Synthesis of bisindolylmethanes and their cytotoxicity properties

International Journal of Molecular Sciences

Volumn 14, Issue 1, 2013, Pages 1843-1853

  Reddi Mohan Naidu, Kalla ^a,b   Khalivulla, Shaik Ibrahim ^c   Rasheed, Syed ^d   Fakurazi, Sharida ^a   Arulselvan, Palanisamy ^a   Lasekan, Ola ^a   Abas, Faridah ^a  

^a UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^b Department of Chemistry Yogananda Inistitute of Technology and Science ^*  (India)

^c UCSI UNIVERSITY   (Malaysia)

^d SRI VENKATESWARA UNIVERSITY   (India)

Author keywords

Bisindolylmethanes; Cytotoxicity properties; Dibisindolylmethanes; Green catalyst

Indexed keywords

ALDEHYDE; BISINDOLYLMETHANE; INDOLE; METHANE; POLYMER; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CYTOTOXIN; INDOLE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; COLON CANCER; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROPHILICITY; HUMAN; HUMAN CELL; IC 50; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; ROOM TEMPERATURE; CHEMISTRY; DRUG SCREENING; HELA CELL LINE; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CYTOTOXINS; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HUMANS; INDOLES;

EID: 84878643088     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms14011843     Document Type: Article

References (35)

1. Jemal, A.; Bray, F.; Center, M.M.; Ferlay, J.; Ward, E.F. Global cancer statistics. Cancer J. Clin. 2011, 61, 69-90.
2. Arulselvan, P.; Wen, C.C.; Lan, C.W.; Chen, Y.H.; Wei, W.C.; Yang, N.S. Dietary administration of scallion extract effectively inhibits colorectal tumor growth: Cellular and molecular mechanisms in mice. PLoS One 2012, 7, e44658.
3. Halliwell, B. Oxidative stress and cancer. Biochem. J. 2007, 401, 1-11.
4. Mostafa, Y.A.H.; Hussein, M.A.; Radwan, A.A.; Kfafy, A.E.H.N. Synthesis and antimicrobial activity of certain new 1,2,4-triazolo[1,5-a]pyrimidine derivatives. Arch. Pharm. Res. 2008, 31, 279-293.
5. Habib, N.S.; Soliman, R.; El-Tombary, A.A.; El-Hawash, S.A.; Shaaban, O.G. Synthesis ofthiazolo[4,5-d]pyrimidine derivatives as potential antimicrobial agents. Arch. Pharm. Res. 2007, 30, 1511-1520.
6. Sundberg, R.J. The Chemistry of Indoles; Academic Press: New York, NY, USA, 1970.
7. Sivaprasad, G.; Perumal, P.T.; Prabavathy, V.R.; Mathivanan, N. Synthesis antimicrobial activity of pyrazolylbisindoles. Bioorg. Med. Chem. Lett. 2006, 16, 6302-6305.
8. Kamal, A.; Khan, M.N.A.; Reddy, K.S.; Srikanth, Y.V.V.; Ahmed, S.K.; Kumar, K.P.; Murthy, U.S.N. An efficient synthesis of bis(indolyl)methanes and evaluation of their antimicrobial activities. J. Enzyme Inhib. Med. Chem. 2009, 24, 559-565.
9. Sujatha, K.; Perumal, P.T.; Muralidharan, D.; Rajendran, M. Synthesis, analgesic and anti-inflammatory activities of bis(indolyl)methanes. Indian J. Chem. 2009, 48, 267-272.
10. Benabadji, S.H.; Wen, R.; Zheng, J.; Dong, X.; Yuan, S. Anticarcinogenic and antioxidant activity of diindolylmethane derivatives. Acta Pharmacol. Sin. 2004, 25, 666-671.
11. Shiri, M.; Zolfigol, M.A.; Kruger, H.G.; Tanbakouchian, Z. Bis-and trisindolylmethanes. Chem. Rev. 2010, 110, 2250-2293.
12. Kirkus, M.; Tsai, M.H.; Grazulevicius, J.V.; Wu, C.C.; Chi, L.C.; Wong, K.T. New indole-carbazole hybrids as glass-forming high-triplet-energy materials. Synth. Met. 2009, 159, 729-734.
13. Stupnikova, T.V.; Reybenko, L.A.; Skorobogotova, Z.M.; Sheinkman, A.K. Tri(3-indolyl)-methyl perchlorates-New dyes of the triarylmethane series. Khim. Geterotsikl. Soedin. 1978, 3, 314.
14. He, X.; Hu, S.; Liu, K.; Guo, Y.; Xu, J.; Shao, S. Oxidized bis(indolyl)methane: A simple and efficient chromogenic-sensing molecule based on the proton transfer signaling mode. Org. Lett. 2006, 8, 333-336.
15. Martinez, R.; Espinosa, A.; Tarraga, A.; Molina, P. Bis(indolyl)methane derivatives as highly selective colourimetric and ratiometric fluorescent molecular chemosensors for Cu2+ cations. Tetrahedron 2008, 64, 2184-2191.
16. Liao, B.S.; Chen, J.T.; Liu, S.T. An efficient preparation of bis(indole)methanes catalyzed by tetrakis[3,5-bis(trifluoromethyl)phenyl]borate salts in aqueous medium. Synthesis 2007, 20, 3125-3128.
17. Noguchi-Yachide, T.; Tetsuhashi, M.; Aoyama, H.; Hashimoto, Y. Enhancement of chemically-induced HL-60 cell differentiation by 3,3'-diindolylmethane derivatives. Chem. Pharm. Bull. 2009, 57, 536-540.
18. Najmodin, A.; Lalleh, T.; Mohammad, R.S. Highly efficient synthesis of bis(indolyl)methanes in water. J. Mol. Catal. A 2007, 275, 109-112.
19. Najmadin, A.; Zohreh, M. Eutectic salts promote green synthesis of bis(indolyl)methanes. Res. Chem. Intermed. 2012, 38, 1495-1500.
20. Mi, X.L.; Luo, S.Z.; He, J.Q.; Cheng, J.P. Dy(OTf)3 in ionic liquid: An efficient catalytic system for reactions of indole with aldehydes/ketones or imines. Tetrahedron Lett. 2004, 45, 4567-4570.
21. Samuel, R.M.; Samuel, T.; Margiani, P.F.; Filipe, P.; Eder, J.L.; Diego, A.; Gelson, P.; Raquel, G.J. Synthesis of bis(indolyl)methanes using silica gel as an efficient and recyclable surface. Tetrahedron Lett. 2012, 53, 5402-5406.
22. Ke, B.W.; Qin, Y.; Wang, Y.; Wang, F.P. Amberlyst-catalyzed reaction of indole: Synthesis of bisindolylalkane. Synth. Commun. 2005, 35, 1209-1212.
23. Yadav, J.S.; Reddy, B.V.S.; Murthy, C.V.S.R.; Kumar, G.M.; Madan, C. Lithium perchlorate catalyzed reactions of indoles: An expeditious synthesis of bis(indolyl)methanes. Synthesis 2001, 5, 783-787.
24. Nagarajan, R.; Perumal, P.T. InCl3 and In(OTf)3 catalyzed reactions: Synthesis of 3-acetyl indoles, bis-indolylmethane and indolylquinoline derivatives. Tetrahedron 2002, 58, 1229-1232.
25. Ma, S.M.; Yu, S.C.; Peng, Z.H. Sc(OTf)3-catalyzed efficient synthesis of 1,1-bis(indolyl)ketones by the double indolylation of acetic acid 2-methylene-3-oxobutyl ester. Org. Biomol. Chem. 2005, 3, 1933-1936.
26. Bandgar, B.P.; Shaikh, K.A. Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions. Tetrahedron Lett. 2003, 44, 1959-1961.
27. Deb, W.L.; Bhuyan, P.J. An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature. Tetrahedron Lett. 2006, 47, 1441-1443.
28. Nagawade, R.R.; Shinde, D.B. Synthesis of bis(indolyl)methanes. Acta Chim. Slov. 2006, 53, 210-213.
29. Babu, G.; Sreedhar, N.; Perumal, P.T. A convenient method of synthesis of bis(indolyl)-methane indiumtrichloride catalyzed reactions of indole with aldehydes and schiff bases. Synth. Commun. 2000, 30, 1609-1614.
30. Firouzabadi, H.; Iranpoor, N.; Ali Jafari, A.A. Aluminumdodecatungstophosphate (AlPW12O40), a versatile and a highly water tolerant green lewis acid catalyzes efficient preparation of indole derivatives. J. Mol. Catal. 2006, 244, 168-172.
31. Ji, S.J.; Zhou, J.F.; Gu, D. G; Wang, S.Y.; Loh, T.P. Efficient synthesis of bis(indolyl)methanes catalyzed by lewis acids in ionic liquids. Synlett 2003, 2077-2079.
32. Kumar, K.S.; Reddy, C.B.; Krishna, B.S.; Srinivasulu, K.; Reddy, C.S. Micelle promoted synthesis of bis-(indolyl)methanes. Lett. Org. Chem. 2012, 9, 294-299.
33. Li, Z.; Yu, J.L.; Ding, R.B.; Wang, Z.Y.; Wang, X.C. Microwave accelerated solvent-free synthesis of 1,3,4-oxadiazoles using polymer supported dehydration reagent. Synth. Commun. 2004, 34, 2981-2986.
34. Reddi Mohan Naidu, K.; Krishna, B.S.; Kumar, M.A.; Selvan, P.A.; Khalivulla, S. I; Lasekan, O. Design, synthesis and antiviral potential of 14-aryl/heteroaryl-14H-dibenzo[a, j]xanthenes using an efficient polymer-supported catalyst. Molecules 2012, 17, 7543-7555.
35. Reddi Mohan Naidu, K.; Dadapeer, E.; Bhupendra Reddy, C.; Janardhan Rao, A.; Suresh Reddy, C.; Naga Raju, C. Polyethylene glycol-promoted dialkyl, aryl/heteroaryl phosphonates. Synth. Commun. 2011, 41, 3462-3468.