Synthesis and Characterization of Some Substituted 3, 4-dihydronaphthalene Derivatives through Different Enaminones as Potent Cytotoxic Agents

M. E. Haiba; E. S. Al-Abdullah; M. M. Edrees; N. M. Khalifa

doi:10.1055/s-0034-1368721

Drug Research, Table of Contents

Drug Res (Stuttg) 2015; 65(1): 9-17
DOI: 10.1055/s-0034-1368721

Original Article

Synthesis and Characterization of Some Substituted 3, 4-dihydronaphthalene Derivatives through Different Enaminones as Potent Cytotoxic Agents

M. E. Haiba

¹Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Saud University, Riyadh, Saudi Arabia

²Department of Therapeutical Chemistry, Pharmaceutical and Drug Industries Division, National Research Center, Cairo, Egypt

,

E. S. Al-Abdullah

¹Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Saud University, Riyadh, Saudi Arabia

,

M. M. Edrees

³Department of Organic Chemistry, National Organization for Drug Control and Research (NODCAR), Giza, Egypt

⁴Department of Chemistry, Faculty of Science, King Khalid University, Abha, Saudi Arabia

,

N. M. Khalifa

²Department of Therapeutical Chemistry, Pharmaceutical and Drug Industries Division, National Research Center, Cairo, Egypt

⁵Department of Pharmaceutical Chemistry, Drug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh, Saudi Arabia

› Author Affiliations

Abstract

A new series of novel substituted 3,4-dihydronaphthalene incorporated to benzo[h]quinoline, benzo[g]indazole, thiazolidin-4-one, pyrazolo[3,4-d]thiazol and thiazolo[4,5-b]pyridine ring systems were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. Some of the tested compounds exhibited promising carcinoma growth inhibition. The detailed synthesis, spectroscopic data and biological activities of the tested compounds were reported.

Key words

3, 4-dihydronaphthalene - enaminone - anticancer agents

Full Text

References

References
1 Grant SK. Cellular processes, and protein phosphorylation is essential for cell growth. Cell Mol Life Sci 2009; 66: 1163-1177
2 Riedl S, Zweytick D, Lohner K. Membrane-active host defense peptides – Challenges and perspectives for the development of novel anticancer drugs. Chem Phys Lipids 2011; 164: 766-781
3 AL-Mutairi MS, AL-Abdullah ES, Haiba ME et al. Synthesis, molecular docking and preliminary in-vitrocytotoxic evaluation of some substituted tetrahydro naphthalene (2',3',4',6'-tetra-o-acetyl-β-d-gluco-/galactopyranosyl) derivatives. Molecules 2012; 17: 4717-4732
4 Haiba ME, AL-Abdullah ES, Hilmy NM. Synthesis and cytotoxicity of some new substituted hydronaphthalene derivatives. Amirican Chemical Science J 2013; 3: 203-220
5 Schoepfer J, Fretz H, Chaudhuri B et al. Structure-based design and synthesis of 2-benzylidenebenzofuran-3-ones as flavopiridol Mimics. J Med Chem 2002; 45: 741-747
6 Ebeid MY, Fathalla OA, EL-Zahar MI et al. New tetralyl thiazoles the anti- HIV and anticancer screening Of 3-{4-[6(1, 2, 3, 4-tetrahydronaphthyl)-thiazol-2-yl-2-(p-chlorophenyl)-thiazolidin-4-one. Bull Fac Pharm Cairo Univ 1996; 34: 125-135
7 Ates-Alagoz Z, Yildiz S, Buyukbingol E. Antimicrobial activities of some tetrahydronaphthaline-benzimidazole derivatives. Chemotherapy 2007; 53: 110-113
8 Haiba ME, Al-Abdullah E, Anwar MM et al. Synthesis of some new substituted tetrahydronaphthalene compounds of effective antimicrobial activity. International Journal of pharmaceutics (recent science) 2013; 29: 1113-1127
9 Kamel MM, Michael JM. Synthesis and schistosomicidal activity of some salicylamido tetralins. Egypt J Bilharziasis 1988; 10: 121-125
10 Hussain RA, Dicky JK, Rosser MP. A novel class of non-peptidic endothelin antagonists isolated from the medicinal herb phyllanthus niruri. J Nat Prod 1995; 58: 1515-1520
11 Murphy PR, Hubbard RE, Manallak AT et al. The Synthesis of novel structural analogues of sialyl lewis X. Tetrahedron Lett 1998; 39: 3273-3276
12 Hara H, Fujihashi T, Sakata T et al. Tetrahydronaphthalene lignan compounds as potent anti-HIV type 1 agents. AIDS Res Hum Retroviruses 1997; 13: 695-705
13 Parker MH, Chen R, Conway KA et al. Synthesis of -5,8-dihydroxy-3r-methyl-2r-(dipropylamino)-1, 2, 3, 4-tetrahydronaphthalene: an inhibitor of β-amyloid1–42 aggregation. Bioorg &. Med Chem 2002; 10: 3565-3569
14 Rogoz Z, Skuza G, Klodzinska A. Anxiolytic- and antidepressant-like effects of 7-oh-dpat, preferential dopamine d3 receptor agonist in rats. Pol J Pharmacol 2004; 56: 519-526
15 Kitamurra Y, Arakib H, Shibatac K et al. 5-HT(1A) receptor full agonist, 8-OH-DPAT, exerts antidepressant-like effects in the forced swim test in ACTH-treated rats. Eur J Pharmacol 2003; 481: 75-77
16 Dreau MAL, Desmaele D, Dumas F et al. A new access to homoerythrina alkaloids. J Org Chem 1993; 58: 2933-2935
17 Obrecht D, Spiegler C, Schoenholzer P et al. A new general approach to enantiomerically pure cyclic and open-chain (r)- and (s)-α,α-disubstituted α-amino acids. Helv Chem Acta 1992; 75: 1666-1696
18 Mugnaini C, Pasquini S, Corelli F. The 4-quinolone-3-carboxylic acid motif as a multivalent scaffold in medicinal chemistry. Curr Med Chem 2009; 16: 1746-1767
19 Srivastava SK, Jha A, Agarwal SK et al. Synthesis and structure-activity relationships of potent antitumor active quinoline and naphthyridine derivatives. Anti-Cancer Agents Med Chem 2007; 7: 685-709
20 Shaharyar M, Abdullah MM, Bakht MA et al. Pyrazoline bearing benzimidazoles: search for anticancer agent. J Eur J Med Chem 2010; 45: 114-119
21 Luo Y, Xiao F, Qian S et al. Synthesis and in vitro cytotoxic Eur. J. Med Chem 2011; 46: 417-422
22 Alley MC, Scudiero DA, Monks PA et al. Lines using a microculture tetrazolium assay feasibility of drug screening with panels of human tumor Cell. Cancer Research 1988; 48: 589-601
23 Grever MR, Schepartz SA, Chabner BA. The National Cancer Institute: cancer drug discovery and development program. Seminars in Oncology 1992; 19: 622
24 Boyd MR, Paull KD. Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Development Research 1995; 34: 91-109
25 Shoemeker RH. Review. The NCI. 60 Human tumor cell line anticancer drug screen. Nature Reviews 2006; 6: 813
26 Skehan P, Storeng R, Scudiero D et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990; 8: 1107-1112