Synthesis and biological evaluation of 4-phenylquinazoline-2-carboxamides designed as a novel class of potent ligands of the translocator protein

Journal of Medicinal Chemistry

Volumn 55, Issue 9, 2012, Pages 4506-4510

  Castellano, Sabrina ^a   Taliani, Sabrina ^b   Milite, Ciro ^a   Pugliesi, Isabella ^b   Da Pozzo, Eleonora ^b   Rizzetto, Elisa ^c   Bendinelli, Sara ^b   Costa, Barbara ^b   Cosconati, Sandro ^d   Greco, Giovanni ^e   Novellino, Ettore ^e   Sbardella, Gianluca ^a   Stefancich, Giorgio ^c   Martini, Claudia ^b   Da Settimo, Federico ^b  

^a UNIVERSITY OF SALERNO   (Italy)

^b UNIVERSITY OF PISA   (Italy)

^c UNIVERSITY OF TRIESTE   (Italy)

^d SECOND UNIVERSITY OF NAPLES   (Italy)

^e UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BENZODIAZEPINE RECEPTOR; N ALKYL 4 PHENYL QUINAZOLINE 2 CARBOXAMIDE DERIVATIVE; N ALKYL N METHYL 4 PHENYLQUINAZOLINE 2 CARBOXAMIDE DERIVATIVE; N SEC BUTYL 1 (2 CHLOROPHENYL) N METHYL 3 ISOQUINOLINECARBOXAMIDE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; DRUG BINDING; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING, COMPETITIVE; CARRIER PROTEINS; CELL LINE, TUMOR; CELL SURVIVAL; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; QUINAZOLINES; RATS; RECEPTORS, GABA-A; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861054375     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201703k     Document Type: Article

References (19)

1. Papadopoulos, V.; Baraldi, M.; Guilarte, T. R.; Knudsen, T. B.; Lacapere, J. J.; Lindemann, P.; Norenberg, M. D.; Nutt, D.; Weizman, A.; Zhang, M. R.; Gavish, M. Translocator protein (18 kDa): new nomenclature for the peripheral-type benzodiazepine receptor based on its structure and molecular function Trends Pharmacol. Sci. 2006, 27, 402-409 (Pubitemid 44069585)
2. Rone, M. B.; Fan, J.; Papadopoulos, V. Cholesterol transport in steroid biosynthesis: role of protein-protein interactions and implications in disease states Biochim. Biophys. Acta 2009, 1791, 646-658
3. Chen, M. K.; Guilarte, T. R. Translocator protein 18 kDa (TSPO): molecular sensor of brain injury and repair Pharmacol. Ther. 2008, 118, 1-17
4. 3H)diazepam binding Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 3805-3809 (Pubitemid 8189972)
5. James, M. L.; Selleri, S.; Kassiou, M. Development of ligands for the peripheral benzodiazepine receptor Curr. Med. Chem. 2006, 13, 1991-2001
6. Taliani, S.; Pugliesi, I.; Da Settimo, F. Structural Requirements to Obtain Highly Potent and Selective 18 kDa Translocator Protein (TSPO) Ligands Curr. Top. Med. Chem. 2011, 11, 860-886
7. Primofiore, G.; Da Settimo, F.; Taliani, S.; Simorini, F.; Patrizi, M. P.; Novellino, E.; Greco, G.; Abignente, E.; Costa, B.; Chelli, B.; Martini, C. N, N -Dialkyl-2-phenylindol-3-ylglyoxylamides. A new class of potent and selective ligands at the peripheral benzodiazepine receptor J. Med. Chem. 2004, 47, 1852-1855 (Pubitemid 38380930)
8. 11C]methylated quinoline-2-carboxamides as potential radioligands for visualization of peripheral benzodiazepine receptors J. Med. Chem. 2001, 44, 579-585 (Pubitemid 32156099)
9. Chaveau, F.; Boutin, H.; Van Camp, N.; Dolle, F.; Tavitian, B. Nuclear imaging of neuroinflammation: a comprehensive review of [11C]PK11195 challengers Eur. J. Nucl. Med. Mol. Imaging 2008, 35, 2304-2319
10. Da Settimo, F.; Simorini, F.; Taliani, S.; La Motta, C.; Marini, A. M.; Salerno, S.; Bellandi, M.; Novellino, E.; Greco, G.; Cosimelli, B.; Da Pozzo, E.; Costa, B.; Simola, N.; Morelli, M.; Martini, C. Anxiolytic-like effects of N, N -dialkyl-2-phenylindol-3-ylglyoxylamides by modulation of translocator protein promoting neurosteroid biosynthesis J. Med. Chem. 2008, 51, 5798-5806
11. Cosimelli, B.; Simorini, F.; Taliani, S.; La Motta, C.; Da Settimo, F.; Severi, E.; Greco, G.; Novellino, E.; Costa, B.; Da Pozzo, E.; Bendinelli, S.; Martini, C. Tertiary amides with a five-membered heteroaromatic ring as new probes for the translocator protein Eur. J. Med. Chem. 2011, 46, 4506-4520
12. Dubroeucq, M. C.; Renault, C.; Le Fur, G. Derivatives of arene and hetero-arene carboxamides and their use as medicaments. US 1983/482082, US19830482082, 19830405, Feb 12, 1985.
13. Campiani, G.; Nacci, V.; Fiorini, I.; De Filippis, M. P.; Garofalo, A.; Ciani, S. M.; Greco, G.; Novellino, E.; Williams, D. C.; Zisterer, D. M.; Woods, M. J.; Mihai, C.; Manzoni, C.; Mennini, T. Synthesis, biological activity, and SARs of pyrrolobenzoxazepine derivatives, a new class of specific "peripheral-type" benzodiazepine receptor ligands J. Med. Chem. 1996, 39, 3435-3450 (Pubitemid 26307848)
14. Sugasawa, T.; Toyoda, T.; Adachi, M.; Sasakura, K. Aminohaloborane in organic synthesis. 1. Specific ortho substitution reaction of anilines J. Am. Chem. Soc. 1978, 100, 4842-4845
15. Chelli, B.; Lena, A.; Vanacore, R.; Da Pozzo, E.; Costa, B.; Rossi., L.; Salvetti, A.; Scatena, F.; Ceruti, S.; Abbracchio, M. P.; Gremigni, V.; Martini, C. Peripheral benzodiazepine receptor ligands: mitochondrial transmembrane potential depolarization and apoptosis induction in rat C6 glioma cells Biochem. Pharmacol. 2004, 68, 125-134 (Pubitemid 38746548)
16. Ruan, S.; Okcu, M. F.; Pong, R. C.; Andreeff, M.; Levin, V.; Hsieh, J. T.; Zhang, W. Attenuation of WAF1/Cip1 expression by an antisense adenovirus expression vector sensitizes glioblastoma cells to apoptosis induced by chemotherapeutic agents 1,3-bis(2-chloroethyl)-1-nitrosourea and cisplatin Clin. Cancer Res. 1999, 5, 197-202 (Pubitemid 29045194)
17. Cappelli, A.; Anzini, M.; Vomero, S.; De Benedetti, P. G.; Menziani, M. C.; Giorgi, G.; Manzoni, C. Mapping the peripheral benzodiazepine receptor binding site by conformationally restrained derivatives of 1-(2-chlorophenyl)- N -methyl- N -(1-methylpropyl)-3- isoquinolinecarboxamide (PK11195) J. Med. Chem. 1997, 40, 2910-2921 (Pubitemid 27382542)
18. 11C]PK11195 and comparison of their behaviours as radioligands for PK binding sites in rats Nucl. Med. Biol. 1994, 21, 573-581 (Pubitemid 24173248)
19. Kugler, W.; Veenman, L.; Shandalov, Y.; Leschiner, S.; Spanier, I.; Lakomek, M; Gavish, M. Ligands of the mitochondrial 18 kDa translocator protein attenuate apoptosis of human glioblastoma cells exposed to erucylphosphohomocholine Cell. Oncol. 2008, 30, 435-450