메뉴 건너뛰기




Volumn 19, Issue 6, 2013, Pages 2399-2412

Prodrugs for masking bitter taste of antibacterial drugs - A computational approach

Author keywords

Antibacterial prodrugs; Cefuroxime prodrugs; DFT calculations; Intramolecular amide hydrolysis; Maleamic acid amides; Masking bitter taste

Indexed keywords

ACICLOVIR; AMIDE; CARBON; CARBOXYLIC ACID; CEFUROXIME; PRODRUG;

EID: 84878759581     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-013-1780-5     Document Type: Article
Times cited : (29)

References (71)
  • 1
    • 3042641200 scopus 로고    scopus 로고
    • Taste masking technologies in oral pharmaceuticals, recent development and approaches
    • 10.1081/DDC-120037477 1:CAS:528:DC%2BD2cXksVSmt7g%3D
    • Sohi H, Sultana Y, Khar RK (2004) Taste masking technologies in oral pharmaceuticals, recent development and approaches. Drug Dev Ind Pharm 30(5):429-448
    • (2004) Drug Dev Ind Pharm , vol.30 , Issue.5 , pp. 429-448
    • Sohi, H.1    Sultana, Y.2    Khar, R.K.3
  • 3
    • 0033667684 scopus 로고    scopus 로고
    • Bitter taste, phytonutrients, and the consumer: A review
    • 1:CAS:528:DC%2BD3cXosl2msbY%3D
    • Drewnowski A, Gomez-Carneros C (2000) Bitter taste, phytonutrients, and the consumer: a review. Am J Clin Nutr 72:1424-1435
    • (2000) Am J Clin Nutr , vol.72 , pp. 1424-1435
    • Drewnowski, A.1    Gomez-Carneros, C.2
  • 4
    • 68649105255 scopus 로고    scopus 로고
    • Identification of the key bitter compounds in our daily diet is a prerequisite for the understanding of the hTAS2R gene polymorphisms affecting food choice
    • 10.1111/j.1749-6632.2009.03914.x 1:CAS:528:DC%2BD1MXhtFSqsLnP
    • Hofmann T (2009) Identification of the key bitter compounds in our daily diet is a prerequisite for the understanding of the hTAS2R gene polymorphisms affecting food choice. Ann N Y Acad Sci 1170:116-125
    • (2009) Ann N y Acad Sci , vol.1170 , pp. 116-125
    • Hofmann, T.1
  • 5
    • 24944559010 scopus 로고    scopus 로고
    • Building a tree of knowledge: Analysis of bitter molecules
    • 10.1093/chemse/bji048 1:CAS:528:DC%2BD2MXpvFGqtLY%3D
    • Rodgers S, Busch J, Peters H, Christ-Hazelhof E (2005) Building a tree of knowledge: analysis of bitter molecules. Chem Senses 30:547-557
    • (2005) Chem Senses , vol.30 , pp. 547-557
    • Rodgers, S.1    Busch, J.2    Peters, H.3    Christ-Hazelhof, E.4
  • 6
    • 33646252229 scopus 로고    scopus 로고
    • Characterizing bitterness: Identification of key structural features and development of a classification model
    • 10.1021/ci0504418 1:CAS:528:DC%2BD28XhtVGqur0%3D
    • Rodgers S, Glen RC, Bender A (2006) Characterizing bitterness: identification of key structural features and development of a classification model. J Chem Inf Model 46:569-576
    • (2006) J Chem Inf Model , vol.46 , pp. 569-576
    • Rodgers, S.1    Glen, R.C.2    Bender, A.3
  • 7
    • 67650686837 scopus 로고    scopus 로고
    • Bitter peptides and bitter taste receptors
    • 10.1007/s00018-009-8755-9 1:CAS:528:DC%2BD1MXosVKjsr4%3D
    • Maehashi K, Huang L (2009) Bitter peptides and bitter taste receptors. Cell Mol Life Sci 66:1661-1671
    • (2009) Cell Mol Life Sci , vol.66 , pp. 1661-1671
    • Maehashi, K.1    Huang, L.2
  • 8
    • 33746639193 scopus 로고    scopus 로고
    • Bitter taste receptors and human bitter taste perception
    • 10.1007/s00018-006-6113-8 1:CAS:528:DC%2BD28XnvFWmsLg%3D
    • Behrens M, Meyerhof W (2006) Bitter taste receptors and human bitter taste perception. Cell Mol Life Sci 63:1501-1509
    • (2006) Cell Mol Life Sci , vol.63 , pp. 1501-1509
    • Behrens, M.1    Meyerhof, W.2
  • 9
    • 79959538797 scopus 로고    scopus 로고
    • Molecular biology of mammalian bitter taste receptors. A review
    • 10.1002/ffj.2041 1:CAS:528:DC%2BC3MXnvFShtrg%3D
    • Meyerhof W, Born S, Brockhoff A, Behrens M (2011) Molecular biology of mammalian bitter taste receptors. A review. Flavour Frag J 26:260-268
    • (2011) Flavour Frag J , vol.26 , pp. 260-268
    • Meyerhof, W.1    Born, S.2    Brockhoff, A.3    Behrens, M.4
  • 10
    • 65449159720 scopus 로고    scopus 로고
    • Mammalian bitter taste perception
    • 1:CAS:528:DC%2BC3cXnvFWmt78%3D
    • Behrens M, Meyerhof W (2009) Mammalian bitter taste perception. Results Probl Cell Differ 47:203-220
    • (2009) Results Probl Cell Differ , vol.47 , pp. 203-220
    • Behrens, M.1    Meyerhof, W.2
  • 11
    • 34547802810 scopus 로고    scopus 로고
    • Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and labdane diterpenoids, strychnine, and denatonium
    • 10.1021/jf070503p 1:CAS:528:DC%2BD2sXmvV2qsbw%3D
    • Brockhoff A, Behrens M, Massarotti A, Appendino G, Meyerhof W (2007) Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and labdane diterpenoids, strychnine, and denatonium. J Agric Food Chem 55:6236-6243
    • (2007) J Agric Food Chem , vol.55 , pp. 6236-6243
    • Brockhoff, A.1    Behrens, M.2    Massarotti, A.3    Appendino, G.4    Meyerhof, W.5
  • 14
    • 0036844351 scopus 로고    scopus 로고
    • The human TAS2R16 receptor mediates bitter taste in response to beta-glucopyranosides
    • 10.1038/ng1014 1:CAS:528:DC%2BD38Xot1Kls7s%3D
    • Bufe B, Hofmann T, Krautwurst D, Raguse JD, Meyerhof W (2002) The human TAS2R16 receptor mediates bitter taste in response to beta-glucopyranosides. Nat Genet 32:397-401
    • (2002) Nat Genet , vol.32 , pp. 397-401
    • Bufe, B.1    Hofmann, T.2    Krautwurst, D.3    Raguse, J.D.4    Meyerhof, W.5
  • 17
    • 60849118380 scopus 로고    scopus 로고
    • Trends in harmaceutical taste masking technologies: A patent review
    • 10.2174/187221109787158364 1:CAS:528:DC%2BD1MXks1Chtbk%3D
    • Ayenew Z, Puri V, Kumar L, Bansal AK (2009) Trends in harmaceutical taste masking technologies: a patent review. Recent Pat Drug Deliv Formul 3:26-39
    • (2009) Recent Pat Drug Deliv Formul , vol.3 , pp. 26-39
    • Ayenew, Z.1    Puri, V.2    Kumar, L.3    Bansal, A.K.4
  • 18
    • 79955377744 scopus 로고    scopus 로고
    • Pop the pills without bitterness taste-masking technologies for bitter drugs
    • Gowthamarajan K, Kulkarni GT, Kumar MN (2004) Pop the pills without bitterness taste-masking technologies for bitter drugs. Resonance 25
    • (2004) Resonance , vol.25
    • Gowthamarajan, K.1    Kulkarni, G.T.2    Kumar, M.N.3
  • 20
    • 34547957533 scopus 로고    scopus 로고
    • Pleasant tasting aqueous liquid composition of a bitter-tasting drug
    • PCT Int Appl WO9805312
    • Fawzy AA (1998) Pleasant tasting aqueous liquid composition of a bitter-tasting drug. PCT Int Appl WO9805312, 2.
    • (1998) , pp. 2
    • Fawzy, A.A.1
  • 21
    • 84856852270 scopus 로고
    • Aliphatic esters as solventless coating pharmaceuticals
    • Can Pat Appl CA2082137:11
    • Gowan WG (1993) Aliphatic esters as solventless coating pharmaceuticals. Can Pat Appl CA2082137:11
    • (1993)
    • Gowan, W.G.1
  • 23
    • 1142274364 scopus 로고    scopus 로고
    • Bitter taste bypass need for sugar spoon
    • Bush L (2004) Bitter taste bypass need for sugar spoon. Pharm Technol 2004. http://pharmtech.findpharma.com/pharmtech/data/articlestandard//pharmtech/ 072004/84521/article.pdf
    • (2004) Pharm Technol 2004
    • Bush, L.1
  • 30
    • 50449085988 scopus 로고    scopus 로고
    • Masking bitter taste by molecules
    • 10.1007/s12078-008-9008-2
    • Ley JP (2008) Masking bitter taste by molecules. Chem Percept 1:58-77
    • (2008) Chem Percept , vol.1 , pp. 58-77
    • Ley, J.P.1
  • 32
    • 34347400020 scopus 로고    scopus 로고
    • Quantitative elucidation of the structure-bittereness relationship of cynaropicrin and grosheimin derivatives
    • 10.1016/j.foodchem.2007.03.038 1:CAS:528:DC%2BD2sXnsVWjsLg%3D
    • Scotti L, Scotti MT, Ishiki HM, Ferreira MGP, Emerenciano VP, Menezes CMS, Ferreira EI (2007) Quantitative elucidation of the structure-bittereness relationship of cynaropicrin and grosheimin derivatives. Food Chem 105:77-83
    • (2007) Food Chem , vol.105 , pp. 77-83
    • Scotti, L.1    Scotti, M.T.2    Ishiki, H.M.3    Ferreira, M.G.P.4    Emerenciano, V.P.5    Menezes, C.M.S.6    Ferreira, E.I.7
  • 33
    • 33845279420 scopus 로고
    • Fast hydrolysis of an aliphatic amide at neutral pH and ambient temperature. A peptidase model
    • 10.1021/ja00228a031 1:CAS:528:DyaL1cXlsVyrsb0%3D
    • Menger FM, Ladika M (1988) Fast hydrolysis of an aliphatic amide at neutral pH and ambient temperature. A peptidase model. J Am Chem Soc 110:6794-6796
    • (1988) J Am Chem Soc , vol.110 , pp. 6794-6796
    • Menger, F.M.1    Ladika, M.2
  • 34
    • 77949489830 scopus 로고    scopus 로고
    • The efficiency of proton transfer in Kirby's enzyme model, a computational approach
    • 10.1016/j.tetlet.2010.02.062 1:CAS:528:DC%2BC3cXjslSntrg%3D
    • Karaman R (2010) The efficiency of proton transfer in Kirby's enzyme model, a computational approach. Tetrahedron Lett 51:2130-2135
    • (2010) Tetrahedron Lett , vol.51 , pp. 2130-2135
    • Karaman, R.1
  • 35
    • 77956414921 scopus 로고    scopus 로고
    • Anti-malarial pro-drugs - A computational aided design
    • 10.1111/j.1747-0285.2010.01018.x 1:CAS:528:DC%2BC3cXht1Cmt7nL
    • Karaman R, Hallak H (2010) Anti-malarial pro-drugs- a computational aided design. Chem Biol Drug Des 76:350-360
    • (2010) Chem Biol Drug des , vol.76 , pp. 350-360
    • Karaman, R.1    Hallak, H.2
  • 36
    • 78651287394 scopus 로고    scopus 로고
    • Prodrugs of aza nucleosides based on proton transfer reactions
    • 10.1007/s10822-010-9389-6 1:CAS:528:DC%2BC3cXhsVektbrL
    • Karaman R (2010) Prodrugs of aza nucleosides based on proton transfer reactions. J Comput Mol Des 24:961-970
    • (2010) J Comput Mol des , vol.24 , pp. 961-970
    • Karaman, R.1
  • 37
    • 79251596024 scopus 로고    scopus 로고
    • Analyzing the efficiency of proton transfer to carbon in Kirby's enzyme model - A computational approach
    • 10.1016/j.tetlet.2010.12.018 1:CAS:528:DC%2BC3MXjvFGjsw%3D%3D
    • Karaman R (2011) Analyzing the efficiency of proton transfer to carbon in Kirby's enzyme model - a computational approach. Tetrahedron Lett 52:699-704
    • (2011) Tetrahedron Lett , vol.52 , pp. 699-704
    • Karaman, R.1
  • 38
    • 84856259611 scopus 로고    scopus 로고
    • Computer-assisted design for paracetamol masking bitter taste prodrugs
    • 10.1007/s00894-011-1040-5 1:CAS:528:DC%2BC38XksVahtw%3D%3D
    • Hejaz H, Karaman R, Khamis M (2012) Computer-assisted design for paracetamol masking bitter taste prodrugs. J Mol Model 18:103-114
    • (2012) J Mol Model , vol.18 , pp. 103-114
    • Hejaz, H.1    Karaman, R.2    Khamis, M.3
  • 39
    • 84861235345 scopus 로고    scopus 로고
    • Computer-assisted design for atenolol prodrugs for the use in aqueous formulations
    • 10.1007/s00894-011-1180-7 1:CAS:528:DC%2BC38XkvVeksb4%3D
    • Karaman R, Dajani KK, Hallak H (2012) Computer-assisted design for atenolol prodrugs for the use in aqueous formulations. J Mol Model 18:1523-1540
    • (2012) J Mol Model , vol.18 , pp. 1523-1540
    • Karaman, R.1    Dajani, K.K.2    Hallak, H.3
  • 40
    • 80054112134 scopus 로고    scopus 로고
    • Computational aided design for dopamine prodrugs based on novel chemical approach
    • 10.1111/j.1747-0285.2011.01208.x 1:CAS:528:DC%2BC3MXhtl2nsrvM
    • Karaman R (2011) Computational aided design for dopamine prodrugs based on novel chemical approach. Chem Biol Drug Des 78:853-863
    • (2011) Chem Biol Drug des , vol.78 , pp. 853-863
    • Karaman, R.1
  • 41
    • 84859420858 scopus 로고    scopus 로고
    • Prodrugs of acyclovir - A computational approach
    • 10.1111/j.1747-0285.2012.01335.x 1:CAS:528:DC%2BC38XlslansLo%3D
    • Karaman R, Dajani KK, Qtait A, Khamis M (2012) Prodrugs of acyclovir - a computational approach. Chem Biol Drug Des 79:819-834
    • (2012) Chem Biol Drug des , vol.79 , pp. 819-834
    • Karaman, R.1    Dajani, K.K.2    Qtait, A.3    Khamis, M.4
  • 42
    • 0023597540 scopus 로고
    • Effect of dose and food on the bioavailability of cefuroxime axetil
    • 10.1002/bdd.2510080604 1:CAS:528:DyaL1cXmvVaisQ%3D%3D
    • Finn A, Straugun A, Meyer M, Chubb J (1987) Effect of dose and food on the bioavailability of cefuroxime axetil. Biopharm Drug Dispos 8:519-526
    • (1987) Biopharm Drug Dispos , vol.8 , pp. 519-526
    • Finn, A.1    Straugun, A.2    Meyer, M.3    Chubb, J.4
  • 43
  • 44
    • 51449119828 scopus 로고    scopus 로고
    • Preparation and evaluation of taste masked famotidine formulation using drug/beta-cyclodextrin/polymer ternary complexation approach
    • 10.1208/s12249-008-9078-0 1:CAS:528:DC%2BC3cXnslGjtLg%3D
    • Patel AR, Vavia PR (2008) Preparation and evaluation of taste masked famotidine formulation using drug/beta-cyclodextrin/polymer ternary complexation approach. AAPS PharmSci Tech 9(2):544-550
    • (2008) AAPS PharmSci Tech , vol.9 , Issue.2 , pp. 544-550
    • Patel, A.R.1    Vavia, P.R.2
  • 45
    • 63649137129 scopus 로고    scopus 로고
    • Taste masking by spray-drying technique
    • 10.1208/s12249-008-9154-5 1:CAS:528:DC%2BC3cXovFanu7w%3D
    • Bora D, Borude P, Bhise K (2008) Taste masking by spray-drying technique. AAPS PharmSci Tech 9(4):1159-1164
    • (2008) AAPS PharmSci Tech , vol.9 , Issue.4 , pp. 1159-1164
    • Bora, D.1    Borude, P.2    Bhise, K.3
  • 46
    • 0030019697 scopus 로고    scopus 로고
    • Particle design for taste-masking using a spray-congealing technique
    • 10.1248/cpb.44.187 1:CAS:528:DyaK28XotVeqtQ%3D%3D
    • Yajima T, Nogata A, Demachi M, Umeki N, Itai S, Yunoki N et al (1996) Particle design for taste-masking using a spray-congealing technique. Chem Pharm Bull 44(1):187-191
    • (1996) Chem Pharm Bull , vol.44 , Issue.1 , pp. 187-191
    • Yajima, T.1    Nogata, A.2    Demachi, M.3    Umeki, N.4    Itai, S.5    Yunoki, N.6
  • 47
    • 0036150607 scopus 로고    scopus 로고
    • Taste masking of diclofenac sodium using microencapsulation
    • 10.1080/02652040110055612
    • Al-Omranm MF, Al-Suwayeh SA, El-Helw AM, Saleh SI (2002) Taste masking of diclofenac sodium using microencapsulation. J Microencapsul 19(1):45-52
    • (2002) J Microencapsul , vol.19 , Issue.1 , pp. 45-52
    • Al-Omranm, M.F.1    Al-Suwayeh, S.A.2    El-Helw, A.M.3    Saleh, S.I.4
  • 48
    • 79959491520 scopus 로고    scopus 로고
    • Taste masked, orally disintegrating tablet containing microspheres for immediate release
    • 1:CAS:528:DC%2BD1MXnsVSmu7k%3D
    • Shidhaye S, Malke S, Kadam V (2008) Taste masked, orally disintegrating tablet containing microspheres for immediate release. J Pharm Res 1:225-229
    • (2008) J Pharm Res , vol.1 , pp. 225-229
    • Shidhaye, S.1    Malke, S.2    Kadam, V.3
  • 49
    • 0029941986 scopus 로고    scopus 로고
    • Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy
    • 10.2165/00003495-199652010-00009 1:CAS:528:DyaK28XksVOnsbo%3D
    • Perry CM, Brogden RN (1996) Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs 52(1):125-158
    • (1996) Drugs , vol.52 , Issue.1 , pp. 125-158
    • Perry, C.M.1    Brogden, R.N.2
  • 50
    • 37049120339 scopus 로고
    • Structure and efficiency in intramolecular and enzymatic catalysis. Catalysis of amide hydrolysis by the carboxy-group of substituted maleamic acids
    • Kirby AJ, Lancaster PW (1972) Structure and efficiency in intramolecular and enzymatic catalysis. Catalysis of amide hydrolysis by the carboxy-group of substituted maleamic acids. J Chem Soc Perkin Trans 2:1206-1214
    • (1972) J Chem Soc Perkin Trans , vol.2 , pp. 1206-1214
    • Kirby, A.J.1    Lancaster, P.W.2
  • 51
    • 84555202654 scopus 로고    scopus 로고
    • Analyzing the efficiency in intramolecular amide hydrolysis of Kirby's N-alkylmaleamic acids - A computational approach
    • 10.1016/j.comptc.2011.07.025 1:CAS:528:DC%2BC3MXht1ehs7bE
    • Karaman R (2011) Analyzing the efficiency in intramolecular amide hydrolysis of Kirby's N-alkylmaleamic acids - a computational approach. J Comput Theor Chem 974:133-142
    • (2011) J Comput Theor Chem , vol.974 , pp. 133-142
    • Karaman, R.1
  • 53
    • 0039968228 scopus 로고
    • Application of a universal force field to main group compounds
    • 10.1021/ja00051a042 1:CAS:528:DyaK38XmsVSis78%3D
    • Casewit CJ, Colwell KS, Rappe AK (1992) Application of a universal force field to main group compounds. J Am Chem Soc 114:10046-10053
    • (1992) J Am Chem Soc , vol.114 , pp. 10046-10053
    • Casewit, C.J.1    Colwell, K.S.2    Rappe, A.K.3
  • 54
    • 37049129198 scopus 로고
    • Symmetries of activated complexes
    • 10.1039/tf9686400371 1:CAS:528:DyaF1cXltlOksw%3D%3D
    • Murrell JN, Laidler KJ (1968) Symmetries of activated complexes. Trans Faraday Soc 64:371-377
    • (1968) Trans Faraday Soc , vol.64 , pp. 371-377
    • Murrell, J.N.1    Laidler, K.J.2
  • 55
    • 0002122384 scopus 로고
    • Reaction paths on multidimensional energy hypersurfaces
    • 10.1002/anie.198000013
    • Muller K (1980) Reaction paths on multidimensional energy hypersurfaces. Angew Chem Int Ed Engl 19:1-13
    • (1980) Angew Chem Int Ed Engl , vol.19 , pp. 1-13
    • Muller, K.1
  • 56
    • 0031209054 scopus 로고    scopus 로고
    • A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics
    • 10.1063/1.474659
    • Cancès MT, Mennucci B, Tomasi J (1997) A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys 107:3032-3041
    • (1997) J Chem Phys , vol.107 , pp. 3032-3041
    • Cancès, M.T.1    Mennucci, B.2    Tomasi, J.3
  • 57
    • 84961979198 scopus 로고    scopus 로고
    • Coninuum solvation models: A new approach to the problem of solute's charge distribution and cavity boundaries
    • 10.1063/1.473558 1:CAS:528:DyaK2sXitVGkt74%3D
    • Mennucci B, Tomasi J (1997) Coninuum solvation models: a new approach to the problem of solute's charge distribution and cavity boundaries. J Chem Phys 106:5151
    • (1997) J Chem Phys , vol.106 , pp. 5151
    • Mennucci, B.1    Tomasi, J.2
  • 58
    • 0031553301 scopus 로고    scopus 로고
    • Evaluation of solvent effects in isotropic and anisotropic dielectrics and in ionic solutions with a unified integral equation method: Theoretical bases, computational implementation, and numerical applications
    • 10.1021/jp971959k 1:CAS:528:DyaK2sXnt1Smsbo%3D
    • Mennucci B, Cancès MT, Tomasi J (1997) Evaluation of solvent effects in isotropic and anisotropic dielectrics and in ionic solutions with a unified integral equation method: theoretical bases, computational implementation, and numerical applications. J Phys Chem B 101:10506-10517
    • (1997) J Phys Chem B , vol.101 , pp. 10506-10517
    • Mennucci, B.1    Cancès, M.T.2    Tomasi, J.3
  • 59
    • 84962428823 scopus 로고    scopus 로고
    • The IEF version of the PCM solvation method: An overview of a new method addressed to study molecular solutes at the QM ab initio level
    • 10.1016/S0166-1280(98)00553-3
    • Tomasi J, Mennucci B, Cancès MT (1997) The IEF version of the PCM solvation method: an overview of a new method addressed to study molecular solutes at the QM ab initio level. J Mol Struct (THEOCHEM) 464:211-226
    • (1997) J Mol Struct (THEOCHEM) , vol.464 , pp. 211-226
    • Tomasi, J.1    Mennucci, B.2    Cancès, M.T.3
  • 61
    • 0038564213 scopus 로고
    • Carboxylic acid participation in amide hydrolysis. Evidence that separation of a nonbonded complex can be rate determining
    • 10.1021/ja00374a032 1:CAS:528:DyaL38XhvFyktb0%3D
    • Kluger R, Chin J (1982) Carboxylic acid participation in amide hydrolysis. Evidence that separation of a nonbonded complex can be rate determining. J Am Chem Soc 104:2891-2897
    • (1982) J Am Chem Soc , vol.104 , pp. 2891-2897
    • Kluger, R.1    Chin, J.2
  • 62
    • 84986431729 scopus 로고
    • AM1 study of acid-catalyzed hydrolysis of maleamic (4-amino-4-oxo-2- butenoic) acids
    • 10.1002/jcc.540110913 1:CAS:528:DyaK3MXitlWmtg%3D%3D
    • Katagi T (1990) AM1 study of acid-catalyzed hydrolysis of maleamic (4-amino-4-oxo-2-butenoic) acids. J Comput Chem 11(9):1094-1100
    • (1990) J Comput Chem , vol.11 , Issue.9 , pp. 1094-1100
    • Katagi, T.1
  • 64
    • 84855186054 scopus 로고    scopus 로고
    • Effective molarities for intramolecular reactions
    • 10.1002/poc.858
    • Kirby AJ (2005) Effective molarities for intramolecular reactions. J Phys Org Chem 18:101-278
    • (2005) J Phys Org Chem , vol.18 , pp. 101-278
    • Kirby, A.J.1
  • 65
    • 78049329519 scopus 로고    scopus 로고
    • Computational analysis of intramolecularity in proton transfer reactions
    • 10.1039/c0ob00252f 1:CAS:528:DC%2BC3cXhtlentL%2FN
    • Karaman R, Pascal RA (2010) Computational analysis of intramolecularity in proton transfer reactions. Org Biomol Chem 8:5174-5178
    • (2010) Org Biomol Chem , vol.8 , pp. 5174-5178
    • Karaman, R.1    Pascal, R.A.2
  • 66
    • 77956229171 scopus 로고    scopus 로고
    • A general equation correlating intramolecular rates with 'attack' parameters: Distance and angle
    • 10.1016/j.tetlet.2010.07.137 1:CAS:528:DC%2BC3cXhtVGrtrzO
    • Karaman R (2010) A general equation correlating intramolecular rates with 'attack' parameters: distance and angle. Tetrahedron Lett 51:5185-5190
    • (2010) Tetrahedron Lett , vol.51 , pp. 5185-5190
    • Karaman, R.1
  • 67
    • 70149084148 scopus 로고    scopus 로고
    • The gem-disubstituent effect - A computational study that exposes the relevance of existing theoretical models
    • 10.1016/j.tetlet.2009.08.072 1:CAS:528:DC%2BD1MXhtFGgu7zL
    • Karaman R (2009) The gem-disubstituent effect - a computational study that exposes the relevance of existing theoretical models. Tetrahedron Lett 50:6083-6087
    • (2009) Tetrahedron Lett , vol.50 , pp. 6083-6087
    • Karaman, R.1
  • 68
    • 67650091591 scopus 로고    scopus 로고
    • The effective molarity (EM) puzzle in proton transfer reactions
    • 10.1016/j.bioorg.2009.04.003 1:CAS:528:DC%2BD1MXosValtrs%3D
    • Karaman R (2009) The effective molarity (EM) puzzle in proton transfer reactions. Bioorg Chem 37:106-110
    • (2009) Bioorg Chem , vol.37 , pp. 106-110
    • Karaman, R.1
  • 69
    • 72049105875 scopus 로고    scopus 로고
    • Effects of substitution on the effective molarity (EM) for five membered ring-closure reactions - A computational approach
    • 10.1016/j.theochem.2009.09.035 1:CAS:528:DC%2BD1MXhsFOrur7I
    • Karaman R (2010) Effects of substitution on the effective molarity (EM) for five membered ring-closure reactions - a computational approach. J Mol Struct (THEOCHEM) 939:69-74
    • (2010) J Mol Struct (THEOCHEM) , vol.939 , pp. 69-74
    • Karaman, R.1
  • 70
    • 72049097664 scopus 로고    scopus 로고
    • The effective molarity (EM) puzzle in intramolecular ring-closing reactions
    • 10.1016/j.theochem.2009.10.006 1:CAS:528:DC%2BD1MXhsFOqtL3I
    • Karaman R (2010) The effective molarity (EM) puzzle in intramolecular ring-closing reactions. J Mol Struct (THEOCHEM) 940:70-75
    • (2010) J Mol Struct (THEOCHEM) , vol.940 , pp. 70-75
    • Karaman, R.1
  • 71
    • 84855168923 scopus 로고    scopus 로고
    • The role of proximity orientation in intramolecular proton transfer reactions
    • 10.1016/j.comptc.2011.03.029 1:CAS:528:DC%2BC3MXlvVWltrY%3D
    • Karaman R (2011) The role of proximity orientation in intramolecular proton transfer reactions. J Comput Theor Chem 966:311-321
    • (2011) J Comput Theor Chem , vol.966 , pp. 311-321
    • Karaman, R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.