Effects of conformational restriction of 2-amino-3-benzoylthiophenes on A1 adenosine receptor modulation

Journal of Medicinal Chemistry

Volumn 53, Issue 18, 2010, Pages 6550-6559

  Aurelio, Luigi ^a   Valant, Celine ^a   Flynn, Bernard L ^a   Sexton, Patrick M ^a   White, Jonathan M ^b   Christopoulos, Arthur ^a   Scammells, Peter J ^a  

^a MONASH UNIVERSITY   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOINDENO[1,2 C]THIOPHEN 8 ONE DERIVATIVE; 2 AMINOINDENO[2,1 B]THIOPHEN 3 YL (PHENYL)METHANONE DERIVATIVE; ADENOSINE A1 RECEPTOR; ADENOSINE A1 RECEPTOR AGONIST; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; PHENYLISOPROPYLADENOSINE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG; ADENOSINE A1 RECEPTOR ANTAGONIST;

ALLOSTERISM; ANIMAL CELL; ARTICLE; CHO CELL; CONCENTRATION RESPONSE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG SYNTHESIS; ENZYME PHOSPHORYLATION; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; CHO CELL LINE; CONFORMATION; CRICETULUS; HAMSTER; METABOLISM; PHOSPHORYLATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALLOSTERIC REGULATION; ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; CRYSTALLOGRAPHY, X-RAY; MITOGEN-ACTIVATED PROTEIN KINASE 1; MITOGEN-ACTIVATED PROTEIN KINASE 3; MOLECULAR CONFORMATION; PHOSPHORYLATION; RECEPTOR, ADENOSINE A1; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES; ADENOSINE A1 RECEPTOR AGONISTS; ADENOSINE A1 RECEPTOR ANTAGONISTS;

EID: 77956730941     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1008538     Document Type: Article

References (15)

1. May, L. T.; Avlani, V. A.; Sexton, P. M.; Christopoulos, A. Allosteric Modulation of G Protein-Coupled Receptors Curr. Pharm. Des. 2004, 10, 2003-2013
2. Schulte, G.; Fredholm, B. B. Signalling from Adenosine Receptors to Mitogen-Activated Protein Kinases Cell. Signalling 2003, 15, 813-827
3. Jacobson, K. A.; Gao, Z.-G. Adenosine Receptors as Therapeutic Targets Nature Rev. Drug Discovery 2006, 5, 247-264
4. 1 Adenosine Receptor Agonists: Medicinal Chemistry and Therapeutic Potential Curr. Pharm. Des. 2004, 10, 2021-2039
5. May, L. T.; Leach, K.; Sexton, P. M.; Christopoulos, A. Allosteric Modulation of G Protein Coupled Receptors Annu. Rev. Pharmacol. Toxicol. 2007, 47, 1-51 (Pubitemid 46277033)
6. 1 Receptor Binding and Function by 2-Amino-3-benzoylthiophenes Mol. Pharmacol. 1990, 38, 939-949
7. 1 Receptor Binding by 2-Amino-3- benzoylthiophenes Mol. Pharmacol. 1990, 38, 950-958
8. 1 Receptor: Synthesis and Pharmacological Evaluation of 4-Substituted 2-Amino-3-benzoylthiophenes J. Med. Chem. 2009, 52, 4543-4547
9. Moorman, A. R; Romagnoli, R; Baraldi, P. G. Preparation of Fused Thiophenes for the Treatment of Neuropathic Pain. PCT Int. Appl. WO02083083, 2002.
10. 4/Base-III. Umsetzungen von Ketonen und α-Halogenketonen mit Malonester Tetrahedron 1973, 29, 635-638
11. Stephens, C. E; Felder, T. M; Sowell, J. W, Sr.; Andrei, G; Balzarini, J; Snoeck, R; Clercq, D. E. Synthesis and Antiviral/Antitumor Evaluation of 2-amino-and 2-Carboximido-3-arylsulfonylthiophenes and Related Compounds as a New Class of Diarylsulfones Bioorg. Med. Chem. Lett. 2001, 9, 1123-1132
12. 1 Adenosine Receptors J. Med. Chem. 2002, 45, 382-389 (Pubitemid 34073455)
13. Tormyshev, V. M.; Trukhin, D. V.; Rogozhnikova, O. U.; Mikhalina, T. V.; Troitskaya, T. I.; Flinn, A. Aryl Alkyl Ketones in a One-Pot Gewald Synthesis of 2-Aminothiophenes Synlett 2006, 2559-2564
14. Farrugia, L. J. ORTEP-3 for windows-a version of ORTEP-III with a graphical user interface (GUI) J. Appl. Crystallogr. 1997, 30, 565
15. Farrugia, L. J. WinGX suite for small-molecule single-crystal crystallography J. Appl. Crystallogr. 1999, 32, 837-338