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http://dx.doi.org/10.15230/SCSK.2015.41.2.143

Improved One-pot Regioselective Synthesis of 3,7-Diarylpyrazolo[1,5-α]pyrimidines and Their CB1R Activity  

Hong, Yong Deog (Amorepacific Corporation R&D Unit)
Byoun, Kyoung Hee (Amorepacific Corporation R&D Unit)
Park, Miyoung (Amorepacific Corporation R&D Unit)
Park, Jun Seong (Amorepacific Corporation R&D Unit)
Shin, Song Seok (Amorepacific Corporation R&D Unit)
Publication Information
Journal of the Society of Cosmetic Scientists of Korea / v.41, no.2, 2015 , pp. 143-150 More about this Journal
Abstract
This study demonstrates an effective one-pot regioselective synthesis of 3,7-diarylpyrazolo [1,5-${\alpha}$]pyrimidines. Moreover, the derivatives obtained were effective CB1R antagonists. These pyrazolo [1,5-${\alpha}$]pyrimidines with diaryl groups at the 3,7-positions are potential pharmacophores for CB1R candidates.
Keywords
aminopyrazoles; aryl ketoesters; regioselective synthesis; 3,7-diarylpyrazolo[1,5-${\alpha}$]pyrimidines;
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1 J. H. M. Lange, Coolen, H. K. A. C. van Stuivenberg, and J. A. R. Dijksman, Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB(1) cannabinoid receptor antagonists, J. Med. Chem., 47, 627 (2004).   DOI
2 M. Ilaria, M. Andrea, O. Francesca, F. Mateo, S. Monica, R. Stefania, L. Giovanni, and L. Paolo, Novel pyrazole derivatives as neutral $CB_1$antagonists with significant activity towards food intake, Eur. J. Med. Chem., 62, 256 (2013).   DOI
3 C. Manera, V. Benetti, M. P. Castelli, T. Cavallini, S. Lazzarotti, F. Pibiri, G. Saccomanni, T. Tuccinardi, A. Vannacci, A. Martinelli, and P. Ferrarini, Design, Synthesis, and Biological Evaluation of New 1,8-Naphthyridin-4(1H)-on-3-carboxamide and Quinolin-4(1H)-on-3-carboxamide Derivatives as $CB_2$ Selective Agonists, J. Med. Chem., 49(20), 5947 (2006).   DOI
4 V. Di. Marzo, $CB_1$ receptor antagonism: biological basis for metabolic effects, Drug Discov. Today, 13(23-24), 1026 (2008).   DOI
5 H. Mukaiyama, T. Nishimura, S. Kobayashi, Y. Komatsu, S. Kikuchi, T. Ozawa, N. Kamada, and H. Ohnota, Bioorg. Med. Chem., 16, 909 (2008).   DOI
6 M. E. Fraley, R. S. Rubino, W. F. Hoffman, S. R. Hambaugh, K. L. Arrington, R. W. Hungate, M. T. Bilodeau, A. J. Tebben, R. L. Kendall, R. C. McFall, W. R. Huckle, K. E. Coll, and K. A. Thomas, Bioorg. Med. Chem. Lett., 13, 3537 (2002).
7 A. S. Kiselyov and L. Smith, Tetrahedron Lett., 47, 2611 (2006).   DOI
8 J. Y. Hwang, M. P. Windisch, S. Jo, K. Kim, S. Kong, H. C. Kim, S. Kim, H. Kim, M. E. Lee, Y. Kim, J. Choi, D-S. Park, E. Park, J. Kwon, S. Ahn, J. Cechetto, J. Kim, M. Liuzzi, Z. No, and J. Lee, Biorog. Med. Chem. Lett., 22, 7297 (2012).   DOI
9 M. R. Shaaban, T. S. Saleh, A. S. Mayhoub, A. Mansour, and A. M. Farag, Bioorg. Med. Chem., 16, 6344 (2008).   DOI
10 S. Bondock, R. Rabie, H. A. Etman, and A. A. Fadda, Eur. J. Med. Chem., 43, 2122 (2008).   DOI
11 R. Aggarwal, G. Sumran, N. Garg, and A. Aggarwal, Eur. J. Med. Chem., 46, 3038 (2011).   DOI
12 O. M. Ahmed, M. A. Mohamed, R. R. Ahmed, and S. A. Ahmed, Eur. J. Med. Chem., 44, 3519 (2009).   DOI
13 K. Senga, T. Novinson, H. R. Wilson, and R. K. Robins, J. Med. Chem., 24, 610 (1981).   DOI
14 W. E. Kirkpatrick, T. Okabe, I. W. Hillyard, R. K. Robins, A. T. Dren, and T. Novinson, J. Med. Chem., 20, 386 (1977).   DOI
15 H. B. Zhou, S. B. Sheng, D. R. Compton, Y. Kim, A. Joachimiak, S. Sharma, K. E. Carlson, B. S. Katzenellenbogen, K. W. Nettles, G. L. Greene, and J. A. Katzenellenbogen, J. Med. Chem., 50, 399 (2007).   DOI
16 M. E. Fraley, R. S. Rubino, W. F. Hoffman, S. R. Hambaugh, K. L. Arrington, R. W. Hungate, M. T. Bilodeau, A. J. Tebben, R. Z. Rutledge, R. L. Kendall, R. C. McFall, W. R. Huckle, K. E. Coll, and K. A. Thomas, Bioorg. Med. Chem. Lett., 12, 3537 (2002).   DOI
17 R. R. Frey, M. L. Curtin, D. H. Albert, K. B. Glaser, L. J. Pease, N. B. Soni, J. J. Bouska, D. Reuter, K. D. Stewart, P. Marcotte, G. Bukofzer, J. Li, S. K. Davidsen, and M. R. Michaelides, J. Med. Chem., 51, 3777 (2008).   DOI
18 R. N. Daniels, K. Kim E. P. Lebois, H. Muchalski, M. Hughes, and C. W. Lindsley, Tetrahedron Lett., 49, 305 (2008).   DOI
19 J. Quiroga, J. Trilleras, B. Insuasty, R. Abonia, M. Noqueras, and J. Cobo, Tertahedron Lett., 49, 3257 (2008).   DOI
20 Y. D. Wang, E. Honores, B. Wu, S. Johnson, D. Powell, M. Miranda, J. P. McGinnis, C. Discafani, S. K. Rabindran, W. Cheng, and G. Krishnamurthy, Bioorg. Med. Chem., 17, 2091 (2009).   DOI
21 H. F. Anwar, D. H. Fleita, H. Kolshorn, H. Meier, and M. H. Elnagdi, Arkivoc, 133 (2006).
22 D. J. Wustrow, T. Capiris, J. A. Knobelsdorf, H. Akunne, M. D. Davis, R. MacKenzie, T. A. Pugsley, K. T. Zoski, T. G. Heffner, and L. D. Wise, Bioorg. Med. Chem. Lett., 8, 2067 (1998).   DOI
23 M. H. Elnagdi and A. W. Erian, Bull. Chem. Soc. Jpn., 63, 1854 (2009).
24 A. Kodimuthali, T. C. Nishad, P. L. Prasunamba, and M. Pal, Tetrahedron Lett., 50, 354 (2009).   DOI