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Volumn 43, Issue 3, 2000, Pages 488-504

Potent and selective non-peptidic inhibitors of endothelin-converting enzyme-1 with sustained duration of action

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 DIBENZOFURAN 3 YL 1 (1H TETRAZOL 5 YL)ETHYLAMINO]METHYLPHOSPHONIC ACID; 2 (4 BIPHENYLYL) 1 (1H TETRAZOL 5 YL)ETHYLAMINOMETHYLPHOSPHONIC ACID; 3 (2 CARBOXYMETHOXY 4 METHOXYPHENYL) 1 (3,4 METHYLENEDIOXYPHENYL) 5 PROPOXY 2 INDANCARBOXYLIC ACID; 3 DIBENZOFURAN 3 YL 2 (PHOSPHONOMETHYLAMINO)PROPIONIC ACID; CGS 34043; CGS 35066; ENDOTHELIN 1; ENDOTHELIN CONVERTING ENZYME; ENDOTHELIN CONVERTING ENZYME INHIBITOR; ENKEPHALINASE INHIBITOR; MEMBRANE METALLOENDOPEPTIDASE; UNCLASSIFIED DRUG;

EID: 0034628537     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990507o     Document Type: Article
Times cited : (108)

References (45)
  • 2
    • 0028311861 scopus 로고
    • Development of agents to modulate the effects of endothelin
    • Cheng, X.-M.; Nikam, S. S.; Doherty, A. M. Development of agents to modulate the effects of endothelin. Curr. Med. Chem. 1994, 1, 271-312.
    • (1994) Curr. Med. Chem. , vol.1 , pp. 271-312
    • Cheng, X.-M.1    Nikam, S.S.2    Doherty, A.M.3
  • 3
    • 0030454012 scopus 로고    scopus 로고
    • Molecular pharmacology and pathophysiological significance of endothelin
    • Goto, K.; Kama, H.; Kasuya, Y. Molecular pharmacology and pathophysiological significance of endothelin. Jpn. J. Pharmacol. 1996, 72, 261-290.
    • (1996) Jpn. J. Pharmacol. , vol.72 , pp. 261-290
    • Goto, K.1    Kama, H.2    Kasuya, Y.3
  • 4
    • 0033068028 scopus 로고    scopus 로고
    • Pathophysiology of endothelin in the cardiovascular system
    • Miyauchi, T.; Masaki, T. Pathophysiology of endothelin in the cardiovascular system. Annu. Rev. Physiol. 1999, 61, 391-415.
    • (1999) Annu. Rev. Physiol. , vol.61 , pp. 391-415
    • Miyauchi, T.1    Masaki, T.2
  • 5
    • 0032056046 scopus 로고    scopus 로고
    • Biosynthesis, distribution and metabolism of endothelins in the pulmonary system
    • Battistini, B.; Dussault, P. Biosynthesis, distribution and metabolism of endothelins in the pulmonary system. Pulm. Pharmacol. Ther. 1998, 11, 79-88.
    • (1998) Pulm. Pharmacol. Ther. , vol.11 , pp. 79-88
    • Battistini, B.1    Dussault, P.2
  • 8
    • 0030731003 scopus 로고    scopus 로고
    • Endothelin-converting enzyme inhibitors
    • (a) Jeng, A. Y.; De Lombaert, S. Endothelin-converting enzyme inhibitors. Curr. Pharm. Des. 1997, 3, 597-614.
    • (1997) Curr. Pharm. Des. , vol.3 , pp. 597-614
    • Jeng, A.Y.1    De Lombaert, S.2
  • 10
    • 0000319750 scopus 로고    scopus 로고
    • In vivo role of endothelin-converting enzyme-1 as examined by adenovirus-mediated overexpression in rats
    • Telemaque, S.; Emoto, N.; Dewit, D.; Yanagisawa, M. In vivo role of endothelin-converting enzyme-1 as examined by adenovirus-mediated overexpression in rats. J. Cardiovasc. Pharmacol. 1998, 31, S548-S550.
    • (1998) J. Cardiovasc. Pharmacol. , vol.31
    • Telemaque, S.1    Emoto, N.2    Dewit, D.3    Yanagisawa, M.4
  • 11
    • 0030032386 scopus 로고    scopus 로고
    • Molecular pharmacology of endothelin converting enzymes
    • Turner, A. J.; Murphy, L. J. Molecular pharmacology of endothelin converting enzymes. Biochem. Pharmacol. 1996, 51, 91-102.
    • (1996) Biochem. Pharmacol. , vol.51 , pp. 91-102
    • Turner, A.J.1    Murphy, L.J.2
  • 13
    • 0032527754 scopus 로고    scopus 로고
    • Recombinant human endothelin-converting enzyme ECE-1b is located in an intracellular compartment when expressed in polarized Madin-Darby canine kidney cells
    • Azarani, A.; Boileau, G.; Crine, P. Recombinant human endothelin-converting enzyme ECE-1b is located in an intracellular compartment when expressed in polarized Madin-Darby canine kidney cells. Biochem. J. 1998, 333, 439-448.
    • (1998) Biochem. J. , vol.333 , pp. 439-448
    • Azarani, A.1    Boileau, G.2    Crine, P.3
  • 15
    • 0031940499 scopus 로고    scopus 로고
    • Dual genetic pathways of endothelin-mediated intercellular signaling revealed by targeted disruption of endothelin converting enzyme-1 gene
    • Yanagisawa, H.; Yanagisawa, M.; Kapur, R. P.; Richardson, J. A.; Williams, S. C.; Clouthier, D. E.; deWit, D.; Emoto, N.; Hammer, R. E. Dual genetic pathways of endothelin-mediated intercellular signaling revealed by targeted disruption of endothelin converting enzyme-1 gene. Development 1998, 125, 825-836.
    • (1998) Development , vol.125 , pp. 825-836
    • Yanagisawa, H.1    Yanagisawa, M.2    Kapur, R.P.3    Richardson, J.A.4    Williams, S.C.5    Clouthier, D.E.6    DeWit, D.7    Emoto, N.8    Hammer, R.E.9
  • 16
    • 0031921321 scopus 로고    scopus 로고
    • Cell surface metallopeptidases involved in blood pressure regulation: Structure, inhibition and clinical perspectives
    • Roques, B. P. Cell surface metallopeptidases involved in blood pressure regulation: structure, inhibition and clinical perspectives. Pathol. Biol. 1998, 46, 191-200.
    • (1998) Pathol. Biol. , vol.46 , pp. 191-200
    • Roques, B.P.1
  • 18
    • 0031738285 scopus 로고    scopus 로고
    • Potential pathophysiological role of endothelin-1 in asthma
    • Hay, D. W. P.; Goldie, R. G. Potential pathophysiological role of endothelin-1 in asthma. Drug News Perspect. 1998, 11, 411-418.
    • (1998) Drug News Perspect. , vol.11 , pp. 411-418
    • Hay, D.W.P.1    Goldie, R.G.2
  • 19
    • 0028287969 scopus 로고
    • Aminophosphonate endothelin converting enzyme inhibitors: Potency-enhancing and selectivity-improving modifications of phosphoramidon
    • Fukami, T.; Hayama, T.; Amano, Y.; Nakamura, Y.; Arai, Y.; Matsuyama, K.; Yano, M.; Ishikawa, K. Aminophosphonate endothelin converting enzyme inhibitors: potency-enhancing and selectivity-improving modifications of phosphoramidon. Bioorg. Med. Chem. Lett. 1994, 4, 1257-1262.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 1257-1262
    • Fukami, T.1    Hayama, T.2    Amano, Y.3    Nakamura, Y.4    Arai, Y.5    Matsuyama, K.6    Yano, M.7    Ishikawa, K.8
  • 23
    • 0032544132 scopus 로고    scopus 로고
    • Synthesis of novel substituted pyridines as inhibitors of endothelin converting enzyme-1 (ECE-1)
    • Massa, M. A.; Patt, W. C.; Ahn, K.; Sisneros, A. M.; Herman, S. B.; Doherty, A. Synthesis of novel substituted pyridines as inhibitors of endothelin converting enzyme-1 (ECE-1). Bioorg. Med. Chem. Lett. 1998, 8, 2117-2122.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2117-2122
    • Massa, M.A.1    Patt, W.C.2    Ahn, K.3    Sisneros, A.M.4    Herman, S.B.5    Doherty, A.6
  • 24
    • 0032584684 scopus 로고    scopus 로고
    • Endothelin converting enzyme inhibitor protects development of right ventricular overload and medial thickening of pulmonary arteries in rats with monocrotaline-induced pulmonary hypertension
    • Takahashi, T.; Kanda, T.; Inoue, M.; Sumino, H.; Kobayashi, I.; Iwamoto, A.; Nagai, R. Endothelin converting enzyme inhibitor protects development of right ventricular overload and medial thickening of pulmonary arteries in rats with monocrotaline-induced pulmonary hypertension. Life Sci. 1998, 63, PL137-PL143.
    • (1998) Life Sci. , vol.63
    • Takahashi, T.1    Kanda, T.2    Inoue, M.3    Sumino, H.4    Kobayashi, I.5    Iwamoto, A.6    Nagai, R.7
  • 25
    • 0033514321 scopus 로고    scopus 로고
    • Effects of a specific endothelin-converting enzyme inhibitor on cardiac, renal, and neurohumoral functions in congestive heart failure: Comparison of effects with those of endothelin A receptor antagonism
    • Wada, A.; Tsutamoto, T.; Ohnishi, M.; Sawaki, M.; Fukai, D.; Maeda, Y.; Kinoshita, M. Effects of a specific endothelin-converting enzyme inhibitor on cardiac, renal, and neurohumoral functions in congestive heart failure: Comparison of effects with those of endothelin A receptor antagonism. Circulation 1999, 99, 570-577.
    • (1999) Circulation , vol.99 , pp. 570-577
    • Wada, A.1    Tsutamoto, T.2    Ohnishi, M.3    Sawaki, M.4    Fukai, D.5    Maeda, Y.6    Kinoshita, M.7
  • 26
    • 0028171845 scopus 로고
    • Pharmacological profile of a non-peptidic dual inhibitor of neutral endopeptidase 24.11 and endothelin-converting enzyme
    • De Lombaert, S.; Ghai, R. D.; Jeng, A. Y.; Trapani, A. J.; Webb, R. L. Pharmacological profile of a non-peptidic dual inhibitor of neutral endopeptidase 24.11 and endothelin-converting enzyme. Biochem. Biophys. Res. Commun. 1994, 204, 407-412.
    • (1994) Biochem. Biophys. Res. Commun. , vol.204 , pp. 407-412
    • De Lombaert, S.1    Ghai, R.D.2    Jeng, A.Y.3    Trapani, A.J.4    Webb, R.L.5
  • 27
    • 0029832067 scopus 로고    scopus 로고
    • Systemic administration of an inhibitor of endothelin-converting enzyme for attenuation of cerebral vasospasm following experimental subarachnoid hemorrhage
    • Caner, H. H.; Kwan, A.-L.; Arthur, A.; Jeng, A. Y.; Lappe, R. W.; Kassell, N. F.; Lee, K. S. Systemic administration of an inhibitor of endothelin-converting enzyme for attenuation of cerebral vasospasm following experimental subarachnoid hemorrhage. J. Neurosurg. 1996, 85, 917-922.
    • (1996) J. Neurosurg. , vol.85 , pp. 917-922
    • Caner, H.H.1    Kwan, A.-L.2    Arthur, A.3    Jeng, A.Y.4    Lappe, R.W.5    Kassell, N.F.6    Lee, K.S.7
  • 28
    • 0030799481 scopus 로고    scopus 로고
    • Prevention and reversal of cerebral vasospasm by an endothelin-converting enzyme inhibitor, CGS 26303, in an experimental model of subarachnoid hemorrhage
    • Kwan, A.-L.; Bavbek, M.; Jeng, A. Y.; Maniara, W.; Toyoda, T.; Lappe, R. W.; Kassell, N. F.; Lee, K. S. Prevention and reversal of cerebral vasospasm by an endothelin-converting enzyme inhibitor, CGS 26303, in an experimental model of subarachnoid hemorrhage. J. Neurosurg. 1997, 87, 281-286.
    • (1997) J. Neurosurg. , vol.87 , pp. 281-286
    • Kwan, A.-L.1    Bavbek, M.2    Jeng, A.Y.3    Maniara, W.4    Toyoda, T.5    Lappe, R.W.6    Kassell, N.F.7    Lee, K.S.8
  • 29
    • 0000231723 scopus 로고    scopus 로고
    • Attenuation of experimental subarachnoid hemorrhage-induced cerebral vasospasm by CGS 26303, an endothelin-converting enzyme inhibitor
    • Kwan, A.-L.; Bavbek, M.; Jeng, A. Y.; Toyoda, T.; Kassell, N. F.; Lee, K. S. Attenuation of experimental subarachnoid hemorrhage-induced cerebral vasospasm by CGS 26303, an endothelin-converting enzyme inhibitor. J. Cardiovasc. Pharmacol. 1998, 31, S320-S322.
    • (1998) J. Cardiovasc. Pharmacol. , vol.31
    • Kwan, A.-L.1    Bavbek, M.2    Jeng, A.Y.3    Toyoda, T.4    Kassell, N.F.5    Lee, K.S.6
  • 30
  • 33
    • 0032554967 scopus 로고    scopus 로고
    • Synthesis of tetrazole analogues of a-amino acids by alkylation of a Schiff base of α-aminomethyltetrazole
    • Satoh, Y.; De Lombaert, S.; Marcopoulos, N.; Moliterni, J.; Moskal, M.; Tan, J.; Wallace, E. Synthesis of tetrazole analogues of a-amino acids by alkylation of a Schiff base of α-aminomethyltetrazole. Tetrahedron Lett. 1998, 39, 3367-3370.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3367-3370
    • Satoh, Y.1    De Lombaert, S.2    Marcopoulos, N.3    Moliterni, J.4    Moskal, M.5    Tan, J.6    Wallace, E.7
  • 34
    • 0028840084 scopus 로고
    • Non-peptidic inhibitors of neutral endopeptidase 24.11. 1. Discovery and optimization of potency
    • De Lombaert, S.; Blanchard, L.; Tan, J.; Sakane, Y; Berry, C.; Ghai, R. D. Non-peptidic inhibitors of neutral endopeptidase 24.11. 1. Discovery and optimization of potency. Bioorg. Med. Chem. Lett. 1995, 5, 145-150.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 145-150
    • De Lombaert, S.1    Blanchard, L.2    Tan, J.3    Sakane, Y.4    Berry, C.5    Ghai, R.D.6
  • 35
    • 2142742056 scopus 로고
    • The synthesis of isoprenoid (phosphinylmethy)phosphonates
    • Biller, S. A.; Forster, C. The synthesis of isoprenoid (phosphinylmethy)phosphonates. Tetrahedron 1990, 46, 6645-6658.
    • (1990) Tetrahedron , vol.46 , pp. 6645-6658
    • Biller, S.A.1    Forster, C.2
  • 36
    • 33847801634 scopus 로고
    • Palladium-promoted cyclization of diphenyl ether, diphenylamine, and related compounds
    • Akermark, B.; Eberson, L.; Jonsson, E.; Pettersson, E. Palladium-promoted cyclization of diphenyl ether, diphenylamine, and related compounds. J. Org. Chem. 1975, 40, 1365-1367.
    • (1975) J. Org. Chem. , vol.40 , pp. 1365-1367
    • Akermark, B.1    Eberson, L.2    Jonsson, E.3    Pettersson, E.4
  • 38
    • 0028895725 scopus 로고
    • Non-peptidic inhibitors of neutral endopeptidase 24.11. 2. Design of orally active phosphonate prodrugs and pharmacological evaluation
    • De Lombaert, S.; Blanchard, L.; Tan, J.; Trapani, A. J. Non-peptidic inhibitors of neutral endopeptidase 24.11. 2. Design of orally active phosphonate prodrugs and pharmacological evaluation. Bioorg. Med. Chem. Lett. 1995, 5, 151-154.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 151-154
    • De Lombaert, S.1    Blanchard, L.2    Tan, J.3    Trapani, A.J.4
  • 39
    • 0024789549 scopus 로고
    • Chiral purity determination by proton NMR spectroscopy. Novel use of 1,1′-binaphthyl-2,2'-diylphosphoric acid
    • Shapiro, M. J.; Archinal, A. E.; Jarema, M. A. Chiral purity determination by proton NMR spectroscopy. Novel use of 1,1′-binaphthyl-2,2'-diylphosphoric acid. J. Org. Chem. 1989, 54, 5826-5828.
    • (1989) J. Org. Chem. , vol.54 , pp. 5826-5828
    • Shapiro, M.J.1    Archinal, A.E.2    Jarema, M.A.3
  • 40
    • 0028269336 scopus 로고
    • N-Phosphonomethyl dipeptides and their phophonate prodrugs, a new generation of neutral endopeptidase (NEP, EC 3.4.24.11) inhibitors
    • De Lombaert, S.; Erion, M. D.; Tan, J.; Blanchard, L.; El-Chehabi, L.; Ghai, R.; Sakane, Y.; Berry, C.; Trapani, A. J. N-Phosphonomethyl dipeptides and their phophonate prodrugs, a new generation of neutral endopeptidase (NEP, EC 3.4.24.11) inhibitors. J. Med. Chem. 1994, 37, 498-511.
    • (1994) J. Med. Chem. , vol.37 , pp. 498-511
    • De Lombaert, S.1    Erion, M.D.2    Tan, J.3    Blanchard, L.4    El-Chehabi, L.5    Ghai, R.6    Sakane, Y.7    Berry, C.8    Trapani, A.J.9
  • 41
    • 0028003993 scopus 로고
    • Dual inhibition of neutral endopeptidase and angiotensin-converting enzyme by N-phosphonomethyl and N-carboxyalkyl dipeptides
    • De Lombaert, 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. Bioorg. Med. Chem. Lett. 1994, 4, 2715-2720.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 2715-2720
    • De Lombaert, S.1    Tan, J.2    Stamford, L.J.3    Sakane, Y.4    Berry, C.5    Ghai, R.D.6
  • 42
    • 0001494523 scopus 로고
    • A new route to N-substituted aminomethylphosphonates
    • Ha, H. I.; Nam, G. S.; Park, K. P. A new route to N-substituted aminomethylphosphonates. Bull. Korean Chem. Soc. 1990, 11, 485-486.
    • (1990) Bull. Korean Chem. Soc. , vol.11 , pp. 485-486
    • Ha, H.I.1    Nam, G.S.2    Park, K.P.3
  • 44
    • 0342266896 scopus 로고    scopus 로고
    • (Novartis), personal communication
    • W. Maniara, E. Walter (Novartis), personal communication.
    • Maniara, W.1    Walter, E.2
  • 45
    • 0032442820 scopus 로고    scopus 로고
    • Molecular modelling and site-directed mutagenesis of the active site of endothelin-converting enzyme
    • Sansom, C. E.; Hoang, M. V.; Turner, A. J. Molecular modelling and site-directed mutagenesis of the active site of endothelin-converting enzyme. Prot. Eng. 1998, 11, 1235-1241.
    • (1998) Prot. Eng. , vol.11 , pp. 1235-1241
    • Sansom, C.E.1    Hoang, M.V.2    Turner, A.J.3


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