Medicinal Chemistry Research

, Volume 24, Issue 5, pp 1942–1951 | Cite as

Synthesis and anticancer activity evaluation of some acridine derivatives

  • Surbhi Arya
  • Anuj Kumar
  • Nikhil Kumar
  • Partha Roy
  • S. M. SondhiEmail author
Original Research


9-Amino acridine derivatives (1a1h) on condensation with 9, 10-dihydroanthracene-9, 10-α, β-succinic anhydride (2) at room temperature gave condensation products (3a3h). Microwave-assisted condensation of 9-amino acridine derivatives (1a1d) with phthalic anhydride, cis 1,2,3,6-tetrahydrophthalimide, and 2,5-pyrroledione gave corresponding condensation products 4a4d, 5a5d & 6a6d, respectively, in good yields. All these compounds were screened for in vitro anticancer activity against five human cancer cell lines i.e., breast (T47D), lung (NCl H-522), colon (HCT-15), ovary (PA-1), and liver (Hep G2). Compounds 3a (breast T47D), 3 g (lung NCl H-522), 4a (liver Hep G2), and 6b (colon HCT-15) exhibited IC50 values 5.4, 4.2, 4.5, and 2.4 µM, respectively, and hence possess good anticancer activity.


Synthesis Acridine derivatives Human cancer cell lines Anticancer 



We are thankful to technical staff of the Chemistry Department, I. I. T. Roorkee, for spectroscopic studies and elemental analysis. Thanks also due to Head I.I.C. for providing NMR facility. Ms. Surbhi Arya (SRF) to CSIR New Delhi and Mr. Anuj Kumar to MHRD, New Delhi are thankful for financial assistance.


  1. Albert A, Gledhill W (1945) Improved syntheses of aminoacridines. IV. Substituted 9-aminoacridines. J Soc Chem Ind-L 64:169–172Google Scholar
  2. Albert A, Ritchie B (1960) 9-Aminoacridine. Org Synthesis Coll 3:53–56Google Scholar
  3. Ali TE-S, El-Kazak AM (2010) Synthesis and antimicrobial activity of some new 1,3-thiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles and 1,3-thiazines incorporating acridine and1,2,3,4-tetrahydroacridine moieties. Eur J Chem 1:6–11CrossRefGoogle Scholar
  4. Allen CFH, Mckee GHW (1959) Acridone. Org Synthesis Coll 2:15–17Google Scholar
  5. Aly EI, Abadi AH (2004) Synthesis and antitubercular activity of 6-chloro (unsubstituted)-2-methoxy-9-substituted acridine derivatives. Arch Pharm Res 27:713–719CrossRefPubMedGoogle Scholar
  6. Aly ME-M, Ebeid MY, Aly EI, Seri SMA (1997) Potential anti-HIV agents: synthesis and anti-HIV-1 activity of some N-substituted 9-(4-sulfamoylphenylamino)-2-acridinyl-, 9-oxo-9,10-dihydro-2-acridinyl- and 9-amino-2-acridinyl-[N-(4-sulfamoylphenyl)] carboxamide derivatives. Bull Fac Pharm (Cairo University) 35:185–197Google Scholar
  7. Chen Y-L, Lu C-M, Chen I-L, Tsao L-T, Wang J-P (2002) Synthesis and antiinflammatory evaluation of 9-anilinoacridine and 9-phenoxyacridine derivatives. J Med Chem 45:4689–4694CrossRefPubMedGoogle Scholar
  8. Di Giorgio C, De Meo M, Chiron J, Delmas F, Nikoyan A, Jean S, Dumenil G, Timon-David P, Galy J-P (2005) Synthesis and antileishmanial activities of 4,5-di-substituted acridines as compared to their 4-mono-substituted homologues. Bioorg Med Chem 13:5560–5568CrossRefGoogle Scholar
  9. El-Deiry WS (2008) Acridine compound activation of p53 and use for the treatment of cancer. WO 2008010984 A2 20080124Google Scholar
  10. Goodell JR, Madhok AA, Hiasa H, Ferguson DM (2006) Synthesis and evaluation of acridine- and acridone-based anti-herpes agents with topoisomerase activity. Bioorg Med Chem 14:5467–5480CrossRefPubMedGoogle Scholar
  11. Gopalan B, Gharat LA, Khairatkar-Joshi N (2006) Preparation of acridine, phenazine and oxanthrene-1-carboxamides as PDE4 inhibitors for treatment of asthma and chronic pulmonary disease. WO 2006040650 A1 20060420Google Scholar
  12. Gupta HC, Jaiswal V (2010) Synthesis and antiviral activity of some acridin-9-yl aryldithiocarbamates. Indian J Heterocycl Chem 19:409–410Google Scholar
  13. Kumar A, Srivastava K, Kumar SR, Puri SK, Chauhan MS (2009) Synthesis of 9-anilinoacridine triazines as new class of hybrid antimalarial agents. Bioorg Med Chem Lett 19:6996–6999CrossRefPubMedGoogle Scholar
  14. Lp NY, Lp FCF, Hu Y, Han Y, Chung SK (2008) Preparation of acridine derivatives as cholinesterase inhibitors. WO 2008091901 A1 20080731Google Scholar
  15. Maurice HB, Phillips R, Karodia N (2009) Design, synthesis and biological evaluation of novel acridine-polyamine conjugates against prostate cancer. Afr J Pharm Pharacol 3:602–610Google Scholar
  16. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63CrossRefPubMedGoogle Scholar
  17. Prabakaran K, Yamuna E, Prasad KJR (2011) Synthesis and antimicrobial activities of nitro substituted indolo[3,2-c]acridines. Indian J Chem, Sect B 50B:906–909Google Scholar
  18. Sondhi SM, Singh J, Rani R, Gupta PP, Agarwal SK, Saxena AK (2010) Synthesis, anti-inflammatory and anticancer activity evaluation of some novel acridine derivatives. Eur J Med Chem 45:555–563CrossRefPubMedGoogle Scholar
  19. Sondhi SM, Kumar S, Rani R, Chakraborty A, Roy P (2013) Synthesis of bis acridine derivatives exhibiting anticancer and anti-inflammatory activity. J Heterocycl Chem 50:252–260CrossRefGoogle Scholar
  20. Srivastava A, Nizamuddin (2004) Synthesis and fungicidal activity of some acridine derivatives. Indian J Heterocycl Chem 13:261–264Google Scholar
  21. Tomer V, Bhattacharjee G, Kamaluddin, Rajakumar S, Srivastava K, Puri SK (2010) Synthesis of new chalcone derivatives containing acridinyl moiety with potential antimalarial activity. Eur J Med Chem 45:745–751CrossRefGoogle Scholar
  22. Tonelli M, Vettoretti G, Tasso B, Novelli F, Boido V, Sparatore F, Busonera B, Ouhtit A, Farci P, Blois S, Giliberti G, La Colla P (2011) Acridine derivatives as anti-BVDV agents. Antiviral Res 91:133–141CrossRefPubMedGoogle Scholar
  23. Tripathi RP, Verma SS, Pandey J, Agarwal KC, Chaturvedi V, Manju YK, Srivastva AK, Gaikwad A, Sinha S (2006) Search of antitubercular activities in tetrahydroacridines: synthesis and biological evaluation. Bioorg Med Chem Lett 16:5144–5147CrossRefPubMedGoogle Scholar
  24. Vogel AI (1968) A textbook of practical organic chemistry, ELBS LondonGoogle Scholar
  25. Wurster S, Engstroem M, Savola J-M, Hoeglund I, Sallinen J, Haapalinna A, Tauber A, Hoffren A-M, Salo H (2001) Preparation of 4-(phenylamino)quinolines and 9-(phenylamino)acridines as α2-adrenoceptor antagonists. WO 2001064645 A2 20010907Google Scholar
  26. Yartseva LV, Isayev SG, Svechnikova OM (2003) Synthesis, physicochemical properties, and biological activity of 9-acetylamino and arylamino derivatives of 5-nitroacridine. Farmatsevtichnii Zhurnal 3:60–64Google Scholar
  27. Yu X-M, Ramiandrasoa F, Guetzoyan L, Pradines B, Quintino E, Gadelle D, Forterre P, Cresteil T, Mahy J-P, Pethe S (2012) Synthesis and biological evaluation of acridine derivatives as antimalarial agents. Chem Med Chem 7:587–605CrossRefPubMedGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Surbhi Arya
    • 1
  • Anuj Kumar
    • 1
  • Nikhil Kumar
    • 2
  • Partha Roy
    • 2
  • S. M. Sondhi
    • 1
    Email author
  1. 1.Department of ChemistryIndian Institute of Technology-RoorkeeRoorkeeIndia
  2. 2.Department of BiotechnologyIndian Institute of Technology-RoorkeeRoorkeeIndia

Personalised recommendations