Journal of the American Chemical Society
Article
Kassack, M. U.; Schepmann, D.; Wunsch, B.; Jurva, U.; Wellner, E.
̈
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
ChemMedChem 2008, 3, 152−164.
S
(6) (a) Bains, W.; Tacke, R. Curr. Opin. Drug Discov. Devel. 2003, 6,
526−543. (b) Pooni, P. K.; Showell, G. A. Mini-Rev. Med. Chem. 2006,
6, 1169−1177. (c) Tacke, R.; Dorrich, S.; Topics in Medicinal
̈
Chemistry; Springer: Berlin/Heidelberg, 2014; Vol. 55, pp 1−31.
(7) (a) Sieburth, S. M.; Manly, C. J.; Gammon, D. W. Pestic. Sci.
1990, 28, 289−307. (b) Moberg, W. K.; Basarab, G. S.; Cuomo, J.;
Liang, P. H. Synth. Chem. Agrochem. 1987, 355, 288−301.
(8) (a) Shishkina, A. A.; Ivanenko, T. I.; Zarubina, N. A.; Volzhina,
O. N.; Angarskaya, V. G.; Pivnitskii, K. K. Pharm. Chem. J. 1986, 20,
143−148. (b) Lukevics, E.; Ignatovich, L. Appl. Organomet. Chem.
1992, 6, 113−126.
(9) (a) Lesuisse, D.; Lange, G.; Deprez, P.; Benard, D.; Schoot, B.;
Delettre, G.; Marquette, J.-P.; Broto, P.; Jean-Baptiste, V.; Bichet, P.;
Sarubbi, E.; Mandine, E. J. Med. Chem. 2002, 45, 2379−2387.
(b) Hajduk, P. J.; Greer, J. Nat. Rev. Drug Discovery 2007, 6, 211−219.
(c) Jacoby, E.; Davies, J.; Blommers, M. Curr. Top. Med. Chem. 2003,
3, 11−23. (d) Carr, R. A. E.; Congreve, M.; Murray, C. W.; Rees, D. C.
Drug Discovery Today 2005, 10, 987−992.
General experimental information, detailed experimental
procedures, characterization data, NMR spectra, compu-
tational data, biological protocols, additional figures,
schemes, and tables (PDF)
AUTHOR INFORMATION
Corresponding Author
ORCID
■
Notes
The authors declare no competing financial interest.
(10) Bulman Page, P. C.; McKenzie, M. J.; Klair, S. S.; Rosenthal, S.
Acyl Silanes. In The Chemistry of Organic Silicon Compounds;
Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; Vol. 2, pp
1599−1665.
ACKNOWLEDGMENTS
■
This work was generously supported by Janssen Research and
Development LLC, San Diego; particular appreciation for
advice and assistance is owed to Curt Dvorak and Nicholas
Carruthers. We are indebted to Andrew F. Zahrt for the free-
energy calculations and computational modeling. We are also
grateful for the support services of the NMR and mass
spectrometry laboratories of the University of Illinois at
Urbana−Champaign. Additionally, special thanks to Lucas W.
Hernandez, Sean McCarty, and Kuo Zhao for their assistance.
(11) (a) Wieber, M.; Schmidt, M. J. Organomet. Chem. 1963, 1, 22−
27. (b) Voss, P.; Meinicke, C.; Popowski, E.; Kelling, H. J. Prakt. Chem.
1978, 320, 34−42. (c) Nikonov, A. Y.; Sterkhova, I. V.; Lazarev, I. M.;
Albanov, A. I.; Lazareva, N. F. J. Mol. Struct. 2016, 1122, 10−17.
(d) Simmler, W. Chem. Ber. 1963, 96, 349−356. (e) Simmler, W.;
Walz, H.; Niederprum, H. Chem. Ber. 1963, 96, 1495−1504.
̈
(f) Mironov, V. F.; Fedotov, N. S.; Rybalka, I. G. Khim. Geterotsikl.
1968, 1124−1127.
(12) (a) Smith, R. J.; Bienz, S. Helv. Chim. Acta 2004, 87, 1681−
1696. (b) Anteunis, M. J. O.; Dedeyne, R. Org. Magn. Reson. 1977, 9,
127−132. (c) Dedeyne, R.; Anteunis, M. J. O. Bull. Soc. Chim. Belg.
1976, 85, 319−331. (d) Shainyan, B. A.; Kirpichenko, S. V.;
Kleinpeter, E. Arkivoc 2012, 175−185. (e) Jachak, G. R.; Ramesh,
R.; Sant, D. G.; Jorwekar, S. U.; Jadhav, M. R.; Tupe, S. G.;
Deshpande, M. V.; Reddy, D. S. ACS Med. Chem. Lett. 2015, 6, 1111−
1116.
REFERENCES
■
(1) (a) Franz, A. K.; Wilson, S. O. J. Med. Chem. 2013, 56, 388−405.
(b) Tacke, R.; Wannagat, U. In Bioactive Organo-Silicon Compounds;
Springer: Berlin/Heidelberg, 1979; Vol. 84. (c) Meanwell, N. A. J.
Med. Chem. 2011, 54, 2529−2591. (d) Allred, A. L.; Rochow, E. G. J.
Inorg. Nucl. Chem. 1958, 5, 269−288. (e) Sekhon, B. S. Res. Pharm. Sci.
2013, 8, 145−158. (f) Corey, J. Y. Historical overview and comparison
of silicon with carbon. In The Chemistry of Organic Silicon Compounds;
Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1989; Vols. 1 and 2,
pp 1−56.
(13) Sato, Y.; Fukami, Y.; Shirai, H. J. Organomet. Chem. 1974, 78,
75−81.
(14) We generally define “complex decomposition” as the formation
of multiple inseparable products, the identities or quantities of which
could not be determined by either NMR or mass spectrometry.
(2) (a) Deerenberg, S.; Schakel, M.; Keijzer, A. H. J. F. d.;
Kranenburg, M.; Lutz, M.; Spek, A. L.; Lammertsma, K. Chem.
Commun. 2002, 348−349. (b) Marciniec, B.; Chojnowski, J. Progress in
Organosilicon Chemistry; Gordon and Breach: Basel, Switzerland, 1995.
(3) (a) Liu, C. T.; Tomsho, J. W.; Benkovic, S. J. Bioorg. Med. Chem.
2014, 22, 4462−4473. (b) Ding, D.; Zhao, Y.; Meng, Q.; Xie, D.;
Nare, B.; Chen, D.; Bacchi, C. J.; Yarlett, N.; Zhang, Y.-K.; Hernandez,
V.; Xia, Y.; Freund, Y.; Abdulla, M.; Ang, K.-H.; Ratnam, J.;
McKerrow, J.-H.; Jacobs, R. T.; Zhou, H.; Plattner, J. J. ACS Med.
Chem. Lett. 2010, 1, 165−169. (c) Tomsho, J. W.; Pal, A.; Hall, D. G.;
Benkovic, S. J. ACS Med. Chem. Lett. 2012, 3, 48−52. (d) Whyte, G.;
Vilar, R.; Woscholski, R. J. Chem. Biol. 2013, 6, 161−174. (e) Zhang, J.;
Zhu, M.; Lin, Y.; Zhou, H. Sci. China: Chem. 2013, 56, 1372−1381.
(4) (a) Mills, J. S.; Showell, G. A. Expert Opin. Invest. Drugs 2004, 13,
1149−1157. (b) Showell, G. A.; Mills, J. S. Drug Discovery Today 2003,
8, 551−556. (c) Singh, S.; Sieburth, S. M. Org. Lett. 2012, 14, 4422−
4425. (d) Kim, J.; Hewitt, G.; Carroll, P.; Sieburth, P. J. Org. Chem.
2005, 70, 5781−5789. (e) Schramm, V. L. Annu. Rev. Biochem. 1998,
67, 693−720. (f) Schramm, V. L. Annu. Rev. Biochem. 2011, 80, 703−
732. (g) Schramm, V. L. ACS Chem. Biol. 2013, 8, 71−81.
(h) Silverman, R. B. The organic chemistry of drug design and drug
action, 2nd ed.; Elsevier Academic Press: Amsterdam/Boston, 2004.
(5) (a) Sieburth, S. M. Designing Safer Chemicals 1996, 640, 74−83.
(b) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher,
A.; Kassack, M. U. Organometallics 2004, 23, 4468−4477. (c) Tacke,
̀
(15) (a) Mignani, S.; Damour, D.; Doble, A.; Labaudiniere, R.;
Malleron, J.-L.; Piot, O.; Gueremy, C. Bioorg. Med. Chem. Lett. 1993, 3,
1913−1918. (b) Damour, D.; Labaudiniere, R.; Malleron, J.-L.;
Mignani, S. French Patent FR2675801(A1), Oct 30, 1992.
(16) Moody, C. J.; Taylor, R. J. J. Chem. Soc., Perkin Trans. 1 1989,
721−731.
(17) (a) Takeuchi, Y.; Ogura, H.; Kanada, A.; Koizumi, T. J. Org.
Chem. 1992, 57, 2196−2199. (b) Katritzky, A. R.; Abdel-Fattah, A. A.
A.; Vakulenko, A. V.; Tao, H. J. Org. Chem. 2005, 70, 9191−9197.
(18) Shi, S.-L.; Wei, X.-F.; Shimizu, Y.; Kanai, M. J. Am. Chem. Soc.
2012, 134, 17019−17022.
(19) (a) Boddaert, T.; Franco
Meerpoel, L.; Angibaud, P.; Durandetti, M.; Maddaluno, J. Chem. -
is, C.; Boddaert, T.;
̧ is, C.; Mistico, L.; Querolle, O.;
Eur. J. 2014, 20, 10131−10139. (b) Franco
̧
Durandetti, M.; Querolle, O.; Van Hijfte, L.; Meerpoel, L.; Angibaud,
P.; Maddaluno, J. Org. Lett. 2012, 14, 2074−2077.
(20) (a) Meyers, A. I.; Hellring, S. Tetrahedron Lett. 1981, 22, 5119−
5122. (b) Meyers, A. I.; Milot, G. J. Org. Chem. 1993, 58, 6538−6549.
(21) (a) Cooper, B. E.; Owen, W. J. J. Organomet. Chem. 1971, 29,
33−40. (b) Yoshida, J.-I.; Maekawa, T.; Murata, T.; Matsunaga, S.-I.;
Isoe, S. J. Am. Chem. Soc. 1990, 112, 1962−1970. (c) Yoshida, J.-I.;
Isoe, S. Tetrahedron Lett. 1987, 28, 6621−6624. (d) Yoon, U. C.;
Mariano, P. S. Acc. Chem. Res. 1992, 25, 233−240.
R.; Popp, F.; Muller, B.; Theis, B.; Burschka, C.; Hamacher, A.;
̈
P
J. Am. Chem. Soc. XXXX, XXX, XXX−XXX