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Volumn , Issue , 2008, Pages 363-379

Conformational Restriction and/or Steric Hindrance in Medicinal Chemistry

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EID: 84882530434     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-374194-3.00017-2     Document Type: Chapter
Times cited : (56)

References (50)
  • 1
    • 0019407381 scopus 로고
    • On the attribution and additivity of binding energies
    • Jencks W. On the attribution and additivity of binding energies. Proc. Natl. Acad. Sci. USA 1981, 78:4046-4050.
    • (1981) Proc. Natl. Acad. Sci. USA , vol.78 , pp. 4046-4050
    • Jencks, W.1
  • 2
    • 0024496899 scopus 로고
    • Thermodynamic analysis of the drug-receptor interaction
    • Raffa R.B., Porreca F. Thermodynamic analysis of the drug-receptor interaction. Life Sci. 1989, 44:245-258.
    • (1989) Life Sci. , vol.44 , pp. 245-258
    • Raffa, R.B.1    Porreca, F.2
  • 3
    • 0021745755 scopus 로고
    • Functional group contributions to drug-receptor interactions
    • Andrews P.R., Craik D.J., Martin J.L. Functional group contributions to drug-receptor interactions. J. Med. Chem. 1984, 27:1657-1684.
    • (1984) J. Med. Chem. , vol.27 , pp. 1657-1684
    • Andrews, P.R.1    Craik, D.J.2    Martin, J.L.3
  • 4
    • 0001535598 scopus 로고
    • Entropie, Bindungsenergie und enzymatische Katalyse
    • Page M.I. Entropie, Bindungsenergie und enzymatische Katalyse. Angew. Chem. 1977, 89:456-467.
    • (1977) Angew. Chem. , vol.89 , pp. 456-467
    • Page, M.I.1
  • 5
    • 0030905238 scopus 로고    scopus 로고
    • Structure-based thermodynamic analysis of HIV-1 protease inhibitors
    • Bardi S.J., Luque I., Freire E. Structure-based thermodynamic analysis of HIV-1 protease inhibitors. Biochemistry 1997, 36:6588-6596.
    • (1997) Biochemistry , vol.36 , pp. 6588-6596
    • Bardi, S.J.1    Luque, I.2    Freire, E.3
  • 6
    • 0034093758 scopus 로고    scopus 로고
    • HIV-1 Protease inhibitors: enthalpic versus entropic optimization of the binding affinity
    • Velazquez-Campoy A., Todd M.J., Freire E. HIV-1 Protease inhibitors: enthalpic versus entropic optimization of the binding affinity. Biochemistry 2000, 39:2201-2207.
    • (2000) Biochemistry , vol.39 , pp. 2201-2207
    • Velazquez-Campoy, A.1    Todd, M.J.2    Freire, E.3
  • 7
    • 9644258919 scopus 로고
    • The cost of conformational order: entropy changes in molecular associations
    • Searle M.S., Williams D.H. The cost of conformational order: entropy changes in molecular associations. J. Am. Chem. Soc. 1992, 114:10690-10697.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10690-10697
    • Searle, M.S.1    Williams, D.H.2
  • 9
    • 10944261243 scopus 로고    scopus 로고
    • Understanding noncovalent interactions: ligand binding energy and catalytic efficiency from ligand-induced reductions in motion within receptors and enzymes
    • Williams D.H., Stephens E., O'Brien D.P., Zhou M. Understanding noncovalent interactions: ligand binding energy and catalytic efficiency from ligand-induced reductions in motion within receptors and enzymes. Angew. Chem. Int. Ed. 2004, 43:6596-6616.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 6596-6616
    • Williams, D.H.1    Stephens, E.2    O'Brien, D.P.3    Zhou, M.4
  • 10
    • 0033559918 scopus 로고    scopus 로고
    • Hydrogen bonding hydrophobic interactions, and failure of the rigid receptor hypothesis
    • Davis A.M., Teague S.J. Hydrogen bonding hydrophobic interactions, and failure of the rigid receptor hypothesis. Angew. Chem. Int. Ed. 1999, 38:736-749.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 736-749
    • Davis, A.M.1    Teague, S.J.2
  • 11
    • 0028454828 scopus 로고
    • The development of a simple empirical scoring function to estimate the binding constant for a protein-ligand complex of known three-dimensional structure
    • Böhm H.J. The development of a simple empirical scoring function to estimate the binding constant for a protein-ligand complex of known three-dimensional structure. J. Comput.-Aided Mol. Des. 1994, 8:243-256.
    • (1994) J. Comput.-Aided Mol. Des. , vol.8 , pp. 243-256
    • Böhm, H.J.1
  • 12
    • 33751157207 scopus 로고
    • Enthalpy-entropy compensation in drug-receptor binding
    • Gilli P., Ferretti V., Gilli G. Enthalpy-entropy compensation in drug-receptor binding. J. Phys. Chem. 1994, 98:1515-1518.
    • (1994) J. Phys. Chem. , vol.98 , pp. 1515-1518
    • Gilli, P.1    Ferretti, V.2    Gilli, G.3
  • 13
    • 0035861396 scopus 로고    scopus 로고
    • The application of themodynamic methods in drug design
    • Velazquez-Campoy A., Luque I., Freire E. The application of themodynamic methods in drug design. Thermochim. Acta 2001, 380:217-227.
    • (2001) Thermochim. Acta , vol.380 , pp. 217-227
    • Velazquez-Campoy, A.1    Luque, I.2    Freire, E.3
  • 14
    • 0018607313 scopus 로고
    • Fundamental difference between the molecular interactions of agonists and antagonists with the beta;-adrenergic receptor
    • Weiland G.A., Minnemann K.P., Molinoff P.B. Fundamental difference between the molecular interactions of agonists and antagonists with the β-adrenergic receptor. Nature 1979, 281:114-117.
    • (1979) Nature , vol.281 , pp. 114-117
    • Weiland, G.A.1    Minnemann, K.P.2    Molinoff, P.B.3
  • 15
    • 0025100420 scopus 로고
    • On the fundamental difference in the thermodynamics of agonist and antagonist interactions with beta;-adrenergic receptors and the mechanism of entropy driven binding
    • Miklavc A., Kocjan D., Mavri J., Koller J., Hadzi D. On the fundamental difference in the thermodynamics of agonist and antagonist interactions with β-adrenergic receptors and the mechanism of entropy driven binding. Biochem. Pharmacol. 1990, 40:663-669.
    • (1990) Biochem. Pharmacol. , vol.40 , pp. 663-669
    • Miklavc, A.1    Kocjan, D.2    Mavri, J.3    Koller, J.4    Hadzi, D.5
  • 18
    • 0030884435 scopus 로고    scopus 로고
    • Design of peptides, proteins and peptidomimetics in chi space
    • and references cited therein.
    • Hruby V.J., Li G., Hacksell-Luevano C., Shenderovich M. Design of peptides, proteins and peptidomimetics in chi space. Biopolymers 1997, 43:219-266. and references cited therein.
    • (1997) Biopolymers , vol.43 , pp. 219-266
    • Hruby, V.J.1    Li, G.2    Hacksell-Luevano, C.3    Shenderovich, M.4
  • 19
    • 84986532188 scopus 로고
    • A racing-bracing approach to computer-assisted ligand design
    • Leach A.R., Lewis R.A. A racing-bracing approach to computer-assisted ligand design. J. Comp. Chem. 1994, 15:233-240.
    • (1994) J. Comp. Chem. , vol.15 , pp. 233-240
    • Leach, A.R.1    Lewis, R.A.2
  • 21
    • 5244381937 scopus 로고
    • Steric effects in drug design
    • Charton M., Motoc I. Steric effects in drug design. Top. Curr. Chem. 1983, 114:1-6.
    • (1983) Top. Curr. Chem. , vol.114 , pp. 1-6
    • Charton, M.1    Motoc, I.2
  • 23
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 1997, 23:4-25.
    • (1997) Adv. Drug Deliv. Rev. , vol.23 , pp. 4-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 24
    • 11144355212 scopus 로고    scopus 로고
    • SSR240612 [(2R)-2-[((3R)-3-(1,3-Benzodioxol-5-yl)-3-{[(6-methoxy-2-naphthyl)sulfon yl]amino}propanoyl)amino]-3-(4-{[2R,6S)-2,6-dimethylpiperidinyl]methyl}p henyl)-N-isopropyl-N-methylpropanamide Hydrochloride], a new nonpeptide antagonist of the bradykinin B1 receptor: biochemical and pharmacological characterization
    • Gougat J., Ferrari B., Sarran L., Planchenault C., Poncelet M., Maruani J., Alonso R., Cudennec A., Tiziano Croci T., Fabio Guagnini F., Katalin Urban-Szabo K., Martinolle J.P., Soubrié P., Finance O., Le Fur G. SSR240612 [(2R)-2-[((3R)-3-(1,3-Benzodioxol-5-yl)-3-{[(6-methoxy-2-naphthyl)sulfon yl]amino}propanoyl)amino]-3-(4-{[2R,6S)-2,6-dimethylpiperidinyl]methyl}p henyl)-N-isopropyl-N-methylpropanamide Hydrochloride], a new nonpeptide antagonist of the bradykinin B1 receptor: biochemical and pharmacological characterization. J. Pharmacol. Exp. Ther. 2004, 309:661-669.
    • (2004) J. Pharmacol. Exp. Ther. , vol.309 , pp. 661-669
    • Gougat, J.1    Ferrari, B.2    Sarran, L.3    Planchenault, C.4    Poncelet, M.5    Maruani, J.6    Alonso, R.7    Cudennec, A.8    Tiziano Croci, T.9    Fabio Guagnini, F.10    Katalin Urban-Szabo, K.11    Martinolle, J.P.12    Soubrié, P.13    Finance, O.14    Le Fur, G.15
  • 26
    • 0001895261 scopus 로고
    • Prediction and entropy
    • Shannon C.E. Prediction and entropy. Bell Sys. Tech. J. 1951, 16:50-64.
    • (1951) Bell Sys. Tech. J. , vol.16 , pp. 50-64
    • Shannon, C.E.1
  • 27
    • 33845282016 scopus 로고
    • Assessment of bond rotation interdependence in polymer chains: an information theory approach
    • Viswanadham V.N., Mattice W.L. Assessment of bond rotation interdependence in polymer chains: an information theory approach. Macromolecules 1987, 20:685-688.
    • (1987) Macromolecules , vol.20 , pp. 685-688
    • Viswanadham, V.N.1    Mattice, W.L.2
  • 28
    • 0034801468 scopus 로고    scopus 로고
    • An enthalpic component in cooperativity: the relationship between enthalpy, entropy, and noncovalent structure in weak associations
    • Calderone C.T., Williams D.H. An enthalpic component in cooperativity: the relationship between enthalpy, entropy, and noncovalent structure in weak associations. J. Am. Chem. Soc. 2001, 123:6262-6267.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 6262-6267
    • Calderone, C.T.1    Williams, D.H.2
  • 29
    • 33748547737 scopus 로고    scopus 로고
    • Stereochemical diversity-oriented conformational restriction strategy. Development of potent histamine H3 and/or H4 receptor antagonists with an imidazolylcyclopropane structure
    • Watanabe M., Kazuta Y., Hayashi H., Yamada S., Matsuda A., Shuto D. Stereochemical diversity-oriented conformational restriction strategy. Development of potent histamine H3 and/or H4 receptor antagonists with an imidazolylcyclopropane structure. J. Med. Chem. 2006, 49:5587-5596.
    • (2006) J. Med. Chem. , vol.49 , pp. 5587-5596
    • Watanabe, M.1    Kazuta, Y.2    Hayashi, H.3    Yamada, S.4    Matsuda, A.5    Shuto, D.6
  • 30
    • 0033545582 scopus 로고    scopus 로고
    • Design, synthesis, and structure-activity relationships of acetylene-based histamine H3 receptor antagonists
    • Ali S.M., Tedford C.E., Gregory R., Handley M.K., Yates S.L., Hirth W.W., Phillips J.G. Design, synthesis, and structure-activity relationships of acetylene-based histamine H3 receptor antagonists. J. Med. Chem. 1999, 42:903-909.
    • (1999) J. Med. Chem. , vol.42 , pp. 903-909
    • Ali, S.M.1    Tedford, C.E.2    Gregory, R.3    Handley, M.K.4    Yates, S.L.5    Hirth, W.W.6    Phillips, J.G.7
  • 31
    • 0038644592 scopus 로고    scopus 로고
    • Cyclopropane-based conformational restriction of histamine. (1S,2S)-2-(2-Aminoethyl)-1-(1H-imidazol-4-yl)cyclopropane, a highly selective agonist for the histamine H3 receptor, having a cis-cyclopropane structure
    • Kazuta Y., Hirano K., Natsume K., Yamada S., Kimura R., Matsumoto S.-i., Furuichi K., Matsuda A., Shuto S. Cyclopropane-based conformational restriction of histamine. (1S,2S)-2-(2-Aminoethyl)-1-(1H-imidazol-4-yl)cyclopropane, a highly selective agonist for the histamine H3 receptor, having a cis-cyclopropane structure. J. Med. Chem. 2003, 46:1980-1988.
    • (2003) J. Med. Chem. , vol.46 , pp. 1980-1988
    • Kazuta, Y.1    Hirano, K.2    Natsume, K.3    Yamada, S.4    Kimura, R.5    Matsumoto, S.-I.6    Furuichi, K.7    Matsuda, A.8    Shuto, S.9
  • 32
    • 0344550397 scopus 로고    scopus 로고
    • A method for designing conformationally restricted analogues based on allylic strain: synthesis of a novel class of noncompetitive NMDA receptor antagonists having the acrylamide structure
    • Ohmori Y., Yamashita A., Tsujita R., Yamamoto T., Taniuchi K., Matsuda A., Shuto S. A method for designing conformationally restricted analogues based on allylic strain: synthesis of a novel class of noncompetitive NMDA receptor antagonists having the acrylamide structure. J. Med. Chem. 2003, 46:5326-5333.
    • (2003) J. Med. Chem. , vol.46 , pp. 5326-5333
    • Ohmori, Y.1    Yamashita, A.2    Tsujita, R.3    Yamamoto, T.4    Taniuchi, K.5    Matsuda, A.6    Shuto, S.7
  • 33
    • 0034678033 scopus 로고    scopus 로고
    • Target-oriented and diversity-oriented organic synthesis in drug discovery
    • Schreiber S.L. Target-oriented and diversity-oriented organic synthesis in drug discovery. Science 2000, 287:1964-1969.
    • (2000) Science , vol.287 , pp. 1964-1969
    • Schreiber, S.L.1
  • 34
    • 3042799070 scopus 로고    scopus 로고
    • A planning strategy for diversity-oriented synthesis
    • Burke M.D., Schreiber S.L. A planning strategy for diversity-oriented synthesis. Angew. Chem. Int. Ed. 2004, 43:46-58.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 46-58
    • Burke, M.D.1    Schreiber, S.L.2
  • 35
    • 0034058306 scopus 로고    scopus 로고
    • Alkaloids from frog skin: the discovery of epibatidine and the potential for developing novel non-opioid analgesics
    • Daly J.W., Garraffo H.M., Spande T.F., Decker M.W., Sullivan J.P., Williams M. Alkaloids from frog skin: the discovery of epibatidine and the potential for developing novel non-opioid analgesics. Nat. Prod. Rep. 2000, 17:131-135.
    • (2000) Nat. Prod. Rep. , vol.17 , pp. 131-135
    • Daly, J.W.1    Garraffo, H.M.2    Spande, T.F.3    Decker, M.W.4    Sullivan, J.P.5    Williams, M.6
  • 36
    • 0037474599 scopus 로고    scopus 로고
    • Synthesis of conformationally constrained spirodihydrofuropyridine analogues of epibatidine
    • Abe H., Arai Y., Aoyagi S., Kibayashi C. Synthesis of conformationally constrained spirodihydrofuropyridine analogues of epibatidine. Tetrahedron Lett. 2003, 44:2971-2973.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2971-2973
    • Abe, H.1    Arai, Y.2    Aoyagi, S.3    Kibayashi, C.4
  • 37
    • 0035806272 scopus 로고    scopus 로고
    • Synthesis of bridged analogs of epibatidine 3-Chloro-5,7,8,9,9a,10-hexahydro-7,10-methanopyrrolo[1,2-b]-2,6-naphthyr idine and 2-chloro-5,5a,6,7,8,10-hexahydro-5,8-methanopyrrolo[2,1-b]-1,7-naphthyri dine
    • Brieaddy L.E., Mascarella S.W., Navarro H.A., Atkinson R.N., Damaj M.I., Martin B.R., Carroll F.Y. Synthesis of bridged analogs of epibatidine 3-Chloro-5,7,8,9,9a,10-hexahydro-7,10-methanopyrrolo[1,2-b]-2,6-naphthyr idine and 2-chloro-5,5a,6,7,8,10-hexahydro-5,8-methanopyrrolo[2,1-b]-1,7-naphthyri dine. Tetrahedron Lett. 2001, 42:3795-3797.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 3795-3797
    • Brieaddy, L.E.1    Mascarella, S.W.2    Navarro, H.A.3    Atkinson, R.N.4    Damaj, M.I.5    Martin, B.R.6    Carroll, F.Y.7
  • 38
    • 33746700189 scopus 로고    scopus 로고
    • Benzimidazole derivatives bearing substituted biphenyls as hepatitis C virus NS5B RNA-dependent RNA polymerase inhibitors: structure-activity relationship studies and identification of a potent and highly selective inhibitor JTK-109
    • Hirashima S., Suzuki T., Ishida T., Noji S., Yata S., Ando I., Komatsu M., Ikeda S., Hashimoto H. Benzimidazole derivatives bearing substituted biphenyls as hepatitis C virus NS5B RNA-dependent RNA polymerase inhibitors: structure-activity relationship studies and identification of a potent and highly selective inhibitor JTK-109. J. Med. Chem. 2006, 49:4721-4736.
    • (2006) J. Med. Chem. , vol.49 , pp. 4721-4736
    • Hirashima, S.1    Suzuki, T.2    Ishida, T.3    Noji, S.4    Yata, S.5    Ando, I.6    Komatsu, M.7    Ikeda, S.8    Hashimoto, H.9
  • 41
    • 0033576679 scopus 로고    scopus 로고
    • Discovery of the first potent and selective small molecule opioid receptor-like (ORL1) antagonist: 1-[(3R,4R)-1-cyclooctylmethyl-3- hydroxymethyl-4-piperidyl]-3-ethyl- 1,3-dihydro-2H-benzimidazol-2-one (J-113397)
    • Kawamoto H., Ozaki S., Itoh Y., Miyaji M., Arai S., Nakashima H., Kato T., Ohta H., Iwasawa Y. Discovery of the first potent and selective small molecule opioid receptor-like (ORL1) antagonist: 1-[(3R,4R)-1-cyclooctylmethyl-3- hydroxymethyl-4-piperidyl]-3-ethyl- 1,3-dihydro-2H-benzimidazol-2-one (J-113397). J. Med. Chem. 1999, 42:5061-5063.
    • (1999) J. Med. Chem. , vol.42 , pp. 5061-5063
    • Kawamoto, H.1    Ozaki, S.2    Itoh, Y.3    Miyaji, M.4    Arai, S.5    Nakashima, H.6    Kato, T.7    Ohta, H.8    Iwasawa, Y.9
  • 42
    • 0346887162 scopus 로고    scopus 로고
    • The design and synthesis of a novel quinolizidine template for potent opioid and opioid receptor-like (ORL1, NOP) receptor ligands
    • Jong L., Zaveri N., Toll L. The design and synthesis of a novel quinolizidine template for potent opioid and opioid receptor-like (ORL1, NOP) receptor ligands. Bioorg. Med. Chem. Lett. 2004, 14:181-185.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 181-185
    • Jong, L.1    Zaveri, N.2    Toll, L.3
  • 43
    • 15444345625 scopus 로고    scopus 로고
    • Investigation of the N-substituent conformation governing potency and receptor subtype-selectivity in (+)-(3R,4R)-dimethyl-4-(3-hydroxyphenyl)- piperidine opioid antagonists
    • Thomas J.B., Mascarella S.W., Rothman R.B., Partilla J.S., Xu H., McCullough K.B., Dersch C.M., Cantrell B.E., Zimmerman D.M., Carroll F.I. Investigation of the N-substituent conformation governing potency and receptor subtype-selectivity in (+)-(3R,4R)-dimethyl-4-(3-hydroxyphenyl)- piperidine opioid antagonists. J. Med. Chem. 1998, 41:1980-1990.
    • (1998) J. Med. Chem. , vol.41 , pp. 1980-1990
    • Thomas, J.B.1    Mascarella, S.W.2    Rothman, R.B.3    Partilla, J.S.4    Xu, H.5    McCullough, K.B.6    Dersch, C.M.7    Cantrell, B.E.8    Zimmerman, D.M.9    Carroll, F.I.10
  • 45
    • 0035979029 scopus 로고    scopus 로고
    • Olefin metathesis in the design and synthesis of a globally constrained Grb2 SH2 domain inhibitor
    • Gao Y., Wei C.-Q., Burke T.R. Olefin metathesis in the design and synthesis of a globally constrained Grb2 SH2 domain inhibitor. Org. Lett. 2001, 3:1617-1620.
    • (2001) Org. Lett. , vol.3 , pp. 1617-1620
    • Gao, Y.1    Wei, C.-Q.2    Burke, T.R.3
  • 47
    • 33846928472 scopus 로고    scopus 로고
    • Preorganization in biological systems: Are conformational constraints worth the energy?
    • Martin S.F. Preorganization in biological systems: Are conformational constraints worth the energy?. Pure Appl. Chem. 2007, 79:193-200.
    • (2007) Pure Appl. Chem. , vol.79 , pp. 193-200
    • Martin, S.F.1


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