Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions

Molecules

Volumn 18, Issue 7, 2013, Pages 8046-8062

  Nor, Siti Mariam Mohd ^a   Sukari, Mohd Aspollah Hj Md ^a   Azziz, Saripah Salbiah Syed Abdul ^b   Fah, Wong Chee ^b   Alimon, Hasimah ^b   Juhan, Siti Fadilah ^a  

^a UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^b SULTAN IDRIS EDUCATION UNIVERSITY   (Malaysia)

Author keywords

Acylation; Amination; Aminoanthraquinone; Cytotoxic; Hep G2; MCF 7; Mechanism; Methylation; Reduction; Substitution

Indexed keywords

1,4-DIHYDROXYANTHRAQUINONE; ANTHRAQUINONE DERIVATIVE; QUINIZARIN;

CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; HEPG2 CELL LINE; HUMAN; MCF 7 CELL LINE; STRUCTURE ACTIVITY RELATION; SYNTHESIS; ARTICLE; CELL STRAIN HEPG2; CELL STRAIN MCF 7; DRUG EFFECT;

ANTHRAQUINONES; CELL PROLIFERATION; HEP G2 CELLS; HUMANS; MCF-7 CELLS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84880847204     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18078046     Document Type: Article

References (36)

1. Ashnagar, A.; Bruce, M.; Dutton, L.; Prince, R.C. One- and two-electron reduction of hydroxy- 1, 4-naphthoquinones and hydroxy-9, 10-anthraquinones: The role of internal hydrogen bonding and its bearing on the redox chemistry of the anthracycline antitumour quinones. BBA-Gen Subjects 1984, 801, 351-359.
2. Ge, P.; Russel, R.A. The synthesis of anthraquinone derivatives as potential anticancer agent. Tetrahedron 1997, 53, 17469-17476.
3. Hua, D.H.; Lou, K.; Havens, J.; Perchellet, E.M.; Wang, Y.; Perchellet, J.P.; Iwamotoc, T. Synthesis and in vitro antitumor activity of substituted anthracene-1, 4-diones. Tetrahedron 2004, 60, 10155-10163.
4. Chang, P.; Chen, C. Isolation and characterisation of antitumour anthraquinones from Morinda umbellata. Chin. Pharm. J. (Taipei) 1995, 47, 347-353.
5. Yadav, J.P.; Arya, V.; Yadav, S.; Panghal, M.; Kumar, S.; Dhankhar, S. Cassia occidentalis L.: A review on its ethnobotany, phytochemical and pharmacological profile. Fitoterapia 2010, 81, 223-230.
6. Osman, C.P.; Ismail, N.H.; Ahmad, R.; Ahmat, N.; Awang, K.; Jaafar, F.M. Anthraquinones with antiplasmodial activity from the roots of Rennellia elliptica Korth. (Rubiaceae). Molecules 2010, 15, 7218-7226.
7. Sittie, A.A.; Lemmich, E.; Olsen, C.E.; Hviid, L.; Kharazmi, A.; Nkrumah, F.K.; Christensen, S.B. Structure-Activity studies: In vitro antileishmanial and antimalarial activities of anthranones from Morinda lucida. Planta Med. 1999, 65, 259-261.
8. Xiang, W.; Song, Q.S.; Zhang, H.J.; Guo, S.P. Antimicrobial anthraquinones from Morinda angustifolia. Fitoterapia 2008, 79, 501-504.
9. Rath, G.; Ndonzao, M.; Hostettmann, K. Antifungal anthraquinones from Morinda lucida. Int. J. Pharmacogn. 1995, 33, 107-114.
10. Chang, P.; Lee, K.H. Cytotoxic antileukemic anthraquinones from Morinda parvifolia. Phytochemistry 1984, 23, 1733-1736.
11. Ismail, N.H.; Ali, A.M.; Aimi, N.; Kitajima, M.; Takayama, H.; Lajis, N.H. Anthraquinone from Morinda ellintica. Phytochem. 1997, 45, 1723-1725.
12. Schinazi, R.F.; Chu, C.K.; Babu, J.R.; Oswald, B.J.; Saalmann, V.; Cannon, D.L.; Eriksson, B.F. H.; Nasr, M. Anthraquinones as a new class of antiviral agents against human immunodeficiency virus. Antiviral Res. 1990, 13, 265-272.
13. Alves, D.S.; Pérez-Fons, L.; Estepa, A.; Micol, V. Membrane-related effects underlying the biological activity of the anthraquinones emodin and barbaloin. Biochem. Pharmacol. 2004, 68, 549-561.
14. Andersen, D.O.; weber, N.D.; Wood, S.G.; Hughes, B.G.; Murray, B.K.; North, J.A. In vitro virucidal activity of selected anthraquinones and anthraquinones derivatives. Antiviral Res. 1991, 16, 185-196.
15. Barnard, D.L.; Huffman, J.H.; Morris, J.L.; Wood, S.G.; Hughes, B.G.; Sidwell, R.W. Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinones derivatives against human cytomegalovirus. Antiviral Res. 1992, 17, 63-77.
16. Yen, G.C.; Duh, P.D.; Chuang, D.Y. Antioxidant activity of anthraquinones and anthrones. Food Chem. 2000, 70, 437-441.
17. Sokolyuk, N.T.; V.V. Romanov, L.P.; Pisulina, L.P. Naphthacenequinones: Synthesis and properties. Russ. Chem. Rev. 1993, 62, 1005-1024.
18. Bechtold, T.; Burtscher, E.; Turcanu, A. Anthraquinones as mediators for the indirect cathodic reduction of dispersed organic dyestuffs. J. Electroanal Chem. 1999, 465, 80-87.
19. Guo, J.; Zhou, J.; Wang, D.; Tian, C.; Wang, P.; Salah Uddin, M.; Yu, H. Biocatalyst effects of immobilised anthraquinone on the anaerobic reduction of azo dyes by the salt-tolerant bacteria. Water Res. 2007, 41, 426-432.
20. Ahn, K.D.; Yoo, K.W.; Soh, J.H.; Kang, J.H. Fluorescent photoimaging with polymers having protected quinizarin dye precursors by a dry process based on chemical amplification. React. Funct. Polym. 2009, 69, 111-116.
21. Shchekotikhin, A.E.; Glazunova, V.A.; Dezhenkova, L.G.; Shevtsova, E.K.; Traven, V.F.; Balzarini, J.; Huang, H.S.; Shtil, A.A.; Preobrazhenskaya. M.N. The first series of 4, 11-bis[(2-aminoethyl)amino]anthra[2, 3-b]furan-5, 10-diones: Synthesis and anti-proliferative characteristics. Eur. J. Med. Chem. 2011, 46, 423-428.
22. Lee, C.C.; Huang, K.F.; Lin, P.Y.; Huang, F.C.; Chen, C.L.; Chen, T.C.; Guh, J.H.; Lin, J.J.; Huang, H.S. Synthesis, antiproliferative activities and telomerase inhibition evaluation of novel asymmetrical 1, 2-disubstituted amidoanthraquinone derivatives. Eur. J. Med. Chem. 2012, 47, 323-336.
23. Jin, G.Z.; Song, G.Y.; Zheng, X.G.; Kim, Y.; Sok, D.E.; Ahn, B.Z. 2-(1 -Oxyalkyl)-1, 4-dioxy- 9, 10-anthraquinones: Synthesis and evaluation of antitumor activity. Arch. Pharm. Res. 1998, 21, 198-206.
24. Teich, L.; Daub, K.S.; Krugel, V.; Nissler, L.; Gebhardt, R.; and Eger, K. Synthesis and biological evaluation of new derivatives of emodin. Bioorg. Med. Chem. 2004, 12, 5961-5971.
25. Shchekotikhin, A.E.; Glazunova, V.A.; Luzikov, Y.N.; Buyanov, V.N.; Susova, O.Y.; Shtil, A.A.; Preobrazhenskaya, M.N. Synthesis and structure-activity relationship studies of 4, 11- diaminophtho[2, 3-f]indole-5, 10-diones. Bioorg. Med. Chem. 2006, 14, 5241-5251.
26. Shchekotikhin, A.E.; Shtil, A.A.; Luzikov, Y.N.; Bobrysheva, T.V.; Buyanov, V.N.; Preobrazhenskaya, M.N. 3-Aminomethyl derivatives of 4, 11-dihydroxynaphtho[2, 3-f]indole-5, 10- dione for circumvention of anticancer drug resistance. Bioorg. Med. Chem. 2005, 13, 2285-2291.
27. Krapcho, A.P.; Shaw, K.J.; Landi, J.J., Jr.; Phinney, D.J. Synthesis of unsymmetrical 1, 4-Bis[(aminoalkyl)amino]anthracene-9, 10-diones for Antineoplastic Evaluation. J. Org. Chem. 1984, 49, 5253-5255.
28. Glänzel, M.; Bültmann, R.; Starke, K.; Frahm, A.W. Structure-activity relationships of novel P2-receptor antagonists structurally related to reactive blue 2. Eur. J. Med. Chem. 2005, 40, 1262-1276.
29. Baqi, Y.; Müller, C.E. Efficient and mild deamination procedure for 1-Aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity. Tetrahedron Lett. 2012, 53, 6739-6742.
30. Jin, G.Z.; Jin, H.S.; Jin, L.L. Synthesis and antiproliferative activity of 1, 4-Bis(dimethylamino)- 9, 10-anthraquinone derivatives against P388 mouse leukemic tumor cells. Arch Pharm. Res. 2011, 34, 1071-1076.
31. Sugimoto, N.; Kawasaki, Y.; Sato, K.; Aoki, H.; Ichi, T.; Koda, T.; Yamazaki, T.; Maitani, T. Structure of Acid-Stable Carmine. J. Food Hyg. Soc. Jpn. 2002, 43, 18-23.
32. Zielske, A.G. (Tosyloxy)anthraquinones: Versatile synthones for the preparation of various aminoanthraquinones. J. Org. Chem. 1987, 52, 1305-1309.
33. Camara, C.A.; Pinto, A.C.; Rosa, M.A.; Vargas, M.D. Secondary amine and unexpected 1-Aza-anthraquinone from 2-Methoxylapachol. Tetrahedron 2001, 57, 9569-9574.
34. Saha, K.; Lam, K.W.; Abas, F.; Hamzah, A.S.; Stanslas, J.; Hui, L.S.; Lajis, N.H. Synthesis of damnacanthal, a naturally occurring 9, 10-Anthraquinone and its analogues, and its biological evaluation against five cancer cell lines. Med. Chem. Res. 2013, 22, 2093-2104.
35. Sukari, M.A.; Tang, S.W.; Neoh, B.K.; Ee, G.C.L.; Rahmani, M. Antileukemic activity and chemical constituents of some Zingiberaceae species. Asian J. Chem. 2010, 22, 7891-7896.
36. Garba, S.; Okenyi, S.O. Antimicrobial activities of total alkaloids extracted from some nigerian medicinal plants. J. Microbiol. Antimicrob. 2012, 4, 60-63.