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Volumn 39, Issue 18, 1996, Pages 3547-3555

Orally active, nonpeptide vasopressin V2 receptor antagonists: A novel series of 1-[4-(benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepines and related compounds

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; ARGIPRESSIN; ARGIPRESSIN RECEPTOR; BENZAZEPINE DERIVATIVE; MOZAVAPTAN; RECEPTOR BLOCKING AGENT; VASOPRESSIN ANTAGONIST; VASOPRESSIN V2 RECEPTOR;

EID: 9544238082     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960133o     Document Type: Article
Times cited : (101)

References (30)
  • 1
    • 0027532677 scopus 로고
    • Synthesis and some uses of receptor-specific agonists and antagonists of vasopressin and oxytocin
    • Manning, M.; Sawyer, W. H. Design, Synthesis and some uses of receptor-specific agonists and antagonists of vasopressin and oxytocin. J. Recept. Res. 1993, 13, 195-214.
    • (1993) J. Recept. Res. , vol.13 , pp. 195-214
    • Manning, M.1    Design, S.W.H.2
  • 2
    • 0023852168 scopus 로고
    • Antagonists of the antidiuretic activity of vasopressin
    • Kinter, L. B.; Huffman, W. F.; Stassen, F. L. Antagonists of the antidiuretic activity of vasopressin. Am. J. Phisiol. 1988, 254, F165-F177.
    • (1988) Am. J. Phisiol. , vol.254
    • Kinter, L.B.1    Huffman, W.F.2    Stassen, F.L.3
  • 3
    • 0026062086 scopus 로고
    • Pharmacology and clinical perspectives of vasopressin antagonists
    • László, F. A.; László, F., Jr.; De Wied, D. Pharmacology and clinical perspectives of vasopressin antagonists. Pharmacol. Rev. 1991, 43, 73-108.
    • (1991) Pharmacol. Rev. , vol.43 , pp. 73-108
    • László, F.A.1    László Jr., F.2    De Wied, D.3
  • 4
    • 0024801647 scopus 로고
    • Discovery, development, and some uses of vasopressin and oxytocin antagonists
    • Manning, M.; Sawyer, W. H. Discovery, development, and some uses of vasopressin and oxytocin antagonists. J. Lab. Clin. Med. 1989, 114, 617-632.
    • (1989) J. Lab. Clin. Med. , vol.114 , pp. 617-632
    • Manning, M.1    Sawyer, W.H.2
  • 5
    • 0027207594 scopus 로고
    • Design of cyclic and linear peptide antagonists of vasopressin and oxytocin: Current status and future directions
    • Manning, M.; Chan, W. Y.; Sawyer, W. H. Design of cyclic and linear peptide antagonists of vasopressin and oxytocin: current status and future directions. Regul. Pept. 1993, 45, 279-283.
    • (1993) Regul. Pept. , vol.45 , pp. 279-283
    • Manning, M.1    Chan, W.Y.2    Sawyer, W.H.3
  • 6
    • 0023899699 scopus 로고
    • Evaluation of the pharmacologic properties of a vasopressin antagonists in brattleboro rats
    • Mah, S. C.; Hofbauer, K. G. Evaluation of the pharmacologic properties of a vasopressin antagonists in brattleboro rats. J. Pharmacol. Exp. Ther. 1988, 245, 1028-1032.
    • (1988) J. Pharmacol. Exp. Ther. , vol.245 , pp. 1028-1032
    • Mah, S.C.1    Hofbauer, K.G.2
  • 10
    • 37049058490 scopus 로고
    • Azabenzocycloheptenones. Part III. 2,3,4,5-Tetrahydro-5-oxo-1-toluene-p-sulphonylbenz[b]azepine
    • Proctor, G. R. Azabenzocycloheptenones. Part III. 2,3,4,5-Tetrahydro-5-oxo-1-toluene-p-sulphonylbenz[b]azepine. J. Chem. Soc. 1961, 3989-3994.
    • (1961) J. Chem. Soc. , pp. 3989-3994
    • Proctor, G.R.1
  • 11
    • 8944237154 scopus 로고
    • A new synthesis of 3,4-dihydro-2H-1,4-benzoxazines using solid-liquid phase transfer catalysis
    • For compound 7, see: Coudert, G.; Guillaumet, G.; Loubinoux, B. A new synthesis of 3,4-dihydro-2H-1,4-benzoxazines using solid-liquid phase transfer catalysis. Synthesis 1979, 541-543.
    • (1979) Synthesis , pp. 541-543
    • Coudert, G.1    Guillaumet, G.2    Loubinoux, B.3
  • 12
    • 9544250124 scopus 로고    scopus 로고
    • Eur. Patent 283162, 1988
    • For compound 8, see: Watjen, F.; Hansen, H. C. Eur. Patent 283162, 1988.
    • Watjen, F.1    Hansen, H.C.2
  • 13
    • 0000614533 scopus 로고
    • Diisobutylaluminum hydride, a novel reagent for the reduction of oximes
    • For compound 9, see: Sasatani, S.; Miyazaki, T.; Maruoka, K.; Yamamoto, H. Diisobutylaluminum hydride, a novel reagent for the reduction of oximes. Tetrahedron Lett. 1983, 24, 4711-4712.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 4711-4712
    • Sasatani, S.1    Miyazaki, T.2    Maruoka, K.3    Yamamoto, H.4
  • 14
    • 0013618921 scopus 로고
    • Condensed heterocycles. Beckmann rearrangement of xanthone and thioxanthone oximes as a route to dibenz[b,f][1,4]-oxazepines and thiazepines
    • For compound 10, see: Nagarajan, K.; Kulkarni, C. L.; Venkateswarlu, A. Condensed heterocycles. Beckmann rearrangement of xanthone and thioxanthone oximes as a route to dibenz[b,f][1,4]-oxazepines and thiazepines. Indian J. Chem. 1974, 12, 247-251.
    • (1974) Indian J. Chem. , vol.12 , pp. 247-251
    • Nagarajan, K.1    Kulkarni, C.L.2    Venkateswarlu, A.3
  • 15
    • 33646149680 scopus 로고
    • Substances active on central nervous system. XLIV. 3,5-Dihydro-4,1-benzoxazepin-2(1H)-ones and 1,2,3,5-tetrahydro-4,1-benzoxazepines
    • For compound 11, see: Testa, E.; Fontanella, L. Substances active on central nervous system. XLIV. 3,5-Dihydro-4,1-benzoxazepin-2(1H)-ones and 1,2,3,5-tetrahydro-4,1-benzoxazepines. Farmaco (Pavia), Ed. Sci. 1965, 20, 323-335; Chem. Abstr. 1965, 63, 18088c.
    • (1965) Farmaco (Pavia), Ed. Sci. , vol.20 , pp. 323-335
    • Testa, E.1    Fontanella, L.2
  • 16
    • 33646149680 scopus 로고
    • For compound 11, see: Testa, E.; Fontanella, L. Substances active on central nervous system. XLIV. 3,5-Dihydro-4,1-benzoxazepin-2(1H)-ones and 1,2,3,5-tetrahydro-4,1-benzoxazepines. Farmaco (Pavia), Ed. Sci. 1965, 20, 323-335; Chem. Abstr. 1965, 63, 18088c.
    • (1965) Chem. Abstr. , vol.63
  • 17
    • 84987378274 scopus 로고
    • 1,2,3,5-Tetrahydro-4H-1,5-benzodiazepin-4-ones and 1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-ones from the reaction of hydrazoic acid on 1,2,3,4-tetrahydroquinoline-4one-5
    • For compound 12; see: Misiti, D.; Gatta, F.; Landi-Vittory, R. 1,2,3,5-Tetrahydro-4H-1,5-benzodiazepin-4-ones and 1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-ones from the reaction of hydrazoic acid on 1,2,3,4-tetrahydroquinoline-4one-5. J. Heterocycl. Chem. 1971, 8, 231-236.
    • (1971) J. Heterocycl. Chem. , vol.8 , pp. 231-236
    • Misiti, D.1    Gatta, F.2    Landi-Vittory, R.3
  • 18
    • 0021135036 scopus 로고
    • Amphiphilic compounds, I. Synthesis of 1-aryl-, 1-aroyl- and 1-benzyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepines
    • For compound 13, see: Lehmann, J.; Kraft, G. Amphiphilic compounds, I. Synthesis of 1-aryl-, 1-aroyl- and 1-benzyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepines. Arch. Pharm. 1984, 317, 595-606.
    • (1984) Arch. Pharm. , vol.317 , pp. 595-606
    • Lehmann, J.1    Kraft, G.2
  • 19
    • 9544232413 scopus 로고
    • 1,2,3,4,5,6-Hexahydro-1-benzazocine, Czech. Patent 210993, 1984
    • For compound 14, see: Jedrichovsky, J.; Rybar, A.; Frimm, R. 1,2,3,4,5,6-Hexahydro-1-benzazocine, Czech. Patent 210993, 1984; Chem. Abstr. 1984, 101, 130603.
    • (1984) Chem. Abstr. , vol.101 , pp. 130603
    • Jedrichovsky, J.1    Rybar, A.2    Frimm, R.3
  • 20
    • 37049044187 scopus 로고
    • Azabenzocycloheptenones. Part V. 2,3,4,5-Tetrahydro-5-oxobenz[b]azepines
    • For compound 15, see: Bell, W. H.; Hannah, E. D.; Proctor, G. R. Azabenzocycloheptenones. Part V. 2,3,4,5-Tetrahydro-5-oxobenz[b]azepines. J. Chem. Soc. 1964, 4926-4930.
    • (1964) J. Chem. Soc. , pp. 4926-4930
    • Bell, W.H.1    Hannah, E.D.2    Proctor, G.R.3
  • 21
    • 0018151325 scopus 로고
    • Neurohypophyseal hormone-responsive renal adenylate hormone-sensitive adenylate cyclase in bovine renal medullary membranes prepared using a double phase polymer system
    • Nakahara, T.; Terada, S.; Pincus, J.; Flouret, G.; Hechter, O. Neurohypophyseal hormone-responsive renal adenylate hormone-sensitive adenylate cyclase in bovine renal medullary membranes prepared using a double phase polymer system. J. Biol. Chem. 1978, 253, 3211-3218.
    • (1978) J. Biol. Chem. , vol.253 , pp. 3211-3218
    • Nakahara, T.1    Terada, S.2    Pincus, J.3    Flouret, G.4    Hechter, O.5
  • 22
    • 0020972549 scopus 로고
    • Acquisition of a β-adrenergic response by adult rat hepato-cytes during primary culture
    • Nakamura, T.; Tomomura, A.; Noda, C.; Shimoji, M.; Ichihara, A. Acquisition of a β-adrenergic response by adult rat hepato-cytes during primary culture. J. Biol. Chem. 1983, 258, 9283-9289.
    • (1983) J. Biol. Chem. , vol.258 , pp. 9283-9289
    • Nakamura, T.1    Tomomura, A.2    Noda, C.3    Shimoji, M.4    Ichihara, A.5
  • 25
    • 9544240112 scopus 로고    scopus 로고
    • note
    • 28 of compounds 31b and 31s. Compound 31b adopts an extended trans conformation compared to the N-methyl amide 31s. These findings suggest that the conformational change by the N-methylation of benzanilide may be a predominant factor in lowering the binding affinity to the receptors.
  • 28
    • 0000438409 scopus 로고
    • Crystallographic studies on retinoidal-active and -inactive aromatic anilides
    • Toriumi, Y.; Kasuya, A.; Itai, A. Crystallographic studies on retinoidal-active and -inactive aromatic anilides. J. Org. Chem. 1990, 55, 259-263.
    • (1990) J. Org. Chem. , vol.55 , pp. 259-263
    • Toriumi, Y.1    Kasuya, A.2    Itai, A.3
  • 29
    • 9544238833 scopus 로고    scopus 로고
    • note
    • Energy minimization calculations were carried out with use of CHARMM, and molecular modeling was performed with the QUANTA software (Molecular Simulations Inc.).
  • 30
    • 3743048540 scopus 로고
    • Synthesis of pyrido[3,2,1-de]phenanthridine derivatives
    • Nagarajan, K.; Madhavan Pillai, P.; Bhute, R. S. Synthesis of pyrido[3,2,1-de]phenanthridine derivatives. Indian J. Chem. 1969, 7, 848-858.
    • (1969) Indian J. Chem. , vol.7 , pp. 848-858
    • Nagarajan, K.1    Madhavan Pillai, P.2    Bhute, R.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.