메뉴 건너뛰기




Volumn 55, Issue 3, 2010, Pages 1137-1142

Spectroscopic determination and evaluation of acidity constants for some drug precursor 2-amino-4-(3- or 4-substituted phenyl) thiazole derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ACID DISSOCIATION CONSTANTS; ACIDITY CONSTANTS; STRUCTURE ELUCIDATION; TAUTOMERIZATIONS; THIAZOLE DERIVATIVES; UV-VIS SPECTROSCOPIC TECHNIQUES;

EID: 77949476266     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je9005739     Document Type: Article
Times cited : (11)

References (42)
  • 2
    • 31144474402 scopus 로고    scopus 로고
    • Synthesis and biological activity of natural thiazoles: An important class of heterocyclic compounds
    • De Souza, M. V. N. Synthesis and biological activity of natural thiazoles: An important class of heterocyclic compounds. J. Sulfur Chem. 2005, 26, 429-449.
    • (2005) J. Sulfur Chem. , vol.26 , pp. 429-449
    • De Souza, M.V.N.1
  • 4
    • 24944521495 scopus 로고    scopus 로고
    • Novel inhibitor of p38 MAP kinase as an anti-TNF-R drug: Discovery of N-[4-[2-ethyl- 4-(3-methylphenyl)-1, 3-thiazol-5-yl]-2-pyridyl]benzamide (TAK-715) as a potent and orally active anti-rheumatoid arthritis agent
    • Miwatashi, S.; Arikawa, Y.; Kotani, E.; Miyamoto, M.; Naruo, K.-I.; Kimura, H.; Tanaka, T.; Asahi, S.; Ohkawa, S. Novel Inhibitor of p38 MAP Kinase as an Anti-TNF-R Drug: Discovery of N-[4-[2-Ethyl- 4-(3-methylphenyl)-1, 3-thiazol-5-yl]-2-pyridyl]benzamide (TAK-715) as a Potent and Orally Active Anti-Rheumatoid Arthritis Agent. J. Med. Chem. 2005, 48, 5966-5979.
    • (2005) J. Med. Chem. , vol.48 , pp. 5966-5979
    • Miwatashi, S.1    Arikawa, Y.2    Kotani, E.3    Miyamoto, M.4    Naruo, K.-I.5    Kimura, H.6    Tanaka, T.7    Asahi, S.8    Ohkawa, S.9
  • 5
    • 27744522539 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of new thiazolyl/benzothiazolyl- amides, derivatives of 4-phenyl-piperazine
    • Papadopoulou, C.; Geronikaki, A.; Hadjipavlou-Litina, D. Synthesis and biological evaluation of new thiazolyl/benzothiazolyl-amides, derivatives of 4-phenyl-piperazine. Farmaco 2005, 60, 969-973.
    • (2005) Farmaco , vol.60 , pp. 969-973
    • Papadopoulou, C.1    Geronikaki, A.2    Hadjipavlou-Litina, D.3
  • 6
    • 0027138655 scopus 로고
    • Synthesis of 2, 4-disubstituted thiazoles and selenazoles as potential antitumor and antifilarial agents. 1. Methyl 4-(isothiocyanatomethyl) thiazole-2-carbamates, -selenazole-2-carbamates, and related derivatives
    • Kumar, Y.; Green, R.; Borysko, K. Z.; Wise, D. S.; Wotring, L. L.; Townsend, L. B. Synthesis of 2, 4-disubstituted thiazoles and selenazoles as potential antitumor and antifilarial agents. 1. Methyl 4-(isothiocyanatomethyl) thiazole-2-carbamates, -selenazole-2-carbamates, and related derivatives. J. Med. Chem. 1993, 36, 3843-3848.
    • (1993) J. Med. Chem. , vol.36 , pp. 3843-3848
    • Kumar, Y.1    Green, R.2    Borysko, K.Z.3    Wise, D.S.4    Wotring, L.L.5    Townsend, L.B.6
  • 7
    • 0029906776 scopus 로고    scopus 로고
    • 2, 4-Disubstituted thiazole II A novel class of antitumor agents, synthesis and biological evaluation
    • El-Subbagh, H. I.; Al-Obaid, A. M. 2, 4-Disubstituted thiazole II A novel class of antitumor agents, synthesis and biological evaluation. Eur. J. Med. Chem. 1996, 31, 10171021>.
    • (1996) Eur. J. Med. Chem. , vol.31 , pp. 10171021
    • El-Subbagh, H.I.1    Al-Obaid, A.M.2
  • 9
    • 0028825317 scopus 로고
    • WS75624 A and B, new endothelin converting enzyme inhibitors isolated from saccharothrix sp. No. 75624
    • Tsuruni, Y.; Ueda, H.; Hayashi, K.; Takase, S.; Nishikawa, M.; Kiyoto, S.; Okuhara, M. WS75624 A and B, New Endothelin Converting Enzyme Inhibitors Isolated from Saccharothrix sp. No. 75624. J. Antibiot. 1995, 48, 1066-1072.
    • (1995) J. Antibiot. , vol.48 , pp. 1066-1072
    • Tsuruni, Y.1    Ueda, H.2    Hayashi, K.3    Takase, S.4    Nishikawa, M.5    Kiyoto, S.6    Okuhara, M.7
  • 10
    • 26844541494 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel bisheterocycle- containing compounds as potential anti-influenza virus agents
    • Wang, W.-L.; Yao, D.-Y.; Gu, M.; Fan, M.-Z.; Li, J.-Y.; Xing, Y.- C.; Nan, F.-J. Synthesis and biological evaluation of novel bisheterocycle- containing compounds as potential anti-influenza virus agents. Bioorg. Med. Chem. Lett. 2005, 15, 5284-5287.
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 5284-5287
    • Wang, W.-L.1    Yao, D.-Y.2    Gu, M.3    Fan, M.-Z.4    Li, J.-Y.5    Xing, Y.-.C.6    Nan, F.-J.7
  • 11
    • 1842585913 scopus 로고    scopus 로고
    • Versatile 2-amino-4-substituted-1, 3-thiazoles: Synthesis and reactions
    • Metwally, M. A.; Abdel-Latif, E.; Amer, F. A.; Kaupp, G. Versatile 2-amino-4-substituted-1, 3-thiazoles: synthesis and reactions. J. Sulfur Chem. 2004, 25, 63-85.
    • (2004) J. Sulfur Chem. , vol.25 , pp. 63-85
    • Metwally, M.A.1    Abdel-Latif, E.2    Amer, F.A.3    Kaupp, G.4
  • 13
    • 0011514181 scopus 로고    scopus 로고
    • Derwent Information: 14 Great Queen Street, London WC2B 5DF, UK
    • Derwent World Drug Index; Derwent Information: 14 Great Queen Street, London WC2B 5DF, UK.
    • Derwent World Drug Index
  • 14
    • 0020955969 scopus 로고
    • N-(4-Substitutedthiazolyl) oxamic acid derivatives, a new series of potent, orally active antiallergy agents
    • Hargrave, K. D.; Hess, F. K.; Oliver, J. T. N-(4-Substitutedthiazolyl) oxamic Acid Derivatives, a New Series of Potent, Orally Active Antiallergy Agents. J. Med. Chem. 1983, 26, 1158-1163.
    • (1983) J. Med. Chem. , vol.26 , pp. 1158-1163
    • Hargrave, K.D.1    Hess, F.K.2    Oliver, J.T.3
  • 17
    • 0028365057 scopus 로고
    • Synthesis and anti-pseudomonal activity of new 2-isocephems with a dihydroxypyridone moiety at C-7
    • Tsuji, K.; Ishikawa, H. Synthesis and anti-pseudomonal activity of new 2-isocephems with a dihydroxypyridone moiety at C-7. Bioorg. Med. Chem. Lett. 1994, 4, 1601-1606.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 1601-1606
    • Tsuji, K.1    Ishikawa, H.2
  • 19
    • 11144323894 scopus 로고    scopus 로고
    • a values of the prototype imidazolium cation
    • a Values of the Prototype Imidazolium Cation. Aust. J. Chem. 2004, 120, 5-1210.
    • (2004) Aust. J. Chem. , vol.120 , pp. 5-1210
    • Magill, A.M.1    Yates, B.F.2
  • 20
    • 0037364162 scopus 로고    scopus 로고
    • ADMET in silico modelling: Towards prediction paradise
    • Van de Waterbeemd, H.; Gifford, E. ADMET in silico modelling: towards prediction paradise. Nat. Rev. Drug Discovery 2003, 2, 192- 204.
    • (2003) Nat. Rev. Drug Discovery , vol.2 , pp. 192-204
    • Van De Waterbeemd, H.1    Gifford, E.2
  • 22
    • 0025826451 scopus 로고
    • Structure-activity relationships for mitomycin C and mitomycin A analogues
    • Kunz, K. R.; Iyengar, B. S.; Dorr, R. T.; Alberts, D. S.; Remers, W. A. Structure-Activity Relationships for Mitomycin C and Mitomycin A Analogues. J. Med. Chem. 1991, 34, 2281-2286.
    • (1991) J. Med. Chem. , vol.34 , pp. 2281-2286
    • Kunz, K.R.1    Iyengar, B.S.2    Dorr, R.T.3    Alberts, D.S.4    Remers, W.A.5
  • 24
    • 0016741904 scopus 로고
    • Microelectrometric titration measurement of the pKa's and partition and drug distribution coefficients of narcotics and narcotic antagonists and their pH and temperature dependence
    • Kaufman, J. J.; Semo, N. M.; Koski, W. S. Microelectrometric Titration Measurement of the pKa's and Partition and Drug Distribution Coefficients of Narcotics and Narcotic Antagonists and Their pH and Temperature Dependence. J. Med. Chem. 1975, 18, 647-655.
    • (1975) J. Med. Chem. , vol.18 , pp. 647-655
    • Kaufman, J.J.1    Semo, N.M.2    Koski, W.S.3
  • 25
    • 0018291660 scopus 로고
    • Differential potentiometric method for determining dissociation constants of very slightly water-soluble drugs applied to the sulfonamide diuretic chlorthalidone
    • Fleuren, H. L. J.; Van Ginneken, C. A. M.; Van Rossum, J. M. Differential potentiometric method for determining dissociation constants of very slightly water-soluble drugs applied to the sulfonamide diuretic chlorthalidone. J. Pharm. Sci. 1979, 68, 1056-1058.
    • (1979) J. Pharm. Sci. , vol.68 , pp. 1056-1058
    • Fleuren, H.L.J.1    Van Ginneken, C.A.M.2    Van Rossum, J.M.3
  • 26
    • 29244464648 scopus 로고    scopus 로고
    • Determination of dissociation constants of compounds with potential cognition enhancing activity by capillary zone electrophoresis
    • Lišková, A.; Køivánková, L. Determination of dissociation constants of compounds with potential cognition enhancing activity by capillary zone electrophoresis. Electrophoresis 2005, 26, 4429-4439.
    • (2005) Electrophoresis , vol.26 , pp. 4429-4439
    • Lišková, A.1    Køivánková, L.2
  • 27
    • 41749113059 scopus 로고    scopus 로고
    • Determination and evaluation of acid dissociation constants of some substituted 2-aminobenzothiazole derivatives
    • Öǧretir, C.; Demirayak, Ş.; Tay, N. F.; Duran, M. Determination and evaluation of acid dissociation constants of some substituted 2-aminobenzothiazole derivatives. J. Chem. Eng. Data 2008, 53, 422-426.
    • (2008) J. Chem. Eng. Data , vol.53 , pp. 422-426
    • Öǧretir, C.1    Demirayak, Ş.2    Tay, N.F.3    Duran, M.4
  • 28
    • 0003474609 scopus 로고
    • Akadémiai Kiadü/Ellis Horwood Ltd. Publisher Coll House: Budapest/Chichester, England
    • Inczédy, J. Analytical Application of Complex Equilibria; Akadémiai Kiadü/Ellis Horwood Ltd. Publisher Coll House: Budapest/Chichester, England, 1976.
    • (1976) Analytical Application of Complex Equilibria
    • Inczédy, J.1
  • 29
    • 27844520774 scopus 로고    scopus 로고
    • Spectrophotometric determination of the dissociation constants of crown ethers with grafted acridone unit in methanol based on Benesi-Hildebrand evaluation. Spectrochim
    • Kádár, M.; Biró, A.; Tóth, K.; Vermes, B.; Huszthy, P. Spectrophotometric determination of the dissociation constants of crown ethers with grafted acridone unit in methanol based on Benesi-Hildebrand evaluation. Spectrochim. Acta, Part A 2005, 62, 1032-1038.
    • (2005) Acta, Part A , vol.62 , pp. 1032-1038
    • Kádár, M.1    Biró, A.2    Tóth, K.3    Vermes, B.4    Huszthy, P.5
  • 33
    • 0000787839 scopus 로고
    • The applicability of Hammett acidity functions to substituted pyridines and pyridines 1-oxides
    • Johnson, C. D.; Katritzky, A. R.; Ridgewell, B. J.; Shakir, N.; White, A. M. The applicability of Hammett acidity functions to substituted pyridines and pyridines 1-oxides. Tetrahedron 1965, 21, 1055-1065.
    • (1965) Tetrahedron , vol.21 , pp. 1055-1065
    • Johnson, C.D.1    Katritzky, A.R.2    Ridgewell, B.J.3    Shakir, N.4    White, A.M.5
  • 34
    • 0002893877 scopus 로고
    • Études physico-chimiques du cycle thiazoligue. V. Détermination des pKa des bases hétérocycligues azotées
    • Phan Tan Luu, R.; Surzur, J. M.; Metzger, J.; Aune, J. P.; Dupuy, C. Études physico-chimiques du cycle thiazoligue. V. Détermination des pKa des bases hétérocycligues azotées. Bull. Soc. Chim. Fr. 1967, 9, 3274-3283.
    • (1967) Bull. Soc. Chim. Fr. , vol.9 , pp. 3274-3283
    • Phan Tan Luu, R.1    Surzur, J.M.2    Metzger, J.3    Aune, J.P.4    Dupuy, C.5
  • 35
    • 0041757592 scopus 로고
    • Konstitution und Bildung der Arylsulfonyl-Derivate von Aminoheterocyclen
    • Dorn, H.; Hilgetag, G.; Rieche, A. Konstitution und Bildung der Arylsulfonyl-Derivate von Aminoheterocyclen. Angew. Chem. 1961, 73, 560-577.
    • (1961) Angew. Chem. , vol.73 , pp. 560-577
    • Dorn, H.1    Hilgetag, G.2    Rieche, A.3
  • 36
    • 0038138857 scopus 로고
    • Reactions of 3-thiocyano-2-butanone. II. the preparation of 2-arylamino- and 2-alkylamino-4, 5-dimethylthiazoles
    • Mathes, R. A.; Gregory, J. T. Reactions of 3-Thiocyano-2-butanone. II. The Preparation of 2-Arylamino- and 2-Alkylamino-4, 5-dimethylthiazoles. J. Am. Chem. Soc. 1952, 74, 3867-3868.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 3867-3868
    • Mathes, R.A.1    Gregory, J.T.2
  • 37
    • 33947434980 scopus 로고
    • Characterization of the ultraviolet absorption spectra of some substituted benzene-sulfonamides
    • Vandenbelt, J. M.; Doub, L. Characterization of the Ultraviolet Absorption Spectra of Some Substituted Benzene-sulfonamides. J. Am. Chem. Soc. 1944, 66, 1633-1636.
    • (1944) J. Am. Chem. Soc. , vol.66 , pp. 1633-1636
    • Vandenbelt, J.M.1    Doub, L.2
  • 38
    • 77949428482 scopus 로고
    • Vergleich der dissoziationskonstanten von 2-amino-thiazol- und 2-amino-oxazol-derivaten
    • Strauss, U.; Haerter, H. P.; Schindler, O. Vergleich der Dissoziationskonstanten von 2-Amino-thiazol- und 2-Amino-oxazol-Derivaten. Chimia 1973, 27, 99-102.
    • (1973) Chimia , vol.27 , pp. 99-102
    • Strauss, U.1    Haerter, H.P.2    Schindler, O.3
  • 39
    • 0002251219 scopus 로고
    • The tautomerism of N-hetero-aromatic amines. Part I
    • Angyl, S. J.; Angyal, C. L. The tautomerism of N-hetero-aromatic amines. Part I. J. Chem. Soc. 1952, 146, 1-1466.
    • (1952) J. Chem. Soc. , vol.146 , pp. 1-1466
    • Angyl, S.J.1    Angyal, C.L.2
  • 40


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.