Ненасыщенные трифторметилзамещенные ?-аминокислоты и их металлокатализируемые трансформации
Диссертация
Вместе с тем известно, что модификация аминокислот атомами фтора или фторалкильными группами значительно улучшает физико-химические и биологические свойства как аминокислот, так и пептидов на их основе. Среди фторсодержащих ос-аминокислот наибольшее внимание уделяется производным, содержащим атомы фтора в Р-положении. Эти соединения способны селективно и необратимо блокировать активность ряда… Читать ещё >
Содержание
- Глава I. ЛИТЕРАТУРНЫЙ ОБЗОР
- Ненасыщенные алифатические а-аминокислоты в металлорганическом синтезе"
- Предисловие
- 1. 1. Реакции кросс-сочетания ненасыщенных а-аминокислот
- 1. 1. 1. Реакция Хека
- 1. 1. 2. Реакция Стилле
- 1. 1. 3. Реакция Сузуки
- 1. 1. 4. Реакция Сопогаширы
- 1. 2. Реакции метатезиса ненасыщенных а-аминокислот
- 1. 2. 1. Внутримолекулярный олефиновый метатезис (ВОМ)
- 1. 2. 2. Внутримолекулярный метатезис ениное (ВМЕ)
- 1. 2. 3. Внутримолекулярный метатезис диацетиленов
- 1. 2. 4. Кросс-метатезис диолефинов и енинов
- 1. 3. Ненасыщенные фторсодержащие а-аминокислоты
- 1. 1. Реакции кросс-сочетания ненасыщенных а-аминокислот
- Глава II. ОБСУЖДЕНИЕ РЕЗУЛЬТАТОВ
- 2. 1. Синтез ненасыщенных производных а-СЕз-замещенных а-аминокислог
- 2. 1. 1. Синтез иминов алкилтрифторпируватов
- 2. 1. 2. Реакции иминов с ненасыщенными С-нуклеофилами
- 2. 1. 3. Синтез a-CFs-a-оминокислот с эндоциклической двойной связью. Термическая ен-реакция ацил- и сульфонилиминов метилтрифторпирувата
- 2. 1. 4. Синтез диолефинов, енинов и диацетиленов
- 2. 2. Металлокатализируемые трансформации ненасыщенных производных a-CFj-замещенных a-аминокислот
- 2. 2. 1. Метатезис циклосодержащш. азадиенов с раскрытием-замыканием цикла
- 2. 2. 2. Рутепий-катачизируемая реакция циклизации/циклопропанированш
- 2. 2. 3. Каталитическая реакция циклотримеризации 1,6- и 1,7-азадиинов
- 2. 3. Диполярное [3+2]-циклоприсоединение а-пропаргилсодержащих аминокислот к органическим азидам
- 2. 1. Синтез ненасыщенных производных а-СЕз-замещенных а-аминокислог
- Глава III. ЭКСПЕРИМЕНТАЛЬНАЯ ЧАСТ
- ВЫВОДЫ
Список литературы
- H. Ishida, Y. Inoue, Peptides that contain unnatural amino acids: Toward artificial proteins, Rev. Heleroat. Chem., 1999,19, 79.
- R. R. Schrock and A. H. Hoveyda, Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts, Angew. Chem., Int. Ed., 2003, 42, 4592.
- F. Lacombe, K. Radkowski, G. Seidel, A. Fuerstner, (?)-Cycloalkenes and (E, E)-cycloalkadienes by ring closing diyne- or enyne-yne metathesis/semi-reduction, Tetrahedron, 2004,60, 7315.
- J. Kaiser, S. S. Kinderman, В. C. J. van Esseveldt, F. L. van Delft, H. E. Schoemaker, R. H. Blaauw, F. P. J. T. Rutjes, Synthetic applications of aliphatic unsaturated a-H-a-amino acids, Org. Biomol. Chem., 2005,3,3435.
- G. N. Dardenne, J. Casimir, M. Marlier, P. O. Larsen, Acide 2(/?)-amino-3-butenoique (vinylglycine) dans les carpophores de Rhodophyllus nidorosus, Phytochemistry, 1974, 13, 1897.
- C. J. Easton, A. J. Edwards, S. B. McNabb, M. C. Merrett, J. L. O’Connell, G. W. Simpson, J. S. Simpson, A. C. Willis, Allylic halogcnation of unsaturated amino acids, Org. Biomol. Chem., 2003,1,2492.
- Ed. by F. Diederich, P.J. Stang, Metal-catalyzed Cross-coupling Reactions, Wiley-VCH Verlag GmbH, 1998
- M. K. Gurjar, A. Talukdar, Heck Reaction of (S)-iV-Cbz-Allyl Glycine /-Butyl Ester with Aromatic Halides, Synthesis, 2002,315.
- P. N. Collier, I. Patel, R. J. K. Taylor, Heck reactions of amino acid building blocks: application to the synthesis of pyrrololine analogues, Tetrahedron Lett., 2002,43,3401.
- T. D. Penning, M. A. Russell, В. B. Chen, H. Y. Chen, B. N. Desai, S. H. Docter, D. J. Edwards, G. J. Gesicki, C.-D. Liang, J. W. Malecha, S. S. Yu, V. W. Engleman, S. K.
- Freeman, M. L. Hanneke, К. E. Shannon, M. M. Westlin, G. A. Nickols, Synthesis of cinnamic acids and related isosteres as potent and selective av|i3 receptor antagonists, Bioorg. Med. Chem. Lett., 2004,14,1471.
- С. V. C. Prasad, S. E. Mercer, G. M. Dubowchik, J. E. Macor, Enantioselective synthesis of aminobenzazepinones, Tetrahedron Lett., 2007,48, 2661.
- E. Tullberg, D. Peters, T. Frejd, The Heck reaction under ball-milling conditions, J. Organomet. Chem., 2004,689,3778.
- S.E. Gibson, N. Guillo, R.J. Middleton, A. Thuilliez, M.J. Tozer, Synthesis of conformationally constrained phenylalanine analogues via 7-, 8- and 9-endo Heck cyclisations, Chem. Soc., Perkin Trans. 1,1997,447.
- S.E. Gibson, N. Guillo, S.B. Kalindjian, M.J. Tozer, incorporation of conformationally constrained phenylalanine derivatives TIC, SIC, HIC and NIC into a cholecystokinin-b/Gastrin receptor antagonist, Bioorg. Med. Chem. Lett. 1997, 7, 1289.
- S. E. Gibson, J. O. Jones, S. B. Kalindjian, J. D. Knight, N. Mainolfi, M. Rudd, J. W. Steed, M. J. Tozerb, P. T. Wrigh, Synthesis of meta- and paracyclophanes containing unsaturated amino acid residues, Tetrahedron, 2004, 60, 6945.
- V. Gracias, J. D. Moore, S. W. Djuric, Sequential Ugi/Heck cyclization strategies for the facile construction of highly functionalized N-heterocyclic scaffolds, Tetrahedron Lett., 2004,45,417.
- S. A. Giacobbe, R. Di Fabio, Versatile assembly of the 2-carboxybenzob.azepine ring system, Tetrahedron Lett., 2001,42,2027.
- G. L. Bolton, J. C. Hodges, Solid-Phase Synthesis of Substituted Benzazepines via Intramolecular Heck Cyclization, J. Comb. Chem., 1999,1,130.
- P.A. Donets, E.V. Van der Eycken, Efficient Synthesis of the 3-Benzazepine Framework via Intramolecular Heck Reductive Cyclization, Org. Lett., 2007,9,3017.
- D. B. Berkowitz, J. M. McFadden, E. Chisowa, C. L. Semerad, Organoselenium-Based Entry into Versatile, a-(2-Tributylstannyl)vinyl Amino Acids in Scalemic Form: A New Route to Vinyl Stannanes, J. Am. Chem. Soc., 2000,122,11 031.
- S. Chen, R. M. Williams, Syntheses of highly functionalized 8, y-unsaturated-a-amino acids, Tetrahedron, 2006, 62, 11 572.
- N. Miyaura, К. Yamada, A. Suzuki, A new stereospecifie cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides, Tetrahedron Lett. 1979, 3437
- G. J. Roff, R. C. Lloyd, N. J. Turner, A Versatile Chemo-Enzymatic Route to Enantiomerically Pure P-Branched a-Amino Acids, J. Am. Chem. Soc., 2004, 126,4098.
- G. Guillena, C. A. Kruithof, M. A. Casado, M. R. Egmond, G. van Koten, The Suzuki cross-coupling reaction: a powerful tool for the attachment of organometallic 'NCN'-pincer units to biological scaffolds, J. Organomet. Chem., 2003, 668, 3.
- J. S. Potuzak, D. S. Tan, Synthesis of Cl-alkyl- and acylglycals from glycals using a B-alkyl Suzuki-Miyaura cross coupling approach, Tetrahedron Lett., 2004,45,1797.
- S. Collet, F. Carreaux, J.-L. Boucher, S. Pethe, M. Lepoivre, R. Danion-Bougot, D. Danion, Synthesis and evaluation of co-borono-a-amino acids as active-site probes of arginase and nitric oxide synthases, J. Chem. Soc., Perkin Trans. 1, 2000, 177.
- S. Collet, R. Danion-Bougot, D. Danion, Suzuki cross-coupling reactions of nonracemic vinylborono-a-amino acids, Synth. Commun., 2001,31,249.
- M. Isaac, A. Slassi, K. Da Silva, T. Xin, Synthesis of chiral and geometrically defined 5,5-diaryl-2-amino-4-pentenoates: novel amino acid derivatives, Tetrahedron Lett., 2001,42,2957.
- G. T. Crisp, Y.-L. Jiang, Intramolecular hydrogen bonding studies for a series of dipurinyl-2,6-pyridinedicarboxamides, Tetrahedron, 1999,55,549.
- G. Lassalle, J. M. Altenburger, SSR182289A, a selective and potent orally active thrombin inhibitor, Bioorg. Med. Chem., 2004,12, 1713.
- R. J. Brea, M. P. Lopez-Deber, L. Castedo, J. R. Granja, Synthesis of o-(Hetero)arylalkynylated a-Amino Acid by Sonogashira-Type Reactions in Aqueous Media, J. Org. Chem., 2006, 71, 7870.
- Y. Du, C. J. Creighton, Z. Yan, D. A. Gauthier, J. P. Dahl, B. Zhao, S. M. Belkowski, A. B. Reitz, The synthesis and evaluation of 10- and 12-membered ring benzofused enediyne amino acids, Bioorg. Med. Chem. 5936,13,2005.
- M. A. Fagan, D. W. Knight, Tetrahedron Lett., A new approach to the core of roseophilin, 1999,40,6117.
- L. В. Wolf, К. С. М. F. Tjen, Н. Т. ten Brink, R. Н. Blaauw, Н. Hiemstra, Н. Е. Sehoemaker, F. P. J. Т. Rutjes, Palladium-Catalyzed Cyclization Reactions of Acetylene-Containing Amino Acids, Adv. Synlh. Catal., 2002,344, 70.
- Bart C. J. van Esseveldt, Paul W. H. Vervoort, Floris L. van Delft, Floris P. J. T. Rutjes, Novel Approach to 5-Substituted Proline Derivatives Using a Silver-Catalyzed Cyclization as the Key Step, J. Org. Chem., 2005, 70,1791.
- S. Ma, F. Yu, W. Gao, Studies on Pd (II)-Catalyzed Coupling-Cyclization of a- or P-Amino Allenes with Allylic Halides, J. Org. Chem., 2003,68,5943.
- S. Werner, D. Kasi, К. M. Brummond, Design and Synthesis of a 3,4-Dehydroproline Amide Discovery Library, J. Comb. Chem. 2007,9, 677.
- S. L. Castle, G. S. C. Srikanth, Catalytic Asymmetric Synthesis of the Central Tryptophan Residue of Celogentin C, Org. Lett., 2003,5,3611.
- Alkenyl Metathesis in Organic Synthesis in Topics in Organometallic Chemistry, Eds. A. Fuerstner, Springer, Berlin, 1998.
- B. Mohr, D.M. lynn, R.H. Grubbs, Synthesis of Water-Soluble, Aliphatic Phosphines and Their Application to Well-Defined Ruthenium Olefin Metathesis Catalysts Organometallics, 1996,15,4317.
- P. Schwab, R. H. Grubbs, J. W. Ziller, Synthesis and Applications of RuCl2(=CHR')(PR3)2: The Influence of the Alkylidene Moiety on Metathesis Activity, J. Am. Chem. Soc., 1996,118,100.
- S. J. Miller, H. E. Blackwell, R. H. Grubbs, Application of Ring-Closing Metathesis to the Synthesis of Rigidified Amino Acids and Peptides, J. Am. Chem. Soc., 1996, 118, 9606.
- F. P. J. T. Rutjes, H. E. Sehoemaker, Ruthenium-Catalyzed Ring Closing Olefin Metathesis of Non-Natural a-Amino Acids, Tetrahedron Lett., 1997,38,677.
- S. Varray, С. Gauzy, F. Lamaty, R. Lazaro, J. Martinez, J. Org. Chem., 2000,65,6787.
- S.Varray, R. Lazaro, F. Martine, F. Lamaty, Eur. J. Org. Chem., 2002,2308.
- A. Fiirstner, M. Picquet, C. Bruneau, P. H. Dixneuf, Cationic ruthenium allenylidene complexes as a new class of performing catalysts for ring closing metathesis, Chem. Commun., 1998,1315.
- R. Akiyama, S. Kobayashi, A Novel Polymer-Supported Arene-Ruthenium Complex for Ring-Closing Olefin Metathesis, Angew. Chem., Int. Ed., 2002,41,2602.
- S. Kotha, K. Singh, N-Alkylation of diethyl acetamidomalonate: synthesis of constrained amino acid derivatives by ring-closing metathesis, Tetrahedron Lett., 2004, 45, 9607.
- S. S. Kinderman, R. de Gelder, J. H. Van Maarseveen, II. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, Amidopalladation of Alkoxyallenes Applied in the Synthesis of an Enantiopure 1-Ethylquinolizidine Frog Alkaloid, J. Am. Chem. Soc., 2004,126,4100-
- J. Gardiner, К. H. Anderson, A. Downard, A. D. Abell, Synthesis of Cyclic a-Amino Acid Esters from Methionine, Allylglycine, and Serine, J. Org. Chem., 2004,69,3375.
- J. Gardiner, A. D. Abell, Synthesis and solid state conformation of phenylalanine mimetics constrained in a proline-like conformation, Org. Biomol. Chem., 2004, 2, 2365.
- J. S. Clark, M. D. Middleton, Synthesis of Novel x-Substituted and a, a -Disubstituted Amino Acids by Rearrangement of Ammonium Ylides Generated from Metal Carbenoids, Org. Lett., 2002,4, 765.
- M. Kummeter, U. Kazmaier, Synthesis of Polyhydroxylated Aminocyclopentanes, Eur. J. Org. Chem., 2003, 3325.
- R. V. Hoffman, S. Madan, Synthesis and Reactions of 2-Substituted Ethyl N-Alkylmalonylhydroxamic Acids,./ Org. Chem., 2003,68,4876.
- C. J. Creighton, A. B. Reitz, Synthesis of an Eight-Membered Cyclic Pseudo-Dipeptide Using Ring Closing Metathesis, Org. Lett., 2001,3, 893.
- J. A. Horton, J. M. Bostock, I. Chopra, L. Hesse, S. E. V. Phillips, D. J. Adams, A. P. Johnson, C. W. G. Fishwick, Macrocyclic inhibitors of the bacterial cell wall biosynthesis enzyme mur D, Bioorg. Med. Chem. Lett., 2003,13, 1557.
- T. Hoffmann, R. Waibel and P. Gmeiner, A General Approach to Dehydro-Freidinger Lactams: Ex-Chiral Pool Synthesis and Spectroscopic Evaluation as Potential Reverse Turn Inducers, J. Org. Chem., 2003,68, 62.
- L. Banfi, A. Basso, G. Guanti, R. Riva, Application of tandem Ugi reaction/ring-closing metathesis in multicomponent synthesis of unsaturated nine-membered lactams Tetrahedron Lett., 2003, 44, 7655.
- N. Ghalit, J. Kemmink, H. W. Hilbers, C. Versluis, D. T. S. Rijkers, R. M. J. Liskamp, Step-wise and pre-organization induced synthesis of a crossed alkene-bridged nisin Z DE-ring mimic by ring-closing metathesis. Org. Biomol. Chem., 2007,5, 924.
- W. J. N. Meester, R. van Dijk, J. H. van Maarseveen, F. P. J. T. Rutjes, P. H. H. Hermkens, H. Hiemstra, Highly diastereoselective synthesis of |}-amino alcohols, J. Chem. Soc., Perkin Trans. 1,2001,2909.
- G. F. Busscher, F. P. J. T. Rutjes, F. L. van Delft, Synthesis of a protected enantiomerically pure 2-deoxystreptamine derivative from D-allylglycine, Tetrahedron Lett., 2004,45,3629.
- U. Voigtmann, S. Blechert, Enantioselective Synthesis of a, a-Disubstituted Piperidines via Ruthenium-Catalyzed Ring Rearrangement, Synthesis, 2000, 893.
- H. Villar, М. Fringsa, С. Bolm, Ring closing enyne metathesis: A powerful tool for the synthesis of heterocycles, Chem. Soc. Rev., 2007,36,55
- В. M. Trost, M. J. Krische, Transition Metal Catalyzed Cycloisomerizations, Synlett, 1998,1.
- M. Mori, N. Sakakibara, A. Kinoshita, Remarkable Effect of Ethylene Gas in the Intramolecular Enyne Metathesis of Terminal Alkynes, J. Org. Chem., 1998, 63,6082.
- S. Kotha, N. Sreenivasachary, A new synthetic approach to 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives via enyne metathesis and the Diels-Alder reaction, Chem. Commun., 2000, 503
- N. Chatani, II. Inoue, T. Kotsuma, S. Murai, Skeletal Reorganization of Enynes to 1-Vinylcycloalkenes Catalyzed by GaCl3, J. Am. Chem. Soc., 2002,124, 10 294.
- T. Kitamura, Y. Satom, M. Mori, Synthetic study of (C)-anthramycin using ring-closing enyne metathesis and cross-metathesis, Tetrahedron 2004,60, 9649.
- S. Kotha, N. Sreenivasachary, E. Brahmachary, Constrained Phenylalanine Derivatives by Enyne Metathesis and Diels-Alder Reaction, Eur. J. Chem., 2001, 787.
- M. I. Jsselstijn, J. Kaiser, F. L. van Delft, H. E. Schoemaker, F. P. J. T. Rutjes, Synthesis of novel acetylene-containing amino acids, Amino Acids, 2003,24,263.
- K. Biswas, D. M. Coltart, S. J. Danishefsky, Construction of carbohydrate-based antitumor vaccines: synthesis of glycosyl amino acids by olefin cross-metathesis, Tetrahedron Lett., 2002,43,6107.
- G. J. McCarvey, Т. E. Benedum, F.W. Schmidtmann, Development of Co- and Post-Translational Synthetic Strategies to C'-Neoglycopeptides, Org. Lett., 2002,4, 3591.
- M. Zanda, Trifluoromethyl group: an effective xenobiotic function for peptidebackbone modification, New J. Chem., 2004,28, 1401
- V.P. Kukhar, V.A. Soloshonok (Eds.), Fluorine-Containing Amino Acids. Synthesis and Properties., John Wiley and Sons Ltd: Chichester, 1995.
- D. Semeril, J. Le Notre, C. Bruneau, P. H. Dixneuf, A. F. Kolomiets, S. N. Osipov, Fluorine-containing a-alkynyl amino esters and access to a new family of 3,4-dehydroproline analogues, New J. Chem., 2001,25, 16,
- V. De Matteis, F. L. van Delft, H. Jakobi, S. Lindell, J. Tiebes, F. P. J. T. Rutjes, RCM-Mediated Synthesis of Trifluoromethyl-Containing Nitrogen Heterocycles, J. Org. Chem., 2006, 71,7527.
- K. Burger, E. Hoss, K. Gaa, N. Sewald, C. Schierlinger, Neue Strategien zur Synthese von 3,3,3-Trifluoralanin, 2-Deutero-3,3,3-trifluoralanin und ihren Derivaten, Z. Naturforsch., Teil B, 1991,46,361.
- C.H. Осипов, А. Ф. Коломиец, А. В. Фокин, Фторсодержащие кетимины, Успехи Химии, 1992,61,1457.
- C.H. Осипов, P. Dixneuf, Метезис с замыканием цикла в синтезе циклических а-аминокислот, Ж. Орг. Хим., 2003,39,1211.
- W.J. Zuercher, М. Hashimoto, R.H. Grubbs, Tandem Ring Opening-Ring Closing Metathesis of Cyclic Olefins, J. Am. Chem. Soc., 1996,118,6634.
- S. Saito, Y. Yamamoto Recent Advances in the Transition-Metal-Catalyzed Regioselective Approaches to Polysubstituted Benzene Derivatives, Chem. Rev. 2000, 100, 2901-
- I.Nakamura, Y. Yamamoto, Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis, Chem. Rev. 2004,104, 2127.
- Y. Yamamoto, Т. Arakawa, R. Ogawa, K. Itoh, Ruthenium (II)-Catalyzed Selective Intramolecular 2 + 2 + 2. Alkyne Cyclotrimerizations J. Am. Chem. Soc., 2003, 125, 12 143.
- H. C. Kolb, M. G. Finn, К. B. Sharpless, Click Chemistry: Diverse Chemical Function from a Few Good Reactions, Angew. Chem. Int. Ed, 2001,40, 2004-
- C. W. Tornoe, C. Christensen, M. Meldal, Peptidotriazoles on Solid Phase: 1,2,3.-Triazoles by Regiospecific Copper (I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides, J. Org. Chem., 2002,67, 3057-
- V. V. Rostovtsev, L. G. Green, V. V. Fokin, К. B. Sharpless, A Stepwise Huisgen Cycloaddition Process: Copper (I)-Catalyzed Regioselective «Ligation» of Azides and Terminal Alkynes, Angew. Chem. Int. Ed. 2002,41,2596.
- C.H. Осипов, Канд. диссер., ИНЭОСРАН, 1991.
- C.H. Осипов, Н. Д. Чкаников, А. Ф. Коломиец, А. В. Фокин, Синтез и С-алкилирующие свойства метилового эфира 2-(бензолсульфонилимино)-3,3,3-трифторпропионовой кислоты, Изв. АН СССР, Сер. Хим., 1986, 6,1385.
- С.Н. Осипов, Н. Д. Чкаников, А. Ф. Коломиец, А. В. Фокин, Реакции метиловых эфиров замещенных 2-амино-3,3,3-трифторпропионовых кислот с ариламинами, Изв. АН СССР, Сер. Хим., 1989,5,1648.