Nucleophilic Addition of Thiol to Peripheral C=C Bonds of Tetraaryltetracyanoporphyrazine Macrocycle

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Abstract

An irreversible addition reaction of benzylmercaptan to the macrocycle of the cyanoarylporphyrazine family (Ar = p -MeOPh and Nph) was established for the first time. The reaction proceeds along the polarized peripheral semi-isolated double bonds of the macrocycle and takes place under mild conditions. Mass spectrometry and 1H NMR spectroscopy confirm the composition and structure of the products.

About the authors

T. S Lyubova

G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

S. A Lermontova

G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

L. G Klapshina

G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

E. Yu. Ladilina

G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

Email: eladilina@gmail.ru

References

  1. Wood Z.A., Schrosder E., Harris J.R., Poole L.B. // Trends Biochem. Sci. 2003. Vol. 28. N 1. P. 32. doi: 10.1016/S0968-0004(02)00003-8
  2. Dalton T.P., Shertzer H.G., Puga A. // Ann. Rev. Pharmacol. Toxicol. 1999. Vol. 39. P. 67. doi: 10.1146/annurev.pharmtox.39.1.67
  3. Oballa R.M., Truchon J.-F., Bayly C.I., Chauret N., Day S., Crane S., Berthelette C. // Bioorg. Med. Chem. Lett. 2007. Vol. 17. P. 998. doi: 10.1016/j.bmcl.2006.11.044
  4. Nomura T., Katunuma N. // J. Med. Invest. 2005. Vol. 52. N 1-2. P. 1. doi: 10.2152/jmi.52.1
  5. D'Arcy P., Wang X., Linder S. // Pharmacol. Therapeut. 2015. Vol. 147. P. 32. doi: 10.1016/j.pharmthera.2014.11.002
  6. Harris I.S., Endress J.E., Coloff J.L., Selfors L.M., McBrayer S.K., Rosenbluth J.M., Takahashi N., Dhakal S., Koduri V., Oser M.G., Schauer N.J., Doherty L.M., Hong A.L., Kang Y.P., Younger S.T., Doench J.G., Hahn W.C., Buhrlage S.J., DeNicola G.M., Kaelin W.G. Jr., Brugge J.S. // Cell Metabolism. 2019. Vol. 29. P. 1166. doi: 10.1016/j.cmet.2019.01.020
  7. Colland F., Formstecher E., Jacq X., Reverdy C., Planquette C., Conrath S., Trouplin V., Bianchi J., Aushev V.N., Camonis J., Calabrese A., Borg-Capra C., Sippl W., Collura V., Boissy G., Rain J.-C., Guedat P., Delansorne R., Daviet L. // Mol. Cancer Therapeut. 2009. Vol. 8. P. 2286. doi: 10.1158/1535-7163.MCT-09-0097
  8. Лермонтова С.А., Григорьев И.С., Ладилина Е.Ю., Балалаева И.В., Шилягина Н.Ю., Клапшина Л.Г. // Коорд. хим. 2018. Т. 44. № 2. C. 151
  9. Lermontova S.A., Grigor'ev I.S., Ladilina E.Yu., Balalaeva I.V., Shilyagina N.Yu., Klapshina L.G. // Russ. J. Coord. Chem. 2018. Vol. 44. P. 301. doi: 10.1134/S1070328418040061
  10. Maltsev O.V., Walter V., Brandl M.J., Hintermann L. // Synthesis. 2013. Vol. 45. P. 2763. doi: 10.1055/s-0033-1339492
  11. Berteotti A., Vacondio F., Lodola A., Bassi M., Silva C., Mor M., Cavalli A. // ACS Med. Chem. Lett. 2014. Vol. 5. P. 501. doi: 10.1021/ml400489b
  12. Pereira M.M., Monteiro C.J.P., Simoes A.V.C., Pinto S.M.A., Abreu A.R., Sa G.F.F., Silva E.F.F., Rocha L.B., Dabrowski J.M., Formosinho S.J., Simoes S., Arnaut L.G. // Tetrahedron. 2010. Vol. 66. P. 9545. doi: 10.1016/j.tet.2010.09.106
  13. Brückner C., Dolphin D. // Tetrahedron Lett. 1995. Vol. 36. N 52. P. 9425. doi: 10.1016/0040-4039(95)02052-7
  14. Silva A.M.G., Cavaleiro J.A.S. // Progr. Heterocycl. Chem. 2008. Vol. 19. Р. 44. doi: 10.1016/s0959-6380(08)80004-9
  15. Tome A.C., Neves M.G.P.M.S., Cavaleiro J.A.S. // J. Porph. Phthal. 2009. Vol. 13. Р. 408. doi: 10.1142/S1088424609000619
  16. Kadish K., Smith K.M., Guilard R. The Porphyrin Handbook. San Diego, San Francisco, New York, Boston, London, Sydney, Toronto: Academic Press, 1999. Vol. 1. P. 210.
  17. Khelevina O.G., Chizhova N.V., Stuzhin P.A. // J. Porph. Phthal. 2000. Vol. 4. P. 555. doi: 10.1002/1099-1409(200008)4:5<555::AID-JPP271>3.0.CO;2-6
  18. Hoffman D.R. // J. Org. Chem. 1965. Vol. 30. N 10. P. 3512. doi. 10.1021/jo01021a053
  19. Srinivasan N., Haney C.A., Lindsey J.S., Zhang W., Chait B.T.J. // J. Porph. Phthal. 1999. Vol. 4. P. 283. doi: 10.1002/(SICI)1099-1409(199904)3:4<283::AID-JPP132>3.0.CO;2-F
  20. Zhabanov Y.A., Zakharov A.V., Giricheva N.I., Shlykov S.A., Koifman O.I., Girichev G.V. // J. Mol. Struct. 2015. Vol. 1092. P. 104. doi: 10.1016/j.molstruc.2015.03.010
  21. Gryko D.T., Clausen C., Lindsey J.S. // J. Org. Chem. 1999. Vol. 64. N 23. P. 8635. doi: 10.1021/jo9911084
  22. MacFaul P.A., Morley A.D., Crawford J.J. // Bioorg. Med. Chem. Lett. 2009. Vol. 19. P. 1136. doi: 10.1016/j.bmcl.2008.12.105
  23. Oballa R.M., Truchon J.-F., Bayly C.I., Chauret N., Day S., Crane S., Berthelette C. // Bioorg. Med. Chem. Lett. 2007. Vol. 17. N 4. P. 998. doi: 10.1016/j.bmcl.2006.11.044
  24. Serafimova I.M., Pufall M.A., Krishnan S., Duda K., Cohen M.S., Maglathlin R.L., McFarland J.M., Miller R.M., Frödin M., Taunton J. // Nature Chem. Biol. 2012. Vol. 8. P. 471. doi: 10.1038/NChemBio.925
  25. Pritchard R.B., Lough C.E., Currie D.J., Holmes H.L. // Can. J. Chem. 1968. Vol. 46. P. 775. doi: 10.1139/v68-128
  26. Лермонтова С.А., Любова Т.С., Ладилина Е.Ю., Плеханов В.И., Балалаева И.В., Боярский В.П., Клапшина Л. Г. // ЖОХ 2020. Т. 90. Вып. 2. С. 274
  27. Lermontova S.A., Lyubova T.S., Ladilina, E.Yu., Plekhanov V.I., Balalaeva I.V., Boyarskii V.P., Klapshina L.G. // Russ. J. Gen. Chem. 2020. Vol. 90. N 2. P. 249. doi: 10.1134/S1070363220020140
  28. Лермонтова С.А., Григорьев И.С., Шилягина Н.Ю., Пескова Н.Н., Балалаева И.В., Ширманова М.В., Клапшина Л.Г. // ЖОХ 2016. Т. 86. Вып. 6. C. 1000
  29. Lermontova S.A., Grigoryev I.S., Shilyagina N.Yu., Peskova N.N., Balalaeva I.V., Shirmanova M.V., Klapshina L.G. // Russ. J. Gen. Chem. 2016. Vol. 86. N 6. P. 1330. doi: 10.1134/S1070363216060189

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