Design, synthesis, and structure-activity relationships of novel spiro-piperidines as acetyl-CoA carboxylase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 11, 2012, Pages 3643-3647

  Kamata, Makoto ^a   Yamashita, Tohru ^a   Kina, Asato ^a   Funata, Masaaki ^a   Mizukami, Atsushi ^a   Sasaki, Masako ^a   Tani, Akiyoshi ^a   Funami, Miyuki ^a   Amano, Nobuyuki ^a   Fukatsu, Kohji ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

ACC; Acetyl CoA carboxylase; Lipophilicity; Metabolic stability; Spiro piperidine

Indexed keywords

6 METHYLTHIENO[2,3 B]PYRIDINE; ACETYL COENZYME A CARBOXYLASE; BENZOTHIOPHENE; ENZYME INHIBITOR; PIPERIDINE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; MOUSE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ACETYL-COA CARBOXYLASE; ANIMALS; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; LACTONES; LIVER; PIPERIDINES; RATS; SPIRO COMPOUNDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 84861193920     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.04.047     Document Type: Article

References (16)

1. J.M. Friedman Science 299 2003 856
2. J.O. Hill, H.R. Wyatt, G.W. Reed, and J.C. Peters Science 299 2003 853
3. X. Pi-Sunyer Science 299 2003 859
4. M.R. Munday, and C.J. Hemingway Adv. Enzyme Regul. 39 1999 205
5. N.B. Ruderman, A.K. Saha, D. Vavvas, and L.A. Witters Am. J. Physiol. 276 1999 E1
6. N.B. Ruderman, A.K. Saha, and E.W. Kraegen Endocrinology 144 2003 5166
7. N. Rudermen, and M. Prentki Nat. Rev. Drug Disc. 3 2004 340
8. J. Mao, S.S. Chirala, and S.J. Wakil Proc. Natl. Acad. Sci. U.S.A. 100 2003 7515
9. L. Abu-Elheiga, D.B. Almarza-Ortega, A. Baldini, and S.J. Wakil J. Biol. Chem. 272 1997 10669
10. L. Abu-Elheiga, M.M. Matzuk, P. Kordari, W. Oh, T. Shaikenov, Z. Gu, and S.J. Wakil Proc. Natl. Acad. Sci. U.S.A. 102 2005 12011
11. L. Abu-Elheiga, M.M. Matzuk, K.A. Abo-Hashema, and S.J. Wakil Science 291 2001 2613
12. T. Yamashita, M. Kamata, S. Endo, M. Yamamoto, K. Kakegawa, H. Watanabe, K. Miwa, T. Yamano, M. Funata, J. Sakamoto, A. Tani, C.D. Mol, H. Zou, D.R. Dougan, B. Sang, G. Snell, and K. Fukatsu Bioorg. Med. Chem. Lett. 21 2011 6314
13. S. Tsukamoto, M. Ichihara, F. Wanibuchi, S. Usada, K. Hidaka, M. Harada, and T. Tamura J. Med. Chem. 36 1993 2292
14. M.J. Queiroz, R.C. Calhelha, L.A. Vale-Silva, E. Pinto, and M. São-José Nascimento Eur. J. Med. Chem. 44 2009 1893
15. C. Bernal, C. Palacin, A. Boronat, and S. Imperial Anal. Biochem. 337 2005 55
16. T. Koike, T. Takai, Y. Hoashi, M. Nakayama, Y. Kosugi, M. Nakashima, S. Yoshikubo, K. Hirai, and O. Uchikawa J. Med. Chem. 54 2011 4207