S. Okovytyy
320
8. Apparu M, Barrelle M (1978) Reactivite des epoxydes—III: Methodes de synthese
d’hydroxyalkyl-1 vinyl-2 cyclopropanes: reactions d’epoxydes γ,δ-ethyleniques avec les
amidures de lithium dans l’HMTP. Tetrahedron 34(11):1691–1697
9. Rickborn B, Thumell RP (1969) Stereoselectivity of the base-induced conversion of epoxides
to allylic alcohols. J Org Chem 34(11):3583–3586
10. Norman ROC, Coxon JM (1993) Principles of organic synthesis, 3rd edn. Chapman and Hall,
Blackie
11. Chacos N, Capdevila J, Falck JR, Manna S, Martin-Wixtrom C, Gill SS, Hammock BD,
Estabrook, RW (1983) The reaction of arachidonic acid epoxides (epoxyeicosatrienoic acids)
with a cytosolic epoxide hydrolase. Arch Biochem Biophys 223:639–648
12. Yu Z, Xu F, Huse LM, Morisseau C, Draper AJ, Newman JW, Parker C, Graham L, Engler
MM, Hammock BD, Zeldin DC, Kroetz DL (2000) Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ Res 87:992–998
13. Lonsdale R, Harvey JN, Mulholland AJ (2010) Compound I reactivity defines alkene oxidation selectivity in cytochrome P450cam. J Phys Chem B 114(2):1156–1162
14. Jean DJ St Jr, Fotsch C (2012) Mitigating heterocycle metabolism in drug discovery. J Med
Chem 55(13):6002–6020
15. Koskinen M, Plna K (2000) Specific DNA adducts induced by some mono-substituted epoxides in vitro and in vivo. Chem Biol Interact 129(3):209–229
16. Suresh CH, Vijayalakshmi KP, Mohan N, Ajitha M (2011) Mechanism of epoxide hydrolysis
in microsolvated nucleotide bases adenine, guanine and cytosine: a DFT study. Org Biomol
Chem 9:5115–5122
17. Oesch F (1973) Mammalian epoxide hydrases. Inducible enzymes catalyzing inactivation
of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds.
Xenobiotica 3:305–340
18. Oesch F, Hengstler JG, Arand M (2004) Detoxification strategy of epoxide hydrolase—the
basis for a novel threshold for definable genotoxic carcinogens. Nonlinearity Biol Toxicol
Med 2(1):21–26
19. Jones RB, Mackrodt WC (1983) Structure–genotoxicity relationship for aliphatic epoxides.
Biochem Pharmacol 32:2359–2362
20. Ross WC (1950) The reactions of certain epoxides in aqueous solutions. J Chem Soc 2257–
2272
21. Jones RB, Mackrodt WC (1982) Structure–mutagenicity relationships for chlorinated ethylenes: a model based on the stability of the metabolically derived epoxides. Biochem Pharmacol 31:3710–3712
22. Kirkovsky LI, Lermontov SA, Zavorin SI, Sukhozhenko II, Zavelsky VI, Thier R, Bolt
HM (1998) Hydrolysis of genotoxic methyl-substituted oxiranes: experimental kinetic and
semiempirical studies. Environ Toxicol Chem 17:2141–2147
23. Gervasi PG, Citti L, Delmonte M, Longo V, Benetti D (1985) Mutagenicity and chemicalreactivity of epoxidic intermediates of the isoprene metabolism and other structurally relatedcompounds. Mutat Res 156:77–82
24. Polansky OE, Fratev F (1976) Pars orbital method: character orders in CNDO calculations and a new definition for bond orders in all valence electron methods. Chem Phys Lett
37(3):602–607
25. Fujimoto H, Katata M, Yamabe S, Fukui K (1972) An MO-theoretical interpretation of the
nature of chemical reactions III. Bond interchange. Bull Chem Soc Jpn 45(5):1320–1324
26. Kas’yan LI (1999) Steric strain and reactivity of epoxynorbornanes (3-oxatricyclo[3.2.1.02,4]
octanes). Rus J Org Chem 35(5):635–665
27. Kas’yan LI, Gorb LG, Seferova MF, Chernousov DA, Svyatkin VA, Boldeskul IE (1990)
Quantum-chemical investigation of alicyclic epoxide compounds. Zh Org Khim 26(1):3–10
28. Kas’yan LI, Gorb LG, Seferova MF, Dryuk VG (1990) Quantum-chemical study of electronic structure and reactivity of spirooxiranes. Ukr Khim Zhurn 56(10):1071–1076
29. Kretova EN, Podgornova VA, Shpekht NA, Ustavshchikov BF (1983) Theoretical and experimental studies of the reactivity of alkene oxides with acids. I. Calculation of the electronic
320
8. Apparu M, Barrelle M (1978) Reactivite des epoxydes—III: Methodes de synthese
d’hydroxyalkyl-1 vinyl-2 cyclopropanes: reactions d’epoxydes γ,δ-ethyleniques avec les
amidures de lithium dans l’HMTP. Tetrahedron 34(11):1691–1697
9. Rickborn B, Thumell RP (1969) Stereoselectivity of the base-induced conversion of epoxides
to allylic alcohols. J Org Chem 34(11):3583–3586
10. Norman ROC, Coxon JM (1993) Principles of organic synthesis, 3rd edn. Chapman and Hall,
Blackie
11. Chacos N, Capdevila J, Falck JR, Manna S, Martin-Wixtrom C, Gill SS, Hammock BD,
Estabrook, RW (1983) The reaction of arachidonic acid epoxides (epoxyeicosatrienoic acids)
with a cytosolic epoxide hydrolase. Arch Biochem Biophys 223:639–648
12. Yu Z, Xu F, Huse LM, Morisseau C, Draper AJ, Newman JW, Parker C, Graham L, Engler
MM, Hammock BD, Zeldin DC, Kroetz DL (2000) Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ Res 87:992–998
13. Lonsdale R, Harvey JN, Mulholland AJ (2010) Compound I reactivity defines alkene oxidation selectivity in cytochrome P450cam. J Phys Chem B 114(2):1156–1162
14. Jean DJ St Jr, Fotsch C (2012) Mitigating heterocycle metabolism in drug discovery. J Med
Chem 55(13):6002–6020
15. Koskinen M, Plna K (2000) Specific DNA adducts induced by some mono-substituted epoxides in vitro and in vivo. Chem Biol Interact 129(3):209–229
16. Suresh CH, Vijayalakshmi KP, Mohan N, Ajitha M (2011) Mechanism of epoxide hydrolysis
in microsolvated nucleotide bases adenine, guanine and cytosine: a DFT study. Org Biomol
Chem 9:5115–5122
17. Oesch F (1973) Mammalian epoxide hydrases. Inducible enzymes catalyzing inactivation
of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds.
Xenobiotica 3:305–340
18. Oesch F, Hengstler JG, Arand M (2004) Detoxification strategy of epoxide hydrolase—the
basis for a novel threshold for definable genotoxic carcinogens. Nonlinearity Biol Toxicol
Med 2(1):21–26
19. Jones RB, Mackrodt WC (1983) Structure–genotoxicity relationship for aliphatic epoxides.
Biochem Pharmacol 32:2359–2362
20. Ross WC (1950) The reactions of certain epoxides in aqueous solutions. J Chem Soc 2257–
2272
21. Jones RB, Mackrodt WC (1982) Structure–mutagenicity relationships for chlorinated ethylenes: a model based on the stability of the metabolically derived epoxides. Biochem Pharmacol 31:3710–3712
22. Kirkovsky LI, Lermontov SA, Zavorin SI, Sukhozhenko II, Zavelsky VI, Thier R, Bolt
HM (1998) Hydrolysis of genotoxic methyl-substituted oxiranes: experimental kinetic and
semiempirical studies. Environ Toxicol Chem 17:2141–2147
23. Gervasi PG, Citti L, Delmonte M, Longo V, Benetti D (1985) Mutagenicity and chemicalreactivity of epoxidic intermediates of the isoprene metabolism and other structurally relatedcompounds. Mutat Res 156:77–82
24. Polansky OE, Fratev F (1976) Pars orbital method: character orders in CNDO calculations and a new definition for bond orders in all valence electron methods. Chem Phys Lett
37(3):602–607
25. Fujimoto H, Katata M, Yamabe S, Fukui K (1972) An MO-theoretical interpretation of the
nature of chemical reactions III. Bond interchange. Bull Chem Soc Jpn 45(5):1320–1324
26. Kas’yan LI (1999) Steric strain and reactivity of epoxynorbornanes (3-oxatricyclo[3.2.1.02,4]
octanes). Rus J Org Chem 35(5):635–665
27. Kas’yan LI, Gorb LG, Seferova MF, Chernousov DA, Svyatkin VA, Boldeskul IE (1990)
Quantum-chemical investigation of alicyclic epoxide compounds. Zh Org Khim 26(1):3–10
28. Kas’yan LI, Gorb LG, Seferova MF, Dryuk VG (1990) Quantum-chemical study of electronic structure and reactivity of spirooxiranes. Ukr Khim Zhurn 56(10):1071–1076
29. Kretova EN, Podgornova VA, Shpekht NA, Ustavshchikov BF (1983) Theoretical and experimental studies of the reactivity of alkene oxides with acids. I. Calculation of the electronic