Novel route to chaetomellic acid A and analogues: Serendipitous discovery of a more competent FTase inhibitor

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 1, 2013, Pages 348-358

  Bellesia, Franco ^a   Choi, Seoung Ryoung ^b   Felluga, Fulvia ^c   Fiscaletti, Giuliano ^a   Ghelfi, Franco ^a   Menziani, Maria Cristina ^a   Parsons, Andrew F ^d   Poulter, C Dale ^b   Roncaglia, Fabrizio ^a   Sabbatini, Massimo ^e   Spinelli, Domenico ^f  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^b UNIVERSITY OF UTAH   (United States)

^c UNIVERSITY OF TRIESTE   (Italy)

^d UNIVERSITY OF YORK   (United Kingdom)

^e UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^f UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Chaetomellic acid A; Farnesyl pyrophosphate; FTase inhibitors; Modelling studies; Radical cyclization

Indexed keywords

1,1' (3,3' DISULFANEDIYLBIS(PROPANE 3,1 DIYL))BIS (3 METHYL 4 (NON 8 ENYL) 1H PYRROLE 2,5 DIONE); 1,1' [3,3' DISULFANEDIYLBIS(PROPANE 3,1 DIYL)]BIS (3 METHYL 4 TETRADECYL 1H PYRROLE 2,5 DIONE); 3 (2,2 DICHLOROPROPANOYL) 2 (DEC 9 ENYLIDENE) 1,3 THIAZINANE; 3 (2,2 DICHLOROPROPANOYL) 2 [10 (BUTYLTHIO)DECYLIDENE] 1,3 THIAZINANE; 3 (2,2 DICHLOROPROPANOYL) 2 PENTADECYLIDENE 1,3 THIAZINANE; 3 (9 (BUTYLTHIO)NONYL) 4 METHYLFURAN 2,5 DIONE; 3 METHYL 1 [3 (8 METHYL 6 OXO 7 TETRADECYL 3,4,6,8A TETRAHYDRO 2H PYRROLO [2,1 B] [1,3] THIAZIN 8A YLTHIO)PROPYL] 4 TETRADECYL 1H PYRROLE 2,5 DIONE; 3 METHYL 4 (NON 8 ENYL)FURAN 2,5 DIONE; BUTANE 1 THIOL 3 METHYL 4 (NON 8 ENYL)FURAN 2,5 DIONE; CHAETOMELLIC ACID A; ENZYME INHIBITOR; FARNESYL DIPHOSPHATE; UNCLASSIFIED DRUG;

ACUTE KIDNEY FAILURE; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING SITE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CONTROLLED STUDY; CYCLIZATION; DEPROTECTION REACTION; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; HYDROLYSIS; HYDROPHOBICITY; MASS SPECTROMETRY; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; PROTEIN PROCESSING; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; RAT; REPERFUSION INJURY; STEREOCHEMISTRY;

ANIMALS; CATALYSIS; COPPER; CYCLIZATION; ENZYME INHIBITORS; FARNESYLTRANSTRANSFERASE; MALEATES; MOLECULAR DOCKING SIMULATION; RATS; YEASTS;

EID: 84870877847     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.10.034     Document Type: Article

References (102)

1. D.M. Leonard J. Med. Chem. 40 1997 2971
2. L.A. Beck, T.J. Hosick, and M. Sinensky J. Cell Biol. 107 1988 1307
3. S.L. Wolda, and J.A. Glomset J. Biol. Chem. 263 1988 5997
4. K.T. Lane, and L.S. Beese J. Lipid Res. 47 2006 681
5. A.M. Winter-Vann, and P.J. Casey Nat. Rev. Cancer 5 2005 405
6. R.J. Anderegg, R. Betz, S.A. Carr, J.W. Crabb, and W. Duntze J. Biol. Chem. 263 1988 18236
7. C.C. Farnsworth, C.L. Wolda, M.H. Gelb, and J.A. Glomset J. Biol. Chem. 264 1989 20422
8. P.J. Casey, P.A. Solski, C.J. Der, and J.E. Buss Proc. Natl. Acad. Sci. U.S.A. 86 1989 8323
9. W.A. Maltese, and J.D. Robishaw J. Biol. Chem. 265 1990 18071
10. Y. Fukada, T. Takao, H. Ohguru, T. Yoshizawa, T. Akino, and Y. Shimonishi Nature (London) 346 1990 658
11. R.K. Lai, D. Perez-Sala, F.J. Canada, and R.R. Rando Proc. Natl. Acad. Sci. U.S.A. 87 1990 7673
12. S.L. Moores, M.D. Schaber, S.D. Mosser, E. Rands, M.B. O'Hara, V.M. Garsky, M.S. Marshall, D.L. Pompliano, and J.B. Gibbs J. Biol. Chem. 266 1991 14603
13. M. Chow, C.J. Der, and J.E. Buss Curr. Opin. Cell Biol. 4 1992 629
14. W.R. Schafer, and J. Rine Annu. Rev. Genet. 26 1992 209
15. J.F. Hancock, A.I. Magee, J.E. Chilad, and C.J. Marshall Cell 57 1989 1167
16. W.R. Schafer, R. Kim, R. Sterne, J. Thorner, S.H. Kim, and J. Rine Science 245 1989 379
17. J.B. Gibbs, A. Oliff, and N.E. Kohl Cell 77 1994 175
18. I.M. Bell J. Med. Chem. 47 2004 1869
19. V. Santagada, G. Caliendo, B. Severino, A. Lavecchia, E. Perissutti, F. Fiorino, A. Zampella, V. Sepe, D. Califano, G. Santelli, and E. Novellino J. Med. Chem. 49 2006 1882
20. S.F. Sousa, P.A. Fernandes, and M. Ramos J. Phys. Chem. B 112 2008 8681
21. P. Dunten, U. Kammlott, R. Crowther, D. Weber, R. Palermo, and J. Birktoft Biochemistry 37 1998 7907
22. D.L. Pompliano, M.D. Schaber, S.D. Mosser, C.A. Omer, J.A. Shafer, and J.B. Gibbs Biochemistry 32 1993 8348
23. J.D. Scholten, K. Zimmerman, M. Oxender, J. Sebolt-Leopold, R. Gowan, D. Leonard, and D.J. Hupe Bioorg. Med. Chem. 4 1996 1537
24. D. Vilella, M. Sánchez, G. Platas, O. Salazar, O. Genilloud, I. Royo, C. Cascales, I. Martin, T. Diez, K.C. Silverman, R.B. Lingham, S.B. Singh, H. Jayasuriya, and F. Peláez J. Ind. Microbiol. Biotech. 25 2000 315
25. S.B. Singh, D.L. Zink, J.M. Liesch, M.A. Goetz, R.G. Jenkins, M. Nallin-Omstead, K.C. Silverman, G.F. Bills, R.T. Mosley, J.B. Gibbs, G. Albers-Schonberg, and R.B. Lingham Tetrahedron 49 1993 5917
26. R.B. Lingham, K.C. Silvermann, G.F. Bills, C. Cascales, M. Sanchez, R.G. Jenkins, S.E. Gartner, I. Martin, M.T. Diez, F. Peláez, S. Mochales, Y.-L. Kong, R.W. Burg, M.S. Meinz, L. Huang, M. Nallin-Omstead, S.D. Mosser, M.D. Schaber, C.A. Omer, D.L. Pompliano, J.B. Gibbs, and S.B. Singh Appl. Microbiol. Biotechnol. 40 1993 370
27. J.B. Gibbs, D.L. Pompliano, S.D. Mosser, E. Rands, R.B. Lingham, S.B. Singh, E.M. Scolnick, N.E. Kohl, and A. Oliff J. Biol. Chem. 268 1993 7617
28. A.A. Scholte, L.M. Eubanks, C.D. Poulter, and J.C. Vederas Bioorg. Med. Chem. 12 2004 763
29. H. Andréa, I. Fischt, and T.J. Bach Physiol. Plant 110 2000 342
30. C.J.D. Mau, S. Garneau, A.A. Scholte, J.E. Van Fleet, J.C. Vederas, and K. Cornish Eur. J. Biochem. 270 2003 3939
31. S. Garneau, L. Qiao, L. Chen, S. Walker, and J.C. Vederas Bioorg. Med. Chem. 12 2004 6473
32. M. Sabattini, M. Santillo, A. Pisani, R. Paternò, F. Uccello, R. Serù, G. Matrone, G. Spagnuolo, M. Andreucci, V. Serio, P. Esposito, B. Cianciaruso, G. Fiano, and E.V. Avvedimento Am. J. Physiol. Renal Physiol. 290 2006 F1408
33. M. Sabattini, F. Uccello, V. Serio, G. Troncone, V. Varone, M. Andreucci, T. Faga, and A. Pisani Nephrol. Dial. Transplant. 25 2010 1443
34. A. Ruocco, M. Santillo, M. Cicale, R. Serù, G. Cuda, J. Anrather, C. Iadecola, A. Postiglione, E.V. Avvedimento, and R. Paternò Eur. J. Neurosci. 26 2007 3261
35. (a) Singh, S. B.; Bills, G. F.; Lingham, R. B.; Silverman, K. G.; Zink, D. L. EP 547671, 1992; Chem. Abstr. 1993, 119, 225753;
36. (b) Caskey, C. T.; Nishimura, S.; Yonemoto, M. WO 9701275, 1997; Chem. Abstr. 1997, 126, 171903.
37. E.S. Ratemi, J.M. Dolence, C.D. Poulter, and J.C. Vederas J. Org. Chem. 61 1996 6296
38. S. Poigny, M. Guyot, and M. Samadi J. Chem. Soc., Perkin Trans. 1 1997 2175
39. S.B. Desai, and N.P. Argade J. Org. Chem. 62 1997 4862
40. A.M. Deshpande, A.A. Natu, and N.P. Argade J. Org. Chem. 63 1998 9557
41. R.M. Slade, and B.P. Branchaud J. Org. Chem. 63 1998 3544
42. A. Kar, and N.P. Argade J. Org. Chem. 67 2002 7131
43. K.P. Haval, and N.P. Argade J. Org. Chem. 73 2008 6936
44. U.A. Kshirsagar, and N.P. Argade Synthesis 2011 1804
45. N.P. Argade, and R.H. Naik Bioorg. Med. Chem. 4 1996 881
46. M.J. Kates, and J.H. Schauble J. Org. Chem. 61 1996 4164
47. S.B. Singh, H. Jayasuriya, K.C. Silverman, C.A. Bonfiglio, J.M. Williamson, and R.B. Lingham Bioorg. Med. Chem. 8 2000 571
48. M. Takimoto, M. Kawamura, M. Mori, and Y. Sato Synlett 2005 2019
49. T. Yoshimitsu, Y. Arano, T. Kaji, T. Ino, H. Nagaoka, and T. Tanaka Heterocycles 77 2009 179
50. L. De Buyck, R. Cagnoli, F. Ghelfi, G. Merighi, A. Mucci, U.M. Pagnoni, and A.F. Parsons Synthesis 2004 1680
51. F. Bellesia, C. Danieli, L. De Buyck, R. Galeazzi, F. Ghelfi, A. Mucci, M. Orena, U.M. Pagnoni, A.F. Parsons, and F. Roncaglia Tetrahedron 62 2006 746
52. F. Ghelfi, M. Pattarozzi, F. Roncaglia, V. Giangiordano, and A.F. Parsons Synth. Commun. 40 2010 1040
53. F. Ghelfi, M. Pattarozzi, F. Roncaglia, A.F. Parsons, F. Felluga, U.M. Pagnoni, E. Valentin, A. Mucci, and F. Bellesia Synthesis 2008 3131
54. M. Pattarozzi, F. Ghelfi, F. Roncaglia, U.M. Pagnoni, and A.F. Parsons Synlett 2009 2172
55. A. Cornia, F. Felluga, V. Frenna, F. Ghelfi, A.F. Parsons, M. Pattarozzi, F. Roncaglia, and D. Spinelli Tetrahedron 68 2012 5863
56. F. Bellesia, F. D'Anna, F. Felluga, V. Frenna, F. Ghelfi, A.F. Parsons, and D. Spinelli Synthesis 2012 605
57. C. Fuganti, F.G. Gatti, and S. Serra Tetrahedron 63 2007 4762
58. A.R. Hajipour, A. Zarei, L. Khazdooz, and A.E. Ruoho Synthesis 2006 1480
59. T. Ozturk, E. Ertas, and O. Mert Chem. Rev. 110 2010 3419
60. T.J. Curphey J. Org. Chem. 67 2002 6461
61. L. Forti, F. Ghelfi, R. Grandi, E. Libertini, and U.M. Pagnoni Synth. Commun. 26 1996 3517
62. J.K. Kim, Y. Souma, N. Beutow, C. Ibbeson, and M.C. Caserio J. Org. Chem. 54 1989 1714
63. von K. Thewalt, and G. Renchhoff Fette Seifen Anstrichmittel 70 1968 648
64. P.G.M. Wuts, and T.W. Greene Greene's Protective Groups in Organic Synthesis 4th ed. 2007 Wiley Interscience New York pp 477-500
65. H. Kim, and J. Hong Org. Lett. 12 2010 2880
66. N.C. Ganguly, and S.K. Barik Synthesis 2009 1393
67. W.-M. Dai, G. Feng, J. Wu, and L. Sun Synlett 2008 1013
68. M. Kirihara, A. Harano, H. Tsukiji, R. Takizawa, T. Uchiyama, and A. Hatano Tetrahedron Lett. 46 2005 6377
69. A. De Brauwere, W. Baeyens, F. De Ridder, and M. Elskens Talanta 80 2009 1034
70. G. Franc, and A.K. Kakkar Chem. Soc. Rev. 39 2010 1536
71. A.B. Lowe Polym. Chem. 1 2010 17
72. C.E. Hoyle, and C.N. Bowman Angew. Chem., Int. Ed. 49 2010 1540
73. K. Griesbaum Angew. Chem., Int. Ed. 9 1970 273
74. M. Van der Steen, and C.V. Stevens ChemSusChem 2 2009 692
75. V.S. Dalavoy, and U.R. Nayak J. Sci. Ind. Res. 40 1981 520
76. H. Mutlu, and M.A.R. Meier Eur. J. Lipid Sci. Technol. 112 2010 10
77. D.S. Ogunniyi Bioresour. Technol. 97 2006 1086
78. O. Ito, and M.D.C.M. Fleming J. Chem. Soc., Perkin Trans. 2 1989 689
79. O. Ito, and M. Matsuda J. Am. Chem. Soc. 101 1979 5732
80. B. Giese Angew. Chem., Int. Ed. 22 1983 753
81. A.-P. Schaffner, and P. Renaud Eur. J. Org. Chem. 2004 2291
82. C. Ollivier, and P. Renaud Chem. Rev. 101 2001 3415
83. D.L. Pompliano, R.P. Gomez, and N.J. Anthony J. Am. Chem. Soc. 114 1992 7945
84. P.B. Cassidy, J.M. Dolence, and C.D. Poulter Methods Enzymol. 250 1995 30
85. C. Bolchi, M. Pallavicini, S.K. Bernini, S. Chiodini, A. Corsini, N. Ferri, L. Fumagalli, V. Straniero, and E. Valoti Bioorg. Med. Chem. Lett. 21 2011 5408
86. J.L. Houghland, C.L. Lamphear, S.A. Scott, R.A. Gibbs, and C.A. Fierke Biochemistry 48 2009 1691
87. D.V. Patel, R.J. Schmidt, S.A. Biller, E.M. Gordon, S.S. Robinson, and V. Manne J. Med. Chem. 38 1995 2906
88. S.B. Long, P.J. Casey, and L.S. Beese Biochemistry 37 1998 9612
89. T.S. Reid, K.L. Terry, P.J. Casey, and L.S. Beese J. Mol. Biol. 343 2004 417
90. C.L. Strickland, W.T. Windsor, R. Syto, L. Wang, R. Bond, Z. Wu, J. Schwartz, H.V. Le, L.S. Beese, and P.C. Weber Biochemistry 37 1998 16601
91. K.F. Brameld, B. Kuhn, D.C. Reuter, and M. Stahl J. Chem. Inf. Model. 48 2008 1
92. J. Drabowicz, B. Bujnicki, and M. Mikolajczyk J. Lab. Compd. Radiopharm. 46 2003 1001
93. L.-P. Guan, X. Sui, X.-Q. Deng, D.-H. Zhao, Y.-L. Qu, and Z.-S. Quan Med. Chem. Res. 20 2011 601
94. G. Shen, H. Fang, Y. Song, A.A. Bielska, Z. Wang, and J.-S.A. Taylor Bioconjugate Chem. 20 2009 1729
95. K.J. Fraunhoffer, N. Prabagaran, L.E. Sirois, and C. White J. Am. Chem. Soc. 128 2006 9032
96. J.H. Dodd, J. Guan, and C.F. Schwender Synth. Commun. 23 1993 1003
97. H. Yasuda, Y. Uenoyama, O. Nobuta, S. Kobayashi, and I. Ryu Tetrahedron Lett. 49 2008 367
98. Q.B. Broxterman, B. Kaptein, J. Kamphuis, and H.E. Schoemaker J. Org. Chem. 57 1992 6286
99. M.S. Kharasch, J. Read, and F.R. Mayo Chem. Ind. 57 1938 752
100. M.P. Mayer, G.D. Prestwich, J.M. Dolence, P.D. Bond, H.-W. Wu, and C.D. Poulter Gene 132 1993 41
101. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne Nucleic Acids Res. 28 2000 235
102. B.R. Brooks, R.E. Bruccoleri, B.D. Olafson, D.J. States, S. Swaminathan, and M. Karplus J. Comput. Chem. 4 1983 187