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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

Construction of the CSIRO Fragment Library

Craig L. Francis A , Peter W. Kenny B , Olan Dolezal B , Simon Saubern A , Megan Kruger A , G. Paul Savage A , Thomas S. Peat B C and John H. Ryan A C
+ Author Affiliations
- Author Affiliations

A CSIRO Materials Science and Engineering, Bayview Avenue, Clayton, Vic. 3168, Australia.

B CSIRO Materials Science and Engineering, 343 Royal Parade, Parkville, Vic. 3052, Australia.

C Corresponding authors. Email: tom.peat@csiro.au; jack.ryan@csiro.au

Australian Journal of Chemistry 66(12) 1473-1482 https://doi.org/10.1071/CH13325
Submitted: 25 June 2013  Accepted: 12 September 2013   Published: 17 October 2013

Abstract

A fundamental component of a successful fragment screening program is a productive fragment library, one that delivers hit fragments with potential for pharmaceutical development. A proprietary fragment library was developed by identifying and extracting subsets of CSIRO’s Compound Collection using two complimentary approaches. Over time, the use of surface plasmon resonance as a front-line screening tool has enabled identification and exclusion of problematic compounds and led to a more reliable fragment screening library.


References

[1]  T. V. Hughes, I. Baldwin, I. Churcher, International Drug Discovery 2011, 6, 34.
         | 1:CAS:528:DC%2BC38XhtVClt7k%3D&md5=deab71fe1b133e6c4188dc2a0c36ce2dCAS |

[2]  J. Tsai, J. T. Lee, W. Wang, J. Zhang, H. Cho, S. Mamo, R. Bremer, S. Gillette, J. Kong, N. K. Haass, K. Sproesser, L. Li, K. S. M. Smalley, D. Fong, Y.-L. Zhu, A. Marimuthu, H. Nguyen, B. Lam, J. Liu, I. Cheung, J. Rice, Y. Suzuki, C. Luu, C. Settachatgul, R. Shellooe, J. Cantwell, S.-H. Kim, J. Schlessinger, K. Y. J. Zhang, B. L. West, B. Powell, G. Habets, C. Zhang, P. N. Ibrahim, P. Hirth, D. R. Artis, M. Herlyn, G. Bollag, Proc. Natl. Acad. Sci. USA 2008, 105, 3041.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjtVSitrk%3D&md5=f55aba0c859344d2b26ba6a77cc3eefeCAS | 18287029PubMed |

[3]  G. Bollag, P. Hirth, J. Tsai, J. Zhang, P. N. Ibrahim, H. Cho, W. Spevak, C. Zhang, Y. Zhang, G. Habets, E. A. Burton, B. Wong, G. Tsang, B. L. West, B. Powell, R. Shellooe, A. Marimuthu, H. Nguyen, K. Y. J. Zhang, D. R. Artis, J. Schlessinger, F. Su, B. Higgins, R. Iyer, K. D’Andrea, A. Koehler, M. Stumm, P. S. Lin, R. J. Lee, J. Grippo, I. Puzanov, K. B. Kim, A. Ribas, G. A. McArthur, J. A. Sosman, P. B. Chapman, K. T. Flaherty, X. Xu, K. L. Nathanson, K. Nolop, Nature 2010, 467, 596.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1ajtbfK&md5=7013e9a231333a70eb593597f24bf61eCAS | 20823850PubMed |

[4]  D. E. Scott, A. G. Coyne, S. A. Hudson, C. Abell, Biochemistry 2012, 51, 4990.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XosV2qsLY%3D&md5=030bf432b8b339185a4d728a226abbdaCAS | 22697260PubMed |

[5]  A. Schuffenhauer, S. Ruedisser, A. L. Marzinzik, W. Jahnke, M. Blommers, P. Selzer, E. Jacoby, Curr. Top. Med. Chem. 2005, 5, 751.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXpsFGht78%3D&md5=6d34ee45ae9d1d7ca504b170cefa20e3CAS | 16101415PubMed |

[6]  I.-J. Chen, R. E. Hubbard, J. Comput. Aided Mol. Des. 2009, 23, 603.
         | Crossref | GoogleScholarGoogle Scholar | 19495994PubMed |

[7]  S. M. Boyd, G. E. de Kloe, Drug Discov. Today: Technol. 2010, 7, e173.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVegsLs%3D&md5=61fa1ae20a91d344c38899375db4c0a9CAS |

[8]  N. Baurin, F. Aboul-Ela, X. Barril, B. Davis, M. Drysdale, B. Dymock, H. Finch, C. Fromont, C. Richardson, H. Simmonite, R. E. Hubbard, J. Chem. Inf. Comput. Sci. 2004, 44, 2157.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXotlaru78%3D&md5=ca9944f6cf28590bdb248cd8616f6b6fCAS | 15554686PubMed |

[9]  B. A. Tounge, M. H. Parker, in Methods in Enzymology (Ed. L. C. Kuo) 2011, Vol. 493, Ch. 1. pp. 3–20 (Elsevier: Amsterdam).

[10]  J. Barker, S. Courtney, T. Hesterkamp, D. Ullmann, M. Whittaker, Expert Opin. Drug Dis. 2006, 1, 225.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XpvVyjurc%3D&md5=488efa5836ae997979c7528ea64081ffCAS |

[11]  C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Deliv. Rev. 1997, 23, 3.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXktlKlsQ%3D%3D&md5=80a15d2724291c04488c40d4b5be7db6CAS |

[12]  C. A. Lipinski, Drug Discov. Today: Technol. 2004, 1, 337.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtlSqsrg%3D&md5=0cc27e5105fc9ff2102da48397cefbe7CAS |

[13]  M. Congreve, R. Carr, C. Murray, H. Jhoti, Drug Discov. Today 2003, 8, 876.
         | Crossref | GoogleScholarGoogle Scholar | 14554012PubMed |

[14]  G. Siegal, E. AB, J. Shultz, Drug Discov. Today 2007, 12, 1032.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVSmurnI&md5=5ce4a6f9098452c07152435d2169a213CAS | 18061882PubMed |

[15]  G. M. Rishton, Drug Discov. Today 2003, 8, 86.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXmt1ansQ%3D%3D&md5=195c29aee55b6a9a4f8a4afebe4f2414CAS | 12565011PubMed |

[16]  P. J. Edwards, C. Sturino, Curr. Med. Chem. 2011, 18, 3116.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXpsl2qsr4%3D&md5=16d17f1c4d436a68b6804483e17f96feCAS | 21651480PubMed |

[17]  N. A. Meanwell, J. Med. Chem. 2011, 54, 2529.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjsVCnu7o%3D&md5=7ed0104849009c3209a6b76eea158406CAS | 21413808PubMed |

[18]  S. W. Muchmore, J. J. Edmunds, K. D. Stewart, P. J. Hadjuk, J. Med. Chem. 2010, 53, 4830.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjvVaru7k%3D&md5=2c10f8015ed3fffa885b64202318f27fCAS | 20329801PubMed |

[19]  J. Wielens, S. J. Headey, D. I. Rhodes, R. J. Mulder, O. Dolezal, J. J. Deadman, J. Newman, D. K. Chalmers, M. W. Parker, T. S. Peat, M. J. Scanlon, J. Biomol. Screen. 2013, 18, 147.
         | Crossref | GoogleScholarGoogle Scholar | 23139382PubMed |

[20]  T. S. Peat, D. I. Rhodes, N. Vandegraaff, G. Le, E. D. Jones, J. Smith, J. A. V. Coates, N. Thienthong, J. Newman, O. Dolezal, J. H. Ryan, G. P. Savage, C. L. Francis, J. J. Deadman, PLoS ONE 2012, 7, e40147.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVGmtrfI&md5=f5671c1f8aa85b4ace9448633bc09851CAS | 22808106PubMed |

[21]  J. Newman, O. Dolezal, V. Fazio, T. Caradoc-Davies, T. S. Peat, J. Comput. Aided Mol. Des. 2012, 26, 497.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XptFCgtLw%3D&md5=b3d6c671e7a5550d89b7c0dcbf1dea07CAS | 22187139PubMed |

[22]  D. I. Rhodes, T. S. Peat, N. Vandegraaff, D. Jeevarajah, G. Le, E. D. Jones, J. A. Smith, J. A. V. Coates, L. J. Winfield, N. Thienthong, J. Newman, D. Lucent, J. H. Ryan, G. P. Savage, C. L. Francis, J. J. Deadman, Antivir. Chem. Chemother. 2011, 21, 155.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXivF2mtLc%3D&md5=9fe6bef6d64f384ed3d8313c4c99f2f8CAS | 21602613PubMed |

[23]  M. Vieth, M. G. Siegel, R. E. Higgs, I. A. Watson, D. H. Robertson, K. A. Savin, G. L. Durst, P. A. Hipskind, J. Med. Chem. 2004, 47, 224.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXptlGqurk%3D&md5=8c807f6b93460717dfdf372d4c9a2587CAS | 14695836PubMed |

[24]  G. W. Bemis, M. A. Murcko, J. Med. Chem. 1996, 39, 2887.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XjvVejtro%3D&md5=7a62ebaf060072217a7929cdd6833989CAS | 8709122PubMed |

[25]  N. Schindler, Chem. Ber. 1973, 106, 56.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXosVajuw%3D%3D&md5=28224c8e667e7246b71fe4a8a166fdf3CAS |

[26]  L. N. Markovskii, Y. G. Shermolovich, V. I. Shevchenko, J. Org. Chem. USSR (Engl. Transl.) 1973, 9, 644.
         | 1:CAS:528:DyaE3sXhtlKhtrw%3D&md5=442bdf1b25f50756c50ee9b44d564058CAS |

[27]  L. N. Markovskii, Y. G. Shermolovich, V. I. Shevchenko, J. Org. Chem. USSR (Engl. Transl.) 1974, 10, 492.

[28]  M. Knollmüller, P. Kosma, Monatsh. Chem. 1985, 116, 1321.
         | Crossref | GoogleScholarGoogle Scholar |

[29]  H. Schröder, E. Fischer, M. Michalik, J. Prakt. Chem. 1988, 330, 900.
         | Crossref | GoogleScholarGoogle Scholar |

[30]  G. D. Fallon, S. Jahangiri, A. J. Liepa, R. C. J. Woodgate, Aust. J. Chem. 2005, 58, 332.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjvV2ksbg%3D&md5=8065b0728046dba5314fb8448062a636CAS |

[31]  C. M. Forsyth, C. L. Francis, S. Jahangiri, A. J. Liepa, M. V. Perkins, A. P. Young, Aust. J. Chem. 2010, 63, 785.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmtlGjtL8%3D&md5=e87f2ad9e9cd62f7bc559b6be69677d1CAS |

[32]  (a) G. D. Fallon, C. L. Francis, K. Johansson, A. J. Liepa, R. C. J. Woodgate, Aust. J. Chem. 2005, 58, 891.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtlejsL3O&md5=f63e8a85ecabd36dfd1985ff12e60c0fCAS |
      (b) T. Cablewski, E. J. Carter, C. L. Francis, A. J. Liepa, M. V. Perkins, Aust. J. Chem. 2007, 60, 105.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) T. Cablewski, C. L. Francis, A. J. Liepa, Aust. J. Chem. 2008, 61, 59.
         | Crossref | GoogleScholarGoogle Scholar |

[33]  T. Cablewski, C. L. Francis, A. J. Liepa, Aust. J. Chem. 2008, 61, 332.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXmtFGgt7Y%3D&md5=93602f868f5946ee6a74ffe19b380fa9CAS |

[34]  C. M. Forsyth, C. L. Francis, S. Jahangiri, A. J. Liepa, M. V. Perkins, A. P. Young, Aust. J. Chem. 2010, 63, 659.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXksFSgtL0%3D&md5=84c1c8baac6806c58c3c14f94f1391b5CAS |

[35]  T. Cablewski, C. L. Francis, A. J. Liepa, Aust. J. Chem. 2007, 60, 113.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhs1yqt7o%3D&md5=76a194149329a95bf31f61172cdf3d2eCAS |

[36]  T. Cablewski, C. M. Forsyth, C. L. Francis, A. J. Liepa, V. Tran, Aust. J. Chem. 2008, 61, 785.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1Siu7nF&md5=9840b7c4a25411a34416f24fccf2918cCAS |

[37]  G. W. Bemis, M. A. Murcko, J. Med. Chem. 1999, 42, 5095.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXnsFymtLw%3D&md5=4004e73bb16100bcc54c4203c6025d59CAS | 10602694PubMed |

[38]  N. Blomberg, D. A. Cosgrove, P. W. Kenny, K. Kolmodin, J. Comput. Aided Mol. Des. 2009, 23, 513.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXot1Gmur8%3D&md5=ded0a21b07af5db1d31d1c2a33459e56CAS | 19283339PubMed |

[39]  S. M. A. R. T. S. Theory Manual (Daylight Chemical Information Systems, Inc.: Laguna Niguel, CA). Available at http://www.daylight.com/dayhtml/doc/theory/theory.smarts.html (accessed 16 December 2012).

[40]  B. J. Davis, D. A. Erlanson, Bioorg. Med. Chem. Lett. 2013, 23, 2844.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXltlOns7s%3D&md5=3c69458b6ebf979de109ae610fcd898dCAS | 23562240PubMed |

[41]  C. Engeloch, U. Schopfer, I. Muckenschnabel, F. Le Goff, H. Mees, K. Boesch, M. Popov, J. Biomol. Screen. 2008, 13, 999.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXkslGrtr4%3D&md5=1c6cbf32bed8aabb1ab6f95bcf35789cCAS | 19029012PubMed |

[42]  S. J. Lane, D. S. Eggleston, K. A. Brinded, J. C. Hollerton, N. L. Taylor, S. A. Readshaw, Drug Discov. Today 2006, 11, 267.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XjtFagsbc%3D&md5=7a15d5f2ce02f774571078671fda1c48CAS | 16580604PubMed |

[43]  P. E. Ilouga, D. Winkler, C. Kirchhoff, B. Schierholz, J. Wölcke, J. Biomol. Screen. 2007, 12, 21.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXjtFGgsrk%3D&md5=8ce2cda033b4e4a79ad7ee4c47c3535dCAS | 17099243PubMed |

[44]  O. Dolezal, L. Doughty, M. K. Hattarki, V. J. Fazio, T. T. Caradoc-Davies, J. Newman, T. S. Peat, Aust. J. Chem. 2013, 66, 1507.
         | Crossref | GoogleScholarGoogle Scholar |

[45]  G. A. Papalia, M. Baer, K. Luehrsen, H. Nordin, P. Flynn, D. G. Myszka, Anal. Biochem. 2006, 359, 112.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1Sjs7rO&md5=c85b0685e005a82f4b7d4ad4f98ff032CAS | 17027901PubMed |

[46]  T. Bravman, V. Bronner, K. Lavie, A. Notcovich, G. A. Papalia, D. G. Myszka, Anal. Biochem. 2006, 358, 281.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFSksL7K&md5=1ff8a8ef99326cbb605fc1e887e3c66cCAS | 16962556PubMed |

[47]  A. M. Giannetti, B. D. Koch, M. F. Browner, J. Med. Chem. 2008, 51, 574.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjt1entg%3D%3D&md5=df07996f2b663d8e23a25ff70a89e963CAS | 18181566PubMed |

[48]  S. L. McGovern, B. K. Shoichet, J. Med. Chem. 2003, 46, 1478.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhvFeksLs%3D&md5=dd0ffc568d550992402f48008d7351dcCAS | 12672248PubMed |

[49]  H. Nordin, M. Jungnelius, R. Karlsson, O. P. Karlsson, Anal. Biochem. 2005, 340, 359.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjtlWqtbk%3D&md5=6bfae7da410d4f2f0c39a65f019659daCAS | 15840510PubMed |

[50]  H. Ohno, K. Kubo, H. Murooka, Y. Kobayashi, T. Nishitoba, M. Shibuya, T. Yoneda, T. Isoe, Mol. Cancer Ther. 2006, 5, 2634.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1els7jF&md5=1418722d230b1c57c2c8e4200c0130f1CAS | 17121910PubMed |

[51]  R. Karlsson, P. S. Katsamba, H. Nordin, E. Pol, D. G. Myszka, Anal. Biochem. 2006, 349, 136.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XotVGmtg%3D%3D&md5=efb6daacdbad92140fdc361e8a0937e7CAS | 16337141PubMed |

[52]  M. Zender, T. Klein, C. Henn, B. Kirsch, C. K. Maurer, D. Kail, C. Ritter, O. Dolezal, A. Steinbach, R. W. Hartmann, J. Med. Chem. 2013, 56, 6761.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1Wlt7jI&md5=52991cb106bdd8db43a4e6430f8e51a0CAS | 23919758PubMed |

[53]  R. E. Hubbard, J. B. Murray, Methods in Enzymol. 2011, 493, 509.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXoslers70%3D&md5=52a299bf4f4841140ac791aca2bc4319CAS |

[54]  J. Clardy, C. Walsh, Nature 2004, 432, 829.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVOht7jP&md5=b6a14ec4a09ce807ae44e2ecf94951a6CAS | 15602548PubMed |

[55]  P. J. Hajduk, J. Greer, Nat. Rev. Drug Discov. 2007, 6, 211.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXit12rtr4%3D&md5=9b633b9505974f9f6a71c476120c0d78CAS | 17290284PubMed |

[56]  A. W. Hung, A. Ramek, Y. Wang, T. Kaya, J. A. Wilson, P. A. Clemons, D. W. Young, Proc. Natl. Acad. Sci. USA 2011, 108, 6799.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXlslyru7k%3D&md5=f889684902809627394b8dd2c87360e2CAS | 21482811PubMed |

[57]  S. M. Pereira, G. P. Savage, G. W. Simpson, R. J. Greenwood, M. F. Mackay, Aust. J. Chem. 1993, 46, 1401.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXitFOgtbY%3D&md5=dcc40d60ce1f63e7cc526d47b99f1c6eCAS |

[58]  C. K. Y. Lee, C. J. Easton, G. P. Savage, G. W. Simpson, ARKIVOC 2006, 3, 175.

[59]  B. M. Kelly-Basetti, M. F. Mackay, S. M. Pereira, G. P. Savage, G. W. Simpson, Heterocycles 1994, 37, 529.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXkvVeqsro%3D&md5=325f780c35a79819f70c0ec62c9d0e0bCAS |

[60]  R. Newton, G. P. Savage, Aust. J. Chem. 2008, 61, 432.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXntlGjs70%3D&md5=c8907dfe7b054d50a70658304f4f8f39CAS |

[61]  S. L. Harding, G. P. Savage, Org. Biomol. Chem. 2012, 10, 4759.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XnvVSrt7o%3D&md5=105e8a89dac05a718933858e7656f1eaCAS | 22588428PubMed |

[62]  N. J. Beattie, C. L. Francis, A. J. Liepa, G. P. Savage, Aust. J. Chem. 2010, 63, 445.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjvV2rsbg%3D&md5=e88a5ccf05f27e437c0f09b4f65d5f87CAS |

[63]  A. M. Said, G. P. Savage, J. Org. Chem. 2011, 76, 6946.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXptFKnu7k%3D&md5=a31df04f9cce97a372c3c6c2c5918f24CAS | 21739981PubMed |

[64]  S. J. Ryan, C. L. Francis, G. P. Savage, Aust. J. Chem. 2013, 66, 874.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1Ois7zP&md5=1d1197ee4294390fbe93138d12eb0125CAS |

[65]  P. Grunanger, P. Vita-Finzi, Isoxazoles – Part 1. Chemistry of Heterocyclic Compounds 1991, Vol. 49 (Wiley: New York, NY).

[66]  C. J. Easton, C. M. M. Hughes, G. P. Savage, G. W. Simpson, in Cycloaddition Reactions of Nitrile Oxides with Alkenes (Ed. A. R. Katritzky) 1994, Vol. 60, pp. 261–327 (Academic Press: San Diego, CA).

[67]  G. P. Savage, Curr. Org. Chem. 2010, 14, 1478.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtlCqur3L&md5=731af997b925ac6dc5f7f19a8d30e6faCAS |

[68]  M. R. Berthold, N. Cebron, F. Dill, T. R. Gabriel, T. Kötter, T. Meinl, P. Ohl, C. Sieb, K. Thiel, B. Wiswedel, in Studies in Classification, Data Analysis, and Knowledge Organization (Eds C. Preisach, H. Burkhardt, L. Schmidt-Thieme, R. Decker) 2007, pp. 319–326 (Springer: Berlin). Available at http://knime.org/ (accessed 24 September 2013). https://doi.org/2010.1007/978-3-540-78246-9_38

[69]  C. Steinbeck, Y. Han, S. Kuhn, O. Horlacher, E. Luttmann, E. Willighagen, J. Chem. Inf. Comput. Sci. 2003, 43, 493.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhtVaktbg%3D&md5=bf72720aa6ecf3b627d639dcb9170febCAS | 12653513PubMed |

[70]  S. Chhabra, O. Dolezal, B. M. Collins, J. Newman, J. S. Simpson, I. G. Macreadie, R. Fernley, T. S. Peat, J. D. Swarbrick, PLoS ONE 2012, 7, e29444.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVyks7c%3D&md5=829142e0dc9988934ee711eb10c8e674CAS | 22276115PubMed |

[71]  G. A. Papalia, S. Leavitt, M. A. Bynum, P. S. Katsamba, R. Wilton, H. Qiu, M. Steukers, S. Wang, L. Bindu, S. Phogat, A. M. Giannetti, T. E. Ryan, V. A. Pudlak, K. Matusiewicz, K. M. Michelson, A. Nowakowski, A. Pham-Baginski, J. Brooks, B. C. Tieman, B. D. Bruce, M. Vaughn, M. Baksh, Y. H. Cho, M. De Wit, A. Smets, J. Vandersmissen, L. Michiels, D. G. Myszka, Anal. Biochem. 2006, 359, 94.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1Sjs7jN&md5=2795101ca0e4d16793670eae3c3e9789CAS | 17007806PubMed |