메뉴 건너뛰기




Volumn 39, Issue 2, 1996, Pages 494-502

Dual metalloprotease inhibitors. 6. Incorporation of bicyclic and substituted monocyclic azepinones as dipeptide surrogates in angiotensin-converting enzyme/neutral endopeptidase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

2,3,4,5 TETRAHYDRO 3 (2 MERCAPTO 3 PHENYLPROPIONAMIDO) 2 OXO 1H BENZAZEPINE 1 ACETIC ACID; AZEPINE DERIVATIVE; BENZAZEPINE DERIVATIVE; BICYCLO COMPOUND; BMS 182657; CANDOXATRIL; CAPTOPRIL; DEOXYCORTICOSTERONE ACETATE; DIPEPTIDE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; MEMBRANE METALLOENDOPEPTIDASE; METALLOPROTEINASE INHIBITOR; N (2 MERCAPTOMETHYL 3 PHENYLPROPIONYL) BETA ALANINE; PENTOBARBITAL; UNCLASSIFIED DRUG;

EID: 0030032034     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950677a     Document Type: Article
Times cited : (72)

References (43)
  • 1
    • 0025973972 scopus 로고
    • Antihypertensive activity during inhibition of neutral endopeptidase and angiotensin converting enzyme
    • (a) Seymour, A. A.; Swerdel, J. N.; Abboa-Offei, B. Antihypertensive activity during inhibition of neutral endopeptidase and angiotensin converting enzyme. J. Cardiovasc. Pharmacol. 1991, 17, 456-465.
    • (1991) J. Cardiovasc. Pharmacol. , vol.17 , pp. 456-465
    • Seymour, A.A.1    Swerdel, J.N.2    Abboa-Offei, B.3
  • 2
    • 5244288633 scopus 로고
    • Blood pressure effects during chronic inhibition of angiotensin converting enzyme (ACE) and neutral endopeptidase (NEP) in the telemetered spontaneously hypertensive rat (SHR)
    • (b) Krulan, C.; Ghai, R. D.; Lappe, R. W.; Webb, R. L. Blood pressure effects during chronic inhibition of angiotensin converting enzyme (ACE) and neutral endopeptidase (NEP) in the telemetered spontaneously hypertensive rat (SHR). FABEB J. 1993, 7, A247.
    • (1993) FABEB J. , vol.7
    • Krulan, C.1    Ghai, R.D.2    Lappe, R.W.3    Webb, R.L.4
  • 4
    • 0027448911 scopus 로고
    • Combined inhibition of neutral endopeptidase and angiotensin converting enzyme in cardiomyopathic hamsters with compensated heart failure
    • (d) Trippodo, N. C.; Fox, M.; Natarajan, V.; Panchal, B. C.; Dorso, C. R.; Asaad, M. M. Combined inhibition of neutral endopeptidase and angiotensin converting enzyme in cardiomyopathic hamsters with compensated heart failure. J. Pharmacol. Exp. Ther. 1993, 267, 108-116.
    • (1993) J. Pharmacol. Exp. Ther. , vol.267 , pp. 108-116
    • Trippodo, N.C.1    Fox, M.2    Natarajan, V.3    Panchal, B.C.4    Dorso, C.R.5    Asaad, M.M.6
  • 5
    • 0027519535 scopus 로고
    • Systemic hemodynamics, renal function and hormonal levels during inhibition of neutral endopeptidase 3.4.24.11 and angiotensin-converting enzyme in conscious dogs with pacing-induced heart failure
    • (e) Seymour, A. A.; Asaad, M. M.; Lanoce, V. M.; Langenbacher, K. M.; Fennell, S. A.; Rogers, W. L. Systemic hemodynamics, renal function and hormonal levels during inhibition of neutral endopeptidase 3.4.24.11 and angiotensin-converting enzyme in conscious dogs with pacing-induced heart failure. J. Pharmacol. Exp. Ther. 1993, 266, 872-883.
    • (1993) J. Pharmacol. Exp. Ther. , vol.266 , pp. 872-883
    • Seymour, A.A.1    Asaad, M.M.2    Lanoce, V.M.3    Langenbacher, K.M.4    Fennell, S.A.5    Rogers, W.L.6
  • 6
    • 0025775217 scopus 로고
    • Mixed inhibitors of angiotensin-converting enzyme (EC 3.4.15.1) and enkephalinase (EC 3.4.24.11): Rational design, properties, and potential cardiovascular applications of glycopril and alatriopril
    • (a) Gros, C.; Noel, N.; Souque, A.; Schwartz, J.-C.; Danvy, D.; Plaquevent, J.-C.; Duhamel, L.; Duhamel, P.; Lecomte, J.-M.; Bralet, J. Mixed inhibitors of angiotensin-converting enzyme (EC 3.4.15.1) and enkephalinase (EC 3.4.24.11): Rational design, properties, and potential cardiovascular applications of glycopril and alatriopril. Proc. Natl. Acad. Sci. U.SA. 1991, 88, 4210-4214.
    • (1991) Proc. Natl. Acad. Sci. U.SA. , vol.88 , pp. 4210-4214
    • Gros, C.1    Noel, N.2    Souque, A.3    Schwartz, J.-C.4    Danvy, D.5    Plaquevent, J.-C.6    Duhamel, L.7    Duhamel, P.8    Lecomte, J.-M.9    Bralet, J.10
  • 7
    • 0027034772 scopus 로고
    • Inhibition conjointe de l'enzyme de conversion et de l'endopeptidase neutre: Une nouvelle voie de recherche dans le domaine de l'hypertension
    • (b) Fournie-Zaluski, M. C. Inhibition conjointe de l'enzyme de conversion et de l'endopeptidase neutre: Une nouvelle voie de recherche dans le domaine de l'hypertension. (Dual inhibition of angiotensin-converting enzyme and neutral endopeptidase: a new research pathway in the field of hypertension.) C. R. Seances Soc. Biol. Ses Fil. 1992, 186, 612-625.
    • (1992) C. R. Seances Soc. Biol. Ses Fil. , vol.186 , pp. 612-625
    • Fournie-Zaluski, M.C.1
  • 8
    • 0027244532 scopus 로고
    • Zinc metallopeptidases: Active site structure and design of selective and mixed inhibitors: New approaches in the search for analgesics and anti-hypertensives
    • (c) Roques, B. P. Zinc metallopeptidases: Active site structure and design of selective and mixed inhibitors: New approaches in the search for analgesics and anti-hypertensives. Biochem. Soc. Trans. 1993, 21, 678-685.
    • (1993) Biochem. Soc. Trans. , vol.21 , pp. 678-685
    • Roques, B.P.1
  • 9
    • 0027180453 scopus 로고
    • Application of a conformationally restricted Phe-Leu dipeptide mimetic to the design of a combined inhibitor of angiotensin I-converting enzyme and neutral endopeptidase 24.11
    • (d) Flynn, G. A.; Beight, D. W.; Mehdi, S.; Koehl, J. R.; Giroux, E. L.; French, J. F.; Hake, P. W.; Dage, R. C. Application of a conformationally restricted Phe-Leu dipeptide mimetic to the design of a combined inhibitor of angiotensin I-converting enzyme and neutral endopeptidase 24.11 J. Med. Chem. 1993, 36, 2420-2423.
    • (1993) J. Med. Chem. , vol.36 , pp. 2420-2423
    • Flynn, G.A.1    Beight, D.W.2    Mehdi, S.3    Koehl, J.R.4    Giroux, E.L.5    French, J.F.6    Hake, P.W.7    Dage, R.C.8
  • 10
    • 0027143192 scopus 로고
    • Heterocyclic lactam derivatives as dual angiotensin converting enzyme and neutral endopeptidase 24.11 inhibitors
    • (e) Stanton, J. L.; Sperbeck, D. M.; Trapani, A. J.; Cote, D.; Sakane, Y.; Berry, C. J.; Ghai, R. D. Heterocyclic lactam derivatives as dual angiotensin converting enzyme and neutral endopeptidase 24.11 inhibitors. J. Med. Chem. 1993, 36, 3829-3833.
    • (1993) J. Med. Chem. , vol.36 , pp. 3829-3833
    • Stanton, J.L.1    Sperbeck, D.M.2    Trapani, A.J.3    Cote, D.4    Sakane, Y.5    Berry, C.J.6    Ghai, R.D.7
  • 12
    • 0028299371 scopus 로고
    • New dual inhibitors of neutral endopeptidase and angiotensin-converting enzyme: Rational design, bioavailability, and pharmacological responses in experimental hypertension
    • (g) Fournie-Zaluski, M.-C.; Coric, P.; Turcaud, S.; Rousselet, N.; Gonzalez, W.; Barbe, B.; Pham, I.; Jullian, N.; Michel, J.-B.; Roques, B. P. New dual inhibitors of neutral endopeptidase and angiotensin-converting enzyme: Rational design, bioavailability, and pharmacological responses in experimental hypertension. J. Med. Chem. 1994, 37, 1070-1083.
    • (1994) J. Med. Chem. , vol.37 , pp. 1070-1083
    • Fournie-Zaluski, M.-C.1    Coric, P.2    Turcaud, S.3    Rousselet, N.4    Gonzalez, W.5    Barbe, B.6    Pham, I.7    Jullian, N.8    Michel, J.-B.9    Roques, B.P.10
  • 13
    • 0028243867 scopus 로고
    • New thiol inhibitors of neutral endopeptidase EC 3.4.24.11: Synthesis and enzyme active-site recognition
    • (h) Gomez-Monterrey, I.; Beaumont, A.; Nemecek, P.; Roques, B. P.; Fournie-Zaluski, M.-C. New thiol inhibitors of neutral endopeptidase EC 3.4.24.11: Synthesis and enzyme active-site recognition. J. Med. Chem. 1994, 37, 1865-1873.
    • (1994) J. Med. Chem. , vol.37 , pp. 1865-1873
    • Gomez-Monterrey, I.1    Beaumont, A.2    Nemecek, P.3    Roques, B.P.4    Fournie-Zaluski, M.-C.5
  • 14
    • 0028003993 scopus 로고
    • Dual inhibition of neutral endopeptidase and angiotensin-converting enzyme by N-phosphonomethyl and N-carboxyalkyl dipeptides
    • (i) DeLombaert, S.; Tan, J.; Stamford, L. J.; Sakane, Y.; Berry, C.; Ghai, R. D. Dual inhibition of neutral endopeptidase and angiotensin-converting enzyme by N-phosphonomethyl and N-carboxyalkyl dipeptides. Biomed. Chem. Lett. 1994, 4, 2715-2720.
    • (1994) Biomed. Chem. Lett. , vol.4 , pp. 2715-2720
    • DeLombaert, S.1    Tan, J.2    Stamford, L.J.3    Sakane, Y.4    Berry, C.5    Ghai, R.D.6
  • 15
    • 0028243301 scopus 로고
    • Effect of Alatriopril, a mixed inhibitor of atriopeptidase and angiotensin I-converting enzyme, on cardiac hypertrophy and hormonal responses in rats with myocardial infarction. Comparison with captopril
    • (j) Bralet, J.; Marie, C.; Mossiat, C.; Lecomte, J.-M.; Gros, C.; Schwartz, J.-C. Effect of Alatriopril, a mixed inhibitor of atriopeptidase and angiotensin I-converting enzyme, on cardiac hypertrophy and hormonal responses in rats with myocardial infarction. Comparison with captopril. J. Pharmacol. Exp. Ther. 1994, 270, 8-14.
    • (1994) J. Pharmacol. Exp. Ther. , vol.270 , pp. 8-14
    • Bralet, J.1    Marie, C.2    Mossiat, C.3    Lecomte, J.-M.4    Gros, C.5    Schwartz, J.-C.6
  • 16
    • 0028114412 scopus 로고
    • 4-Substituted proline derivatives that inhibit angiotensin converting enzyme and neutral endopeptidase 24.11
    • (k) Bhagwat, S. S.; Fink, C. A.; Gude, C.; Chan, K.; Qiao, Y.; Sakane, Y.; Berry, C.; Ghai, R. D. 4-Substituted proline derivatives that inhibit angiotensin converting enzyme and neutral endopeptidase 24.11. Biomed. Chem. Lett. 1994, 4, 2673-2676.
    • (1994) Biomed. Chem. Lett. , vol.4 , pp. 2673-2676
    • Bhagwat, S.S.1    Fink, C.A.2    Gude, C.3    Chan, K.4    Qiao, Y.5    Sakane, Y.6    Berry, C.7    Ghai, R.D.8
  • 17
    • 0028838979 scopus 로고
    • Hypotensive and natriuretic effects of RB 105, a new dual inhibitor of angiotensin converting enzyme and neutral endopeptidase in hypertensive rats
    • (l) Vera, W. G.; Fournie-Zaluski, M.-C.; Pham, I.; Laboulandine, I.; Roques, B.-P.; Michel, J.-P. Hypotensive and natriuretic effects of RB 105, a new dual inhibitor of angiotensin converting enzyme and neutral endopeptidase in hypertensive rats. J. Pharmacol. Exp. Ther. 1995, 272, 343-351.
    • (1995) J. Pharmacol. Exp. Ther. , vol.272 , pp. 343-351
    • Vera, W.G.1    Fournie-Zaluski, M.-C.2    Pham, I.3    Laboulandine, I.4    Roques, B.-P.5    Michel, J.-P.6
  • 18
    • 0028959948 scopus 로고
    • α-Mercaptoacyl dipeptides that inhibit angiotensin converting enzyme and neutral endopeptidase 24.11
    • (m) Bhagwat, S. S.; Fink, C. A.; Gude, C.; Chan, K.; Qiao, Y.; Sakane, Y.; Berry, C.; Ghai, R. D. α-Mercaptoacyl dipeptides that inhibit angiotensin converting enzyme and neutral endopeptidase 24.11. Biomed. Chem. Lett. 1995, 5, 735-738.
    • (1995) Biomed. Chem. Lett. , vol.5 , pp. 735-738
    • Bhagwat, S.S.1    Fink, C.A.2    Gude, C.3    Chan, K.4    Qiao, Y.5    Sakane, Y.6    Berry, C.7    Ghai, R.D.8
  • 24
    • 85033857957 scopus 로고    scopus 로고
    • note
    • In virtually all cases we have examined, the mercaptopropanoyl-containing conformationally restricted inhibitors are significantly less potent as ACE inhibitors in vivo (AI pressor) than their mercaptoacetyl counterparts, despite similar in vitro potencies versus ACE. Numerous examples have been cited in this laboratory (see refs 3a,b,e). For this reason we have concentrated our efforts in this work on the mercaptoacetyl class of inhibitors.
  • 25
    • 0029619616 scopus 로고
    • Cardiovascular effects of the novel dual inhibitor of neutral endopeptidase and angiotensin converting enzyme BMS-182657 in experimental hypertension and heart failure
    • Trippodo, N. C., Robl, J. A.; Asaad, M. M.; Bird, J. E.; Panchal, B. C.; Schaeffer, T. R.; Fox, M.; Giancarli, M. R.; Cheung, H. S. Cardiovascular effects of the novel dual inhibitor of neutral endopeptidase and angiotensin converting enzyme BMS-182657 in experimental hypertension and heart failure. J. Pharmacol. Exp. Ther. 1995, 275, 745-752.
    • (1995) J. Pharmacol. Exp. Ther. , vol.275 , pp. 745-752
    • Trippodo, N.C.1    Robl, J.A.2    Asaad, M.M.3    Bird, J.E.4    Panchal, B.C.5    Schaeffer, T.R.6    Fox, M.7    Giancarli, M.R.8    Cheung, H.S.9
  • 27
    • 0010315718 scopus 로고
    • Conformationally restricted inhibitors of angiotensin converting enzyme
    • (b) Thorsett, E. D. Conformationally restricted inhibitors of angiotensin converting enzyme. Actual. Chim. Ther. 1986, 13, 257-268.
    • (1986) Actual. Chim. Ther. , vol.13 , pp. 257-268
    • Thorsett, E.D.1
  • 30
    • 0028047179 scopus 로고
    • Peptidomimetic synthesis: Utilization of N-acyliminium ion cyclization chemistry in the generation of 7,6- and 7,5-fused bicyclic lactams
    • Robl, J. R. Peptidomimetic synthesis: Utilization of N-acyliminium ion cyclization chemistry in the generation of 7,6- and 7,5-fused bicyclic lactams. Tetrahedron Lett. 1994, 35, 393-396.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 393-396
    • Robl, J.R.1
  • 32
    • 0028215536 scopus 로고
    • A synthetic route for the generation of C-7 substituted azepinones
    • (b) Robl, J. R.; Cimarusti, M. P. A synthetic route for the generation of C-7 substituted azepinones. Tetrahedron Lett. 1994, 35, 1393-1396.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 1393-1396
    • Robl, J.R.1    Cimarusti, M.P.2
  • 33
    • 33845375871 scopus 로고
    • N2 substitution using cesium thiocarboxylates
    • N2 substitution using cesium thiocarboxylates. J. Org. Chem. 1986, 51, 3664-3671.
    • (1986) J. Org. Chem. , vol.51 , pp. 3664-3671
    • Strijtveen, B.1    Kellogg, R.M.2
  • 34
    • 0002760103 scopus 로고
    • Cyclopropanation of terminal olefins using diazomethane/palladium(II) acetate
    • Suda, M. Cyclopropanation of terminal olefins using diazomethane/palladium(II) acetate. Synthesis 1981, 714.
    • (1981) Synthesis , pp. 714
    • Suda, M.1
  • 36
    • 0028925678 scopus 로고
    • Dual metalloprotease inhibitors V. Utilization of bicyclic azepinonethiazolidines and azepinonetetrahydrothiazines in constrained peptidomimetics of mercaptoaeyl dipeptides
    • Slusarchyk, W. A.; Robl, J. A.; Taunk, P. C.; Asaad, M. M.; Bird, J. E.; DiMarco, J.; Pan, Y. Dual metalloprotease inhibitors V. Utilization of bicyclic azepinonethiazolidines and azepinonetetrahydrothiazines in constrained peptidomimetics of mercaptoaeyl dipeptides. Bioorg. Med. Chem. Lett. 1995, 5, 753-758.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 753-758
    • Slusarchyk, W.A.1    Robl, J.A.2    Taunk, P.C.3    Asaad, M.M.4    Bird, J.E.5    DiMarco, J.6    Pan, Y.7
  • 37
    • 0026332097 scopus 로고
    • The pharmacology of SQ 28,603, an inhibitor of neutral endopeptidase 3.4.24.11. Cardiovasc
    • (a) Seymour, A. A. The pharmacology of SQ 28,603, an inhibitor of neutral endopeptidase 3.4.24.11. Cardiovasc. Drug Rev. 1991, 9, 285-298.
    • (1991) Drug Rev. , vol.9 , pp. 285-298
    • Seymour, A.A.1
  • 40
    • 0020675817 scopus 로고
    • Membrane-bound kidney neutral metalloendopeptidase: Interaction with synthetic substrates, Neutral Peptides, and Inhibitors
    • Almenoff, J.; Orlowski, M. Membrane-bound kidney neutral metalloendopeptidase: Interaction with synthetic substrates, Neutral Peptides, and Inhibitors. Biochemistry 1983, 22, 590-599.
    • (1983) Biochemistry , vol.22 , pp. 590-599
    • Almenoff, J.1    Orlowski, M.2
  • 41
    • 0015083353 scopus 로고
    • Spectrophotometric assay and properties of the angiotensin-converting enzyme of rabbit lung
    • Cushman, D. W.; Cheung, H. S. Spectrophotometric assay and properties of the angiotensin-converting enzyme of rabbit lung. Biochem. Pharmacol. 1971, 20, 1637-1648.
    • (1971) Biochem. Pharmacol. , vol.20 , pp. 1637-1648
    • Cushman, D.W.1    Cheung, H.S.2
  • 42
    • 0017801959 scopus 로고
    • SQ 14,225 (D-3-Mercapto-2-methylpropanoyl-L-proHne), a novel orally active inhibitor of angiotensin converting enzyme
    • Rubin, B.; Laffan, R. J.; Kotler, D. G.; O'Keefe, E. H.; Demaio, D. A.; Goldberg, M. E. SQ 14,225 (D-3-Mercapto-2-methylpropanoyl-L-proHne)), a novel orally active inhibitor of angiotensin converting enzyme. J. Pharmacol. Exp. Ther. 1978, 204, 271.
    • (1978) J. Pharmacol. Exp. Ther. , vol.204 , pp. 271
    • Rubin, B.1    Laffan, R.J.2    Kotler, D.G.3    O'Keefe, E.H.4    Demaio, D.A.5    Goldberg, M.E.6
  • 43
    • 0024435563 scopus 로고
    • SCH 39370, a neutral metalloendopeptidase inhibitor, potentiates biological responses to atrial natriuretic factor and lowers blood pressure in desoxycorticosterone acetate-sodium hypertensive rats
    • Sybertz, E. J.; Chiu, P. J. S.; Vemulapalli, S.; Pitts, B.; Foster, C. J.; Watkins, R. W.; Barnett, A.; Haslanger, M. F. SCH 39370, a neutral metalloendopeptidase inhibitor, potentiates biological responses to atrial natriuretic factor and lowers blood pressure in desoxycorticosterone acetate-sodium hypertensive rats. J. Pharmacol. Exp. Ther. 1989, 250, 624-631.
    • (1989) J. Pharmacol. Exp. Ther. , vol.250 , pp. 624-631
    • Sybertz, E.J.1    Chiu, P.J.S.2    Vemulapalli, S.3    Pitts, B.4    Foster, C.J.5    Watkins, R.W.6    Barnett, A.7    Haslanger, M.F.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.