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Volumn 46, Issue 12, 2003, Pages 2436-2445

Synthesis and biological activity of various derivatives of a novel class of potent, selective, and orally active prostaglandin D2 receptor antagonists. 1. Bicyclo[2.2.1]heptane derivatives

Author keywords

[No Author keywords available]

Indexed keywords

3 BENZYL 5 (6 CARBOXYHEXYL) 1 (2 CYCLOHEXYL 2 HYDROXYETHYLAMINO)HYDANTOIN; ANTIALLERGIC AGENT; CYCLIC AMP; NORBORNANE DERIVATIVE; PROSTACYCLIN RECEPTOR; PROSTAGLANDIN D2 RECEPTOR BLOCKING AGENT; PROSTAGLANDIN RECEPTOR BLOCKING AGENT; RADIOLIGAND; SULFONAMIDE; THROMBOXANE A2; UNCLASSIFIED DRUG;

EID: 12444339842     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020517g     Document Type: Article
Times cited : (46)

References (59)
  • 1
    • 0032823306 scopus 로고    scopus 로고
    • Prostanoid receptors: Structures, properties, and functions
    • (a) Narumiya, S.; Sugimoto, Y.; Ushikubi, F. Prostanoid receptors: structures, properties, and functions. Physiol. Rev. 1999, 79, 1193-1226.
    • (1999) Physiol. Rev. , vol.79 , pp. 1193-1226
    • Narumiya, S.1    Sugimoto, Y.2    Ushikubi, F.3
  • 5
    • 0016635266 scopus 로고
    • Prostaglandins and congeners. Synthesis of simplified prostaglandins. Inhibition of gastric acid secretion by 2-(ω-carboxyalkyl)-3-alkylcycloalkanones
    • (e) Poletto, J. F.; Bernady, K. F.; Kupter, D.; Partidge, R.; Weiss, M. J. Prostaglandins and Congeners. Synthesis of Simplified Prostaglandins. Inhibition of Gastric Acid Secretion by 2-(ω-Carboxyalkyl)-3-alkylcycloalkanones. J. Med. Chem. 1975, 18, 359-362.
    • (1975) J. Med. Chem. , vol.18 , pp. 359-362
    • Poletto, J.F.1    Bernady, K.F.2    Kupter, D.3    Partidge, R.4    Weiss, M.J.5
  • 6
    • 0015237263 scopus 로고
    • Indomethacin and aspirin abolish prostaglandin release from the spleen
    • (f) Ferreira, S. H.; Moncada, S.; Vane, J. R. Indomethacin and Aspirin Abolish Prostaglandin Release from the Spleen. Nature (London), New Biol. 1971, 231, 237-239.
    • (1971) Nature (London), New Biol. , vol.231 , pp. 237-239
    • Ferreira, S.H.1    Moncada, S.2    Vane, J.R.3
  • 7
    • 0020858787 scopus 로고
    • Protective effects of prostaglandins against gastric mucosal damage: Current knowledge and proposed mechanisms
    • (g) Miller, T. A. Protective Effects of Prostaglandins against Gastric Mucosal Damage: Current Knowledge and Proposed Mechanisms. Am. J. Physiol. 1983, 245, G601-G623.
    • (1983) Am. J. Physiol. , vol.245
    • Miller, T.A.1
  • 10
    • 0025670021 scopus 로고
    • Physiologic responses to intranasal dose-response challenges with histamine, methacholine, bradykinin, and prostaglandin in adult volunteers with and without nasal allergy
    • (b) Doyle, W. J.; Boehm, S.; Skoner, D. P. Physiologic responses to intranasal dose-response challenges with histamine, methacholine, bradykinin, and prostaglandin in adult volunteers with and without nasal allergy. J. Allergy Clin. Immunol. 1990, 86, 924-935.
    • (1990) J. Allergy Clin. Immunol. , vol.86 , pp. 924-935
    • Doyle, W.J.1    Boehm, S.2    Skoner, D.P.3
  • 14
    • 0029134144 scopus 로고
    • Molecular cloning and characterization of the human prostanoid DP receptor
    • (f) Boie, Y.; Sawyer, N.; Slipetz, D. M.; Metters, K. M.; Abramovitz, M. Molecular cloning and characterization of the human prostanoid DP receptor. J. Biol. Chem. 1995, 270, 18910-18916.
    • (1995) J. Biol. Chem. , vol.270 , pp. 18910-18916
    • Boie, Y.1    Sawyer, N.2    Slipetz, D.M.3    Metters, K.M.4    Abramovitz, M.5
  • 20
    • 0001216272 scopus 로고
    • Hydantoin prostaglandin analogues, potent and selective inhibitors of platelet aggregation
    • (c) Caldwell, A, G.; Harris, C. J.; Stepney, R.; Whittaker, N. Hydantoin Prostaglandin Analogues, Potent and Selective Inhibitors of Platelet Aggregation J. Chem. Soc., Chem. Commun. 1979, 13, 561-562.
    • (1979) J. Chem. Soc., Chem. Commun. , vol.13 , pp. 561-562
    • Caldwell, A.G.1    Harris, C.J.2    Stepney, R.3    Whittaker, N.4
  • 23
    • 12444271764 scopus 로고    scopus 로고
    • Japan Patent Kokai 59-157072, 1984
    • (f) Caldwell, A. G. Japan Patent Kokai 59-157072, 1984.
    • Caldwell, A.G.1
  • 24
    • 12444290473 scopus 로고    scopus 로고
    • Caldwell, A. G. European Patent 126849 Al, 1984
    • (g) Caldwell, A. G. European Patent 126849 Al, 1984.
    • Caldwell, A.G.1
  • 26
    • 0036135587 scopus 로고    scopus 로고
    • Pronounced Eosinophilic lung inflammation and Th2 cytokine release in human lipocalin-type prostaglandin D synthase transgenic mice
    • 2 receptors CRTH2 and DP. J. Allergy Clin. Immunol, 2001, 108, 982-988. (b) Fujitani, Y.; Kanaoka, Y.; Aritake, K.; Uodome, N.; Okazaki-Hatake, K.; Urade, Y. Pronounced Eosinophilic Lung Inflammation and Th2 Cytokine Release in Human Lipocalin-Type Prostaglandin D Synthase Transgenic Mice. J. Immunol. 2002, 168, 443-449.
    • (2002) J. Immunol. , vol.168 , pp. 443-449
    • Fujitani, Y.1    Kanaoka, Y.2    Aritake, K.3    Uodome, N.4    Okazaki-Hatake, K.5    Urade, Y.6
  • 27
    • 0023711375 scopus 로고
    • Synthesis and in vitro activity of various derivatives of a novel thromboxane receptor antagonist, (±)-(5Z)-7-[3-endo[(phenylsulfonyl)amino]bicyclo [2.2.1]hept-2-exo-yl]heptenoic acid
    • (a) Narisada, M.; Ohtani, M.; Watanabe, F.; Uchida, K.; Arita, H.; Doteuchi, M.; Hanasaki, K.; Kakushi, H.; Otani, K.; Hara, S. Synthesis and in Vitro Activity of Various Derivatives of a Novel Thromboxane Receptor Antagonist, (±)-(5Z)-7-[3-endo[(Phenylsulfonyl)amino]bicyclo [2.2.1]hept-2-exo-yl]heptenoic Acid. J. Med. Chem. 1988, 31, 1847-1854.
    • (1988) J. Med. Chem. , vol.31 , pp. 1847-1854
    • Narisada, M.1    Ohtani, M.2    Watanabe, F.3    Uchida, K.4    Arita, H.5    Doteuchi, M.6    Hanasaki, K.7    Kakushi, H.8    Otani, K.9    Hara, S.10
  • 32
    • 12444293345 scopus 로고
    • Benzenesulfonyl chloride
    • (a) Adams, R.; Marvel, C. S. Benzenesulfonyl chloride. Org. Synth. 1941, 1, 84-87.
    • (1941) Org. Synth. , vol.1 , pp. 84-87
    • Adams, R.1    Marvel, C.S.2
  • 33
    • 0002479857 scopus 로고
    • L-10-camphorsulfonyl chloride
    • (b) Bartlett, P. D.; Knox, L. H. D. L-10-Camphorsulfonyl chloride, Org. Synth. 1973, 5, 196-198.
    • (1973) Org. Synth. , vol.5 , pp. 196-198
    • Bartlett, P.D.1    Knox, L.H.D.2
  • 34
    • 0001583767 scopus 로고
    • Studies in the diphenyl ether series. II. Preparation and structure of some sulfonic acids and related derivatives
    • (c) Suter, C. M. Studies in the Diphenyl Ether Series. II. Preparation and Structure of Some Sulfonic Acids and Related Derivatives. J. Am. Chem. Soc. 1931, 53, 1112-1116.
    • (1931) J. Am. Chem. Soc. , vol.53 , pp. 1112-1116
    • Suter, C.M.1
  • 35
    • 0000820291 scopus 로고
    • A kinetic study of alkylation by ethyl arylsulfonates
    • (d) Morgan, M. S.; Cretcher, L. H. A Kinetic Study of Alkylation by Ethyl Arylsulfonates. J. Am. Chem. Soc. 1948, 70, 375-378.
    • (1948) J. Am. Chem. Soc. , vol.70 , pp. 375-378
    • Morgan, M.S.1    Cretcher, L.H.2
  • 36
    • 0030923065 scopus 로고    scopus 로고
    • N-methyl-2-(4-(2-methylpropyl)phenyl)-3- (3-methoxy-5-methylpyrazin-2-ylsulfamoyl)benzamide; one of a class of novel benzenesulfonamides which are orally-active, etaselective endothelin antagonists
    • (e) Mortlock, A. A.; Bath, C.; Butlin, R. J.; Heys, C.; Hunt, S. J.; Reid, A. C.; Sumner, N. F.; Tang, E. K.; Whiting, E.; Wilson, C.; Wright, N. D. N-Methyl-2-(4-(2-methylpropyl)phenyl)-3- (3-methoxy-5-methylpyrazin-2-ylsulfamoyl)benzamide; One of a Class of Novel Benzenesulfonamides Which Are Orally-Active, ETASelective Endothelin Antagonists. Bioorg. Med. Chem. Lett. 1997, 7, 1399-1402.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 1399-1402
    • Mortlock, A.A.1    Bath, C.2    Butlin, R.J.3    Heys, C.4    Hunt, S.J.5    Reid, A.C.6    Sumner, N.F.7    Tang, E.K.8    Whiting, E.9    Wilson, C.10    Wright, N.D.11
  • 37
    • 0001993921 scopus 로고
    • An improved synthesis of arylsulfonyl chlorides from aryl halides
    • (f) Hamada, T.; Yonemitsu, U. An Improved Synthesis of Arylsulfonyl Chlorides from Aryl Halides. Synthesis 1986, 4, 852-854.
    • (1986) Synthesis , vol.4 , pp. 852-854
    • Hamada, T.1    Yonemitsu, U.2
  • 39
    • 0038520746 scopus 로고
    • Reaction of arylmethanesulfonyl and styrylmethanesulfonyl chlorides with triethylamine
    • Nakayama, J.; Tanuma, M.; Honda, Y.; Hoshino, M. Reaction of Arylmethanesulfonyl and Styrylmethanesulfonyl Chlorides with Triethylamine. Tetrahedron Lett. 1984, 25, 4553-4556.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 4553-4556
    • Nakayama, J.1    Tanuma, M.2    Honda, Y.3    Hoshino, M.4
  • 40
    • 0011879089 scopus 로고
    • Resioselective preparation of 2- and 3-nitrodibenzofurans by the direct nitration of dibenzofuram
    • (a) Keumi, T.; Yamada, H.; Takahashi, H.; Kitajima, H. Resioselective Preparation of 2- and 3-Nitrodibenzofurans by the Direct Nitration of Dibenzofuram Bull. Chem. Soc. Jpn. 1982, 55, 629-630.
    • (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 629-630
    • Keumi, T.1    Yamada, H.2    Takahashi, H.3    Kitajima, H.4
  • 42
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of oraganoboran
    • (a) Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Oraganoboran Compounds. Chem. Rev. 1995, 95, 2457-2483.
    • (1995) Compounds. Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 43
    • 84989498349 scopus 로고
    • A convenient synthesis of ethynylarenes diethynylarenes
    • (b) Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. A Convenient Synthesis of Ethynylarenes and Diethynylarenes. Synthesis 1980, 8, 627-630.
    • (1980) Synthesis , vol.8 , pp. 627-630
    • Takahashi, S.1    Kuroyama, Y.2    Sonogashira, K.3    Hagihara, N.4
  • 44
    • 0001306949 scopus 로고
    • Condensed heteroaromatic ring systems. XI. A facile synsthesis of isoquinoline n-oxides
    • (c) Sakamoto, T.; Kondo, Y.; Miura, N.; Hayashi, K.; Yamanaka, H. Condensed Heteroaromatic Ring Systems. XI. A Facile Synsthesis of Isoquinoline N-Oxides. Heterocycles 1986, 24, 2311-2314.
    • (1986) Heterocycles , vol.24 , pp. 2311-2314
    • Sakamoto, T.1    Kondo, Y.2    Miura, N.3    Hayashi, K.4    Yamanaka, H.5
  • 45
    • 0001613090 scopus 로고
    • Palladium-catalyzed vinylic substitution reactions with heterocylic bromides
    • (d) Frank, W. C.; Kim, Y. C.; Heck, R. F. Palladium-Catalyzed Vinylic Substitution Reactions with Heterocylic Bromides. J. Org. Chem. 1978, 43, 2947-2958.
    • (1978) J. Org. Chem. , vol.43 , pp. 2947-2958
    • Frank, W.C.1    Kim, Y.C.2    Heck, R.F.3
  • 46
    • 0001025730 scopus 로고
    • New applications of palladium in organic syntheses
    • (e) Heck, R. F. New Applications of Palladium in Organic Syntheses. Pure. Appl. Chem. 1978, 50, 691-701.
    • (1978) Pure. Appl. Chem. , vol.50 , pp. 691-701
    • Heck, R.F.1
  • 47
    • 37049111808 scopus 로고
    • Palladium-catalyzed vinylation of organic halides under solid-liquid phase transfer conditions
    • (a) Jeffery, T. Palladium-Catalyzed Vinylation of Organic Halides under Solid-Liquid Phase Transfer Conditions. J. Chem. Soc., Chem. Commun. 1984, 1287-1289.
    • (1984) J. Chem. Soc., Chem. Commun. , pp. 1287-1289
    • Jeffery, T.1
  • 48
    • 46549101525 scopus 로고
    • Highly stereospecific palladium-catalyzed vinylation of vinylic halides under solid-liquid phase transfer conditions
    • (b) Jeffery, T. Highly Stereospecific Palladium-Catalyzed Vinylation of Vinylic Halides under Solid-Liquid Phase Transfer Conditions. Tetrahedron Lett. 1985, 26, 2667-2670.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2667-2670
    • Jeffery, T.1
  • 49
    • 0001628407 scopus 로고
    • Palladium catalyzed reaction of 2-alkynylanilines with allyl chlorides. Formation of 3-allylindoles
    • (a) Iritani, K.; Matsubara, S.; Utimoto, K. Palladium Catalyzed Reaction of 2-Alkynylanilines with Allyl Chlorides. Formation of 3-Allylindoles. Tetrahedron Lett. 1988, 29, 1799-1802.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 1799-1802
    • Iritani, K.1    Matsubara, S.2    Utimoto, K.3
  • 50
    • 0000973319 scopus 로고
    • Palladium homogeneous and supported catalysis: Synthesis of functional acetylenics and cyclisation to heterocycles
    • (b) Villemin, D.; Goussu, D. Palladium Homogeneous and Supported Catalysis: Synthesis of Functional Acetylenics and Cyclisation to Heterocycles. Heterocycles 1989, 29, 1255-1261.
    • (1989) Heterocycles. , vol.29 , pp. 1255-1261
    • Villemin, D.1    Goussu, D.2
  • 51
    • 0001798464 scopus 로고    scopus 로고
    • Efficient synthesis of alpha-chloro ketones via reaction of organome tallic reagents with n-methoxy-n-methylchloroacetamide
    • (a) Tillyer, R.; Frey, L. F.; Tschaen, D. M.; Dolling, U.-H. Efficient Synthesis of alpha-Chloro Ketones via Reaction of Organome tallic Reagents with N-Methoxy-N-methylchloroacetamide. Synlett 1996, 225-226.
    • (1996) Synlett , pp. 225-226
    • Tillyer, R.1    Frey, L.F.2    Tschaen, D.M.3    Dolling, U.-H.4
  • 52
    • 0027383213 scopus 로고
    • Stereoselective synthesis of a hydroxyethylene dipeptide isostere
    • (b) Diederich, A. M.; Ryckman, D. M. Stereoselective Synthesis of a Hydroxyethylene Dipeptide Isostere. Tetrahedron Lett. 1993, 34, 6169-6172.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6169-6172
    • Diederich, A.M.1    Ryckman, D.M.2
  • 53
    • 0018643960 scopus 로고
    • Synthesis and biological activity of carbonyl-terminus modified prostaglandin analogs
    • (a) Schaaf, T. K.; Hess, H. J. Synthesis and Biological Activity of Carbonyl-Terminus Modified Prostaglandin Analogs. J. Med. Chem. 1979, 22, 1340-1346.
    • (1979) J. Med. Chem. , vol.22 , pp. 1340-1346
    • Schaaf, T.K.1    Hess, H.J.2
  • 56
    • 0025980415 scopus 로고
    • Prednisone inhibits the appearance of inflammatory mediators and the influx of eosinophils and basophils associated with the cutaneous late-phase response to allergen
    • (b) Charlesworth, E. N.; Kagey-Sobotka, A.; Schleimer, R. P.; Norman, P. S.; Lichtenstein, L. M.; Prednisone inhibits the appearance of inflammatory mediators and the influx of eosinophils and basophils associated with the cutaneous late-phase response to allergen. J. Immunol. 1991, 149, 671-676.
    • (1991) J. Immunol. , vol.149 , pp. 671-676
    • Charlesworth, E.N.1    Kagey-Sobotka, A.2    Schleimer, R.P.3    Norman, P.S.4    Lichtenstein, L.M.5


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