Синтез производных пиразино[1, 2-a]пиразинов — потенциальных миметиков ?-поворота в белках
Диссертация
Практическая значимость работы. Разработан метод стереоселективного синтеза производных 2,4,7,8-замещенных пергидропиразинопиразин-3-онов из доступных аминоспиртов, позволивший синтезировать большую серию этих соединений, перспективную для тестирования на биологическую активность. В условиях разработанного метода получены и охарактеризованы производные 2,4,7,8-замещенных… Читать ещё >
Список литературы
- Граник В. Г. Основы медицинской химии. М.: «Вузовская книга». 2001. с 34.
- Bonner, G. G., Davis, P., Stropova, D., Ferguson, R., Yamamura, H. I., Porreca, F., Hruby, V. J. Simultaneous 5-agonism and antagonism in somatostatin analogues // Peptides 1997, 18, 93 100.
- Овчинников Ю. А. Биоорганическая химия. M., Просвещение, 1987, с 101.
- Hruby, V. J., Hadley, M. E. In: Design and synthesis of organic molecules based on molecular recognition// G. VanBinst, Ed., Springer-Verlog: Heidelberg, 1986, 269−289.
- Hruby, V. J. Conformational restriction of biologically active peptides via amino acid chain groups II Life Sci. 1982, 31, 189−199.
- Marshall, G. R. A hierarchical approach to peptido-mimetic design // Tetrahedron 1993, 49, 3547−3552.
- Piscopio, A. D., Miller, J. F., Koch, K. Solid phase heterocyclic syntesis via ring closing metathesis: traceless linking and cyclative cleavage through a carbon-carbon double bond // Tetrahedron Lett., 1997, 38, 7143−7146.
- Bennett III, R. В., Choi, J.-R. Montgomery, W. D., Cha, J. K. A Short, Enantioselective Synthesis of (-) — Swainsonine II J. Am. Chem. Soc, 1989, 111, 2580−2582.
- Murray, P. J., Starkey, I. D., Davies, J. E. The enantiospecific synthesis of novel lysine analoques incorporating a pyrrolidine containing side chain // Tetrahedron Lett. 1998, 39, 6721−6724.
- Шульц Г., Ширмер P. Принципы структурной организации белков. М., Мир, 1982, с 23.
- Gething M.J. Sambrook К. Protein folding in the cell IINature 1992, 355, 33−45.
- Adkins J. C., Faulds D. Amprenavir II Drugs 1998, 55(6), 837−842.
- Caroline M. P., Paul B. Nelfinavir // Drugs 1997, 54(1), 81−87.
- Арчаков А. И. Наука: Геномика, протеомика и биоинформатика — науки XXI столетия // Фармацевтический вестник 2001, № 9, 208.
- Woody R. W., В lout Е. R., Bovery F. A., Goodman М., Loton N., Wiley J. Peptides, polypeptides and proteins. New York, 1974, 338−350.
- Goldberg D. E. Genetic algoritms in search, optimization and machine learning. Reading (Mass.), Addison-Wesley, 1989, 457.
- Privalov P. L. Stability of proteins II Adv. Protein Chem. 1979, 33, 167−241.
- Marshall, G. R. A hierarchical approach to peptidomimetic design // Tetrahedron 1993, 49, 3547−3558.
- Chou, К. C. Prediction of Tight Turns and Their Types in Proteins // Anal. Biochem. 2000, 286, 1−16.
- Ball, J. В., Alewood, P. F. Conformational constraints: nonpeptide beta-turn mimics // J. Mol. Recognit. 1990, 3, 55−64.
- Venkatachalam С. M. Stereochemical criteria for polypeptides and proteins. Conformation of a system of three linked peptide units // Biopolimers 1968, 6, 1425—1436.
- Lewis P. N., Momary F. A., Scherada H. A. Chain reversais in proteins // Biochem. Biophys. Acta 1913, 303, 211−229.
- Hutchinson E. G., Thornton J. M. A revised set of potentials for turn formation in proteins // Protein sci. 1994, 3, 2207−2216.
- Lim V.I. Structural principles of globular protein secondary structure // J. Mol. Biol. 1974, 88, 857−872.
- Gamier J., Osguthorpe D., Robson B. Analysis of the accuracy and implications of simple methods for predicting the secondary structure of globular proteins // J. Mol. Biol. 1978,120, 97−120.
- Nagai U., Sato K., Nakamura R., Kato R. Bicyclic turned dipeptide (BTD) as a /?-turn mimetic- its desing, synthesis and incorporation into bioactive peptide // Tetrohedron 1993, 49, 3577−3592.
- Virgilio, A. A., Ellman, J. A. Simultaneous solid-phase synthesis of yff-turn mimetics incorporating side-chane functionality // J. Am. Chem. Soc. 1994,116, 11 580−11 581.
- Chou К. C. Prediction of turns II J. Peptide Res. 1997, 49, 120−144.
- Финкелыптейн А. В., Птицын О. Б. Физика белка., М., 2002, 130−132.
- Ueki T., Ashida T., Kakudo M., Sasada Y., Katsube Y. Structure of p-bromocarbobenzoxyglycylprolylleucylglycine II Acta crystallogr. 1969, B25, 1840−1849.
- Kawai M., Fasman G. D. A model /?-turn. Circular dichroism and infrared spectra of a tetrapeptide // J. Am. Chem. Soc., 1978, 100, 3630−3632.
- Han, S. L., Stimson, E. R., Maxfield, F. R., Scheraga, H. A. Conformational study of Leu5.-enkephalin by laser Raman spectroscopy // Int. J. Pept. Protein Res., 1980,16, 173−181.
- Nair, R. M., Kastin, A. J., Schally, A.V. Isolation and structure of hypothalamic MSH release-inhibiting hormone// Biochem. Biophys. Res. Comm. 1971, 43, 1376−1381.
- Maxfield, F. R., Bandekar, S., Krimm, D. J., Evans, S. J., Leach, S. J., Nemethy, G., Scheraga,
- H. A. Conformation of cyclo (L-alanylglycyl-s-aminocaproyl), a cyclized dipeptide model for a P bend. 3. Infrared and Raman spectroscopic studies // Macromolecules 1981, 14, 9 971 003.
- Perly, B., Forchioni, A., Helbeque, N., Loucheux-Lefevre, M. H. NMR studies of a free and protected tetrapeptide glycyl-L-prolylglycylglycine in-turn-supporting environment // Biopolymers, 1983, 22, 1853−1868.
- Garland, S. L., Dean P. M. Design criteria for molecular mimics of fragments of the beta-turn.
- C alpha atom analysis. II J. Comput. AidedMol. Des. 1999,13(5), 469−483.
- Lipinski, C. A., Lombardo, F., Dominy, B. W. and Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings II Adv. Drug Delivery Rev. 1997, 23(1−3), 3−25.
- Ball, J. B.- Alewood, P. F. Conformational constraints: nonpeptide beta-turn mimics //J. Mol Recognit. 1990, 3, 55−67.
- Kahn, M., Ed. Peptide secondary structure mimetics // Tetrahedron 1993, 49, Symposia 50, 3433−3689.
- Gillespie, P.- Cicariello, J., Olson, G. H. Conformational analysis of dipeptide mimetics // Biopolymers 1997, 43, 191−217.
- Olson, G. L., Voss, M. E., Hill, D. E., Kahn, M., Madison, V. S., Cook, C.M. Design and syntesis of a protein y^-turn mimetic// J. Am. Chem. Soc. 1990,772,323−325.
- Freidinger, R. M., Veber, D.F., Perlow, D. S., Brooks, J. R., Saperstein, R. Bioactive conformation of luteinizing hormone-releasing hormone: evidence from a conformationally constrained analog // Science 1980, 210, 656−658.
- Nagai U., Sato K. Synthesis of a bicyclic turned dipeptide with the shape of /7-turn central part // Tetrahedron Lett. 1985, 26, 647−650.
- Alig, L., Edenhofer, A., Hadvary, P., Hurzeler, M., Knopp, D., Muller, M., Steiner, В., Trzeciak, A., Weller, T. Low molecular weight, non-peptide fibrinogen receptor antagonists // J. Med.Chem. 1992, 35, 4393−4407.
- Feng, Y. Z. Wang, S. Jin, K. Burgess, Y. R. SnAr cyclization to form cyclic peptidomimetics ofy^turnII J. Am. Chem. Soc. 1998, J20, 10 768−10 769.
- Зефиров H. С., Кулов H. H. Химическая энциклопедия, 1988, M., 602.
- Zhang A. J., Khare S., Gokulan K., Linthicum S., Burgess K. Dimeric /?-turn peptidomimeticsas ligands for the neurotrophin receptor Trk С // Bioorg. Med. Chem. Lett. 2001,11, 207−210.
- Feng, Y., Pattarawarapan, M., Wang, Z., Burgess, K. Stereochemical implications on diversityin уЗ-turn peptidomimetic libraries // J. Org. Chem. 1999, 38, 9175−9177.
- Piscopio A. D., Miller J. F., Koch K. A second generation solid phase approach to freidingerlactams application of fukuyama’s amine synthesis and cyclative release via ring closig metathesis // Tetrahedron Lett. 1998, 39, 2667−2670.
- Furstner A. Olefin metatesis and beyond //Angew. Chem., 2000, 39, 3012−3043.
- Brickmann K., Somfai P., Kihlberg J. An approach to enantiomerically pure inverse y-turn mimetics for use in solid-phase synthesis // Tetrahedron Lett., 1997, 38, 3651−3654.
- Piscopio, A. D., Miller, J. F., Koch, K. Ring closing metathesis in organic syntesis: evolution of a high speed, solid phase method for the preparation of turn mimetics // Tetrahedron, 1999, 55,8189−8198.
- Virgilio, A. A., Ellman, J. A. Simultaneous solid-phase syntensis of p-turn mimetics incorporating side-chane functionality II J. Am. Chem. Soc. 1994,116, 11 580−11 581.
- Maeji, N. J.- Valerio, R. M.- Bray, A. M.- Campbell, R. A.- Geyson, H. M. Grafted supports used with the multipin method of peptide synthesis // React.Polym. 1994, 22, 203−212.
- Virgilio, A. A., Scurer, S. C., Ellman, J. A. Expedient solid-phase synthesis of putative p-turn mimetics incorporating the i+l, i+2, and i+3 sidechains // Tetrahedron Lett. 1996, 37, 69 616 965.
- Patel, Y.C. Molecular pharmacology of somatostatin receptor subtypes // J. Endocrinol. Invest. 1997, 20, 348−353.
- Veber, D. F., Saperstein, R., Nutt, R. F., Freidinger, R.M., Brady, S. F., Curley, P., Perlow, D.
- Souers, A. J., Rosenquist, A., Jarvie, E. M., Ladlow, M., Feniuk, W., Ellman, J. A. Optimization of a somatostatin mimetic via constrained amino acid and backbone incorporation // Bioorg. Med. Chem. Lett. 2000,10, 2731−2733.
- Kurokawa K., Kumihara H., Kondo H. A solid-phase synthesis for P-turn mimetics of sialyl Lewis X // Bioorg. Med. Chem. Lett. 2000,10,1827−1830.
- Souers A. J., Ellman J. A. /?-Turn mimetic library synthesis: scaffolds and applications // Tetrahedron, 2001,12, 7431−7448.
- Eguchi, M., Lee, M. S., Nakanishi, H., Stasiak, M., Lovell, S., Kahn, M. Solid-phase synthensis and structural analysis of bicyclic /?-turn mimetics incorporating functionality at the i to i+1 position// J. Am. Chem. Soc. 1999,121, 12 204−12 205.
- Golebiowski A., Klopfenstein S. R., Chen J. J., Shao X. Solid supported high-throughput organic synthesis of peptide b-turn mimetics via Petasis reaction/diketopiperazine formation // Tetrahedron Lett. 2000, 41, 4841−4844.
- Kim H., Nakanishi H., Lee M. S., Kahn M. Design and syntesis of novel conformationally restricted peptide secondary structure mimetics // Org. Lett., 2000, 2, 301—302.
- Karlson, S., Hogberg H.-E. Assymetric 1,3-dipolar cycloadditions for the construction of enantiomerically pure heterocycles. A review // Organic preparations and procedures Inc. 2001,103−172.
- Sha C. K" Mohanakrishnan A. K. Azides // Chem. ofHeterocycl. Comp. 2002, 59, 623−679.
- Michaelis A., Hermens R. Ueber das P-succinyl-phenyl-hydrazid oder das l-phenyl-3,6-orthopiperazon // Chem. Ber., 1893, 676.
- Strub H., Strehler C., Streith J. Photoinduced nitrene, carbene, and atomic oxygen transfer reactions starting from the corresponding pyridinium N-, C-, and O-ylides // Chem. Ber. 1987, 120, 355−363.
- Halpern A. M., Ramachadran B. R., Sharma S. Structural effects on photophysical processes in saturated amines. 6. Excited-state interactions in piperazine derivatives // J. Phys. Chem. 1982, 86,2049−2052.
- Anastassiou C. Reaction of cyanonitrene with cyclooctatetraene 1,4 and 1,2 addition II J. Am. Chem. Soc. 1968, 90, 1527−1536.
- L’Abbe G. Decomposition and addition reaction of organic azides // Chemical reviews. 1969, 69(3), 354−363.
- Koumbis, A. E., Gallos, J. K. 1,3-Dipolar cycloadditions in the syntesis of carbohydrate mimics.// Cur. Org. Chem. 2003, 7, 771−797.
- Huisgen, R., Konig, H., Binsch G., Sturm. 1,3-dipolare additionen der ketocarbene // Angew. Chem., 1961, 73, 368−370.
- Anderson, G.T., Henry, J. R., Weinreb S.M. High-pressure induced 1,3-dipolar cycloaddition of azides with electron-deficient olefins II J. Org. Chem., 1991, 56, 24, 6946−6948.
- Просяник А. В., Федосеенко Д. В., Марков В. И. Диэтиловые эфиры 1-ацилазиридин-2,2-дикарбоновых кислот//ХГС, 1982,18, 11, 1216.
- Alvernhe G., Laurent A., Touhami К. Synthesis de fluoro- 3 azacyclanes: action de l’acide fluorhydrique sur les aza-1 bicyclon. l .OJalcanes II J. of Fluor. Chem. 1985, 29, 363−384.
- Kadaba P.K. Triazolines. 1,3-Cycloaddition of aryl azides to enamides and the synthesis of 1-aryl-5-amido-l, 2,3-triazolines // J. Org. Chem. 1992, 57, 3075−3097.
- Chakrasali R. Т., Ila H., Junjappa H. Cycloaddition of sodium azide to polarized ketene S, S-and iS^TV-acetals: synthesis of novel substituted triazole and tetrazole derivatives.// Synthesis 1988, 453−459.
- De Kimpe N., Boeykens M. Synthesis of lactam derivatives by cycloaddition of 2-methyleneazetidines with azides // J. Org. Chem. 1994, 59, 5189−5191.
- Erba E., Pocar D., Valle M. Triazolines. A new synthesis of 2-alkylquinazolines and 2,9-dialkylpyrimido4,5-&.indoles // J. Chem. Soc. Perkin Trans. 1- 1999, 4, 421 -426.
- Goldsmith D. J., Soria J. J. Ultrasonically accelerated cycloaddition-rearrangement of enol ethers // Tetrohedron Lett. 1991, 32, 2457−2459.
- Moss W. О., Bradbury R. H., Hales N. J., Gallagher T. Ketene-S, S-acetals as 1,3dipolarophiles. Reactivity towards electron-deficient azides //Tetrahedron Lett, 1988, 29, 6475−6476.
- Rieber N., Bohn H. 1,3-Dipolare addithionen an 3,4-diazatricyclo4.2.1.0.nona-3.7-dien und 3,4-diazatricyclo[4.2.1.0]nona-7-en-derivate // J. Heter. Chem., 1981,18, 1−7.
- Васильева С. А.,.Абзалов A. 3., Сафаров M. Г. Реакция тетрагидропиранилазидов с 5-R-бицикло2.2.1.-2-гептенами // ХГС, 1997, 7, 893−897.
- Jego J. М., Carboni В., Vaultier М. Synthesis of azetidine, pyrrolidines and piperidines by intramolecular cyclization of omega-azidoborane // Bull. Soc. Chim. Fr. 1992,129, 554−565.
- Anderson G. T" Henry J. R. High-pressure induced 1,3-dipolar cycloadditions of azides with electron-deficient olefins II J. Org. Chem. 1991, 56, 24, 6947−6950.
- Subbaraj A., Subba R., Lwowski W. Functionalization of olefins by alkoximidoylnitrenes // J. Org. Chem. 1989, 54, 3945−3951.
- Dabbagh H. A., Modarresi-Alam A. R. The stereoselective synthesis and the nitrogen interconversion studies of 2-(tert-butoxymethyl)-l-N'-(4-methylbenzenesulfonyl)(4-methylphenoxy)imidoyl.aziridine // J. Chem. Reseach, 2000, 3, 190−192.
- Лановая Г. А., Мищенко В. Ф., Корниец Е. Д. Образование 1,4- и 1,5-региоизомеров триазолинов в реакциях 2-этоксиэтилазида с монозамещенными этиленами // ЖОрХ, 1987, б, 798−803.
- Keshava М., Murthy К., Hassner A. Fused /^-lactams via intramolecular dipolar cycloaddition.// Tetrahedron Lett., 1987, 28, 97−100.
- Koumbis A. E., Gallos J. K. 1,3-Dipolar cycloadditions in the synthesis of carbohydrate mimics. Part3: Azides, diazo compounds and other dipoles // Cur. Org. Chem. 2003, 7(8), 771−797.
- Shea, K. J., Kim, J. S. Influence of Strain on Chemical Reactivity. Relative Reactivity of Torsionally Strained Double Bonds in 1,3-Dipolar Cycloadditions // J. Am. Chem. Soc. 1992, 114,4846—4851.
- Hassner, A., Amarasekara, A.C., Andisik, D. Intramolecular Azide-Olefin Cycloadditions. A Novel Synthesis of2,5-Dihydrooxazoles И J. Org. Chem, 1988, 53, 27−30.
- Lin, Z., Kadaba, P. K., Studies on Isoxazole and Pyrazole Formation by the Reaction of Trifluoromethyl-Substituted Anilines with Oxime and Hydrazone Dianions // J. Heter. Chem., 1997, 34, 1645−1648.
- Pearson, W. H, Walavalkar, R. Syntesis of (+/-)-tylophorine by the intramolecular cycloaddition of azide with an a-chloroalkene // Tetrahedron 1994, 50, 12 293−12 304.
- Kozikowski, P., Greco, M.N. Total synthesis of the clavicipitic acids by an intramolecular azide cycloaddition strategy // J. Org. Chem. 1984,49, 2310−2314.
- Bennett III, R. В., Choi, J.-R., Montgomery, W.D., Cha, J. K. A Short, enantioselective synthesis of (-)-swainsonine // J. Am. Chem. Soc, 1989, 111, 2580−2582.
- Орлова Т. И., Гаврилов II. И. Электровосстановление как метод исследования белка // Журнал органической химии, 1957, 27, 3314—3319.
- Chu D., Nordeen С., Hardy D., Swanson R., Giardina W. Synthesis, Antibacterial activities, and pharmacological properties of enantiomers of temafloxacin hydrochloride // J. Med. Chem. 1991, 34, 1, 168−174
- Ovakimian G., Christman С. С., Кипа M., Levene P. A. The reaction of the esters of dl-leucine and of /-leucine on the raney catalyst // J. Biol. Chem. 1940,134, 151−161.
- Naylor A., Judd D.B., Lloyd J. E., Scopes D. I., Hayes A. G., Birch P. J. A potent new classof k- receptor agonist: 4-substituted l-(arylacetyl)-2-(dialkilamino)methyl.piperasines // J. Med. Chem. 1993,35,2075−2083.
- Greene T.W., Wuts P.G. Protective groups in organic synthesis., John Wiley & Sons, Inc., 1999, 495.
- Meyers A.I., Reider P.J. Stereoselective synthesis of threo-3-hydroxy-2-methylcarboxylic acids using alkoxyalkyl propionates // J. Am. Chem. Soc. 1979,101, 2501−2502.
- Perich J. W., Johns R. B. An improved one-pot synthensis of N-(tert-butoxycarbonyl)-0-(0', 0"-dialkylphosphorc)-L-tyrosines using dialkyl N, N-diethylphosphoramidites // Synthesis, 1989, 9, 701−703.
- S. D. Barton, W. D. Ollis. Общая органическая химия, M., 1983, 4 т., стр. 460−462.
- Д. Марч, Органическая химия, М., «Мир» 1987, 2 т., стр. 164.
- S. D. Barton, W. D. Ollis., Общая органическая химия, М., 1983, 3 т., стр. 313−315.
- Ponnusamy Е., Fotadar U., Spisni A., Fiat D. A novel method for rapid, non-aqueous t-butoxycarbonylation of some O-labeled amino acids and o-N.M.R. parameters of the products // Synthesis, 1986, 48−49.
- Kawanami H., Ikushima Y. Regioselectivity and selective enhancement of carbon dioxidefixation of 2-substituted aziridines to 2-oxazolidinones under supercritical conditions // Tetrahedron Lett., 2002, 43, 3841−3844.
- Гордон А., Форд P. Спутник химика, M., 1976, с. 56.
- Opplzer W., Bienayme H., Genevois-Borella A. Enantioselective syntesis of (+)-3isorauniticine via a catalytic tandem «Palladium-Ene'Vcarbonylation reaction 11 J. Am. Chem. Soc., 1991,113, 9660−9661.
- Heathcock С. H., Blumenkopf T. A., Smith К. M. Total synthesis of (+/-)-fawcettimine (Burnett's base A) II J. Am. Chem. Soc., 1986,108, 5022−5024.
- Kudav D. P., Samant S. P., Hosangadi B. D. Perchloric acid-acetic acid: a reagent system fordetosylation // Synth. Commun. 1987,17, 1185−1188.
- Vedejs E., Lin S., Klapars A., Wang J. Heteroarene-2-sulfonyl chlorides (BtsCl, ThsCl): reagents for nitrogen protection and 99percent racemization-free phenylglycine activation with SOCL2II J. Am. Chem. Soc., 1996,118, 40, 9796−9797.
- Fieser M., Fieser L. F Reagents for organic syntesis, John Wiley & Sons, Inc., 1972, v. 10, 237.
- Keshava M., Hassner, A. Fused-lactams via intramolecular dipolar cycloaddition. II Tetrahedron Lett. 1987, 28, 97−100.
- Hassner, A.- Amarasekara, A. S.- Andisik, D. Intramolecular azide-olefin cycloadditions. A novel synthesis of 2,5-dihydrooxazoles II J. Org. Chem. 1988, 53, 27−30.
- Rai, К. M. L- Hassner, A. Versatile methods of synthesis of 5 to 8-membered ring N-heterocycles via intramolecular cycloaddition of allylamines // Heterocycles 1990, 30, 817— 830.
- Bernet В., Murty A. R. С. В., Vasella A. Analogues of sialic acids as potential sialidaseinhibitors. Synthesis of 2-C-hydroxymethyl derivatives of N-acetyl-6-amino-2,6-dideoxyneuraminic acid.// Helv. Chim. Acta 1990, 73, 940−958.
- Orlek B. S., Sammes P.G., Weller D.J. Steric acceleration of intramolecular azide cycloadditions.// J. Chem. Soc. Chem. Comm., 1993, 7, 607−608.
- Pearson W. H., Suga H. Total synthesis of (±)-Quinolizidine 217A II J. Org. Chem. 1998, 63, 9910−9918.
- Матье Ж., Панико P., Вейль-Рейналь Ж. Изменение и введение функций в органическом синтезе. М., «Мир», 1980.
- Walborsky Н.М. Chemical Effects of the Trifluoromethyl Group: III. Synthesis of 2-Amino-4,4,4-trifluorobutyric acid II J. Org. Chem. 1956, 21, 538−539.
- Bouzide A., Sauve G., Yelle J. Lysine derivatives as potent HIV protease inhibitors 11 Bioorg. Med. Chem. Lett. 2005,15, 1509- 1514.
- Pohlmann, A.- Schanen, V.- Guillaume, D.- Quirion, J.- Husson, H. Efficient synthesis of conformationally constrained peptidomimetics containing 2-oxopiperazines // J. Org. Chem., 1997,62, 1016−1022.