Synthesis and pharmacological evaluation of novel unsubstituted indole-anthraquinone carboxamide derivatives as potent antihyperlipidemic agents

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 69 C, Issue 1-2, 2014, Pages 21-28

  AL Najdawi, Manal ^a   Al Hiari, Yusuf ^a   Al Qirim, Tariq ^b   Shattat, Ghassan ^b   Al Zweri, Mohammad ^a   Sheikha, Ghassan Abu ^b  

^a UNIVERSITY OF JORDAN   (Jordan)

^b AL ZAYTOONAH UNIVERSITY OF JORDAN   (Jordan)

Author keywords

Cholesterol elevation; High density lipoprotein; N (9,10 Dihydro 9,10 dioxoanthracenyl) 1H indole 2 carboxamide; Triglyceride reduction

Indexed keywords

AMIDE; ANTHRAQUINONE DERIVATIVE; ANTILIPEMIC AGENT; CHOLESTEROL; INDOLE DERIVATIVE; TRIACYLGLYCEROL;

ANIMAL; ARTICLE; BLOOD; CHEMISTRY; DOSE RESPONSE; DRUG SCREENING; ELECTROSPRAY MASS SPECTROMETRY; MALE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; SYNTHESIS; WISTAR RAT;

AMIDES; ANIMALS; ANTHRAQUINONES; CHOLESTEROL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; HYPOLIPIDEMIC AGENTS; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MALE; RATS; RATS, WISTAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TRIGLYCERIDES;

EID: 84901448943     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.5560/ZNC.2012-0224     Document Type: Article

References (28)

1. Agren J., Kurvinena J., and Kuksis A. (2005), Isolation of very low density lipoprotein phospholipids enriched in ethanolamine phospholipids from rats injected with Triton WR 1339. Biochim. Biophys. Acta 1734, 34-43.
2. Al-Qirim T., Shahwan M., Shattat G., Al-Hiari Y., Abu Sheikha G., and Zaidi S. (2009), Pharmacological evaluation of novel indole-2-carboxamides as potent lipidlowering agents in Triton-WR1339-induced hyperlipidemic rats. Z. Naturforsch. 64c, 619-625.
3. Alper P., Epple R., Michellys P., Mutnick D., Nikulin V., and Petrassi H. M. J. (2009), Preparation of indoles and benzofurans as therapeutic modulators of GPR119 activity. Patent: US 2008-30897 20080222.
4. Batra S., Srivastava S., Singh K., Chander R., and Khanna A. K. (2000), Synthesis and biological evaluation of 3-substituted amino-1-aryl hydroxy-hex-2-ene-1-one as antioxidant and hypolipidemic agents. Bioorg. Med. Chem. 8, 2195-2209.
5. Beck J. P., Wakefield B. D., Cordier F. L., Dominguez-Manzanares E., Gardinier K. M., Greenen P. M., and Savin K. A. (2004), Preparation of N-benzothiazolyl (or benzoxazolyl) amides as novel MCH receptor antagonists for treating and preventing symptoms associated with obesity and related diseases. Patent: US 637116 P, 20041217.
6. Beyer T. P., Chen Y., Porter R. K., Lu D., Schmidt R. J., Mantlo N. B., Konrad R. J., and Cao G. (2008), Peroxisome proliferator-activated receptor a agonists regulate cholesterol ester transfer protein. Lipids 43, 611-618.
7. Bussolotti D. L. and Gammill R. B. (2004), N-(Pyridin-2-yl)-substituted bicyclic heterocyclic carboxamide derivatives as antidiabetic agents, and their preparation, pharmaceutical compositions, and methods of use as inhibitors of glycogen phosphorylase. Patent Application: WO 2004092158 A1 20041028.
8. Farnier M. and Davignon J. (1998), Current and future treatment of hyperlipidemia: the role of statins. Am. J. Cardiol. 82, 3J-10J.
9. Fruchart J., Sacks F., Hermans M., Assmann G., Brown V., Ceska R., Chapman J., Dodson P., Fioretto P., Ginsberg H., Kadowaki T., Lablanche J., Marx M., Plutzky J., Reiner Z., Rosenson R., Staels B., Stock J., Sy R., Wanner C., Zambon A., and Zimmet Z. (2008), The residual risk reduction initiative: a call to action to reduce residual vascular risk in patients with dyslipidemia. Am. J. Cardiol. 102, 1K-34K.
10. Gammill R. B. (2003), Preparation of substituted 1Hindole-2-carboxamides and 6H-thieno[2,3-b]pyrrole-5-carboxamides as antidiabetic agents. Patent Application: WO 2003072570 A1 20030904.
11. Gotto A. M. (2002), Management of dyslipidemia. Am. J. Med. 112, 8A, 10S-18S.
12. Gouda M. A., Berghot M. A., Shoeib A. I., and Khalil A. M. (2010), Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety. Eur. J. Med. Chem. 45, 1843-1848.
13. Harnafi H., Caid H., Bouanani N., Aziz M., and Amrani S. (2008), Hypolipemic activity of polyphenol-rich extracts from Ocimumbasilicum in Triton WR-1339-induced hyperlipidemic mice. Food Chem. 108, 205-212.
14. Jia L., Pei R., Lin M., and Yang X. (2001), Acute and subacute toxicity and efficacy of S-nitrosylated captopril, an ACE inhibitor possessing nitric oxide activities. Food Chem. Toxicol. 39, 1135-1143.
15. Jun M., Foote C., Jicheng L.V., Neal B., Patel A., Nicholls S. J., Grobbee D. E., Cass A., Chalmers J., and Perkovic V. (2010), Effects of fibrates on cardiovascular outcomes: a systematic review and meta-analysis. Lancet 375, 1875-1884.
16. Kopin A. S., Carey M., andWang D. (2006), Altering intestinal motility and absorption of hydrophobic compounds through the use of agonists and=or antagonists of the cholecystokinin-1 receptor. Patent: US 224869.
17. Koyama H., Boueres J. K., Miller D. J., Berger J. P., Mac-Naul K. L., Wang P., Ippolito M. C., Wright S. D., Agrawal A. K., Moller D. E., and Sahoo S. P. (2005), (2R)-2-Methylchromane-2-carboxylic acids: discovery of selective PPARa agonists as hypolipidemic agents. Bioorg. Med. Chem. Lett. 15, 3347-3351.
18. La Regina G., Silvestri R., Gatti V., Lavecchia A., Novellino E., Befani O., Turini P., and Agostinelli E. (2008), Synthesis, structure-activity relationships and molecular modeling studies of new indole inhibitors of monoamine oxidases A and B. Bioorg. Med. Chem. 16, 9729-9740.
19. Liu G., Zhang Z., Luo X., Shen J., Liu H., Shen X., Chen K., and Jiang H. (2004), Inhibitory mode of indole-2-carboxamide derivatives against HLGPa: Molecular docking and 3D-QSAR analyses. Bioorg. Med. Chem. 15, 4147-4157.
20. Nakajima T., Tanaka N., Kanbe H., Hara A., Kamijo Y., Zhang X., Gonzalez F. J., and Aoyama T. (2008), Bezafibrate at clinically relevant doses decreases serum=liver triglycerides via down-regulation of sterol regulatory element-binding protein-1c in mice: a novel peroxisome proliferator-activated receptor a-independent mechanism. Mol. Pharmacol. 75, 782-792.
21. Olgen S. and Coban T. (2002), Synthesis and antioxidant properties of novel N-substituted indole-2-carboxamide and indole-3-acetamide derivatives. Arch. Pharm. 335, 331-338.
22. Robichaud L. J., Stewart S. F., and Adolphson R. L. (1987), CI-922-a novel, potent antiallergic compound. I. Inhibition of mediator release in vitro. Int. J. Immunopharmacol. 19, 41-49.
23. Schurr P. E., Schultz J. R., and Parkinson T. M. (1972), Triton induced hyperlipidaemia in rats as an animal model for screening hypolipidemic drugs. Lipids 7, 69-74.
24. Shattat G., Al-Qirim R., Al-Hiari Y., Abu Sheikha G., Al-Qirim T., El-Huneidi W., and Shahwan M. (2010), Synthesis and anti-hyperlipidemic evaluation of N-(benzoylphenyl)-5-fluoro-1H-indole-2-carboxamide derivatives in Triton WR-1339-induced hyperlipidemic rats. Molecules 15, 5840-5849.
25. Sher P. M. and Ellsworth B. A. (2004), Triglyceride and triglyceride-like prodrugs of glycogen phosphorylase inhibiting compounds. Patent: US 140474.
26. Venkateswarulu M., Prashanthi K., Chinta G., Sujata D., Pushpa B., and Ranganayakulu D. (2010), Antihyperlipidemic activity of the aqueous extract of the Artocarpusheterophyllus leaves in Triton WR-1339 induced hyperlipidemic rats. Drug Invention Today 2, 25-28.
27. Yamamoto K., Byrne R., Edelstein C., Shen B. and Scanu A. M. (1984), In vitro effect of Triton WR-1339 on canine plasma high density lipoproteins. J. Lipid Res. 25, 770-779.
28. Yoshihisa S. and Yuichi S. (2006), Pharmacokinetic and pharmacodynamic alterations of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors: Drug-drug interactions and interindividual differences in transporter and metabolic enzyme functions. Pharmacol. Ther. 112, 71-105.