Skip to main content

Advertisement

SpringerLink
Log in

Synthesis and evaluation of anticancer and PDE 5 inhibitory activity of spiro-substituted quinazolin-4-ones

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A series of novel spiro-substituted 2,3-dihydroquinazolin-4(1H)-ones was synthesized and structurally confirmed by spectral analysis, screened for their anticancer activity at a concentration of 10 μΜ against a panel of 56 cell lines derived from nine different types of cancers, including leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers. The synthesized compounds screened for their PDE 5 inhibitory activity and it showed encouraged activity compared to sildenafil.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Vasilevsky SF, Baranov DS, Govdi AI, Sorokina IV, Tolstikova TG, Tolstikov GA, Alabugin IV (2014) Arkivoc 4:145

    Google Scholar 

  2. Reddy PSN, Reddy PP, Vasantha T (2003) Heterocycles 60:183

    Article  CAS  Google Scholar 

  3. Cao SL, Guo Y-W, Wang X-B, Zhang M, Feng Y-P, Jiang Y-Y, Wang Y, Gao Q, Ren J (2009) Arch Pharm Chem Life Sci 342:182

    Article  CAS  Google Scholar 

  4. Hongliang D, Zheng J, Qinglin L, Zheng L, Guanghui T, Zhen W, Jianfeng L, Jingshan S (2009) Bioorg Med Chem Lett 19:2777

    Article  Google Scholar 

  5. Rotella DP, Sun Z, Zhu Y, Krupinski J, Pongrac R, Seliger L, Normandin D, Macor JE (2000) J Med Chem 43:1257

    Article  CAS  Google Scholar 

  6. Pattan SR, Reddy VVK, Manvi FV, Desai BG, Bhat AR (2006) Ind J Chem 45B:1778

    CAS  Google Scholar 

  7. Kaour H, Kumar S, Saxena KK, Kumar A (2010) Int J Pharm Biol Sci 1:1

    Google Scholar 

  8. Al-Omary FAM, Hassan GS, El-Messery SM, Nagi MN, Habib EE, El-Subbagh HI (2013) Eur J Med Chem 63:33

    Article  CAS  Google Scholar 

  9. Rajfer J, Aronson WJ, Bush PA, Dorey FJ, Ignarro LJ (1992) N Engl J Med 326:90

    Article  CAS  Google Scholar 

  10. Marmor MF, Kessler R (1999) Surv Ophthalmol 44:153

    Article  CAS  Google Scholar 

  11. Carson CC (2004) Psychosom Med 66:664

    Article  Google Scholar 

  12. Soderling SH, Beavo JA (2000) Curr Opin Cell Biol 12:174

    Article  CAS  Google Scholar 

  13. Ameen MA (2014) J Chem Res 38:701

    Article  CAS  Google Scholar 

  14. Ameen MA, Ahmed EKh, El Malah T, Abd El-Naby HA, Abdel-Kader AA (2015) J Heterocycl Chem 52:1093

    Article  CAS  Google Scholar 

  15. Abdel-Latif FF, Ameen MA, Elhady OM, Kamel MS (2015) Pharm Appl Chem 1:37

    Google Scholar 

  16. Ameen MA, Ahmed EKh (2015) J Sulfur Chem 36:293

    Article  CAS  Google Scholar 

  17. Kai H, Morioka Y, Tomida M, Takahashi T, Hattori M, Hanasaki K, Koike K, Chiba H, Shinohara S, Kanemasa T, Iwamoto Y, Takahashi K, Yamaguchi Y, Baba T, Yoshikawa T, Takenaka H (2007) Bioorg Med Chem Lett 17:3925

    Article  CAS  Google Scholar 

  18. Chen GA, Xia H, Cai Y, Ma D, Yuan J, Yuan C (2011) Med Chem Commun 2:315

    Article  CAS  Google Scholar 

  19. Makarem A, Berg R, Rominger F, Straub BF (2015) Angew Chem Int Ed 54:7431

    Article  CAS  Google Scholar 

  20. Reddy SN, Nagaraju CH (1991) Synth Commun 21:173

    Article  CAS  Google Scholar 

  21. Shaabani A, Maleki A, Mofakham H (2008) Synth Commun 38:3751

    Article  CAS  Google Scholar 

  22. Roschke AV, Tonon G, Gehlhaus KS, McTyre N, Bussey KJ, Lababidi S, Scudiero DA, Weinstein JN, Kirsch IR (2003) Cancer Res 63:8634

    CAS  Google Scholar 

  23. Lorenzi PL, Reinhold WC, Varma S, Hutchinson AA, Pommier Y, Chanock SJ, Weinstein JN (2009) Mol Cancer Ther 8:713

    Article  CAS  Google Scholar 

  24. Mingyi M, Longru S, LouMei J (2013) Chem Cent J 7:179

    Article  Google Scholar 

  25. Spoto G, Berardi S, Ajerba G, De Laurentiis V (1994) Adv Exp Med Biol 370:815

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Minia University, El Minya, Egypt

    Mohamed A. Ameen, Essam Kh. Ahmed, Hisham A. Abd El-Naby & Asmaa A. Abdel-Haseeb

  2. Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Assuit, Egypt

    Mohamed Ramadan

Authors
  1. Mohamed A. Ameen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Essam Kh. Ahmed
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mohamed Ramadan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hisham A. Abd El-Naby
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Asmaa A. Abdel-Haseeb
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohamed Ramadan.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 7628 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ameen, M.A., Ahmed, E.K., Ramadan, M. et al. Synthesis and evaluation of anticancer and PDE 5 inhibitory activity of spiro-substituted quinazolin-4-ones. Monatsh Chem 148, 1513–1523 (2017). https://doi.org/10.1007/s00706-017-1961-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-017-1961-5

Keywords

Search

Navigation