Structural Chemistry

, Volume 22, Issue 1, pp 161–166 | Cite as

Synthesis and NMR elucidation of homoisoflavanone analogues

  • Mahidansha Shaikh
  • Katja Petzold
  • Hendrik G. Kruger
  • Karen du Toit
Original Research

Abstract

A series of five homoisoflavanone analogues have been synthesized from the corresponding 3,5-methoxy phenols via chroman-4-one in three steps. The complete NMR elucidation of these homoisoflavanone analogues is reported. The use of 2D NMR techniques (COSY, NOESY, HSQC and HMBC) proved to be very useful tools in the elucidation of homoisoflavanone analogues. The homoisoflavanone analogues exhibit an AA′BB′ spin pattern in the ring B of the homoisoflavanone. These homoisoflavanone analogues are potential antifungal and anti-inflammatory agents.

Keywords

Homoisoflavanone Synthesis Anti-inflammatory Antifungal 2D NMR 

Supplementary material

11224_2010_9703_MOESM1_ESM.pdf (3.1 mb)
Supplementary material 1 (PDF 3152 kb)

References

  1. 1.
    Kirkiacharian BS, Gomis M, Tongo HG, Mahuteau J, Brion JD (1984) Org Magn Reson 22:106–108CrossRefGoogle Scholar
  2. 2.
    Adinolfi M, Lanzetta R, Laonigro G, Parrilli M, Breitmaier E (1986) Magn Reson Chem 24:663–666CrossRefGoogle Scholar
  3. 3.
    Purushothaman KK, Kalyani K, Subramaniam K, Shanmughanathan SP (1982) Indian J Chem B 21:383Google Scholar
  4. 4.
    McPherson DD, Cordell GA, Soejarto DD, Pezzuto JM, Fong HHS (1983) Phytochemistry 22:2835–2838CrossRefGoogle Scholar
  5. 5.
    Srinivas K, Rao YK, Mahender I, Das B, Krishna K, Kishore KH, Murty USN (2003) Phytochemistry 63:789–793CrossRefGoogle Scholar
  6. 6.
    Zhao P, Iwamoto Y, Kouno I, Egami Y, Yamamoto H (2004) Phytochemistry 65:2455–2461CrossRefGoogle Scholar
  7. 7.
    Saitoh T, Sakashita S, Nakata H, Shimokawa T, Kinjo J, Yamahara J, Yamasaki M, Nohara T (1986) Chem Pharm Bull 34:2506–2511Google Scholar
  8. 8.
    Namikoshi M, Nakata H, Nuno M, Ozawa T, Saitoh T (1987) Chem Pharm Bull 35:3568–3575Google Scholar
  9. 9.
    Du Toit K, Elgorashi EE, Malan SF, Drewes SE, van Staden J, Crouch NR, Mulholland DA (2005) Bioorg Med Chem 13:2561–2568CrossRefGoogle Scholar
  10. 10.
    Du Toit K, Elgorashi EE, Malan SF, Mulholland DA, Drewes SE, Van Staden J (2007) S Afr J Bot 73:236–241CrossRefGoogle Scholar
  11. 11.
    Heller WTC (1981) Fort Chem Org Nat 40:106Google Scholar
  12. 12.
    Della Loggia R, Del Negro P, Tubaro A, Barone G, Parrilli M (1989) Planta Med 55:587–589CrossRefGoogle Scholar
  13. 13.
    Amschler G, Frahm AW, Hatzelmann A, Kilian U, MullerDoblies D, MullerDoblies U (1996) Planta Med 62:534–539CrossRefGoogle Scholar
  14. 14.
    Siddaiah V, Rao CV, Venkateswarlu S, Krishnaraju AV, Subbaraju GV (2006) Bioorg Med Chem 14:2545–2551CrossRefGoogle Scholar
  15. 15.
    Siddaiah V, Maheswara M, Venkata Rao C, Venkateswarlu S, Subbaraju GV (2007) Bioorg Med Chem Lett 17:1288–1290CrossRefGoogle Scholar
  16. 16.
    Foroumadi A, Samzadeh-Kermani A, Emami S, Dehghan G, Sorkhi M, Arabsorkhi F, Heidari MR, Abdollahi M, Shafiee A (2007) Bioorg Med Chem Lett 17:6764CrossRefGoogle Scholar
  17. 17.
    Shaikh MM, Kruger HG, Bodenstein J, Du Toit K (2010) Nat Prod Res (accepted)Google Scholar
  18. 18.
    Wang Y, Xu J, Zhang L, Qu H (2010) Helv Chem Acta 93:980–984CrossRefGoogle Scholar
  19. 19.
    Qian Y, Liang JY, Qu W, Che YY (2010) Chin Chem Lett 21:706–708CrossRefGoogle Scholar
  20. 20.
    Morales-Serna JA, Jimenez C, Estrada-Reyes R, Marquez C, Salmon M (2010) Molecule 15(5):3295–3301CrossRefGoogle Scholar
  21. 21.
    Shaikh MM, Kruger HG, Smith P, Mumro OQ, Bodenstein J, Du Toit K (2010) J Nat Prod (submitted)Google Scholar
  22. 22.
    Meegan MJ, Donelly DMX (1981) J Chem Res Synop 1:4Google Scholar
  23. 23.
    Krishnamurty HG, Prakash B, Seshadri TR (1974) Indian J Chem 12:554Google Scholar
  24. 24.
    Heller W, Andermatt P, Schaad WA, Tamm C (1976) Helv Chem Acta 59:2048–2058CrossRefGoogle Scholar
  25. 25.
    Mahapatra T, Jana N, Nanda S (2008) Tetrahedron Asymmetr 19:1224–1232CrossRefGoogle Scholar
  26. 26.
    Parham WE, Huestis LD (1962) J Am Chem Soc 84:813CrossRefGoogle Scholar
  27. 27.
    Katritzky AR, Akhmedov NG, Guven A, Scriven EFV, Majumder S, Akhmedova RG, Hall CD (2006) J Mol Struct 783:191–203CrossRefGoogle Scholar
  28. 28.
    Dolensky B, Kvicala J, Paleta O, Lang J, Dvorakova H, Cejka J (2010) Magn Reson Chem 48:358–375Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Mahidansha Shaikh
    • 1
    • 2
  • Katja Petzold
    • 1
  • Hendrik G. Kruger
    • 1
  • Karen du Toit
    • 2
  1. 1.School of ChemistryUniversity of KwaZulu-NatalDurbanSouth Africa
  2. 2.School of Pharmacy and PharmacologyUniversity of KwaZulu-NatalDurbanSouth Africa

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