Synthesis of potent and selective inhibitors of Candida albicans N-myristoyltransferase based on the benzothiazole structure

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 7, 2005, Pages 2509-2522

  Yamazaki, Kazuo ^a   Kaneko, Yasushi ^a   Suwa, Kie ^a   Ebara, Shinji ^a   Nakazawa, Kyoko ^a   Yasuno, Kazuhiro ^a  

^a SSP CO LTD   (Japan)

Author keywords

Antifungal; N Myristoyltransferase; Parallel synthesis; Solid supported reagents

Indexed keywords

2 (ACETYLAMINO) N 2 [(2 NAPHTHYLMETHYL)AMINO]ETHYLBENZOTHIAZOLE 6 CARBOXAMIDE; 2 [(2 CYCLOHEXYLCARBONYL)AMINO] 1 METHYL N 2 [(2 NAPHTHYLMETHYL)AMINO]ETHYL 1H BENZIMIDAZOLE 5 CARBOXAMIDE; 2 [(2 CYCLOHEXYLCARBONYL)AMINO] 1 METHYL N 2 [(2 NAPHTHYLMETHYL)AMINO]ETHYL 1H BENZIMIDAZOLE 6 CARBOXAMIDE; 2 [(CYCLOHEXANECARBONYL)AMINO] N [(2 NAPHTHYLMETHYL)AMINO] ETHYLBENZOTHIAZOLE 6 CARBOXAMIDE; 2 [(CYCLOHEXYLCARBONYL)AMINO] N [2 (2 NAPHTHYLAMINO)ETHYL]BENZOXAZOLE 5 CARBOXAMIDE; 2 [(CYCLOHEXYLCARBONYL)AMINO] N [2 (2 NAPHTHYLAMINO)ETHYL]BENZOXAZOLE 6 CARBOXAMIDE; ANTIFUNGAL AGENT; BENZOTHIAZOLE DERIVATIVE; ENZYME INHIBITOR; N [2 [(2 NAPHTHYLMETHYL)AMINO]ETHYL] 2 [(TETRAHYDRO 2H PYRAN 4 YLCARBONYL)AMINO]BENZOTHIAZOLE 6 CARBOXAMIDE; N [2 [(CYCLOPENTYLCARBONYL)AMINO]BENZOTHIAZOL 6 YL] 3 [(2 NAPHTHYLMETHYL)AMINO]CYCLOHEXANECARBOXAMIDE; N [6 [3 [(2 NAPHTHYLMETHYL)AMINO]PROPIONYLAMINO]BENZOTHIAZOL 2 YL]CYCLOHEXANECARBOXAMIDE; PROTEIN N MYRISTOYLTRANSFERASE INHIBITOR; REAGENT; RO 094879; UK 370753; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; STRUCTURE ACTIVITY RELATION;

EID: 14844322778     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.01.033     Document Type: Article

References (24)

1. S. Maure-Stroh, B. Eisenhaber, and F. Eisenhaber J. Mol. Biol. 317 2002 541 557
2. R.A. Weinberg, C.A. McWherter, S.K. Freeman, D.C. Wood, J.I. Gordon, and S.C. Lee Mol. Microbiol. 16 1995 241 250
3. T. Ohtsuka, and Y. Aoki Drugs Future 28 2003 143 152 and references cited therein
4. D.R. Armour, A.S. Bell, M.I. Kemp, M.P. Edwards, and A. Wood Abstracts of papers, 221st national meeting of the American Chemical Society, San Diego, CA 2001 American Chemical Society Washington, DC Abstract MEDI-349
5. A.S. Bell, D.R. Armour, M.P. Edwards, M.I. Kemp, and A. Wood Abstracts of papers, 221st national meeting of the American Chemical Society, San Diego, CA 2001 American Chemical Society Washington, DC Abstract MEDI-350
6. H. Ebiike, M. Masubuchi, P. Liu, K. Kawasaki, K. Morikami, S. Sogabe, M. Hayase, T. Fujii, K. Sakata, H. Shindoh, Y. Shiratori, Y. Aoki, T. Ohtsuka, and N. Shimma Bioorg. Med. Chem. Lett. 12 2002 607 610
7. K. Kawasaki, M. Masubuchi, K. Morikami, S. Sogabe, T. Aoyama, H. Ebiike, S. Niizuma, M. Hayase, T. Fujii, K. Sakata, H. Shindoh, Y. Shiratori, Y. Aoki, T. Ohtsuka, and N. Shimma Bioorg. Med. Chem. Lett. 13 2003 87 91
8. M. Masubuchi, H. Ebiike, K. Kawasaki, S. Sogabe, K. Morikami, Y. Shiratori, S. Tsujii, T. Fujii, K. Sakata, M. Hayase, H. Shindoh, Y. Aoki, T. Ohtsuka, and N. Shimma Bioorg. Med. Chem. 11 2003 4463 4478
9. We utilized the virtual screening to identify the active compounds. The initial database comprised about 2,000,000 entries. Pharmacophore model derived from the crystal structure of the target protein and the flexible docking served as sequential filters to reduce the initial set to about 100 prospective entries. Catalyst was used for the pharmacophore modeling (version 4.6, Molecular Simulations, Inc. now Accelrys Inc., San Diego, CA, USA, 2000). Cerius2 was used for the flexible docking (Version 4.7; Accelrys Inc., San Diego, CA, 2002)
10. S. Bhattacharyya, S. Rana, O.W. Gooding, and J. Labadie Tetrahedron Lett. 44 2003 4957 4960
11. Kunz, W.; Jau, B. U.S. Patent 5770758, 1998
12. Chem. Abstr. 129 1998 81579
13. H. Tsukamoto, T. Suzuki, and Y. Kondo Synlett 2003 1105 1108
14. Y.-Q. Wu, D.C. Limburg, D.E. Wilkinson, and G.S. Hamilton J. Heterocycl. Chem. 40 2003 191 193
15. P.P. Seth, D.E. Robinson, E.A. Jefferson, and E.E. Swayze Tetrahedron Lett. 43 2002 7303 7306
16. N.W. Boaz Tetrahedron: Asymmetry 10 1999 813 816
17. R.V.S. Raju, R.S.S. Datla, and R.K. Sharma Protein Expr. Purif. 7 1996 431 437
18. D. Towler, and L. Glaser Proc. Natl. Acad. Sci. U.S.A. 83 1986 2812 2816
19. K.J. French, Y. Zhuang, R.S. Schrecengost, J.E. Copper, Z. Xia, and C.D. Smith J. Pharmacol. Exp. Ther. 309 2004 340 347
20. R.S. Bhatnagar, K. Fütterer, T.A. Farazi, S. Korolev, C.L. Murray, E. Jackson-Machelski, G.W. Gokei, J.I. Gordon, and G. Waksman Nat. Struct. Biol. 5 1998 1091 1097
21. P. Paderu, S. Park, and D.S. Perlin Antimicrob. Agents Chemother. 48 2004 3845 3849
22. lck have been reported in recent papers, see: J. Das, J. Lin, R.V. Moquin, Z. Shen, S.H. Spergel, J. Wityak, A.M. Doweyko, H.F. De Fex, Q. Fang, S. Pang, S. Pitt, D.R. Shen, G.L. Schieven, and J.C. Barrish Bioorg. Med. Chem. Lett. 13 2003 2145 2149
23. J. Das, R.V. Moquin, J. Lin, C. Liu, A.M. Doweyko, H.F. De Fex, S. Pang, S. Pitt, D.R. Shen, G.L. Schieven, J.C. Barrish, and J. Wityak Bioorg. Med. Chem. Lett. 13 2003 2587 2590
24. National Committee for Clinical Laboratory Standards; Reference Methods for Broth Dilution Antifungal Susceptibility Testing of Yeasts. Approval standard-2nd ed. Document M27-A2. National Committee for Clinical Laboratory Standards, Wayne, Pa; 2002