Synthesis, Antimalarial Activity, and Docking Studies of Monocarbonyl Analogues of Curcumin

[1]. World Malaria Report 2014, http://www.who.int/malaria/publications/world_malaria_report_2014/en/ (accessed December 18, 2017).Search in Google Scholar

[2]. A.P. Zambre, V.M. Kulkarni, S. Padhye, S.K. Sandur and B.B. Aggarwal, Novel curcumin analogs targeting TNF-induced NF-kappaB activation and proliferation in human leukemic KBM-5 cells, Bioorg. Med. Chem. 14 (2006) 7196-7204.10.1016/j.bmc.2006.06.056Search in Google Scholar

[3]. N. Handler, W. Jaeger, H. Puschacher, K. Leisser and T. Erker, Synthesis of novel curcumin analogues and their evaluation as selective cyclooxygenase-1 (COX-1) inhibitors, Chem. Pharm. Bull. 55 (2007) 64-71.10.1248/cpb.55.64Search in Google Scholar

[4]. H. Ohtsu, Z. Xiao, J. Ishida, M. Nagai, H. K. Wang, H. Itokawa, C.Y. Su, C. Shih, T. Chiang, E. Chang, Y. Lee, M.Y. Tsai, C. Chang and K.H. Lee, Antitumor Agents. 217. Curcumin Analogues as Novel Androgen Receptor Antagonists with Potential as Anti-Prostate Cancer Agents, J. Med. Chem. 45 (2002) 5037-5042.10.1021/jm020200gSearch in Google Scholar

[5]. L. Lin, Q. Shi, C.Y. Su, C.C. Shih and K.H. Lee, Antitumor agents 247. New 4-ethoxycarbonylethyl curcumin analogs as potential antiandrogenic agents, Bioorg. Med. Chem. 14 (2006) 2527-2534.10.1016/j.bmc.2005.11.034Search in Google Scholar

[6]. (a) R.L. Thangapazham, A. Sharma and R.K. Maheshwari, Multiple molecular targets in cancer chemoprevention by curcumin AAPS J. 8 (2006) E443; (b) R. Feng, Y. Lu, L.L. Bowman, Y. Qian, V. Castranova and M. Ding, Inhibition of Activator Protein-1, NF-κB, and MAPKs and Induction of Phase 2 Detoxifying Enzyme Activity by Chlorogenic Acid, J. Biol. Chem. 280 (2005) 27888-27895.Search in Google Scholar

[7]. S.S Sardjiman, M.S. Reksohadiprodjo, L. Hakim, H. Goot and H. Timmerman, 1,5-Diphenyl-1,4-pentadiene-3-ones and cyclic analogues as antioxidative agents. Synthesis and structure-activity relationship, Eur. J. Med. Chem. 32 (1997) 625-630.10.1016/S0223-5234(97)83288-6Search in Google Scholar

[8]. R.A. Sharma, W.P. Steward and A.J. Gescher, Pharmacokinetics and pharmacodynamics of curcumin, Adv. Exp. Med. Biol. 595 (2007) 453-470.10.1007/978-0-387-46401-5_2017569224Search in Google Scholar

[9]. R.K. Maheshwari, A.K. Singh, J. Gaddipati and R.C. Srimal, Multiple biological activities of curcumin: a short review, Life Sci. 78 (2006), 2081-2087.10.1016/j.lfs.2005.12.00716413584Search in Google Scholar

[10]. (a) W. Xingchuan, D. Zhi-Yun, Z. Xi, C. Xiao-Xing, H.C. Allan and Z. Kun, Synthesis and evaluation of curcumin-related compounds for anticancer activity, Eur. J. Med. Chem. 53 (2012) 235-245; (b) R.F. James, P. Bulbul, B. Deepak, P.E. Jonathan, R. Nicholas, A. Dalia, L. Chenglong, L. Jiayuh and L. Pui-Kai, Structure-activity relationship studies of curcumin analogues, Bioorg. Med. Chem. Lett. 19 (2009) 2065-2069; (c) O. Hisatsugu, Y. Hiroyuki, T. Masaki, S. Masatoshi, K. Yuichi, T. Atsuko, T. Shin, K. Satoshi, S. Takao, I. Chikashi, I. Yoshiharu and S. Hiroyuki, Synthesis and biological analysis of new curcumin analogues bearing an enhanced potential for the medicinal treatment of cancer, Mol. Cancer Ther. 5 (2006) 2563-2571.Search in Google Scholar

[11]. L. Guang, Y. Shulin, J. Lijuan, Z. Yu, S. Lili, X. Jian, Y. Faqing, L. Yueru and L. Xiaokun, Synthesis and Anti-bacterial Properties of Mono-carbonyl Analogues of Curcumin, Chem. Pharm. Bull. 56 (2008) 162-167.10.1248/cpb.56.16218239300Search in Google Scholar

[12]. H. Lin, G. -X. Hu, J. Guo, Y. Ge, G. Liang, Q. -Q. Lian, Y. Chu, X. Yuan, P. Huang and R. -S. Ge, Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors, Bioorg. Med. Chem. Lett. 23 (2013) 4362-4366.10.1016/j.bmcl.2013.05.08023800686Search in Google Scholar

[13]. Z. Fei, D. Huai-Huai, W. Yuan-Hua, W. Tian-Yi,, Y. Ze-Hao, Y. Fang, Z. Da-Zhi, C. Ying-Ying and J. Yong-Sheng, Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole resistant Candida spp, Med. Chem. Commun. 8 (2017) 1093-1102.10.1039/C6MD00649C607198930108820Search in Google Scholar

[14]. (a) L. Ka-Heng, H.A. Farida, S. Ahmad, A. Faridah, S. Khozirah, A.I. Daud and H.L. Nordin, Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities, Eur. J. Med. Chem. 44 (2009) 3195-3200; (b) L. Guang, L. Xiaokun, C. Li, Y. Shulin, W. Xudong, S. Elaine, G. Emily, B.H. Phillip, Y. Faqing, L. Yueru and Z. Huiping, Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin, Bioorg. Med. Chem. Lett. 18 (2008) 1525-1529.Search in Google Scholar

[15]. (a) L. Gehad, M.S. Mohamed, H.E. El Sayed, H.E. El Sayed, M.A. Yasmine, M.S. Saied and B. Assem, Synthesis, structure combined with conformational analysis, biological activities and docking studies of bis benzylidene cyclohexanone derivatives, J. Saudi Chem. Soc. 21 (2017) 619-632; (b) C. Chatchawan, P.K. Harry, I. Hasan, M.S. Sajid K.G. Matthew and S. Apichart, Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species, Eur. J. Med. Chem. 45 (2010) 941-956.Search in Google Scholar

[16]. B.A. Rahul, W. Gajanan, K. Neha, R.K. Ravi, K.K. Naveen, S. Dinkar and S.C. Virander, Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors, Bioorg. Med. Chem. Lett. 21 (2011) 3034-3036.10.1016/j.bmcl.2011.03.03721493068Search in Google Scholar

[17]. K. Faghihi, M. Hajibeygi and M. Shabanian, Preparation and characterization of new poly(amide-imide) reinforced layer silicate nanocomposite containing N,N′-pyrromellitoyl-bis-l-phenyl acetic acid, J. Polym. Res. 17 (2010) 379-390.10.1007/s10965-009-9324-5Search in Google Scholar

[18]. I. Z. Hanne, S. Dan, C. Jette, H. Lars, H. Henry and W. Jerzy, In Vitro Plasmodium falciparum Drug Sensitivity Assay: Inhibition of Parasite Growth by Incorporation of Stomatocytogenic Amphiphiles into the Erythrocyte Membrane, J. Antimicrob. Agents Chemother. 42 (2002) 1441-1446.10.1128/AAC.46.5.1441-1446.2002Search in Google Scholar

[19]. M.D. Mukhtar, M. Bashir and A.H. Arzai, Comparative in-vitro studies on antiplasmodial quality of some Nigerian and foreign brands of chloroquine oral formulations marketed in kano, Afri. J. Biotechnol. 5 (2006) 2464-2468.Search in Google Scholar

[20]. T. Bodill, A.C. Conibear, G.L. Blatch, K.A. Lobb, and P.T. Kaye, Synthesis and evaluation of phosphonated N-heteroarylcarboxamides as DOXP-reductoisomerase (DXR) inhibitors, Bioorg. Med. Chem. 19 (2011) 1321-1327.10.1016/j.bmc.2010.11.06221216609Search in Google Scholar

[21]. C.M. Adeyemi, Faridoon, M. Isaacs, D. Mnkandhla, H.C. Hoppe, R. Krause and P.T. Kaye, Synthesis and antimalarial activity of N-benzylated (N-arylcarbamoyl)alkylphosphonic acid derivatives, Bioorg. Med. Chem. 24 (2016) 6131-6138.10.1016/j.bmc.2016.04.02127773366Search in Google Scholar

[22]. Dassault Systèmes BIOVIA, Discovery Studio Modelling Environment, Release 2017, San Diego: Dassault Systèmes, 2016.Search in Google Scholar