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2004 | 2 | 4 | 686-695
Tytuł artykułu

Synthesis of a series of vicinal diamines with potential biological activity

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A broad range of vicinal diamines based on styrene oxide are synthesisedvia mixtures of regioisomeric amino alcohols. The ring opening of the intermediate aziridinium ions by primary amines proceeds with high regioselectivity, leading to the target diamines as single regioisomers for all reaction series. The compounds are of potential biological interest as ligands for cisplatin analogues. Anticancer activity tests of both groups of compounds are in progress.
Wydawca

Czasopismo
Rocznik
Tom
2
Numer
4
Strony
686-695
Opis fizyczny
Daty
wydano
2004-12-01
online
2004-12-01
Twórcy
  • Institute of Organic Chemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl.9, 1113, Sofia, Bulgaria, vkurteva@orgchm.bas.bg
  • Institute of Organic Chemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl.9, 1113, Sofia, Bulgaria
Bibliografia
  • [1] L.H. DeRiemer, C.F. Meares, D.A. Goodwin and C.I. Diamanti: “Bledta-II synthesis of a new tumor-visualizing derivative of Co(III)-bleomycin”,J. Labelled Compd. Radiopharm., Vol. 18, (1981), pp. 1517–1534. http://dx.doi.org/10.1002/jlcr.2580181017[Crossref]
  • [2] S. Kasina, A.R. Fritzberg, D.L. Jonhson and D.J. Eshima: “Tissue distribution properties of technetium-99m-diamide-dimercaptide complexes and potential use as renal radiopharmaceuticals”,J. Med. Chem., Vol. 29, (1986), pp. 1933–1940. http://dx.doi.org/10.1021/jm00160a023[Crossref]
  • [3] J.-M. Lehn: “Cryptates: the chemistry of macropolycyclic inclusion complexes”,Acc. Chem. Res., Vol. 11, (1978), pp. 49–57. http://dx.doi.org/10.1021/ar50122a001[Crossref]
  • [4] A.E. Popter: “Pyrazines and their benzo derivatives”, In: A.R. Katritzky and C.W.C. Rees (Eds): Comprehensive Heterocyclic Chemistry, Vol. 3, Pergamon Press, Oxford, 1984, p. 179.
  • [5] Review: D. Leucet, T. Legall and C. Mioskowski: “The chemistry of vicinal diamines”,Angew. Chem., Int. Ed., Vol. 37, (1998), pp. 2580–2627. http://dx.doi.org/10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO;2-L[Crossref]
  • [6] B. Rosenberg, L. VanCamp, J.E. Trosko and V.H. Mansour: “Platinum compounds-a new class of potent antitumor agents”,Nature, Vol. 222, (1969), pp. 385–386.
  • [7] H. Brunner, P. Hankofer, U. Holzinger, B. Treittinger and H. Schönenberger: “Synthesis and antitumor activity of platinum(II) complexes containing substituted ethylenediamine ligands”,Eur. J. Med. Chem., Vol. 25, (1990), pp. 35–44. http://dx.doi.org/10.1016/0223-5234(90)90162-V[Crossref]
  • [8] H. Brunner, P. Hankofer, U. Holzinger and B. Treittinger: “Synthesis and antitumor-activity of Pt(II) complexes of benzyl-1,2-diaminoethane ligands”,Chem. Ber., Vol. 123, (1990), pp. 1029–1038.
  • [9] R. Gust, T. Burgemeister, A. Mannschreck and H. Schönenberger: “Aqua[1-(2,6-dichloro-4-hydroxyphenyl)-2-phenylethylenediamine](sulfato)platinum(II) complexes with variable substituents in the 2-phenyl ring. 1. Synthesis and antitumor and estrogenic properties”,J. Med. Chem., Vol. 33, (1990), pp. 2535–2544. http://dx.doi.org/10.1021/jm00171a031[Crossref]
  • [10] L.R. Kelland, G. Abel, M.J. McKeage, M. Jones, P.M. Goddard, M. Valenti, B.A. Murrer and K.R. Harrap: “Preclinical antitumor evaluation of bis-acetato-amminedichloro-cyclohexylamine platinum (IV): an orally active platinum drug”,Cancer Res., Vol. 53, (1993), pp. 2581–2586.
  • [11] D.-K. Kim, Y.-W. Kim, H.-T. Kim and K.H. Kim: “Synthesis andin vitro cytotoxicity ofcis-dichloro [(2S,3R,4S)-2-aminomethyl-3,4-(O-isopropylidene) dihydroxy-or-3,4-dihydroxypyrrolidine]platinum(II)”,Biiorg. Med. Chem. Lett., Vol. 6, (1996), pp. 643–646. http://dx.doi.org/10.1016/0960-894X(96)00088-1[Crossref]
  • [12] A.R. Khokkar, S. Al-Baker, S. Shamsuddin and Z.H. Siddik: “Chemical and biological studies on a series of novel (trans-(1R,2R)-, trans-(1S,2S)-, and cis-1,2-diaminocyclohexane)platinum(IV) carboxylate complexes”,J. Med. Chem., Vol. 40, (1997), pp. 112–116. http://dx.doi.org/10.1021/jm960587l[Crossref]
  • [13] A. Pasini and F. Zunino: “New cisplatin analogs-on the way to better antitumor agents”,Angew. Chem., Int. Ed., Vol. 26, (1987), pp. 615–624. http://dx.doi.org/10.1002/anie.198706151[Crossref]
  • [14] J. Reedijk: “Improved understanding in platinium antitumour chemistry”,Chem. Commun., (1996), pp. 801–806. [Crossref]
  • [15] S.E. Sousa, P. O'Brien and P. Poumellec: “Two expedient methods for the preparation of chiral diamines”,J. Chem. Soc., Perkin Trans. 1, (1998), pp. 1483–1492.
  • [16] B.E. Rossiter, M. Eguchi, G. Miao, N.M. Swingle, A.E. Hernandez, E. Fluckiger, D. Vickers, R.G. Patterson and K.L. Reddy: “Enantioselective conjugate addition to cyclic enones with scalemic lithium organo(amido) cuprates, Part IV. Relationshipbetween ligand structure and enantioselectivity”,Tetrahedron, Vol. 49, (1993), pp. 965–986. http://dx.doi.org/10.1016/S0040-4020(01)86278-5[Crossref]
  • [17] R.K. Dieter, B. Lagu, J.W. Deiter, N. Deo and W.T. Pennington: „Synthesis of chiral triamine ligands from ephedrine and pseudoephedrine”,Synlett, (1990), pp. 109–110. [Crossref]
  • [18] R.K. Dieter, N. Deo, B. Lagu and J.W. Deiter: „Stereo- and regioselective synthesis of chiral diamines and triamines from pseudoephedrine and ephedrine”,J. Org. Chem., Vol. 57, (1992), pp. 1663–1673. http://dx.doi.org/10.1021/jo00032a013[Crossref]
  • [19] P. O'Brien and T.D. Towers: “Diamine synthesis: Exploring the regioselectivity of ring opening of aziridinium ions”,J. Org. Chem., Vol. 67, (2002), pp. 304–307; and references cited therein. http://dx.doi.org/10.1021/jo010824e[Crossref]
  • [20] D. Bhuniya, A. DattaGupta and V. Singh: “Design, Synthesis, and Application of Chiral Nonracemic Lithium Amide Bases in Enantioselective Deprotonation of Epoxides”,J. Org. Chem., Vol. 61, (1996), pp. 6108–6113. http://dx.doi.org/10.1021/jo960244v[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02482731
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