Синтез и биологическая активность функционально замещенных фосфонатов и амидофосфатов
Диссертация
Предложен новый каталитический вариант получения а-гидроксифосфонатов. Показано, что использование сочетания катализа 1,5-диазабицикло--нон-5-ена (БВИ) и микроволнового облучения позволяет существенно повысить выходы конечных продуктов. Осуществлен направленный синтез неизвестных ранее биологически активных а-аминофосфонатов, аминометиленбисфосфонатов и амидофосфатов, содержащих адамантильный… Читать ещё >
Список литературы
- Нифантьев Э.Е. Химия гидрофосфорильных соединений. М.: Наука. 1983. 262 с.
- Пурдела Д., Вылчану Р. Химия органических соединений фосфора. М.: Химия. 1972. 752 с.
- Корбридж Д. Фосфор. Основы химии, биохии, технологии. М.: Мир. 1982. 670 с.
- Romanenko V.D. Kukhar V.P. Fluorinated phosphonates: synthesis and biomedical application. Chem. Rev. 2006,106, 3868−3935.
- Engel R. Phosphonates and analogues of natural phosphates. Chem. Rev. 1977, 77, 349−367.
- Menn J.J., McBain J.B. New aspects of organophosphorus pesticides. IV. Newer aspects of the methabolism of phosphonate incsecticides. Residue Rev. 1974, 55, 35−51.
- Поляк M.C. Антибиотики группы фосфоновой кислоты. Антибиотики. 1987, 32, 66−75.
- Черкасов Р.А., Галкин В. И. Реакция Кабачника-Филдса: синтетический потенциал и проблема механизма. Успехи химии. 1998, 57 (10), 940−968.
- Кухарь В.П., Свистунова Н. Ю., Солоденко В. А., Слошонок В. А. Асимметрический синтез фтор- и фосфорсодержащих аналогов аминокислот. Успехи химии. 1993, 62 (3), 284−302.
- Uziel J., Genet J.Р. Синтез рацемических и оптически активных а-аминофосфоновых кислот. ЖОрХ. 1997, 33 (И), 1605−1627.
- Ordonez М., Rojas-Cabrera Н., Cativiela С. An overview of stereoselective synthesis of a-aminophosphonic acids and derivatives. Tetrahedron. 2009, 65, 17−49.
- Колодяжный О.И. Хиральные гидроксифосфонаты, синтез, конфигурация, биологические свойства. Успехи химии. 2006, 75 (3), 254−281.
- Kolodiazhnyi O.I. Asymmetric synthesis of hydroxyphosphonates. Tetrahedron: Asymmetry. 2005,16, 3295−3340.
- Kafarski P., Mastalerz P. Aminophosphonates: natural occurance, biochemistry and biological properties. Beilr. Wirkstofforsch. 1984,21, 3−110.
- Albrecht L., Albrecht A., Krawczyk H., Jorgensen K.A. Organocatalytic asymmetric synthesis of organophosphorus compounds. Chem. Eur. J. 2010, 16, 28−48.
- Sobhani S., Tashrifi Z. Synthesis of a-fiinctionalized phosphonates from a-hydroxyphosphonates. Tetrahedron. 2010, 66, 1429−1439.
- Maier L. Advances in the chemistry of aminophosphonic acids. Phosphorus, Sulfer and Silicon. 1983, 14, 295−322.
- Jacobsen N.E., Bartlett P.A. A phosphonamidate dipeptide analog as an inhibitor of carboxypeptidase A.,/. Am. Chem. Soc. 1981,103, 654−657.
- Bartlett P.A., Hanson J.E., Giannousis P.P. Potent inhibition of pepsin and penicillopepsin by phosphorus-containing peptide analogs. J. Org. Chem. 1990, 55, 6268−6274.
- Atherton F.R., Hassall C.H., Lambert R.W. Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. J. Med. Chem. 1986, 29, 29−40.
- Allen M.C., Fuhrer W., Tuck В., Wade R., Wood J.M. Renin inhibitors. Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond. J. Med. Chem. 1989, 32, 1652−1661.
- Пудовик A.H. Присоединение диалкилфосфористых кислот к иминам. Новый метод синтеза эфиров аминофосфоновых кислот. Докл. АН СССР. 1952, 83, 865−869.
- Кабачник М.И., Медведь Т. Я. Новый метод синтеза аминофосфоновых кислот. Докл. АН СССР. 1952, 83, 689−691.
- Fields Е.К. The synthesis of esters of substituted aminophosphonic acids. J. Am. Chem. Soc. 1952, 74 (6), 1528−1531.
- Berlin K.D., Claunch R.T., Gaudy E.T. a-Aminoarylmethylphosphonic acids and diethyl a-aminoarylmethylphosphonates hydrochlorides. Aluminum-amalgamreduction of oximes of diethyl arylphosphonates. J. Org. Chem. 1968, 33, 30 903 095.
- Asano S., Kitahara T., Ogawa T., Matsui M. The synthesis of a-amino phosphonic acids. Agr. Biol. Chem. 1973, 37, 1193−1195.
- Kudzin Z.H., Kotinski A. Synthesis of 0,0-dialkyl 1-aminoalkanephosphonates. Synthesis. 1980,12, 1028−1031.
- Chambers J.R., Isbell A.F. A new synthesis of amino phosphonic acids. J. Org. Chem. 1964, 29, 832−836.
- Redmore D. B Topics in Phosphorus Chemistry. Vol. 8. Willey-Interscience, New-York, 1976, P. 515.
- Yang D., Yan Y.-L., Law K.-L., Zhu N.-Y. Lewis acid-catalyzed atom transfer radical cyclization of unsaturated p-ketoamides. Tetrahedron. 2003, 59, 1 046 510 475.
- Matveeva E.D., Podrugina T.A., Tishkovskaya E.V., Tomilova L.G., Zefirov N.S. A novel catalytic three-component synthesis (Kabachnik-Fields reaction) of a-aminophosphonates from ketones. Synletl. 2003, 2321−2324.
- Qian C., Huang T. One-pot synthesis of a-aminophosphonates from aldehydes using lanthanide triflate as a catalyst. J. Org. Chem. 1998, 63 (12), 4125−4128.
- Ranu B.C., Hajra A., Jana U. General procedure for synthesis of a-aminophosphonates from aldeydes and ketones using indium (III) chloride as a catalyst Org. Lett. 1999,1 (8), 1141−1143.
- Louaisil N., Rabasso N., Fadel A. Asymmetric synthesis of ® — and (S)-a-amino-3-piperidinylphosphonic acids via phosphite addition to iminium ions. Synthesis. 2007, 289−293.
- Heydari A., Karimian A., Ipaktschi J. Lithium perchlorate/diethylether catalyzed aminophosphonation of aldehydes. Tetrahedron Letters 1998, 39 (37), 67 296 732.
- Галкина И.В., Зверева Э. Р., Галкин В. И., Собанов А. А., Черкасов Р. А. Кинетика и механизм реакции Кабачника-Филдса. II. Реакция Кабачника-Филдса в системе диэтилфосфит-бензальдегид-циклогексиламин. ЖОХ. 1998, 68 (9), 1453−1456.
- Галкин В.И., Зверева Э. Р., Собанов А. А., Галкина И. В., Черкасов Р. А. Кинетика и механизм реакции Кабачника-Филдса в системе диалкилфосфит-бензальдегид-анилин. ЖОХ. 1993, 63 (10), 2224−2227.
- Галкина И.В., Галкин В. И., Собанов А. А., Черкасов Р. А. Кинетика и механизм реакции Кабачника-Филдса. IV. Салициловый альдегид в реакции Кабачника-Филдса. ЖОХ. 1998, 68 (9), 1465−1468.
- Галкина И.В., Галкин В. И., Черкасов Р. А. Кинетика и механизм реакции Кабачника-Филдса. V. Влияние природы гидрофосфорильного соединения на механизм реакции Кабачника-Филдса. ЖОХ. 1998, 68 (9), 1469−1475.
- Zeflrov N.S., Matveeva E.D. Catalytic Kabachnik-Fields reaction: new horizons for old reaction. ARKIVOC. 2008, 1−17.
- Chung S.K., Kang D.-H. Asymmetric synthesis of a-aminphosphonates via diastereoselective addition of phosphate to chiral imine derivatives. Tetrahedron: Asymmetry. 1996, 7(1), 21−24. '
- Haak E., Bytschkov I., Doye S. A one pot-procedure for the synthesis of a-aminophosphonates from alkynes. Eur. J. Org. Chem. 2002, 3, 457−463.
- Saidi M.R., Azizi N. A new protocol for a one-pot synthesis of a-aminophosphonates by reaction of imines, prepared in situ with trialkylphosphites. Synlelt. 2002, 8, 1347−1349.
- Пудовик A.H., Шагидулин P.P., Хайрулин В. К., Вандюкова И. И., Чернова А. В., Пудовик М. А. Реакции этилового эфира ДЛ^-(п-метоксибензаль)-«-аминобензойной кислоты с диалкиловыми эфирами фосфористой кислоты. Изв. АН. Сер. Хим. 1996, 5, 1301−1302.
- Soroka М., Zygmunt J. Tritylamine (triphenylmethylamine) in organic synthesis- I. The synthesis of 7V-(Triphenylmethyl)alkaneimines, 1-(Triphenylmethylamino)alkylphosphonic esters, and 1-Aminoalkylphosphonic acids and esters. Synthesis. 1988, 370−372.
- Akiyama Т., Morita H., Itoh J., Fushibe K. Chiral Bronsted acid catalyzed enantioselective hydrophosphorylation of imines: asymmetric synthesis of a-aminhosphonates. Org. Lett. 2005, 7 (13), 2583−2585.
- Sasai H., Arai S., Takara J., Shibasaki M. Catalytic asymmetric synthesis of a-aminophosphonates using lanthanoid-potassium-BINOL complexes. J. Org. Chem. 1995, 60, 6656−6658.
- Chalmers M.E., Kosolapoff G.M. The Synthesis of amino-substituted phosphonic acids. J. Am. Chem. Soc. 1953, 75, 5278−5280.
- Takahashi H., Yoshioka M., Imai N., Onimura K., Kobayashi S. Simple and improved preparation of a-aminophosphonic acid derivatives, key building blocks of phosphonopeptides. Synthesis. 1994, 8, 763−764.
- Kaboudin В., Nazari R. Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions. Tetrahedron Lett. 2001, 42, 82 118 213.
- Bartlett P.A., Hanson J.E., Giannousis P.P. Potent inhibition of pepsin and penicillopepsin by phosphorus-containing peptide analogs. J. Org. Chem. 1990, 55, 6268−6274.
- Fadel A. A useful synthesis of 1-aminocyclopropanephosphonic acid from cyclopropanone acetal. J. Org. Chem. 1999, 64, 4953−4955.
- Scardarian A.R., Kaboudin B. A novel synthesis of diethyl 1-aminoarylmethylphosphonates on the surface of aluminia. Tetrahedron Lett. 1997, 38, 2543−2546.
- Kaboudin B. Surface-mediated solid phase reactions: a simple and new method for the synthesis of a-aminophosphonates under solvent-free conditions. Chem. Lett. 2001,50,880−883.
- Saito B., Egami H., Katsuki T. Synthesis of an optically active Al (salalen) complex and its application to catalytic hydrophosphonylation of aldehydes and aldimines. J. Am. Chem. Soc. 2007,129, 1978−1986.
- Kowalik J., Kupczyk-Subotkowska L., Mastalerz P. Preparation of dialkyl 1-aminoalkanephosphonates by reduction of dialkyl 1-hydroxyiminoalkanephosphonates with zinc in formic acid. Synthesis. 1981, 5759.
- Green D., Patel G., Elgendy S., Baban J.A., Cleason G., Kakkar V.V., Deadman J. The facile synthesis of 0,0-dialkyl 1-aminoalkanephosphonates. Tetrahedron Lett. 1993, 34, 6917−6920.
- Demir A.S., Tanyeli C., Sesenoglu O., Demic S. A simple synthesis of 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds. Tetrahedron Lett. 1996, 57, 407−410.
- Berlin K.D., Roy N.K., Claunch R.T., Bude D. A novel route to a-aminoalkylphosphonic and diethyl a-aminoalkylphosphonate hydrochlorides. J. Am. Chem. Soc. 1968, 90, 4494−4495.
- Kosolapoff G.M. Synthesis of amino-substituted phosphonic acids. II. a-Aminobenzylphosphonic acid. J. Am. Chem. Soc. 1948, 70, 1283.
- Yokomatsu Т., Shibuya S. Enantioselective synthesis of a-amino phosphonic acids by an application of stereoselective opening of homochiral dioxane acetals with triethyl phosphate. Tetrahedron: Asymmetry. 1992, 5, 377−378.
- Gajda Т., Sikora D., Nonas T. Application of 1-azidoalkylphosphonates in the synthesis of phosphonopeptides and other TV-substituted aminophosphonates. Phosphorus, Sulfur and Silicon. 1999, 144, 581−584.
- Bongini A., Camerini R., Panunzio M. Efficient synthesis of the four diastereomers phosphothreonine from lactaldehyde. Tetrahedron: Asymmetry. 1996, 7, 1467−1476.
- Hoffmann S., Witkowski W., Schubert H. Aminophosphonsearen- Hofmannscher Seareamidabbau eine neue Methode zur Darstellung von a-Aminophosphonsearen. Z. Chem. 1974,14, 152−155.
- Soroka M., Mastalerz P. Hofmann degradation and bromination of amides derived from phosphonoacetic acid. Tetrahedron Lett. 1973, 14, 5201−5202.
- Абрамов B.C. О взаимодействии диалкилфосфористых кислот с альдегидами и кетонами. ЖОХ. 1952, 22, 647−652.
- Wroblewski А.Е., Piotrowska D.G. Enantiomerically pure iV-Boc- and N-benzoyl-(S)-phenylglycinals. Tetrahedron: Asymmetry. 2002, 13, 2509−2512.
- Smahi A., Solhy A., Tahir R., Sebti S., Mayoral J.A., Garcia J.I., Fraile J.M., Zahouily M. Preparation of a-hydroxyphosphonates over phosphate catalysts. Catalysis Commun. 2008, 9, 2503−2508.
- Nesterov V.V., Kolodiazhnyi O.I. New method for the asymmetric hydroboration of ketophosphonates and the synthesis of phospho-carnitine. Tetrahedron: Asymmetry. 2006,17, 1023−1026.
- Pogatchnik D.M., Wiemer D.F. Enantioselective synthesis of a-hydroxy phosphonates via oxidation with (camphorsulfonyl)oxaziridines Tetrahedron Letters. 1997,38 (20), 3495−3498.
- Sum V., Kee T.P. Synthetic, stereochemical and mechanistic studies on the asymmetric phosphonylation of aldehydes via 2-triorganosiloxy-1,3,2-oxazaphospholidines. J. Chem. Soc., Perkin Trans. 1.1993,2701 -2711.
- Gancarz R. Nucleophilic addition to carbonyl compounds. Competition between hard (amine) and soft (phosphite) nucleophile. Tetrahedron. 1995, 51 (38), 10 627−10 632.
- Scardarian A. R., Kaboudin B. Surface-mediated solid phase reactions: preparation of diethyl 1 -hydroxyarylmethylphosphonates on the surface of magnesia. Synth. Commun. 1997, 27 (4), 543−551.
- Kaboudin В., Nazari R. The synthesis of a-hydroxyphosphonates mediated by microwave irradiation under solvent-free conditions. J. Chem. Res. (S). 2002, 291−292.
- Baraldi P. G.- Guarneri M.- Moroder F.- Pollini G. P.- Simoni D. Synthesis of 1-phthalimidoalkanephosphonates. Synthesis. 1982, 653−654.
- Пудовик A.H., Зимин М. Г., Собанов А. А., Мусина А. А. Реакции диалкилфософитов с непредельными кетонами. ЖОХ. 1976, 46 (7), 14 551 461.
- Azizi N., Saidi M.R. Lithium perchlorate diethyl ether solution: A highly eficient media for the Abramov reaction. Phosphorus, Sulfur and Silicon. 2003,178, 1255 1259.
- Yamagishi Т., Yokomatsu Т., Suemune K., Shibuya S. Enantioselective synthesis of a-hydroxyphosphonic acid derivatives through hydrophopshynilation of aldehydes catalyzed by Al-Li-BINOL complex. Tetrahedron. 1999, 55, 1 212 512 136.
- Wroblewski A.E., Balcerzak K.B. Synthesis of enetiomeric diethyl (1R, 2R) — and (IS, 2R)-1,2,3-trihydroxypropylphosphonates. Tetrahedron. 1998, 54, 6833.
- Kolodiazhnyi O.I., Grishkun E.V., Sheiko S., Demchuk O., Thoennesen H., Jones P.G., Schmutzler R. Chiral symmetric phosphoric acid esters as sources of optically active organophosphorus compounds. Tetrahedron: Asymmetry. 1998, 9, 1645−1649.
- Cui P., McCalmont W.F., Tomsig J.L., Lynch R.R., Macdonald T.L. a- and p-Substituted phosphonate analogs of LPA as autotaxin inhibitors. Bioorg. Med. Chem. 2008,16, 2212−2225.
- Pham M., Zhang W., Chen V., Whitney T., Yao J., Froese D., Friesen A.D., Diakur J.M., Haque W. Design and synthesis of novel pyridoxine 5'-phosphonates as potential antiischemic agents. J. Med. Chem. 2003, 46, 36 803 687.
- Jankowski S., Marczak J., Olczak A., Glowka M.L. Stereochemistry of 1-hydroxyphosphonate-phosphate rearrangement. Retention of configuration at the phosphorus atom. Tetrahedron Lett. 2006, 47, 3341−3344.
- Wroblewski A.E., Drozd J. Synthesis of four enantiomers of 2-acetamido-l-hydroxypropylphosphonates. Tetrahedron: Asymmetry. 2007, 18, 1134−1141.
- Plazuk D., Zakrzewski J., Rybarczyk-Pirek A. Diastereoselective addition of dimethyl phosphite to 3,3', 4,4'-tetramethyl-l, l '-diphosphaferrocene-2-carboxaldehyde. J. Organometallic Chem. 2006, 691, 3098−3102.
- Plazuk D., Zakrzewski J., Rybarczyk-Pirek A. Resolution and absolute configuration of dimethyl hydroxy-(ferrocenylmethyl)phosphonate Tetrahedron: Asymmetry. 2006, 17, 1975−1978.
- Szymczak M., Szymanska A., Stawinski J., Boryski J., Kraszewski A. Aryl H-phosphonates. 14. Synthesis of new nucleotide analogues with phosphonate-phosphate internucleosidic linkage. Org. Lett. 2003, 5, 3571−3573.
- Chen W., Hui Y., Zhou X., Jiang J., Cai Y., Liu X., Lin L., Feng X. Chiral dioxide-Yb (III) complexes catalyzed enantioselective hydrophosphonylation of aldehydes. Tetrahedron Lett. 2010, 51, 4175−4178.
- Duxbury J.P., Warne J.N.D., Mushtaq R., Ward C., Thornton-Pett M., Jiang M., Greatrex R., Kee T.P. Phospho-aldol catalysis via chiral schiff base complexes of aluminum. Organometallics. 2000,19, 4445−4457.
- Gou S., Zhou X., Wang J., Liu X., Feng X. Asymmetric hydrophosphonylation of aldehydes catalyzed by bifunctional chiral Al (III) complexes. Tetrahedron. 2008, 64, 2864−2870.
- Nakanishi K., Kotani S., Sugiura M., Nakajima M. First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases. Tetrahedron. 2008, 64, 6415−6419.
- Vahdat S.M., Baharfar R., Tajbakhsh M., Heydari A., Baghbanian S.M., Khaksar S. Organocatalytic synthesis of a-hydroxy and a-aminophosphonates. Tetrahedron Lett. 2008, 49, 6501−6504.
- Smahi A., Solhy A., Tahir R., Sebti S., Mayoral J.A., Garcia J.I., Fraile J.M., Zahouily M. Preparation of a-hydroxyphosphonates over phosphate catalysts. Catalysis Commun. 2008, 9, 2503−2508.
- Seyden-Penne J. В Reductions by the Alumino- and Borohydrides in Organic Synthesis (2nd ed.). Wiley-VCH, New York, 1997- P. 6.
- Колодяжный О.И., Гуляйко И. В. Энантиоселективный синтез a-гидроксиалкилфосфонатов. ЖОХ. 2005, 75 (7), 1225−1226.
- Meier С., Laux W.H.G. Asymmetric synthesis of chiral, nonracemic dialkyl-a-hydroxyalkylphosphonates via a (-)-Chlorodiiso-pinocampheylborane (Ipc2B-Cl) reduction. Tetrahedron: Asymmetry. 1996, 7 (1), 89−94
- Gajda T. Enantioselective synthesis of diethyl 1-hydroxyalkylphosphonates via oxazaborolidine catalyzed borane reduction of diethyl a-ketophosphonates. Tetrahedron: Asymmetry. 1994, 5 (10), 1965−1972.
- Fonvielle M., Therisod H., Hemery M., Therisod M. New competitive inhibitors of cytosolic (NADH-dependent) rabbit muscle glycerophosphate dehydrogenase. Bioorg. Med. Chem. Lett. 2007,17, 410−413.
- Nesterov V.V., Kolodiazhnyi O.I. Efficient method for the asymmetric reduction of a- and P-ketophosphonates. Tetrahedron. 2007, 63, 6720−6731.
- Cravotto G., Giovenzana G.B., Pagliarin R., Palmisano G., Sisti M. A straightforward entry into enantiomerically enriched p-amino-a-hydroxyphosphonic acid derivatives. Tetrahedron: Asymmetry. 1998, 9 (5), 745 748.
- Yamagishi Т., Fujii K., Shibuya S., Yokomatsu T. Synthesis of chiral y-Amino-P-hydroxyphosphonate derivatives from unsaturated phosphonates. Synlett. 2004, 14, 2505−2509.
- Yuan Ch., Li J., Zhang W. A facial chemoenzymatic method for the preparation of chiral l, 2-dihydroxy-3,3,3,-trifluoropropanephosphonates. J. Fluorine Chem. 2006,127, 44−47.
- Gordon N.J., Evans S.A. Diastereoselective condensation of oxazaphosphites with aliphatic and aromatic aldehydes. J. Org. Chem. 1993, 58 (20), 5293−5294.
- Kawashima Т., Ishii Т., Inamoto N., Tokitoh N., Okazaki R. The olefin synthesis from P-hydroxyalkylphosphonates induced by fluorides or relatively weak bases. Bull. Chem. Soc. Jpn. 1998, 71 (1), 209−219.
- Cermak D.M., Du Ya., Wiemer D.F. Synthesis of nonracemic dimethyl a-(hydroxyfarnesyl)phosphonates via oxidation of dimethyl farnesylphosphonate with (camphorsulfonyl)oxaziridines. J. Org. Chem. 1999, 64, 388−393.
- Blomen L J.M.J. History of bisphosphonates: Discovery and history of the non-medical uses of bisphosphonates. In Bisphosphonate on Bones- Bijvoet
- O.L.M., Fleisch H.A., Canfield R.E., Russell R.G.G. Eds.- Elsevier: Amsterdam, 1995, 111−124.
- Coleman R.E. Uses and abuses of bisphosphonates. Annuals of Oncology. 2000, 11, 179−188.
- Tubiana-Hulin M. Metastases osseuses des cancers du sein: du bon usage des bisphosphonates. Oncologic. 2004, 6, 129−135.
- Gittens, S. A.- Bansal, G.- Zernicke, R. F.- Uludag, H. Designing proteins for bone targeting. Adv. Drug Delivery Rev. 2005, 57, 1011−1036.
- Obojska A., Berlicki L., Kafarski P., Lejczak В., Chicca M., Forlani G. Herbicidal pyridyl derivatives of aminomethylene-bisphosphonic acid inhibit plant glutamine synthetase. J. Agric. Food Chem. 2004, 53, 3337−3344.
- Soloducho J., Gancarz R., Wieczorek P., Korf J., Hafher J., Lejczak В., Kafarski P. Sposob wytwarzania nowych pochodnych kwasu aminometylenobisfosfonowego. Palelnt PL-93 298 436 93 408.1993.
- Алферьев И.С., Бобков С. Ю., Котляревский И. Jl. Иминобис(метилендифосфоновые) кислоты. Изв. АН СССР. Сер. Хим. 1987, 4, 865−868.
- Dabrowska E., Burzynska A., Mucha A., Matczak-Jon E., Sawka-Dobrowolska W., Berlicki L., Kafarski P. Insight into the mechanism of three component condensation leading to aminomethylenebisphosphonates. J. Organomet. Chem. 2009, 694, 3806−3813.
- Прищенко А.А., Ливанцов M.B., Новикова О. П., Ливанцова Л. И. Синтез TV-анилинометилендифосфорсодержащих кислот и их производных. ЖОХ. 2009, 79,1580−1582.
- Leiras O. Pyridinylbisphosphonates for use as a therapeutical agent. Pat. US5866556 (A). 1999.
- Mlynarz P., Jewginski M., Sliwinska S., Latajka R., Schroeder G., Kafarski P. «Twin» phosphorus atoms of Tetraethyl 2-methyl-piperyd-l-ylmethylenebisphosphonates. Heteroatom. Chem. 2007,18, 774−781.
- Takeuchi M., Sacamoto S., Yoshida M., Abe Т., Isomura Y. Studies on novel bone resorption inhibitors. I. Synthesis and pharmacological activities of aminomethylenebisphosphonate derivatives. Chem Pharm. Bull. 1993, 41(4), 688−693.
- Kubicek V., Kotek J., Hermann P., Lukes I. Aminoalkylbis (phosphonates): their complexation properties in solution and in the solid state. Eur. J. Inorg. Chem. 2007, 2, 333 344.
- Olive G., Jaques A. Optimization, continuation and lack of the one-step diphosphorylation reaction. Assay of modification of the tetraethyl-(pyrrolidine-2,2-dyil)bisphosphonate. Phosphorus, Sulfur and Silicon. 2003,178, 33−46.
- Wu M., Chen R., Huang Y. Convenient synthesis of analogs of aminomethylene gem-diphosphonic acid from amines without catalyst. Synth. Commun. 2004, 34, 1393−1398.
- Gillespie S.G., Lau S.L., Paulson S.C. Stereoselectiv inhibition of cholesterol esterase by enetiomeric phosphonates. Phosphorus, Sulfer and Silicon. 1997,122, 205−208.
- Mucha A., Kunert A., Grembecka J., Pawelczak M., Kafarski P. A phosphonamidate containing aromatic //-terminal amino group as inhibitor of leucine aminopeptidase—design, synthesis and stability. Eur. J. Med. Chem. 2006, 41, 768−772.
- Kafarski P., Lejczak B. Biological activtity of aminophosphonic acids. Phosphorus, Sulfur and Silicon. 1991, 63, 193−215.
- Venkatachalam T.K., Samuel P., Qazi S., Uckun F.M. Effect of change in nucleoside structure on the activation and antiviral activity of. phosphoramidate derivatives. Bioorg. Med. Chem. 2005,13, 5408−5423.
- Muller P., Nury P., Bernardinelli G. Asymmetric catalysis with a phosphoramidite derived from (-)-(aR)-l, r-binaphthalene.-8,8'-diol. Helv. Chim. Ada. 2000, 83, 843−854.
- Kim M., Sanda F., Endo T. Phosphonamidates as thermally latent initiators in the polymerizationof epoxides. Pol. Bull. 2001, 46, 277−282.
- Giannousis P.P., Bartlett P.A. Phosphorus amino acid analogs as inhibitors of leucine aminopeptidase. J. Med. Chem. 1987,30, 1603−1609.
- Jacobsen N.E., Bartlett P.A. A phosphonamidate dipeptide analog as an inhibitor of carboxypeptidase A. J. Am. Chem. Soc. 1981, 103, 654−657.
- Lidstrom P., Tierney J., Wathey B., Westman J. Microwave assisted organic synthesis—a review. Tetrahedron. 2001, 57, 9225−9283.
- Loupy A., Petit A., Hamelin J., Texier-Boullet F., Jaquault P., Mathe D. New solvent-free organic synthesis using focused microwaves. Synthesis. 1998, 1213−1234.
- Jones R.J., Bichofberger R. Minireview: nucleotide prodrugs. Antiviral Res. 1995,27, 1−17.
- Lies T., Plapinger R.E., Wagner-Jauregg T. The preparation of N-dialkylphosphorylated glycine. J. Am. Chem. Soc. 1953, 75, 5755−5756.
- Li S., Eakin R.E. Synthesis of iV-phosphorylated amino acids. J. Am. Chem. Soc. 1955, 77, 1866−1870.
- Sciarini L.J., Fruton J.S. Derivatives of vV-phosphorylated amino acids. J. Am. Chem. Soc. 1949, 71, 2940.
- Atherton F.R., Openshaw H.T., Todd R.R. The reaction of dialkylphosphites with polyhalogen compounds in presence of bases. J. Chem. Soc. 1945, 660−664.
- Atherton F.R., Todd R.R. Studies on phosphorylation. Part III. Further observations on the reaction of phosphites with polygalogen compounds in presence of bases and its application to the phosphorylatoin of alcohols. J. Chem. Soc. 1947, P.674−679.
- Шабарова З.А., Сатарова Л. Г., Прокофьев М. А. Синтез Р-аминокислотных производных адениловой кислоты. Докл. АН СССР, 1958, 123, 864−868.
- Петров К.А., Нифантьев Э. Е., Щеголев А. А., Тусеев А. П. О 6-метилфосфоните 1,2,3,4-диизопропилиденгалактозы. ЖОХ, 1964, 34, 690 695.
- Skropeta D., Schworer R., Schmidt R.R. Stereoselective synthesis of phosphoramidate a (2−6)sialyltransferase transition-state analogue ingibitors. Bioorg. Med. Chem. Lett. 2003, 13, 3351−3354.
- Cui Z., Zhang J., Wang F., Wang Y., Miao Z., Chen R. The diastereoselective synthesis of methyl 5-deoxy-5-(dialkylphosphono)-5-(dialkylphosphorylamido)-2,3−0-isopropylidene-(3-D-ribofuranosides. Carbohydr. Reseach. 2008, 343,2530−2534.
- Hammerschmidt F., Hanbauer M. Transformation of arylmethylamines into a-aminophosphonic acids via metalated phosphoramidates: rearrangement of partly configurationally stable yV-phosphorylated a-aminocarbanions. J. Org. Chem. 2000, 65, 6121−6131.
- Tripathi R., Mishra D., Rizvi A., Singh C. Evaluation of some adamantane-based synthetic trioxanes against Plasmodium knowlesi in rhesus monkeys. Life Sciences. 2007, 81, 1544−1548.
- Balzarini J., Orzeszko B., Maurin J.K., Orzeszko A. Synthesis and anti-HIV studies of 2-adamantyl-substituted thiazolidin-4-ones. Eur. J. Med. Chem. 2007, 42, 993−1003.
- Kesel A.J. A system of protein target sequences for anti-RNA-viral chemotherapy by a vitamin B6-Derived zinc-chelating trioxa-adamantane-triol. Bioorg. Med. Chem. 2003,11, 4599−4613.
- Kabachnik M.M., Zobnina E.V., Beletskaya I.P. Catalyst-free microwave-assisted synthesis of a-aminophosphonates in a three-component system: R’C (0)R?-(Et0)2P (0)H-RNH2. Synlett. 2005, 1393−1396.
- Warner V.D., Mirth D.B., Dey A.S. Synthesis of diethyl N-dodecylphosphoramidate analogs as potential inhibitors of dental plaque. J. Med. Chem., 1973, 16(10), 1185−1186.
- Barbeau D.L. Noncardiotoxic pharmaceutical compounds. American Patent № 35 863. 2006.
- Nyman E.S., Hynninen P.H. Research advances in the use of tetrapyrrolic photosensitizers for fotodynamic therapy. J. of Photochemistry and Photobiology B: Biology. 2004, 73, 1−28.
- Renno R.Z., Miller J.W. Photosensitizer delivery for photodynamic therapy of choroidal neovascularization. Advanced Drug Delivery Reviews. 2001, 52, 63−78.
- Tajiri H., Yokoyama K., Boku N., Ohtsu A., Fujii T., Yoshida S., Sato T., Hakamata K., Hayashi K., Sakata I. Fluorescent diagnosis of experimental gastric cancer using a tumor-localizing photosensitizer. Cancer Letters. 1997, 111, 215 220.
- Mody T.D. Pharmaceutical development and medical applications of porphyrin-type macrocycles. J. Porph. Phth. 2000, 4, 362−368.
- Ali H., van Lier J.E. Metal complexes as photo- and radiosensitizers. Chem. Rev. 1999, 99, 2379−2450.
- Pandey R.K. Recent advances in photodynamic therapy. J. Porph. Phth. 2000, 4, 368−374.
- Wainwright, M. Recent advances in two-photon photodynamic therapy. Anti-Cancer agents Med. Chem. 2008, 8, 280−291.
- Robertson C.A., Hawkins Evans D., Abrahamse H. Photodynamic therapy (PDT): A short review on cellular mechanisms and cancer research applications for PDT. J. of Photochemistry and Photobiology B: Biology 2009, 96, 1 -8.
- Shternberg E.D., Dolfin D., Brukner C. Porphyrin-based photosensitizers for use in photodynamic therapy. Tetrahedron. 1998, 54, 4151−4202.
- Giard D.- Weagle G., Gupta A., Berube G., Chapados C. Preparation and in vitro biological evaluation of tetrapyrrole ethanolamide derivatives as potential anticancer agents. Bioorg. Med. Chem. Lett. 2008,18, 360−365.
- Belykh D.V., Tarabukina I.S., Gruzdev I.V., Kutchin A.V. Unexepted transformations of methylpheophorbide a under the action of bis-(W, yV-dimethylamino)methane. Mendeleev Commun. 2007,17, 340−342.
- Bregadze V.I., Sivaev I.B., Lobanova I.A., Titeev R.A., Brittal D.I., Grin M.A., Mironov A.F. Conjugates of boron clusters with derivatives of natural chlorin and bacteriochlorin. Appl. Radiation and Isotopes 2009, 67, S101 -S104.
- Smith K.M.- Bisset G. M. F., Bushell M.J. Partial syntheses of optically pure methyl bacteriopheophorbides с and d from methyl pheophorbide a. J. Org. Chem. 1980, 45, 2218−2224.
- Гранберг К.И., Кабачник M.M., Новикова 3.C., Теренин В. И. Толстая Т.П. Практические работы по органической химии. Методическое пособие. М. 1995.
- De Savignac A., Bon M., Lattes A. Etude de quelques facteurs intervenant dan l’equilibre imine. Bull. Soc. Chim. Fr. 1972,8, 3167−3171.
- Iqbal A.F.M. Catalytic deoxygenation of organic compounds by carbon monoxide. II. Direct synthesis of Schiff bases from aromatic nitroderivatives, aldehydes, and carbon monoxide. J. Org. Chem. 1972, 37, 2791−2793.
- Cabiddu S., Cadoni E., Ianni A., Gelli G., Melis S., Bernard A.M., Cabiddu M.G., Montis S., Fattuoni C. Addition of 1,3-benzoxathiole 3-oxide anion to azomethines under varying reaction conditions. Eur. J. Org. Chem. 2002, 20, 3393−3401.
- Agarwal R. K, Dutt P. Thorium (IV) halide adducts of aromatic Schiff bases derived from anisaldehyde and substituted anilines. Pol. J. Chem. 1993, 67(4), 575−579.
- Sethi Т., Chaturvedi A., Upadhyay R.K., Mathur S.P. Inhibition effect of nitrogen containing ligands on corrosion of aluminium in acid media with and without KC1. Pol. J. Chem. 2008, 82, 591−598.
- Nakamura M., Komatsu K., Gondo Y., Ohta K., Ueda Y. An infrared study of the C=N stretching frequency in jV-benzylideneaniline derivatives. Chem. Pharm. Bull. 1967, 15, 585−588.
- Sun P., Yang X., Hu Z. One-pot synthesis of a-amino phosphonates in chloroaluminate-based ionic liquid.J. Chem. Res. Syn. 2006, 4, 240−246.
- Wu J., Sun W., Xia H., Sun X. A facile and highly efficient route to a-amino phosphonates via three-component reactions catalyzed by Mg (C104)?, or molecular iodine. Org. Biomol. Chem. 2006, 4, 1663−1667.
- Луговкин. К синтезу диэтиловых эфиров 2-фурфурил (аминопиридил) фосфоновых кислот и эфиров арил (аминоарил)фосфоновых кислот. ЖОХ. 1976, 46, 555−560.
- Kudzin Z.H., Lyzwa P., Luczak J., Andrijewski G. 1-Aminoalkanephosphonates. Part II. A facile conversion of 1-aminoalkanephosphonic acids into 0,0-diethyl 1-aminoalkanephosphonates. Synthesis. 1997,44−46.
- Krzyzanowska В., Stec W.J. A new approach to the synthesis of primary amines, isothiocyanates and 1-aminoalkanephosphonates via vV-phosphinyl aldoximes and ketoximes. Synthesis. 1978, 521−523.
- Kaboudin В., Rahmani A. Silica-supported ammonium hydrogen carbonate as an efficient reagent for one-pot synthesis of 1-aminophosphonates from aldehydes. Synthesis. 2003, 2705−2708.
- В. Vanderhoydonck, C.V. Stevens. Synthesis of l-phosphono-2-aza-l, 3-dienes and scope of their aziridination. Synthesis. 2004, 722−735.
- Gross H., Beisert S., Costisella B. a-Substituierte phosphonate. 37. a-Pyrrolomethanphosphonsaurederivate und iV-vinyl pyrrole. J. Prakt. Chem. 1981, 323, 877−886.
- Azizi N., Rajabi F., Saidi M.R. A mild and highly effiecient protocol for the one-pot synthesis of primary a-amino phosphonates under solvent-free conditions. Tetrahedron Lett. 2004, 45, 9233−9236.
- Kharasch M.S., Mosher R.A. Organophosphorus chemistry. Addition reactions of diethyl phosphonate and the oxidation of triethyl phosphite 1 J. Org. Chem. 1960,25, 1000−1006.
- Абрамов B.C., Капустина А. С. О взаимодействии диалкил фосфористых кислот с альдегидами и кетонами. XII. Эфиры а-окси-а-фурфурилфосфиновой и а-окси-а-тенилфосфиновой кислот. ЖОХ. 1957, 27, 173−176.
- Keglevich G., Sipos М., Takacs D., Greiner I. A study on the Michael addition of dialkylphosphites to methylvinylketone. Heteroatom Chem. 2007, 18, 226−229.
- Olive G.- Le Moigne F.- Mercier A.- Tordo P. Synth. Commun. 2000, 30(4), 619−627.
- L. Maier. ORGANISCHE PHOSPHORVERBINDUNGEN 75: Herstellung und eigenschaften von aminomethylendiphosphinaten und -diphosphonaten, RRiNCHP (0)R2(0R3).2 und derivaten. Phosphorus, Sulfur, and Silicon. 1981,11, 311−322.137 -A