How to cite this paper
Hadidi, S., Norouzibazaz, M & Shiri, F. (2020). A theoretical investigation of the flurbiprofen methyl ester isomerization as the main step in the photopreparation of anti-inflammatory medicine (S)-flurbiprofen: A DFT study.Current Chemistry Letters, 9(4), 161-170.
Refrences
1 Bhasin R., Bhuttani P., Krishnan C., and Sachdev S. (1979) Flurbiprofen and phenylbutazone in rheumatoid arthritis and osteoarthrosis: A double-blind study. The Journal of the Association of Physicians of India, 27 (5), 379-383.
2 Kantor T. G. (1986) Physiology and treatment of pain and inflammation: Analgesic effects of flurbiprofen. The American journal of medicine, 80 (3), 3-9.
3 Frölich J. (1997) A classification of nsaids according to the relative inhibition of cyclooxygenase isoenzymes. Trends in Pharmacological Sciences, 18 (1), 30-34.
4 Flower R. J. (2003) The development of cox2 inhibitors. Nature Reviews Drug Discovery, 2 (3), 179.
5 Greig M. E., and Griffin R. L. (1975) Antagonism of slow reacting substance in anaphylaxis (srs-a) and other spasmogens on the guinea pig tracheal chain by hydratropic acids and their effects on anaphylaxis. Journal of medicinal chemistry, 18 (1), 112-116.
6 Shimura K., Oto A., Hanai Y., Watanabe S., Toda M., Asada K., Ishibashi K., Shimabukuro Y., Yokochi N., and Shiramizu H. (1981) Analgesic effect of fentiazac after tooth extraction or minor oral surgery. Clinical therapeutics, 4 (1), 12-17.
7 Muscat J. E., Stellman S. D., and Wynder E. L. (1994) Nonsteroidal antiinflammatory drugs and colorectal cancer. Cancer, 74 (7), 1847-1854.
8 Hadidi S., Shiri F., and Norouzibazaz M. (2019) A dft study of the degradation mechanism of anticancer drug carmustine in an aqueous medium. Structural Chemistry, 30 (4), 1315-1321.
9 Hadidi S., Shiri F., and Norouzibazaz M. (2020) Mechanistic study of fenoprofen photoisomerization to pure (s)-fenoprofen: A dft study. Structural Chemistry, 31 (1), 115-122.
10 Hadidi S., Shiri F., and Norouzibazaz M. (2019) Conversion mechanism and isomeric preferences of the cis and trans isomers of anti-cancer medicine carmustine; a double hybrid dft calculation. Chemical Physics, 522, 39-43.
11 Hadidi S., Shiri F., and Norouzibazaz M. (2020) Theoretical mechanistic insight into the gabapentin lactamization by an intramolecular attack: Degradation model and stabilization factors. Journal of pharmaceutical and biomedical analysis, 178, 112900.
12 Jamali F., Mehvar R., and Pasutto F. (1989) Enantioselective aspects of drug action and disposition: Therapeutic pitfalls. Journal of pharmaceutical sciences, 78 (9), 695-715.
13 Evans A. M. (1992) Enantioselective pharmacodynamics and pharmacokinetics of chiral non-steroidal anti-inflammatory drugs. European journal of clinical pharmacology, 42 (3), 237-256.
14 Gaut Z. N., Baruth H., Randall L., Ashley C., and Paulsrud J. (1975) Stereoisomeric relationships among anti-inflammatory activity, inhibition of platelet aggregation, and inhibition of prostaglandin synthetase. Prostaglandins, 10 (4), 59-66.
15 Geisslinger G., Muth‐Selbach U., Coste O., Vetter G., Schrödter A., Schaible H. G., Brune K., and Tegeder I. (2000) Inhibition of noxious stimulus‐induced spinal prostaglandin e2 release by flurbiprofen enantiomers: A microdialysis study. Journal of neurochemistry, 74 (5), 2094-2100.
16 Andersen J. V., and Hansen S. H. (1992) Simultaneous determination of (r)-and (s)-naproxen and (r)-and (s)-6-o-desmethylnaproxen by high-performance liquid chromatography on a chiral-agp column. Journal of Chromatography B: Biomedical Sciences and Applications, 577 (2), 362-365.
17 Jamali F., Berry B. W., Tehrani M. R., and Russell A. S. (1988) Stereoselective pharmacokinetics of flurbiprofen in humans and rats. Journal of pharmaceutical sciences, 77 (8), 666-669.
18 Chen C. S., and Sih C. J. (1989) General aspects and optimization of enantioselective biocatalysis in organic solvents: The use of lipases [new synthetic methods (76)]. Angewandte Chemie International Edition in English, 28 (6), 695-707.
19 Mustranta A. (1992) Use of lipases in the resolution of racemic ibuprofen. Applied microbiology and biotechnology, 38 (1), 61-66.
20 Bornscheuer U. T., and Kazlauskas R. J. (2006) Hydrolases in organic synthesis: Regio-and stereoselective biotransformations, Ed, John Wiley & Sons.
21 Ghanem A., and Aboul‐Enein H. Y. (2005) Application of lipases in kinetic resolution of racemates. Chirality: The Pharmacological, Biological, and Chemical Consequences of Molecular Asymmetry, 17 (1), 1-15.
22 Chen C.-S., Shieh W.-R., Lu P.-H., Harriman S., and Chen C.-Y. (1991) Metabolic stereoisomeric inversion of ibuprofen in mammals. Biochimica et Biophysica Acta (BBA)-Protein Structure and Molecular Enzymology, 1078 (3), 411-417.
23 Gill G. (1968) The application of the woodward–hoffmann orbital symmetry rules to concerted organic reactions. Quarterly Reviews, Chemical Society, 22 (3), 338-389.
24 Sato D., Shiba T., Karaki T., Yamagata W., Nozaki T., Nakazawa T., and Harada S. (2017) X-ray snapshots of a pyridoxal enzyme: A catalytic mechanism involving concerted [1,5]-hydrogen sigmatropy in methionine γ-lyase. Scientific Reports, 7 (1), 4874.
25 ŠOlomek T. S., Ravat P., Mou Z., Kertesz M., and JuríČEk M. (2018) Cethrene: The chameleon of woodward–hoffmann rules. The Journal of organic chemistry, 83 (8), 4769-4774.
26 Woodward R. B., and Hoffmann R. (1965) Selection rules for sigmatropic reactions. Journal of the American Chemical Society, 87 (11), 2511-2513.
27 Demchuk O. M., Jasiński R., and Pietrusiewicz K. M. (2015) New insights into the mechanism of reduction of tertiary phosphine oxides by means of phenylsilane. Heteroatom Chemistry, 26 (6), 441-448.
28 Jasiński R. (2015) A stepwise, zwitterionic mechanism for the 1, 3-dipolar cycloaddition between (z)-c-4-methoxyphenyl-n-phenylnitrone and gem-chloronitroethene catalysed by 1-butyl-3-methylimidazolium ionic liquid cations. Tetrahedron Letters, 56 (3), 532-535.
29 Cortizo-Lacalle D., Howells C. T., Pandey U. K., Cameron J., Findlay N. J., Inigo A. R., Tuttle T., Skabara P. J., and Samuel I. D. (2014) Solution processable diketopyrrolopyrrole (dpp) cored small molecules with bodipy end groups as novel donors for organic solar cells. Beilstein journal of organic chemistry, 10 (1), 2683-2695.
30 Neese F., and Wennmohs F. (2013) Orca (3.0. 2)-an ab initio. DFT and semiempirical SCF-MO package,(Max-Planck-Institute for Chemical Energy Conversion Stiftstr. 34-36, 45470 Mulheim ad Ruhr, Germany).
31 Becke A. D. (1993) Density‐functional thermochemistry. Iii. The role of exact exchange. The Journal of chemical physics, 98 (7), 5648-5652.
32 Jacquemin D., Mennucci B., and Adamo C. (2011) Excited-state calculations with td-dft: From benchmarks to simulations in complex environments. Physical chemistry chemical physics, 13 (38), 16987-16998.
33 Perdew J. P., Burke K., and Ernzerhof M. (1996) Generalized gradient approximation made simple. Physical review letters, 77 (18), 3865.
34 Perdew J., Burke K., and Ernzerhof M. (1996) Phys rev lett 77: 3865. Errata:(1997) Phys Rev Lett, 78, 1396.
35 Marenich A. V., Cramer C. J., and Truhlar D. G. (2009) Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. The Journal of Physical Chemistry B, 113 (18), 6378-6396.
36 Jasiński R. J. T. L. (2015) A stepwise, zwitterionic mechanism for the 1, 3-dipolar cycloaddition between (z)-c-4-methoxyphenyl-n-phenylnitrone and gem-chloronitroethene catalysed by 1-butyl-3-methylimidazolium ionic liquid cations. 56 (3), 532-535.
37 Demchuk O. M., Jasiński R., and Pietrusiewicz K. M. J. H. C. (2015) New insights into the mechanism of reduction of tertiary phosphine oxides by means of phenylsilane. 26 (6), 441-448.
2 Kantor T. G. (1986) Physiology and treatment of pain and inflammation: Analgesic effects of flurbiprofen. The American journal of medicine, 80 (3), 3-9.
3 Frölich J. (1997) A classification of nsaids according to the relative inhibition of cyclooxygenase isoenzymes. Trends in Pharmacological Sciences, 18 (1), 30-34.
4 Flower R. J. (2003) The development of cox2 inhibitors. Nature Reviews Drug Discovery, 2 (3), 179.
5 Greig M. E., and Griffin R. L. (1975) Antagonism of slow reacting substance in anaphylaxis (srs-a) and other spasmogens on the guinea pig tracheal chain by hydratropic acids and their effects on anaphylaxis. Journal of medicinal chemistry, 18 (1), 112-116.
6 Shimura K., Oto A., Hanai Y., Watanabe S., Toda M., Asada K., Ishibashi K., Shimabukuro Y., Yokochi N., and Shiramizu H. (1981) Analgesic effect of fentiazac after tooth extraction or minor oral surgery. Clinical therapeutics, 4 (1), 12-17.
7 Muscat J. E., Stellman S. D., and Wynder E. L. (1994) Nonsteroidal antiinflammatory drugs and colorectal cancer. Cancer, 74 (7), 1847-1854.
8 Hadidi S., Shiri F., and Norouzibazaz M. (2019) A dft study of the degradation mechanism of anticancer drug carmustine in an aqueous medium. Structural Chemistry, 30 (4), 1315-1321.
9 Hadidi S., Shiri F., and Norouzibazaz M. (2020) Mechanistic study of fenoprofen photoisomerization to pure (s)-fenoprofen: A dft study. Structural Chemistry, 31 (1), 115-122.
10 Hadidi S., Shiri F., and Norouzibazaz M. (2019) Conversion mechanism and isomeric preferences of the cis and trans isomers of anti-cancer medicine carmustine; a double hybrid dft calculation. Chemical Physics, 522, 39-43.
11 Hadidi S., Shiri F., and Norouzibazaz M. (2020) Theoretical mechanistic insight into the gabapentin lactamization by an intramolecular attack: Degradation model and stabilization factors. Journal of pharmaceutical and biomedical analysis, 178, 112900.
12 Jamali F., Mehvar R., and Pasutto F. (1989) Enantioselective aspects of drug action and disposition: Therapeutic pitfalls. Journal of pharmaceutical sciences, 78 (9), 695-715.
13 Evans A. M. (1992) Enantioselective pharmacodynamics and pharmacokinetics of chiral non-steroidal anti-inflammatory drugs. European journal of clinical pharmacology, 42 (3), 237-256.
14 Gaut Z. N., Baruth H., Randall L., Ashley C., and Paulsrud J. (1975) Stereoisomeric relationships among anti-inflammatory activity, inhibition of platelet aggregation, and inhibition of prostaglandin synthetase. Prostaglandins, 10 (4), 59-66.
15 Geisslinger G., Muth‐Selbach U., Coste O., Vetter G., Schrödter A., Schaible H. G., Brune K., and Tegeder I. (2000) Inhibition of noxious stimulus‐induced spinal prostaglandin e2 release by flurbiprofen enantiomers: A microdialysis study. Journal of neurochemistry, 74 (5), 2094-2100.
16 Andersen J. V., and Hansen S. H. (1992) Simultaneous determination of (r)-and (s)-naproxen and (r)-and (s)-6-o-desmethylnaproxen by high-performance liquid chromatography on a chiral-agp column. Journal of Chromatography B: Biomedical Sciences and Applications, 577 (2), 362-365.
17 Jamali F., Berry B. W., Tehrani M. R., and Russell A. S. (1988) Stereoselective pharmacokinetics of flurbiprofen in humans and rats. Journal of pharmaceutical sciences, 77 (8), 666-669.
18 Chen C. S., and Sih C. J. (1989) General aspects and optimization of enantioselective biocatalysis in organic solvents: The use of lipases [new synthetic methods (76)]. Angewandte Chemie International Edition in English, 28 (6), 695-707.
19 Mustranta A. (1992) Use of lipases in the resolution of racemic ibuprofen. Applied microbiology and biotechnology, 38 (1), 61-66.
20 Bornscheuer U. T., and Kazlauskas R. J. (2006) Hydrolases in organic synthesis: Regio-and stereoselective biotransformations, Ed, John Wiley & Sons.
21 Ghanem A., and Aboul‐Enein H. Y. (2005) Application of lipases in kinetic resolution of racemates. Chirality: The Pharmacological, Biological, and Chemical Consequences of Molecular Asymmetry, 17 (1), 1-15.
22 Chen C.-S., Shieh W.-R., Lu P.-H., Harriman S., and Chen C.-Y. (1991) Metabolic stereoisomeric inversion of ibuprofen in mammals. Biochimica et Biophysica Acta (BBA)-Protein Structure and Molecular Enzymology, 1078 (3), 411-417.
23 Gill G. (1968) The application of the woodward–hoffmann orbital symmetry rules to concerted organic reactions. Quarterly Reviews, Chemical Society, 22 (3), 338-389.
24 Sato D., Shiba T., Karaki T., Yamagata W., Nozaki T., Nakazawa T., and Harada S. (2017) X-ray snapshots of a pyridoxal enzyme: A catalytic mechanism involving concerted [1,5]-hydrogen sigmatropy in methionine γ-lyase. Scientific Reports, 7 (1), 4874.
25 ŠOlomek T. S., Ravat P., Mou Z., Kertesz M., and JuríČEk M. (2018) Cethrene: The chameleon of woodward–hoffmann rules. The Journal of organic chemistry, 83 (8), 4769-4774.
26 Woodward R. B., and Hoffmann R. (1965) Selection rules for sigmatropic reactions. Journal of the American Chemical Society, 87 (11), 2511-2513.
27 Demchuk O. M., Jasiński R., and Pietrusiewicz K. M. (2015) New insights into the mechanism of reduction of tertiary phosphine oxides by means of phenylsilane. Heteroatom Chemistry, 26 (6), 441-448.
28 Jasiński R. (2015) A stepwise, zwitterionic mechanism for the 1, 3-dipolar cycloaddition between (z)-c-4-methoxyphenyl-n-phenylnitrone and gem-chloronitroethene catalysed by 1-butyl-3-methylimidazolium ionic liquid cations. Tetrahedron Letters, 56 (3), 532-535.
29 Cortizo-Lacalle D., Howells C. T., Pandey U. K., Cameron J., Findlay N. J., Inigo A. R., Tuttle T., Skabara P. J., and Samuel I. D. (2014) Solution processable diketopyrrolopyrrole (dpp) cored small molecules with bodipy end groups as novel donors for organic solar cells. Beilstein journal of organic chemistry, 10 (1), 2683-2695.
30 Neese F., and Wennmohs F. (2013) Orca (3.0. 2)-an ab initio. DFT and semiempirical SCF-MO package,(Max-Planck-Institute for Chemical Energy Conversion Stiftstr. 34-36, 45470 Mulheim ad Ruhr, Germany).
31 Becke A. D. (1993) Density‐functional thermochemistry. Iii. The role of exact exchange. The Journal of chemical physics, 98 (7), 5648-5652.
32 Jacquemin D., Mennucci B., and Adamo C. (2011) Excited-state calculations with td-dft: From benchmarks to simulations in complex environments. Physical chemistry chemical physics, 13 (38), 16987-16998.
33 Perdew J. P., Burke K., and Ernzerhof M. (1996) Generalized gradient approximation made simple. Physical review letters, 77 (18), 3865.
34 Perdew J., Burke K., and Ernzerhof M. (1996) Phys rev lett 77: 3865. Errata:(1997) Phys Rev Lett, 78, 1396.
35 Marenich A. V., Cramer C. J., and Truhlar D. G. (2009) Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. The Journal of Physical Chemistry B, 113 (18), 6378-6396.
36 Jasiński R. J. T. L. (2015) A stepwise, zwitterionic mechanism for the 1, 3-dipolar cycloaddition between (z)-c-4-methoxyphenyl-n-phenylnitrone and gem-chloronitroethene catalysed by 1-butyl-3-methylimidazolium ionic liquid cations. 56 (3), 532-535.
37 Demchuk O. M., Jasiński R., and Pietrusiewicz K. M. J. H. C. (2015) New insights into the mechanism of reduction of tertiary phosphine oxides by means of phenylsilane. 26 (6), 441-448.