Design, synthesis, and biological evaluation of benzylamino-methanone based cholesteryl ester transfer protein inhibitors

Molecules

Volumn 15, Issue 8, 2010, Pages 5721-5733

  Sheikha, Ghassan Abu ^a   Khalaf, Reema Abu ^a   Melhem, Areej ^a   Albadawi, Ghadeer ^a  

^a AL ZAYTOONAH UNIVERSITY OF JORDAN   (Jordan)

Author keywords

Benzylamino methanones; CETP inhibitors; High density lipoprotein; Pharmacophore modeling; Quantitative structure activity relationship

Indexed keywords

BENZOXAZINE DERIVATIVE; BENZYL DERIVATIVE; CHOLESTEROL ESTER TRANSFER PROTEIN;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RABBIT; SYNTHESIS;

ANIMALS; BENZOXAZINES; BENZYL COMPOUNDS; CHOLESTEROL ESTER TRANSFER PROTEINS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RABBITS;

EID: 77956096016     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15085721     Document Type: Article

References (16)

1. Hansson, G.K. Inflammation, atherosclerosis, and coronary artery disease. N. Engl. J. Med. 2005, 352, 1685-1695.
2. Lamarche, B.; Despres, J.P.; Moorjani, S.; Cantin, B.; Dagenais, G.R.; Lupien, P.J. Triglycerides and HDL-cholesterol as risk factors for ischemic heart disease, Results from the Quebec cardiovascular study. Atherosclerosis 1996, 119, 235-245.
3. Tall, A.R.; Wang, N.; Mucksavage, P. Is it time to modify the reverse cholesterol transport model? J. Clin. Invest. 2001, 108, 1273-1275.
4. Qiu, X.; Mistry, A.; Ammirati, M.J.; Chrunyk, B.A.; Clark, R.W.; Cong, Y.; Culp, J.S.; Danley, T.B.; Freeman, K.F.; Geoghegan, M.C.; et al. Crystal structure of cholesteryl ester transfer protein reveals a long tunnel and four bound lipid molecules. Nat. Struct. Mol. Biol. 2007, 14, 106-113.
5. Boekholdt, S.M.; Kuivenhoven, J.A.; Wareham, N.J.; Peters, R.J.G.; Jukema, J.W.; Luben, R.; Bingham, S.A.; Day, N.E.; Kastelein, J.J.P.; Khaw, K.T. Plasma levels of cholesteryl ester transfer protein and the risk of future coronary artery disease in apparently healthy men and women. Circulation 2004, 110, 1418-1423.
6. McPherson, R.; Mann, C.J.; Tall, A.R.; Hogue, M.; Martin, L.; Milne, R.W.; Marcel, Y.L. Plasma concentration of cholesteryl ester transfer protein in hyperlipoproteinemia. Arterioscler. Thromb. 1991, 11, 797-804.
7. Castilho; Marcelo, S.; Guido; Rafael, V.C.; Andricopulo; Adriano, D. 2D Quantitative structure- activity relationship studies on a series of cholesteryl ester transfer protein inhibitors. Bioorg. Med. Chem. 2007, 15, 6242-6252.
8. Hanumantharao, P.; Sambasivarao, S.V.; Soni, L.K.; Gupta, A.K.; Kaskhedikar, S.G. QSAR analysis of analogs of bis[2-(acylamino) Ph] disulfides, 2-(acylamino) benzenethiols and S-[2-(acylamino) Ph] alkanethioates as antihyperlipidemic agents. Indian J. Chem. 2005, 44B, 1481-1486.
9. Kelkar; Mandar, A.; Pednekar; Deepa, V.; Pimple; Surekha, R.; Akamanchi; Krishnacharya, G. 3D QSAR studies of inhibitors of cholesterol ester transfer protein (CETP) by CoMFA, CoMSIA and GFA methodologies. Med. Chem. Res. 2004, 13, 590-604.
10. Cronin, M.T.D.; Schultz, T.W. Pitfalls in QSAR. J. Mol. Struct. 2003, 622, 39-51.
11. Akamatsu, M. Current state and perspectives of 3D-QSAR. Curr. Top. Med. Chem. 2002, 12, 1381-1394.
12. Abu Khalaf, R.; Abu Sheikha, G.; Bustanji, Y.; Taha, M.O. Discovery of new cholesteryl ester transfer protein inhibitors via ligand-based pharmacophore modeling and QSAR analysis followed by synthetic exploration. Eur. J. Med. Chem. 2010, 45, 1598-1617.
13. th Ed.; Springer: New York, 2008; Vol.A.
14. Del Amo, V.; Philp, D. Making imines without making water-exploiting a recognition-mediated Aza-Wittig reaction. Org. Lett. 2009, 11, 301-304.
15. Ivanov, I.; Nikolova, S.; Statkova-Abeghe, S. Efficient one-pot friedel-crafts acylation of benzene and its derivatives with unprotected aminocarboxylic acids in polyphosphoric acid. Synth. Commun. 2006, 36, 1405-1411.
16. Reinhard, E.J.; Wang, J.L.; Durley, R.C.; Fobian, Y.M.; Grapperhaus, M.L.; Hickory, M.A.; Massa, M.B.; Norton, M.A.; Promo, M.B.; Tollefson, W.F.; et al. Discovery of a simple picomolar inhibitor of cholesteryl ester transfer protein. J. Med. Chem. 2003, 46, 2152-2168.