 1994, 8, 109-111.
    • (1994) Phytother. Res. , vol.8 , pp. 109-111
    • Koch, H.P.1    Aichinger, A.2    Bohne, B.3    Plank, G.4
  • 41
    • 0026530495 scopus 로고
    • Garlic and onion extracts. In vitro inhibition of adenosine deaminase
    • Koch, H. P.; Jager, W.; Hysek, J.; Korpert, B. Garlic and onion extracts. In vitro inhibition of adenosine deaminase. Phytother. Res. 1992, 6, 50-52.
    • (1992) Phytother. Res. , vol.6 , pp. 50-52
    • Koch, H.P.1    Jager, W.2    Hysek, J.3    Korpert, B.4
  • 42
    • 0021986937 scopus 로고
    • Trazodone, a nontricyclic antidepressant, is an inhibitor of adenosine deaminase
    • Sheid, B. Trazodone, a nontricyclic antidepressant, is an inhibitor of adenosine deaminase. Res. Commun. Chem. Pathol. Pharmacol. 1985, 47, 149-152.
    • (1985) Res. Commun. Chem. Pathol. Pharmacol. , vol.47 , pp. 149-152
    • Sheid, B.1
  • 43
    • 0011510154 scopus 로고
    • Chemistry of the 5:7-fused heteroaromatic systems: A novel rearrangement involving the imidazo-[4,5-e][1,3,4]triazepine and pyrazolo[3,4-e][1,3,4]triazepine systems
    • Hosmane, R. S.; Lim, B. B. Chemistry of the 5:7-fused heteroaromatic systems: A novel rearrangement involving the imidazo-[4,5-e][1,3,4]triazepine and pyrazolo[3,4-e][1,3,4]triazepine systems. Heterocycles 1988, 27, 31-34.
    • (1988) Heterocycles , vol.27 , pp. 31-34
    • Hosmane, R.S.1    Lim, B.B.2
  • 44
    • 0023865496 scopus 로고
    • A novel method for the synthesis of 6-(β-methyl)hydrazinopurine and 4-(β-methyl)hydrazinopyrazolo[3,4-d]pyrimidine
    • Hosmane, R. S.; Lim, B. B. A novel method for the synthesis of 6-(β-methyl)hydrazinopurine and 4-(β -methyl)hydrazinopyrazolo[3,4-d]pyrimidine. Synthesis 1988, 242-244.
    • (1988) Synthesis , pp. 242-244
    • Hosmane, R.S.1    Lim, B.B.2
  • 45
    • 0000170577 scopus 로고
    • Rearrangements in heterocyclic synthesis: A novel translocation of an (N-amino-N-methyl)formamidine side-chain to the vinylogous nitrile function
    • Hosmane, R. S.; Lim, B. B.; Burnett, F. N. Rearrangements in heterocyclic synthesis: A novel translocation of an (N-amino-N-methyl)formamidine side-chain to the vinylogous nitrile function. J. Org. Chem. 1988, 53, 382-386.
    • (1988) J. Org. Chem. , vol.53 , pp. 382-386
    • Hosmane, R.S.1    Lim, B.B.2    Burnett, F.N.3
  • 46
    • 0001647347 scopus 로고
    • Rearrangements in heterocyclic synthesis. 2. Novel transformations of 2-aminonicotino- and anthranilonitriles
    • Hosmane, R. S.; Lim, B. B.; Summers, M. F.; Siriwardane, U.; Hosmane, N. S.; Chu, S. C. Rearrangements in heterocyclic synthesis. 2. Novel transformations of 2-aminonicotino- and anthranilonitriles. J. Org. Chem. 1988, 53, 5309-5315.
    • (1988) J. Org. Chem. , vol.53 , pp. 5309-5315
    • Hosmane, R.S.1    Lim, B.B.2    Summers, M.F.3    Siriwardane, U.4    Hosmane, N.S.5    Chu, S.C.6
  • 47
    • 21844521836 scopus 로고
    • Synthesis of some new imidazole derivatives
    • Ostrowski, S. Synthesis of some new imidazole derivatives. Polish J. Chem. 1994, 68, 2237-2247.
    • (1994) Polish J. Chem. , vol.68 , pp. 2237-2247
    • Ostrowski, S.1
  • 48
    • 0842322595 scopus 로고    scopus 로고
    • note
    • Molecular modeling studies were performed using Insight/DiscoverTM software package, available from Molecular Simulations, Inc., San Diego, California.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.