First Macrocyclic 1,2,3-Triazolyl Uridine Analogues

  • Olga V. Andreeva ИОФХ им. А.Е. Арбузова - ОСП ФИЦ КазНЦ РАН
  • Mayya Belenok Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences
  • Bulat Garifullin Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences
  • Irina Strobykina Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences
  • Liliya Saifina Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences
  • Alexandra Voloshina Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences
  • Vyacheslav Semenov Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences
  • Vladimir Kataev Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences
DOI: https://doi.org/10.6060/mhc224868a
Ключевые слова: Nucleoside analogues, macrocycles, uridine, 1,2,3-triazole, click chemistry, CuAAC reaction

Аннотация

Катализируемой медью реакцией азид-алкинового циклоприсоединения (CuAAC) впервые получены два мароциклических 1,2,3-триазоловых аналогов уридина.  29-Членный макроцикл состоял из одной молекулы урацила, двух молекул D-рибофуранозы и четырех молекул 1,2,3-триазола. 58-Членный макроцикл состоял из двух молекул урацила, четырех молекул D-рибофуранозы и восьми молекул 1,2,3-триазола

Литература

Kataev V.E., Garifullin B.F. Chem. Heterocycl. Compd. 2021, 57, 326-341. https://doi.org/10.1007/s10593-021-02912-8

Pastuch-Gawołek G., Gillner D., Krol E., Walczak K., Wandzik I. Eur. J. Pharm. 2019, 865, 172747. https://doi.org/10.1016/j.ejphar.2019.172747

Seley-Radtke K.L., Yates M.K. Antiviral Res. 2018, 154, 66-86. https://doi.org/10.1016/j.antiviral.2018.04.004

Nakajima M., Itoi K., Takamatsu Y., Kinoshita T., Okazaki T., Kawakubo K., Shindo M., Honma T., Tohjigamori M., Haneishi T. J. Antibiot. 1991, 44, 293-300. https://doi.org/10.7164/antibiotics.44.293

Kumar R., Kumar M., Kumar V., Kumar A., Haque N., Kumar R., Prasad A.K. Synth. Commun. 2020, 50, 3369-3396. https://doi.org/10.1080/00397911.2020.1803914

Koole L.H., Neidle S., Crawford M.D., Krayevski A.A., Gurskaya G.V., Sandstrom A., Wu J.-C., Tong W., Chattopadhyaya J. J. Org. Chem. 1991, 56, 6884-6892, https://doi.org/10.1021/jo00024a034

Marquez V.E., Ezzitouni A., Russ P., Siddiqui M.A., Ford H. Jr., Feldman R.J., Mitsuya H., George C., Barchi J.J. Jr. J. Am. Chem. Soc. 1998, 120, 2780-2789, https://doi.org/10.1021/ja973535

Braasch D.A., Corey D.R. Chem. Biol. 2001, 8, 1-7, https://doi.org/10.1016/S1074-5521(00)00058-2

Zhang Q., He P., Zhou G., Gu Y., Fu T., Xue D., Liu H.-M. Carbohydr. Res. 2013, 382, 65-70, https://doi.org/10.1016/j.carres.2013.10.004

Zhao Y., Shu R., Liu J. Mol. Ther. Nucleic Acids 2021, 26, 997-10133, https://doi.org/10.1016/j.omtn.2021.09.002

Okabe M., Sun R.-C. Tetrahedron Lett. 1989, 30, 2203-2206, https://doi.org/10.1016/S0040-4039(00)99648-5

Beard A. R., Butler P.I., Mann J., Partlett N.K. Carbohydr. Res. 1990, 205, 87-91https://doi.org/10.1016/0008-6215(90)80130-U

Webb T.R., Mitsuya H., Broder S. J. Med. Chem. 1988, 31, 1475-1479, https://doi.org/10.1021/jm00402a038

Callam C.S., Gadikota R.R., Lowary T.L. Synlett 2003, 9, 1271-1274, https://doi.org/10.1055/s-2003-40335

Counde O-Y., Kurz W., Eugui E.M., Mc Roberts M.J., Verheyden J.H.P., Kurz I.J., Walker K.A.M. Tetrahedron Lett. 1992, 33, 41-44, https://doi.org/10.1016/S0040-4039(00)77668-4

Alibes R., Alvarez-Larena A., de March P., Figueredo M., Font J., Parella T., Rustullet A. Org. Lett., 2006, 8, 491-494, https://doi.org/10.1021/ol052794y

Wang G., Girardet J.-L., Gunic E. Tetrahedron 1999, 55, 7707-7724. https://doi.org/10.1016/S0040-4020(99)00394-4

Obika S., Andoh J., Sugimoto T., Miyashita K., Imanishi T. Tetrahedron Lett. 1999, 40, 6465-6468, https://doi.org/10.1016/S0040-4039(99)01324-6

Olsen A.G., Rajwanshi V.K., Nielsen C., Wengel J. J. Chem. Soc. Perkin Trans 1 2000, 21, 3610-3614, https://doi.org/10.1039/b005469k

Srivastava S., Maikhuri V.K., Kumar R., Bohra K., Singla H., Maity J., Prasad A.K. Carbohydr. Res. 2018, 470, 19-25, https://doi.org/10.1016/j.carres.2018.09.007

Zhong S., Mondon M., Pilard S., Len C. Tetrahedron 2008, 64, 7828-7836, https://doi.org/10.1016/j.tet.2008.05.112

Len C., Mondon M., Lebreton J. Tetrahedron 2008, 64, 7453-7475, https://doi.org/10.1016/j.tet.2008.04.095

Mieczkowski A., Roy V., Agrofoglio L.A. Chem. Rev. 2010, 110, 1828-1856, https://doi.org/10.1021/cr900329y

Clark V.M., Todd A.R., Zussman J. J. Chem. Soc. 1951, 2952-2958, https://doi.org/10.1039/jr9510002952

Ikehara M. Acc. Chem. Res. 1969, 2, 47-53, https://doi.org/10.1021/ar50014a003

Holmes R., Robins R.K. J. Org. Chem. 1963, 28, 3483-3486, https://doi.org/10.1021/jo01047a050

Capon R.J., Trotter N.S. J. Nat. Prod. 2005, 68, 1689-1691, https://doi.org/10.1021/np0502692

Wang P., Hollecker L., Pankiewicz K.W., Patterson S.E., Whitaker T., McBrayer T.R., Tharnish P.M., Sidwell R.W., Stuyver L.J., Otto M.J., Schinazi R.F., Watanabe K.A. J. Med. Chem. 2004, 47, 6100-6103, https://doi.org/10.1021/jm0401210

Wang P., Du J., Rachakonda S., Chun B.-K., Tharnish P.M., Stuyver L.J., Otto M.J., Schinazi R.F., Watanabe K.A. J. Med. Chem. 2005, 48, 6454-6460, https://doi.org/10.1021/jm058223t

Chun B.K., Wang P., Hassan A., Du J., Tharnish P.M., Stuyver L.J., Otto M.J., Schinazi R.F., Watanabe K.A. Tetrahedron Lett. 2005, 46, 2825-2827, https://doi.org/10.1016/j.tetlet.2005.02.120

Calcerrada-Munoz N., O'Neil I., Cosstick R. Nucleos. Nucleot. Nucl. 2001, 20, 1347-1350, https://doi.org/10.1081/NCN-100002552

Sengupta J., Mukhopadhyay R., Bhattacharjya A. J. Org. Chem. 2007, 72, 4621-4625, https://doi.org/10.1021/jo062554b

Das S.N., Rana R., Chatterjee S., Kumar G.S., Mandal S.B. J. Org. Chem. 2014, 79, 9958-9969, https://doi.org/10.1021/jo501857k

Gaffney B.L., Jones R.A. Org. Lett. 2014, 16, 158-161, https://doi.org/10.1021/ol403154w

Andreeva O.V., Belenok M.G., Saifina L.F., Shulaeva M.M., Dobrynin A.B., Sharipova R.R., Voloshina A.D., Saifina 36.A.F., Gubaidullin A.T., Khairutdinov B.I., Zuev Y.F., Semenov V.E., Kataev V.E. Tetrahedron Lett. 2019, 60, 151276, https://doi.org/10.1016/j.tetlet.2019.151276

Andreeva O.V., Garifullin B.F., Zarubaev V.V., Slita A.V., Yesaulkova I.L., Volobueva A.S., Belenok M.G., Man'kova M.A., Saifina L.F., Shulaeva M.M., Voloshina A.D., Lyubina A.P., Semenov V.E., Kataev V.E. Molecules 2021, 26, 3678, https://doi.org/10.3390/molecules26123678

Agrahari A.K., Bose P., Jaiswal M.K., Rajkhowa S., Singh A.S., Hotha S., Mishra N., Tiwari V.K. Chem. Rev. 2021, 121, 7638-7956, https://doi.org/10.1021/acs.chemrev.0c00920

Zheng X.-A., Wang R., Gong S.-S., Kong R., Liu R., Sun Q. Nucleos. Nucleot. Nucl. 2018, 37, 79-88, https://doi.org/10.1080/15257770.2017.1414242

Опубликован
2023-05-11
Как цитировать
Andreeva, O., Belenok, M., Garifullin, B., Strobykina, I., Saifina, L., Voloshina, A., Semenov, V., & Kataev, V. (2023). First Macrocyclic 1,2,3-Triazolyl Uridine Analogues. Макрогетероциклы/Macroheterocycles, 16(1), 77-83. https://doi.org/10.6060/mhc224868a
Выпуск
Том 16 № 1 (2023): This issue is dedicated to the anniversary of Academician A. Tsivadze
Раздел
N-Макроциклы