3D-QSAR of amino-substituted pyrido[3,2b]pyrazinones as PDE-5 inhibitors

Medicinal Chemistry Research

Volumn 21, Issue 2, 2012, Pages 202-211

  Tanwar, Omprakash ^a   Saha, Rikta ^a   Alam, M Mumtaz ^a   Akhtar, Mymoona ^a  

^a HAMDARD UNIVERSITY   (India)

Author keywords

3D QSAR; Pharmacophore; PHASE; Phosphodiesterases; Pyrido 3,2b pyrazinones; Schr dinger

Indexed keywords

PHOSPHODIESTERASE V INHIBITOR; PYRIDO[3,2B]PYRAZINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; ENZYME INHIBITION; PHARMACOPHORE; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 84861857678     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9523-y     Document Type: Article

References (21)

1. Almerico AM, Tutone M, Lauria A (2010) 3D-QSAR pharmacophore modeling and in silico screening of new Bcl-xl inhibitors. Eur J Med Chem 45:4774-4782
2. Black KL, Yin D, Ong JM, Hu J, Konda BM, Wang X, Ko MK, Bayan JA, Sacapano MR, Espinoza A, Irvin DK, Shu Y (2008) PDE5 inhibitors enhance tumor permeability and efficacy of chemotherapy in a rat brain tumor model. Brain Res 1230: 290-302
3. Burnett AL (2005) Phosphodiesterase 5 mechanisms and therapeutic applications. Am J Cardiol 96:29-31
4. Dixon SL, Smondyrev AM, Knoll EH, Rao SN, Shaw DE, Friesner RA (2006) PHASE: a new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results. J Comput Aided Mol Des 20:647-671 (Pubitemid 46023928)
5. Eardley I, Donatucci C, Corbin J, El-Meliegy A, Hatzimouratidis K, McVary K, Munarriz R, Lee SW (2010) Pharmacotherapy for erectile dysfunction. J Sex Med 7:524-540
6. Francis SH, Corbin JD (1999) Cyclic nucleotide-dependent protein kinases: intracellular receptors for cAMP and cGMP action. Crit Rev Clin Lab Sci 36:275-328 (Pubitemid 29431414)
7. Haning H, Niewöhner U, Schenke T, Es-Sayed M, Schmidt G, Lampe T, Bischoff E (2002) Imidazo[5, 1-f][1, 2, 4]triazin-4(3H)-ones, a new class of potent PDE 5 inhibitors. Bioorg Med Chem Lett 12:865-868 (Pubitemid 34214962)
8. Hosogai NH, Hamada K, Tomita M, Nagashima A, Takahashi T, Sekizawa T, Mizutani T, Urano Y, Kuroda A, Sawada K, Ozaki T, Seki J, Goto T (2001) FR226807: a potent and selective phosphodiesterase type 5 inhibitor. Eur J Pharmacol 428: 295-302 (Pubitemid 33000153)
9. Lather V, Kristam R, Saini JS, Karthikeyan NA, Balaji VN (2008) QSAR models for prediction of glycogen synthase kinase-3b inhibitory activity of indirubin derivatives. QSAR Comb Sci 27:718-728
10. LigPrep, version 2.3, Schrödinger, LLC, New York, NY, 2009
11. MacroModel, version 9.7, Schrödinger, LLC, New York, NY, 2009
12. Mahipal, Tanwar OP, Karthikeyan C, Moorthy NSHN, Trivedi P (2010) 3D-QSAR of aminophenyl benzamide derivatives as histone deacetylase inhibitors. Med Chem Res 6:277-285
13. Moreland RB, Goldstein I, Kim NN, Traish A (1999) Sildenafil citrate, a selective phosphodiesterase type 5 inhibitor: research and clinical implications in erectile dysfunction. TEM 10:97-104 (Pubitemid 29283892)
14. Narkhede SS, Degani MS (2007) Pharmacophore refinement and 3DQSAR studies of histamine H3 antagonists. QSAR Comb Sci 26:744-753 (Pubitemid 46984720)
15. Owen DR, Walker JK, Jon Jacobsen E, Freskos JN, Hughes RO, Brown DL, Bell AS, Brown DG, Phillips C, Mischke BV, Molyneaux JM, Fobian YM, Heasley SE, Moon JB, Stallings WC, Joseph Rogier D et al (2009) Identification, synthesis and SAR of amino substituted pyrido[3, 2b]pyrazinones as potent and selective PDE5 inhibitors. Bioorg Med Chem Lett 19: 4088-4091
16. PHASE-3.1, Schrödinger, LLC, New York, NY, 2009
17. Samantha L, Cesare M, Aleksey K, Mattia S, Stefano M, Elena C, Dorotea R, Alessandro C (2008) SAR and QSAR study on 2-aminothiazole derivatives, modulators of transcriptional repression in Huntington's disease. Bioorg Med Chem 16:5695-5703
18. Shah UA, Deokar HS, Kadam SS, Kulkarni VM (2010) Pharmacophore generation and atom-based 3D-QSAR of novel 2-(4-methylsulfonylphenyl)pyrimidines as COX-2 inhibitors. Mol Divers 14:559-568
19. Terrett NK, Bell AS, Brown D, Ellis P (1996) Sildenafil (viagra), a potent and selective inhibitor of type 5 cgmp phosphodiesterase with utility for the treatment of male erectile dysfunction. Bioorg Med Chem Lett 6:1819-1824 (Pubitemid 26253884)
20. Wall ME, Francis SH, Corbin JD, Grimes K, Jannetta RR, Kotera J, Macdonald BA, Gibson RR, Trewhella J (2003) Mechanisms associated with cGMP binding and activation of cGMP-dependent protein kinase. PNAS 100:2380-2385 (Pubitemid 36297507)
21. Wallace WD (2005) Available and future treatments for erectile dysfunction. Clinical Cornerstone 1:37-44