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Synthesis and structural studies of novel aminopolychloroethylated chelate acetylacetonate complexes of aluminum (III) and chromium (III)

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Abstract

Novel bio-medicinally promising complexes of amidotrichloroethylated acetylacetonate with Cr(III) and Al(III), which combine synthetically and pharmacologically attractive fragments, have been synthesized. Structural peculiarities of the complexes were investigated by magnetic resonance techniques (EPR, NMR) and some other modern physical-chemical methods (FT-IR, SEM, and elemental analysis). The axial and orthorhombic distortions of octahedral symmetry are observed in the acetylacetonate derivatives due to the presence of structurally different acetylacetonate ligands in the coordination medium that is supported by EPR and X-ray diffraction analysis data.

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References

  1. Arslan E, Lalancette RA, Bernal I (2019) An historic and scientific study of the properties of metal(III) tris-acetylacetonates. Struct Chem 28:201–212

    Article  CAS  Google Scholar 

  2. Trofimov BA, Mal’kina AG, Sapozhnikov AN, Vasil’eva IE, Schmidt AF, Kurokhtina AA, Vakul’skaya TI, Khutsishvili SS (2010) Polymerization of acetylene in aqueous PdCl2-CuCl solutions: novel catalytically active palladium-copper-containing carbon materials. Dokl Chem 431:94–98

    Article  CAS  Google Scholar 

  3. Kargar H, Torabi V, Akbari A, Bejatmanesh-Ardakani R, Sahraei A, Tahir MN (2019) Pd(II) complexes with asymmetric tetradentate NOON Schiff base ligand. Struct Chem 30:2289–2299

    Article  CAS  Google Scholar 

  4. Schmidt FK, Titova YY, Belykh LB, Umanets VA, Khutsishvili SS (2012) Formation of the cobalt hydrogenation catalysts at the action of lithium aluminum hydride and lithium tri(tert-butoxy)aluminohydride and their properties. Russ J Gen Chem 82:1334–1341

    Article  CAS  Google Scholar 

  5. Starikov AG, Chegerev MG, Starikova AA (2019) Heterospin magnetically active bimetallic Fe and Co complexes of aldiminato-functionalized catechol: a DFT study. Struct Chem. https://doi.org/10.1007/s11224-019-01463-1

  6. Tikhonov NI, Khutsishvili SS, Larina LI, Pozdnyakov AS, Emel’yanov AI, Prozorova GF, Vashchenko AV, Vakul’skaya TI (2019) Silver polymer complexes as precursors of nanocomposites based on polymers of 1-vinyl-1,2,4-triazole. J Mol Struct 1180:272–279

    Article  CAS  Google Scholar 

  7. Serrano JL (1996) Metallomesogens: synthesis, properties and applications. Weinheim, VCH

    Google Scholar 

  8. Galyametdinov YG, Ivanova G, Ovchinnikov I, Prosvirin A, Guillon D, Heinrich B, Dunmur DA, Bruce DW (1996) X-ray and magnetic birefringence studies of some lanthanide metallomesogens with Schiff’s base ligands. Liq Cryst 20:831–833

    Article  CAS  Google Scholar 

  9. Jain HG, Karacuban H, Krix D, Becker H-W, Nienhaus H, Buck V (2011) Carbon nanowalls deposited by inductively coupled plasma enhanced chemical vapor deposition using aluminum acetylacetonate as precursor. Carbon 49:4987–4995

    Article  CAS  Google Scholar 

  10. Chadwick DJ, Whelan J (1992) Aluminium in biology and medicine. John Wiley & Sons Inc., Chichester

    Google Scholar 

  11. Crichton RR, Ward RJ, Hider RC (2017) Metal chelation in medicine. RSC Publishing, Croydon

    Google Scholar 

  12. Renfrew AK (2014) Transition metal complexes with bioactive ligands: mechanisms for selective ligand release and applications for drug delivery. Metallomics 6:1324–1335

    Article  CAS  PubMed  Google Scholar 

  13. Henderson IF, Martin AP (1990) Control of slugs with contact-action molluscicides. Ann Appl Biol 116:273–278

    Article  CAS  Google Scholar 

  14. Gillies E, Szarek WA, Baird MC (1971) Application of paramagnetic shift reagents in nuclear magnetic resonance studies of complex alcohols and amines. Can J Chem 49:211–226

    Article  CAS  Google Scholar 

  15. Endo K, Inukai A, Otsu T (1994) Polymerization of methyl methacrylate with metal acetylacetonates and triethylaluminum catalysts. Polym Int 35:287–292

    Article  CAS  Google Scholar 

  16. Greene TW, Wuts PGM (2007) Protective groups in organic synthesis4th edn. Wiley, New York

    Google Scholar 

  17. Chen Y (2016) Recent functionalizations of primary sulfonamides. Synthesis 48:2483–2522

    Article  CAS  Google Scholar 

  18. Ashfaq M, Shah SSA, Najjam T, Shaheen S, Rivera G (2013) Synthetic routes of sulfonamide derivatives: a brief review. Mini-Rev Org Chem 10:160–170

    Article  CAS  Google Scholar 

  19. Vellasco Jr WT, Guedes GP, Facchinetti V, Vasconcelos TRA, Vaz MGF, Cunico W, de Souza MVN, de Paula GR, Fleming MECK, Gomes CRB (2014) Antibacterial activity of thioetherhydroxyethylsulfonamide derivatives. Med Chem 10:271–276

    Article  CAS  PubMed  Google Scholar 

  20. Wilkinson BL, Bornaghi LF, Houston TA, Innocenti A, Vullo D, Supuran CT, Poulsen SA (2007) Carbonic anhydrase inhibitors: inhibition of isozymes I, II, and IX with triazole-linked O-glycosides of benzene sulfonamides. J Med Chem 50:1651–1657

    Article  CAS  PubMed  Google Scholar 

  21. Bechmann N, Kniess T, Koeckerling M, Pigorsch A, Steinbach J, Pietzsch J (2015) Novel (pyrazolyl)benzenesulfonamides with a nitric oxide-releasing moiety as selective cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett 25:3295–3300

    Article  CAS  PubMed  Google Scholar 

  22. Firke SD, Bari SB (2015) Synthesis, biological evaluation and docking study of maleimide derivatives bearing benzenesulfonamide as selective COX-2 inhibitors and anti-inflammatory agents. Bioorg Med Chem 23:5273–5281

    Article  CAS  PubMed  Google Scholar 

  23. Limpachayaporn P, Schaefers M, Haufe G (2015) Isatin sulfonamides: potent caspases-3 and -7 inhibitors, and promising PET and SPECT radiotracers for apoptosis imaging. Future Med Chem 7:1173–1196

    Article  CAS  PubMed  Google Scholar 

  24. Shah SSA, Rivera G, Ashfaq M (2013) Recent advances in medicinal chemistry of sulfonamides. Rational design as anti-tumoral, anti-bacterial and anti-inflammatory agents. Mini-Rev Med Chem 13:70–86

    Article  CAS  PubMed  Google Scholar 

  25. Pingaew R, Prachayasittikul S, Ruchirawat S, Prachayasittikul V (2013) Synthesis and structure–activity relationship of mono-indole-, bis-indole-, and tris-indole-based sulfonamides as potential anticancer agents. Mol Divers 17:595–604

    Article  CAS  PubMed  Google Scholar 

  26. Chen Y, Lan Y, Cao X, Xu X, Zhang J, Yu M, Liu X, Liu B, Zhang G (2015) Synthesis and evaluation of amide, sulfonamide and urea – benzisoxazole derivatives as potential atypical antipsychotics. Med Chem Commun 6:831–838

    Article  CAS  Google Scholar 

  27. Kleemann A, Engel J, Kutscher B, Reichert D (1999) Pharmaceutical substance: syntheses, patents, applications2nd edn. Oxford Press, Stuttgart

    Google Scholar 

  28. Cloudsdale IS, Anderson RJ, Chinn HR, Craig GW, Deng L, Herberich-Patton PN, Pomes JC (1995) Herbicidal sulfonylamides: synthesis and chemistry of agrochemicals IV, vol 584. ACS Symposium Series, Washington, p 37

    Book  Google Scholar 

  29. Ting A, Schaus SE (2007) Organocatalytic asymmetric mannich reactions: new methodology, catalyst design, and synthetic applications. Eur J Org Chem 2007:5797–5815

    Article  CAS  Google Scholar 

  30. Rozentsveig IB, Rozentsveig GN, Mirskova AN, Chernyshev KA, Krivdin LB, Levkovskaya GG (2008) N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides in reactions with secondary amines. Russ J Gen Chem 78:1371–1379

    Article  CAS  Google Scholar 

  31. Levkovskaya GG, Drozdova TI, Rozentsveig IB, Mirskova AN (1999) N-functionally substituted imines of polychlorinated (brominated) aldehydes and ketones. Russ Chem Rev 68:581–604

    Article  CAS  Google Scholar 

  32. Mangelinckx S, Giubellina N, De Kimpe N (2004) 1-Azaallylic anions in heterocyclic chemistry. ACS Chem Rev 104:2353–2400

    Article  CAS  Google Scholar 

  33. Rozentsveig IB, Serykh VY, Chernysheva GN, Chernyshev KA, Kondrashov EV, Tretyakov EV, Romanenko GV (2013) One-pot synthesis of N-(imidazo[1,2-a]pyridin-3-yl)- and N-(imidazo[2,1-b][1,3]thiazol-5-yl)sulfonamides. Eur J Org Chem 2013:368–375

    Article  CAS  Google Scholar 

  34. Rozentsveig IB, Popov AV, Rozentsveig GN, Serykh VY, Chernyshev KA, Krivdin LB, Levkovskaya GG (2010) A novel regiospecific cascade synthesis of sulfonamide derivatives from N-(2-polychloroethyl)sulfonamides via chloroaziridine intermediates in the presence of mercaptoethanol. Mol Divers 14:533–541

    Article  CAS  PubMed  Google Scholar 

  35. Rozentsveig IB, Chernysheva GN, Levkovskaya GG, Fedotova AI, Tret’yakov EV, Romanenko GV (2014) Noncatalytic C-amidoalkylation of acetylacetone and chromium acetylacetonate with N-sulfonyl polychloroacetaldehyde imines. Russ J Org Chem 50:1–5

    Article  CAS  Google Scholar 

  36. Irkutsk Supercomputer Center of the SB RAS (ISDCT SB RAS). https://www.hpc.icc.ru./en/

  37. Stoll S, Schweiger A (2006) EasySpin, a comprehensive software package for spectral simulation and analysis in EPR. J Magn Reson 178:42–55

    Article  CAS  PubMed  Google Scholar 

  38. Domracheva NE, Ovchinnikov IV, Turanov A, Lattermann G, Facher A (2001) Features of the magnetic and dielectric behavior of mesophases of chromium (III) complexes with azacyclic ligands. Phys Sol State 43:1188–1194

    Article  CAS  Google Scholar 

  39. Weckhuysen BM, Rao RR, Pelgrims J, Schoonheydt RA, Bodart P, Debras G, Collart O, van der Voort P, Vansant EF (2000) Synthesis, spectroscopy and catalysis of [Cr(acac)3] complexes grafted onto MCM-41 materials: formation of polyethylene nanofibres within mesoporous crystalline alluminosilicates. Chem Eur J 6:2960–2970

    Article  CAS  PubMed  Google Scholar 

  40. Ardelean I, Peteanu M, Simon V, Bob C, Filip S (1998) EPR and magnetic susceptibility studies of Cr2O3-Bi2O3-GeO2 glasses. J Mater Sci 33:357–362

    Article  CAS  Google Scholar 

  41. Gafurov MR, Volodin MA, Rodionov AA, Sorokina AT, Dolomatov MY, Petrov AV, Vakhin AV, Mamin GV, Orlinskii SB (2018) EPR study of spectra transformations of the intrinsic vanadyl-porphyrin complexes in heavy crude oils with temperature to probe the asphaltenes’ aggregation. J Pet Sci Eng 166:363–368

    Article  CAS  Google Scholar 

  42. Niemann A, Bossek U, Haselhorst G, Wieghardt K, Nuber B (1996) Synthesis and characterization of six-coordinate nitrido complexes of vanadium(V), chromium(V), and manganese(V). Isolation of a dinuclear, mixed-valent μ-nitrido chromium(III)/chromium(V) species. Inorg Chem 35:906–915

    Article  CAS  PubMed  Google Scholar 

  43. Pell AJ, Pintacuda G, Grey CP (2019) Paramagnetic NMR in solution and the solid state. Prog Nucl Magn Reson Spectrosc 111:1–271

    Article  CAS  PubMed  Google Scholar 

  44. Chalmers RA, Umar M (1968) Secondary standards: acetylacetonates. Anal Chim Acta 42:357–364

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are grateful to the Baikal Analytical Center of Collective Use, SB RAS. Research completed in the framework of State contracts No. AAAA-A1611611210009-5 and No. АААА-А16-116112510004-0 of the program of fundamental research.

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Authors and Affiliations

  1. A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk, Russia, 664033

    Spartak S. Khutsishvili, Gulnur N. Chernysheva & Igor B. Rozentsveig

  2. Irkutsk State University, 1 Karl Marx St., Irkutsk, Russia, 664003

    Igor B. Rozentsveig

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  1. Spartak S. Khutsishvili
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Correspondence to Spartak S. Khutsishvili.

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Khutsishvili, S.S., Chernysheva, G.N. & Rozentsveig, I.B. Synthesis and structural studies of novel aminopolychloroethylated chelate acetylacetonate complexes of aluminum (III) and chromium (III). Struct Chem 31, 1793–1800 (2020). https://doi.org/10.1007/s11224-020-01540-w

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