References
- MB Sporn, AB Roberts, and DS Goodman, editors. The Retinoids, Biology, Chemistry and Medicine. New York: Academic Press; (1984) . p 424.
- E Sonneveld, CE Van den Brink, BJ Van der Leede, RK Schulkes, M Petkovich, B Van der Burg, and PT Van der Saag. (1998). Human retinoic acid (RA) 4-hydroxylase (CYP26) is highly specific for all-trans-RA and can be induced through RA receptors in human breast and carcinoma cells. Cell Growth Differ 9:629–637.
- N Ahmad, and H Mukhtar. (2004). Cytochrome P450: A target for drug development for skin diseases. J Investig Dermatol 123:417–425.
- AR Brecher, and SJ Orlow. (2003). Oral retinoid therapy for dermatologic conditions in children and adolescents. J Am Acad Dermatol 49:171–182.
- EH Estey, F Giles, H Kantarjian, S O'Brien, J Cortes, E Freireich, G Lopez-Berestein, and M Keating. (1999). Molecular remissions induced by liposomal-encapsulated all-trans retinoic acid in newly diagnosed acute promyelocytic leukaemia. Blood 94:2230–2235.
- P Fenaux, C Chastang, S Chevret, M Sanz, H Dombret, E Archimbaud, M Fey, C Rayon, F Huguet, JJ Sotto, C Gardin, PC Makhoul, P Travade, E Solary, N Fegueux, D Bordessoule, J San Miguel, H Link, B Desablens, A Stamatoullas, E Deconinck, F Maloisel, S Castaigne, C Preudhomme, and L Degos. (1999). A randomized comparison of all trans retinoic acid (ATRA) followed by chemotherapy and ATRA plus chemotherapy and the role of maintenance therapy in newly diagnosed acute promyelocytic leukaemia. Blood 94:1192–1200.
- WX Guo, PS Gill, and T Antakly. (1995). Inhibition of AIDS-Kaposi's sarcoma cell proliferation following retinoic acid receptor activation. Cancer Res 55:823–829.
- J Marill, T Cresteil, M Lanotte, and GG Chabot. (2000). Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol 58:1341–1348.
- WJ Ray, G Bain, M Yao, and DI Gottlieb. (1997). CYP26, a novel mammalian cytochrome P450, is induced by retinoic acid and defines a new family. J Biol Chem 272:18702–18708.
- MS Gomaa, SW Yee, CE Milbourne, M-C Barbara, A Brancale, and C Simons. (2006). Homology model of human retinoic acid metabolising enzyme cytochrome P450 26A1 (CYP26A1): Active site architecture and ligand binding. J Enz Inhib Med Chem 21:361–369.
- AJ Kirby, R LeLain, P Mason, F Maharlouie, PJ Nicholls, HJ Smith, and C Simons. (2003). Inhibition of retinoic acid metabolising enzymes by 2-(4-aminophenylmethyl)-6-hydroxy-3,4-dihydronaphthalen-1(2H)-one and related compounds. J Enz Inhib Med Chem 18:27–33.
- SW Yee, L Jarno, MS Gomaa, C Elford, L-L Ooi, MP Coogan, R McClelland, RI Nicholson, BAJ Evans, A Brancale, and C Simons. (2005). Novel tetralone-derived retinoic acid metabolism blocking agents: Synthesis and in vitro evaluation with liver microsomal and MCF-7 CYP26A1 cell assays. J Med Chem 48:7123–7131.
- S Pautus, SW Yee, M Jayne, MP Coogan, and C Simons. (2006). Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl)-methyl]-1H-triazoles. Bioorg Med Chem 14:3643–3653.
- MS Gomaa, B Bobillon, JL Armstrong, GJ Veal, A Brancale, CPF Redfern, and C Simons. (2008). Synthesis and in vitro evaluation of novel, 4-[(imidazol-1-yl and triazol-1-yl)(phenyl)methyl]arylamines: Potent CYP26 inhibitors and inducers of retinoic acid in Neuroblastoma cells. Bioorg Med Chem in press
- VCO Njar, L Gediya, P Purushottamachar, P Chopra, TS Vasaitis, A Khandelwal, J Mehta, C Huynh, A Belosay, and J Patel. (2006). Retinoic acid metabolism blocking agents (RAMBAs) for treatment of cancer and dermatological diseases. Bioorg Med Chem 14:4323–4340.
- DD Perrin, and WLF Armarengo. Purification of Laboratory Chemicals .3rd ed. New York: Pergamon Press; (1988).
- B Staskun. (1964). Nuclear acylation of arylamides. J Org Chem 29:2856–2860.
- GJ Bridger, Y Zhou, and R Skerlj. (2005). Preparation of piperidines as chemokine receptor, particularly CCR5, modulators for the treatment of inflammatory and autoimmune disease. PCT Int Appl 384.
- S Massa, G Stefancich, F Corelli, R Silvestri, A Mai, M Artico, S Panico, and N Simonetti. (1989). Researches on antibacterial and antifungal agents. X. Synthesis and antifungal activities of 1-[p-methyl-α-[4-(1H-pyrrol-1-yl)phenyl]benzyl]azoles and some related products. Archiv Pharm 322:369–373.
- Tripos SYBYL 7.0; Tripos Inc., 1699 South Hanley Rd, St. Louis, Missouri 63144, USA. http://www. tripos.com.
- Molecular Operating Environment (MOE). Chemical Computing Group, Inc. Montreal, Quebec, Canada: http://www.chemcomp.com.
- F Janssens, J Torremans, M Janssen, RA Stokbroekx, M Luyckx, and PAJ Janssen. (1985). New antihistaminic N-heterocyclic 4-piperidinamines. Synthesis and antihistaminic activity of N-(4-piperidinyl)-1H-benzimidazole-2-amines. J Med Chem 28:1925–1933.
- W Aelterman, Y Lang, B Willemsens, I Vervest, S Leurs, and F De Knaep. (2001). Conversion of the laboratory synthetic route of the N-aryl-2-benzothiazolamine R116010 to a manufacturing method. Org Proc Res Dev 5:467–471.
- TK Vinh, M Ahmadi, PO Lopez Delgado, S Fernandez Perez, HM Walters, HJ Smith, PJ Nicholls, and C Simons. (1999). 1-[(Benzofuran-2-yl)-triazoles and -tetrazoles -potent competitive inhibitors of aromatase. Bioorg Med Chem Lett 9:2105–2108.
- GPH Lucker, AMC Heremans, PJ Boegheim, PCM Van de Kerkhof, and PM Steijlen. (1997). Oral treatment of ichthyosis by the cytochrome P450 inhibitor liarozole. Brit J Dermatol 136:71–75.
- L Denis, F Debruyne, P De Porre, and J Bruynseels. (1998). Early clinical experience with Liarozole (Liazal (TM)) in patients with progressive prostate cancer. Eur J Cancer 34:469–475.
- P Stoppie, M Borgers, P Borghgraef, L Dillen, J Goossens, G Sanz, H Szel, C Van Hove, G Van Nyen, G Nobels, H Vanden Bossche, M Venet, G Willemsens, and J Van Wauwe. (2000). R115866 inhibits all-trans-retinoic acid metabolism and exerts retinoidal effects in rodent. J Pharmacol Exp Ther 293:304–312.
- MR Saberi, K Shah, and C Simons. (2005). Benzofuran- and furan-2-yl-(phenyl)-3-pyridylmethanols: Synthesis and inhibition of human placental aromatase (CYP19). J Enz Inhib Med Chem 20:135–141.