Structural Chemistry

, Volume 23, Issue 1, pp 209–217 | Cite as

Structural studies of seven homoisoflavonoids, six thiohomoisoflavonoids, and four structurally related compounds

  • Arto Valkonen
  • Katri Laihia
  • Erkki Kolehmainen
  • Reijo Kauppinen
  • Pál Perjési
Original Research

Abstract

1H and 13C NMR chemical shifts have been determined and assigned based on PFG 1H, 13C HMQC, and HMBC experiments for 3-(4′-X-benzyl)-4-chromenones (Ia, X = CN and Ib, X = NO2), 3-(4′-X-benzyl)-4-thiochromenones (IIa, X = Cl and IIb, X = Br), (E)-3-(4′-X-benzylidene)-4-chromanones (IIIaIIIe, X = OCH3, CH3, Cl, N(CH3)2, Br), (Z)-3-(4′-X-benzylidene)4-thiochromanones (IVaIVd, X = Cl, Br, F, OCH3), 2-benzyl-1,2,3,4-tetrahydro-1-naphthol (V), 2-benzyl- and (E)-2-benzylidene-1-tetralones (VI and VII), and (E)-2-benzylidene-1-benzosuberol (VIII). The crystal structures have been determined for the following seven compounds: derivatives of 4-chromanones (IIIaIIId), 1-tetrahydronaphtol (V), and 1-tetralones (VI and VII). The molecular features and intermolecular interactions in crystal state have been discussed.

Keywords

Homoisoflavonoid Thiohomoisoflavonoid NMR Single crystal X-ray structure 

Notes

Acknowledgments

The authors express their thanks to Dr. Tibor Mezei (EGIS Pharmaceuticals, Budapest, Hungary) for his generous contribution to the synthetic works. The corresponding author gratefully acknowledges Academy Professor Kari Rissanen from University of Jyväskylä and the Academy of Finland (project No. 122350) for financial support. The University of Jyväskylä and the Faculty of Medicine of University of Pécs (AOK-KA 34039-12/2009) is also acknowledged for supporting this work.

Supplementary material

11224_2011_9860_MOESM1_ESM.pdf (3.2 mb)
Supplementary material 1 (PDF 3241 kb)

References

  1. 1.
    Kirkiacharian BS, Gomis M, Tongo HG, Mahuteau J, Brion JD (1984) Org Magn Reson 22:106CrossRefGoogle Scholar
  2. 2.
    Miadoková E, Masterová I, Vlcková V, Duhová V, Toth J (2002) J Ethnopharm 81:381CrossRefGoogle Scholar
  3. 3.
    Masterová I, Suchy V, Uhrin D, Ubik K, Grancaiová Z, Bobovnicky B (1991) Phytochemistry 30:713CrossRefGoogle Scholar
  4. 4.
    Koorbanally C, Crouch NR, Langlois A, du Toit K, Mulholland DA, Drewes SE (2006) S Afr J Bot 72:428CrossRefGoogle Scholar
  5. 5.
    Rao VM, Damu GLV, Sudhakar D, Siddaiah V, Rao CV (2008) ARKIVOC (xi):285Google Scholar
  6. 6.
    Maheswara M, Siddaiah V, Rao CV (2006) Chem Pharm Bull 54:1193CrossRefGoogle Scholar
  7. 7.
    Ye G, Ye M, Guo D, Huang C (2005) Chromatographia 61:121CrossRefGoogle Scholar
  8. 8.
    Chang J-M, Shen C–C, Huang Y-L, Chien M-Y, Ou J-C, Shieh B-J, Chen C-C (2002) J Nat Prod 65:1731CrossRefGoogle Scholar
  9. 9.
    Mutanyatta J, Matapa B, Shushu D, Abegaz B (2003) Phytochemistry 62:797CrossRefGoogle Scholar
  10. 10.
    Tait S, Salvati AL, Desideri N, Fiore V (2006) Antiviral Res 72:252CrossRefGoogle Scholar
  11. 11.
    Lévai A (2004) ARKIVOC (vii):15Google Scholar
  12. 12.
    Perjési P, Das U, de Clercq E, Balzarini J, Kawase M, Sakagami H, Stables JP, Lorand T, Rozmer Z, Dimmock JR (2008) Eur J Med Chem 43:839CrossRefGoogle Scholar
  13. 13.
    Perjési P, Perjessy A, Kolehmainen E, Ősz E, Samalikova M, Virtanen E (2004) J Mol Struct 697:41CrossRefGoogle Scholar
  14. 14.
    Perjési P, Linnanto J, Kolehmainen E, Ősz E, Virtanen E (2005) J Mol Struct 740:81CrossRefGoogle Scholar
  15. 15.
    Dimmock JR, Kandepu NM, Nazarali AJ, Kowalchuk TP, Motaganahalli N, Quail JW, Mykytiuk P, Audette GF, Prasad L, Perjési P, Allen TM, Santos CL, Szydlowski J, de Clercq E, Balzarini J (1999) J Med Chem 42:1358CrossRefGoogle Scholar
  16. 16.
    Dimmock JR, Zello GA, Oloo EO, Quail JW, Kraatz H-B, Perjési P, Aradi F, Takacs-Novak K, Allen TM, Santos CL, Balzarini J, de Clercq E, Stables JP (2002) J Med Chem 45:3103CrossRefGoogle Scholar
  17. 17.
    Lévai A, Schág JB (1979) Pharmazie 34:749Google Scholar
  18. 18.
    Lévai A, Dinya Z, Schág JB, Tóth G, Szöllősy Á (1981) Pharmazie 36:465Google Scholar
  19. 19.
    Poisson T, Dalla V, Marsais F, Dupas G, Oudeyer S, Levacher V (2007) Angew Chem Int Ed 46:7090 (Supporting Information)CrossRefGoogle Scholar
  20. 20.
    Yee SW, Jarno L, Gomaa MS, Elford C, Ooi L-L, Coogan MP, McClelland R, Nicholson RI, Evans BAJ, Brancale A, Simons C (2005) J Med Chem 48:7123CrossRefGoogle Scholar
  21. 21.
    Hurd RE, John BK (1991) J Magn Reson 91:648Google Scholar
  22. 22.
    Rance M, Sørensen OW, Bodenhausen G, Wagner G, Ernst RR, Wüthrich K (1983) Biochem Biophys Res Commun 117:479CrossRefGoogle Scholar
  23. 23.
    Derome A, Williamson M (1990) J Magn Reson 88:117Google Scholar
  24. 24.
    Bax A, Griffey RH, Hawkins BL (1983) J Magn Reson 55:301Google Scholar
  25. 25.
    Bax A, Subramanian S (1986) J Magn Reson 67:565Google Scholar
  26. 26.
    Bax A, Summers MF (1986) J Am Chem Soc 108:2093CrossRefGoogle Scholar
  27. 27.
    Otwinowski Z, Minor W (1997) Methods in enzymology, vol. 276: macromolecular crystallography, part A. Academic Press, New York, pp 307–326Google Scholar
  28. 28.
    Burla MC, Camalli M, Carrozzini B, Cascarano GL, Giacovazzo C, Polidori G, Spagna R (2003) J Appl Crystallogr 36:1103CrossRefGoogle Scholar
  29. 29.
    Sheldrick GM (2008) Acta Crystallogr A64:112Google Scholar
  30. 30.
    Spek AL (2009) Acta Crystallogr D65:148Google Scholar
  31. 31.
    Farrugia LJ (1997) J Appl Crystallogr 30:565CrossRefGoogle Scholar
  32. 32.
    Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA (2008) J Appl Crystallogr 41:466CrossRefGoogle Scholar
  33. 33.
    Tóth G, Szöllösy Å, Lévai A, Oszbach G, Dietrich W, Kühne H (1991) Magn Reson Chem 29:801CrossRefGoogle Scholar
  34. 34.
    Pivnenko NS, Orlov VD, Nodel′man OA, Mikhed′kina EI, Lavrushin VF (1980) Zh Org Khim 16:1945Google Scholar
  35. 35.
    Katrusiak A, Ratajczak-Sitarz M, Kałuski Z, Orlov VD (1987) Acta Crystallogr C43:103Google Scholar
  36. 36.
    Augustine APT, Vithiya SM, Ramkumar V, Kanakam CC (2008) Acta Crystallogr E64:o2080Google Scholar
  37. 37.
    Marx A, Manivannan V, Suresh R, Kanagam CC, Sridhar B (2008) Acta Crystallogr E64:o328Google Scholar
  38. 38.
    Marx A, Suresh R, Kanakam CC, Manivannan V, Vasam CS (2008) Acta Crystallogr E64:o27Google Scholar
  39. 39.
    Marx A, Suresh R, Kanagam CC, Manivannan V, Büyükgüngör O (2007) Acta Crystallogr E63:o4530Google Scholar
  40. 40.
    Suresh R, Kanagam CC, Umarani PR, Manivannan V, Büyükgüngör O (2007) Acta Crystallogr E63:o4387Google Scholar
  41. 41.
    Marx A, Manivannan V, Suresh R, Kanagam CC, Büyükgüngör O (2007) Acta Crystallogr E63:o4383Google Scholar
  42. 42.
    Suresh R, Kanagam CC, Umarani PR, Manivannan V, Büyükgüngör O (2007) Acta Crystallogr E63:o4248Google Scholar
  43. 43.
    Chantrapromma S, Boonsri S, Fun H-K, Anjum S, Kanjana-opas A (2006) Acta Crystallogr E62:o1254Google Scholar
  44. 44.
    Boonsri S, Chantrapromma S, Fun H-K, Karalai C, Kanjana-opas A, Anjum S (2005) Acta Crystallogr E61:o3930Google Scholar
  45. 45.
    Allen FR (2002) Acta Crystallogr B58:380 (CSD, version 5.32, February 2011 update)Google Scholar
  46. 46.
    Mölm D, Flörke U, Risch N (1998) Eur J Org Chem 2185Google Scholar
  47. 47.
    Hauer B, Bickley JF, Massue J, Pena PCA, Roberts SM, Skidmore J (2002) 80:546Google Scholar
  48. 48.
    Zhou J-X, Wanga X-S, Shi D-Q (2007) Acta Crystallogr E63:o2082Google Scholar
  49. 49.
    Rong L-C, Li X-Y, Yao C-S, Wang H-Y, Shi D-Q (2006) Acta Crystallogr E62:o35Google Scholar
  50. 50.
    Oloo EO, Quail JW, Perjési P, Dimmock JR (2002) Acta Crystallogr E58:o582Google Scholar
  51. 51.
    Kałuski Z, Skrzypczak-Jankun E, Orlov VD, Borovoi IA (1978) Bull Acad Pol Sci Ser Sci Chim 26:869Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Arto Valkonen
    • 1
  • Katri Laihia
    • 1
  • Erkki Kolehmainen
    • 1
  • Reijo Kauppinen
    • 1
  • Pál Perjési
    • 2
  1. 1.Department of ChemistryUniversity of JyväskyläJyväskyläFinland
  2. 2.Institute of Pharmaceutical ChemistryUniversity of PécsPécsHungary

Personalised recommendations