메뉴 건너뛰기




Volumn 49, Issue 21, 2006, Pages 6371-6390

Identification and optimization of anthranilic sulfonamides as novel, selective cholecystokinin-2 receptor antagonists

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 [(2,1,3 BENZOTHIADIAZOL 4 YLSULFONYL)AMINO] 4 BROMOBENZOYL]PIPERIDINE; 1 [2 [(2,1,3 BENZOTHIADIAZOL 4 YLSULFONYL)AMINO] 5 CHLOROBENZOYL]PIPERIDINE; 4 [4 IODO 2 [(5 QUINOXALINYLSULFONYL)AMINO]BENZOYL]MORPHOLINE; ANTHRANILIC ACID DERIVATIVE; CHOLECYSTOKININ B RECEPTOR; CHOLECYSTOKININ B RECEPTOR ANTAGONIST; RADIOLIGAND; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 33750125268     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060590x     Document Type: Article
Times cited : (35)

References (44)
  • 1
    • 0030902066 scopus 로고    scopus 로고
    • Cholecystokinin(CCK)-A and CCK-B/gastrin receptors in human tumors
    • Reubi, J. C.; Schaer, J. C.; Waser, B. Cholecystokinin(CCK)-A and CCK-B/gastrin receptors in human tumors. Cancer Res. 1997, 57, 1377-1386.
    • (1997) Cancer Res. , vol.57 , pp. 1377-1386
    • Reubi, J.C.1    Schaer, J.C.2    Waser, B.3
  • 2
    • 4444382263 scopus 로고    scopus 로고
    • Activation of NFkappaB represents the central event in the neoplastic progression associated with Barrett's esophagus: A possible link to the inflammation and overexpression of COX-2. PPARgamma and growth factors
    • Konturek, P. C.; Nikiforuk, A.; Kania, J.; Raithel, M.; Hahn, E. G.; Muhldorfer, S. Activation of NFkappaB represents the central event in the neoplastic progression associated with Barrett's esophagus: a possible link to the inflammation and overexpression of COX-2. PPARgamma and growth factors. Dig. Dis. Sci. 2004, 49, 1075-1083.
    • (2004) Dig. Dis. Sci. , vol.49 , pp. 1075-1083
    • Konturek, P.C.1    Nikiforuk, A.2    Kania, J.3    Raithel, M.4    Hahn, E.G.5    Muhldorfer, S.6
  • 3
    • 14644442984 scopus 로고    scopus 로고
    • Gastrin promotes human colon cancer cell growth via CCK-2 receptor-mediated cyclooxygenase-2 induction and prostaglandin E2 production
    • Colucci, R.; Blandizzi, C.; Tanini, M.; Vassalle, C.; Breschi, M. C.; Del Tacca, M. Gastrin promotes human colon cancer cell growth via CCK-2 receptor-mediated cyclooxygenase-2 induction and prostaglandin E2 production. Br. J. Pharmacol. 2005, 144, 338-348.
    • (2005) Br. J. Pharmacol. , vol.144 , pp. 338-348
    • Colucci, R.1    Blandizzi, C.2    Tanini, M.3    Vassalle, C.4    Breschi, M.C.5    Del Tacca, M.6
  • 4
    • 0345735896 scopus 로고    scopus 로고
    • Cancer vaccines entering Phase III clinical trials
    • Durrant, L. G.; Spendlove, I. Cancer vaccines entering Phase III clinical trials. Expert Opin. Emerging Drugs 2003, 8, 489-500.
    • (2003) Expert Opin. Emerging Drugs , vol.8 , pp. 489-500
    • Durrant, L.G.1    Spendlove, I.2
  • 5
    • 33745987278 scopus 로고    scopus 로고
    • G17DT - A new weapon in the therapeutic armoury for gastrointestinal malignancy
    • Watson, S. A.; Gilliam, A. D. G17DT - a new weapon in the therapeutic armoury for gastrointestinal malignancy. Expert Opin. Biol. Ther. 2001, 1, 309-317.
    • (2001) Expert Opin. Biol. Ther. , vol.1 , pp. 309-317
    • Watson, S.A.1    Gilliam, A.D.2
  • 6
    • 2542641563 scopus 로고    scopus 로고
    • Review article: New pharmacological agents for the treatment of gastro-oesophageal reflux disease
    • Vakil, N. Review article: new pharmacological agents for the treatment of gastro-oesophageal reflux disease. Aliment. Pharmacol. Ther. 2004, 19, 1041-1049.
    • (2004) Aliment. Pharmacol. Ther. , vol.19 , pp. 1041-1049
    • Vakil, N.1
  • 7
    • 0042333166 scopus 로고    scopus 로고
    • New molecular targets for treatment of peptic ulcer disease
    • Lehmann, F.; Hildebrand, P.; Beglinger, C. New molecular targets for treatment of peptic ulcer disease. Drugs 2003, 63, 1785-1797.
    • (2003) Drugs , vol.63 , pp. 1785-1797
    • Lehmann, F.1    Hildebrand, P.2    Beglinger, C.3
  • 9
    • 0041919640 scopus 로고    scopus 로고
    • Cholecystokinin antagonists: Pharmacological and therapeutic potential
    • For a review see: Herranz, R. Cholecystokinin antagonists: pharmacological and therapeutic potential. Med. Res. Rev. 2003, 23, 559-605.
    • (2003) Med. Res. Rev. , vol.23 , pp. 559-605
    • Herranz, R.1
  • 10
    • 0030031102 scopus 로고    scopus 로고
    • Improved oral absorption of L-365.260, a poorly soluble drug
    • Lin, J. H.; Storey, D. E.; Chen, I. W.; Xu, X. Improved Oral Absorption of L-365.260, a Poorly Soluble Drug. Biopharm. Drug Dispos. 1996, 17, 1-15.
    • (1996) Biopharm. Drug Dispos. , vol.17 , pp. 1-15
    • Lin, J.H.1    Storey, D.E.2    Chen, I.W.3    Xu, X.4
  • 11
    • 0035114481 scopus 로고    scopus 로고
    • CCK2 receptor antagonists
    • McDonald, I. M. CCK2 Receptor Antagonists. Exp. Opin. Ther. Pat. 2001, 11, 445-462.
    • (2001) Exp. Opin. Ther. Pat. , vol.11 , pp. 445-462
    • McDonald, I.M.1
  • 12
    • 0000319914 scopus 로고
    • Preparation and properties of quaternary ammonium and phosphonium permanganates
    • Karaman, H.; Barton, R. J.; Robertson, B. E.; Lee, D. G. Preparation and Properties of Quaternary Ammonium and Phosphonium Permanganates. J. Org. Chem. 1984, 49, 4509-4516.
    • (1984) J. Org. Chem. , vol.49 , pp. 4509-4516
    • Karaman, H.1    Barton, R.J.2    Robertson, B.E.3    Lee, D.G.4
  • 13
    • 0021364661 scopus 로고
    • Selective reduction of aromatic nitro compounds with stannous chloride in nonacidic and nonaqueous medium
    • Bellamy, F. D.; Ou, K. Selective Reduction of Aromatic Nitro Compounds with Stannous Chloride in Nonacidic and Nonaqueous Medium. Tetrahedron Lett. 1984, 25, 839-842.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 839-842
    • Bellamy, F.D.1    Ou, K.2
  • 14
    • 12044258245 scopus 로고
    • 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive
    • Carpino, L. A. 1-Hydroxy-7-azabenzotriazole. An Efficient Peptide Coupling Additive. J. Am. Chem. Soc. 1993, 115, 4397-4398.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4397-4398
    • Carpino, L.A.1
  • 16
    • 33947334887 scopus 로고
    • Conversion of phenols to thiophenols via dialkylthiocarbamates
    • Newman, M. S.; Karnes, H. A. Conversion of Phenols to Thiophenols Via Dialkylthiocarbamates. J. Org. Chem. 1966, 31, 3980-3984.
    • (1966) J. Org. Chem. , vol.31 , pp. 3980-3984
    • Newman, M.S.1    Karnes, H.A.2
  • 17
    • 0000568534 scopus 로고
    • The vapor phase rearrangement of thionocarbonates and thionocarbamates
    • Kwart, H.; Evans, E. R. The Vapor Phase Rearrangement of Thionocarbonates and Thionocarbamates. J. Org. Chem. 1966, 31, 410-413.
    • (1966) J. Org. Chem. , vol.31 , pp. 410-413
    • Kwart, H.1    Evans, E.R.2
  • 18
    • 17044370417 scopus 로고    scopus 로고
    • Synthesis and characterization of p-phenylenediamine derivatives bearing an electron-acceptor unit
    • Sakurai, H.; Ritonga, M. T. S.; Shibatani, H.; Hirao, T. Synthesis and Characterization of p-Phenylenediamine Derivatives Bearing an Electron-Acceptor Unit. J. Org. Chem. 2005, 70, 2754-2762.
    • (2005) J. Org. Chem. , vol.70 , pp. 2754-2762
    • Sakurai, H.1    Ritonga, M.T.S.2    Shibatani, H.3    Hirao, T.4
  • 21
    • 21244481379 scopus 로고    scopus 로고
    • Molecular cloning, expression and pharmacological characterization of the canine cholecystokinin 1 receptor
    • Morton, M. F.; Pyati, J.; Dai, H.; Li, L.; Moreno, V.; Shankley, N. P. Molecular Cloning, Expression and Pharmacological Characterization of the Canine Cholecystokinin 1 Receptor. Br. J. Pharmacol. 2005, 145, 374-384.
    • (2005) Br. J. Pharmacol. , vol.145 , pp. 374-384
    • Morton, M.F.1    Pyati, J.2    Dai, H.3    Li, L.4    Moreno, V.5    Shankley, N.P.6
  • 24
    • 33750098418 scopus 로고    scopus 로고
    • Ab initio density functional theory calculated using this application; Schrödinger, LLC: San Diego, CA
    • Jaguar Quantum Mechanics, version 4.1; Ab initio density functional theory calculated using this application; Schrödinger, LLC: San Diego, CA.
    • Jaguar Quantum Mechanics, Version 4.1
  • 25
    • 0041555242 scopus 로고
    • Electronic population analysis on LCAO-MO molecular-wave functions. IV. Bonding and antibonding in LCAO and valence-bond theories
    • Mulliken, R. S. Electronic Population Analysis on LCAO-MO Molecular-Wave Functions. IV. Bonding and Antibonding In LCAO and Valence-Bond Theories. J. Chem. Phys. 1955, 23, 2343-2346.
    • (1955) J. Chem. Phys. , vol.23 , pp. 2343-2346
    • Mulliken, R.S.1
  • 26
    • 33750135308 scopus 로고    scopus 로고
    • note
    • a automated computerized potentiometric system equipped with a pH electrode at 25 °C under argon gas (pION, Inc., Woburn. MA).
  • 28
    • 27444434546 scopus 로고    scopus 로고
    • Scaffold hopping with molecular field points: Identification of a cholecystokinin-2 (CCK2) receptor pharmacophore and its use in the design of a prototypical series of pyrrole- and imidazole-based CCK2 antagonists
    • Low, C. M.; Buck, I. M.; Cooke, T.; Cushnir, J. R.; Kalindjian, S. B.; Kotecha, A.; Pether, M. J.; Shankley, N. P.; Vinter, J. G.; Wright, L. Scaffold Hopping With Molecular Field Points: Identification of a Cholecystokinin-2 (CCK2) Receptor Pharmacophore and its use in the Design of a Prototypical Series of Pyrrole- and Imidazole-Based CCK2 Antagonists. J. Med. Chem. 2005, 48, 6790-6802.
    • (2005) J. Med. Chem. , vol.48 , pp. 6790-6802
    • Low, C.M.1    Buck, I.M.2    Cooke, T.3    Cushnir, J.R.4    Kalindjian, S.B.5    Kotecha, A.6    Pether, M.J.7    Shankley, N.P.8    Vinter, J.G.9    Wright, L.10
  • 29
    • 33750096829 scopus 로고    scopus 로고
    • note
    • This intriguing result suggests that a tertiary amide group is required in this series to realize high receptor affinity. This is not necessarily the case, and the results of further studies in this area will be the subject of future disclosures from these laboratories.
  • 30
    • 0035424094 scopus 로고    scopus 로고
    • Synthesis of N-terminal substituted anthranilic acid dimer derivatives for evaluation on CCK receptors
    • Varnavas, A.; Valenta, V.; Berti, F.; Lassiani, L. Synthesis of N-Terminal Substituted Anthranilic Acid Dimer Derivatives for Evaluation on CCK Receptors. Farmaco 2001, 56, 555-564.
    • (2001) Farmaco , vol.56 , pp. 555-564
    • Varnavas, A.1    Valenta, V.2    Berti, F.3    Lassiani, L.4
  • 31
    • 1342300768 scopus 로고    scopus 로고
    • Anthranilic acid based CCKI antagonists: The 2-indole moiety may represent a "needle" according to the recent homonymous concept
    • Varnavas, A.; Lassiani, L.; Valenta, V.; Berti, F.; Tontini, A.; Mennuni, L.; Makovec, F. Anthranilic Acid Based CCKI Antagonists: The 2-Indole Moiety May Represent a "Needle" According to the Recent Homonymous Concept. Eur. J. Med. Chem. 2004, 39, 85-97.
    • (2004) Eur. J. Med. Chem. , vol.39 , pp. 85-97
    • Varnavas, A.1    Lassiani, L.2    Valenta, V.3    Berti, F.4    Tontini, A.5    Mennuni, L.6    Makovec, F.7
  • 33
    • 33750118241 scopus 로고    scopus 로고
    • note
    • These studies will be the subjects of future publications from our laboratories.
  • 34
    • 0028859285 scopus 로고
    • The use of receptor desensitization to analyse CCKA and CCKB/Gastrin receptors coupled to contraction in guinea-pig stomach muscle
    • Bishop, L. A.; Gerskowitch, V. P.; Hull, R. A.; Shankley, N. P.; Black, J. W. The Use of Receptor Desensitization to Analyse CCKA and CCKB/Gastrin Receptors Coupled to Contraction in Guinea-Pig Stomach Muscle. Br. J. Pharmacol. 1995, 114, 339-348.
    • (1995) Br. J. Pharmacol. , vol.114 , pp. 339-348
    • Bishop, L.A.1    Gerskowitch, V.P.2    Hull, R.A.3    Shankley, N.P.4    Black, J.W.5
  • 35
    • 33750093670 scopus 로고
    • A method for the standardization of cholecystokinin in vitro
    • Hultman, E. H. A Method for the Standardization of Cholecystokinin In Vitro. Acta Physiol. Scand. 1955, 33, 291-295.
    • (1955) Acta Physiol. Scand. , vol.33 , pp. 291-295
    • Hultman, E.H.1
  • 36
    • 70449173508 scopus 로고
    • Continuous recording of acid gastric secretion in the rat
    • Ghosh, M. N.; Schild, H. O. Continuous Recording of Acid Gastric Secretion in the Rat. Br. J. Pharmacol. Chemother. 1958, 13, 54-61.
    • (1958) Br. J. Pharmacol. Chemother. , vol.13 , pp. 54-61
    • Ghosh, M.N.1    Schild, H.O.2
  • 39
    • 33750129125 scopus 로고
    • Studies on 2,1,3-thia- and selenadiazole. XXXVI. Sulfonation and Oxidation
    • Pesin, V. G.; Muravnik, R. S. Studies on 2,1,3-thia- and selenadiazole. XXXVI. Sulfonation and Oxidation. Latv. PSR Zinat. Akad. Vestis, Kim. Ser. 1965, 223-232.
    • (1965) Latv. PSR Zinat. Akad. Vestis, Kim. Ser. , pp. 223-232
    • Pesin, V.G.1    Muravnik, R.S.2
  • 40
    • 33750093419 scopus 로고
    • Synthesis of 2,1,3-benzothiadiazole. I. New sulfo derivatives of 2,1,3-benzothiadiazole
    • Mikhailitsyn, F. S. Synthesis of 2,1,3-benzothiadiazole. I. New Sulfo Derivatives of 2,1,3-benzothiadiazole. Khim. Geterotsikl. Soedin. 1973, 19-21.
    • (1973) Khim. Geterotsikl. Soedin. , pp. 19-21
    • Mikhailitsyn, F.S.1
  • 41
    • 0018836097 scopus 로고
    • Synthesis and absolute configuration of substituted morpholines
    • Bettoni, G.; Franchini, C.; Perrone, R.; Tortorella, V. Synthesis and Absolute Configuration of Substituted Morpholines. Tetrahedron 1980, 36, 409-415.
    • (1980) Tetrahedron , vol.36 , pp. 409-415
    • Bettoni, G.1    Franchini, C.2    Perrone, R.3    Tortorella, V.4
  • 42
    • 0028203787 scopus 로고
    • (S,S)-3,5-dimethyl-morpholine, a novel C2-symmetric auxiliary. First application in [4+2]-cycloadditions leading to 4-Oxohexahydropyridazine derivatives
    • Enders, D.; Meyer. O.; Raabe, G.; Runsink, J. (S,S)-3,5-Dimethyl- morpholine, a Novel C2-Symmetric Auxiliary. First Application in [4+2]-cycloadditions Leading to 4-Oxohexahydropyridazine Derivatives. Synthesis 1994, 66-72.
    • (1994) Synthesis , pp. 66-72
    • Enders, D.1    Meyer, O.2    Raabe, G.3    Runsink, J.4
  • 43
    • 33750096036 scopus 로고    scopus 로고
    • Preparation of 5-[[(2-carbamoylphenyl)amino]sulfonyl]-quinoxaline compounds as cholecystokinin 2 modulators
    • U.S. Patent 2005038032, 20050217, 2005
    • Allison, B. D.; Hack, M. D.; Phuong, V. K.; Rabinowitz, M. H.; Rosen, M. D. Preparation of 5-[[(2-carbamoylphenyl)amino]sulfonyl]-quinoxaline compounds as cholecystokinin 2 modulators. U.S. Patent 2005038032, 20050217, 2005.
    • Allison, B.D.1    Hack, M.D.2    Phuong, V.K.3    Rabinowitz, M.H.4    Rosen, M.D.5
  • 44
    • 0015861774 scopus 로고
    • Relationship between the inhibition constant (Kl) and the concentration of inhibitorn which causes 50 per cent inhibition (I50) of an enzymatic reaction
    • Cheng, Y.; Prusoff, W. H. Relationship Between the Inhibition Constant (Kl) and the Concentration of Inhibitorn Which Causes 50 Per Cent Inhibition (I50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
    • (1973) Biochem. Pharmacol. , vol.22 , pp. 3099-3108
    • Cheng, Y.1    Prusoff, W.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.