Combinatorial chemistry in the agrosciences

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 12, 2009, Pages 4035-4046

  Lindell, Stephen D ^a   Pattenden, Lisa C ^a   Shannon, Jonathan ^a  

^a BAYER CROPSCIENCE AG   (Germany)

Author keywords

Agrochemicals; Bioavailability guidelines; Briggs rule of three; Clarke Delaney guide of two; Combinational chemistry; Fungicides; Herbicides; Insecticides; Lead finding; Library design and synthesis; Natural products; Privileged structures; Structure based design; Virtual screening

Indexed keywords

FUNGICIDE; HERBICIDE; INSECTICIDE; NATURAL PRODUCT;

AGRICULTURE; BIOAVAILABILITY; COMBINATORIAL CHEMISTRY; HIGH THROUGHPUT SCREENING; PHASE TRANSITION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; REVIEW; SOLID; SOLUTION AND SOLUBILITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AGROCHEMICALS; ANTIFUNGAL AGENTS; BIOLOGICAL AVAILABILITY; COMBINATORIAL CHEMISTRY TECHNIQUES; COMPUTER-AIDED DESIGN; HERBICIDES; INSECTICIDES; SMALL MOLECULE LIBRARIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 66349092738     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.03.027     Document Type: Review

References (95)

1. Corbett J.R., Wright K., and Baillie A.C. The Biochemical Mode of Action of Pesticides. 2nd ed. (1984), Academic Press, London, New York 347
2. Boger P., and Sandmann G. In: Boger P., and Sandmann G. (Eds). Target Sites of Herbicide Action (1989), CRC Press, Boca Raton, Florida preface
3. Evans D.A. In: Brooks G.T., and Roberts T.R. (Eds). Pesticide Chemistry and Bioscience Vol. 233 (1995), Royal Society of Chemistry Special 3-24
4. Riddley S.M., Elliott A.C., Yeung M., and Youle D. Pestic. Sci. 54 (1998) 327
5. Hay J.V. In: Brooks G.T., and Roberts T.R. (Eds). Pesticide Chemistry and Bioscience Vol. 233 (1999), Royal Society of Chemistry Special 55-65
6. Booth S., Hermkens P.H.H., Ottenheijm H.C.J., and Rees D.C. Tetrahedron 54 (1998) 15385
7. Bunin B.A. The Combinatorial Index (1998), Academic Press, London, New York
8. Booth S.E., Dreef-Tromp C.M., Hermkens P.H.H., de Man J.A.P.A., and Ottenheijm H.C.J. Combinatorial Chemistry (1999), Elsevier, Amsterdam Chapter 2, pp 35-76
9. Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., and Taylor S.J. J. Chem. Soc. (2000) 3815
10. Lahana R. Drug Discovery Today 4 (1999) 447
11. Wilhelm S., Carter C., Lynch M., Lowinger T., Dumas J., Smith R.A., Schwarz B., Simantov R., and Kelley S. Nat. Rev. Drug Discovery 5 (2006) 835
12. Wilhelm S., Carter C., Lynch M., Lowinger T., Dumas J., Smith R.A., Schwarz B., Simantov R., and Kelley S. Nat. Rev. Drug Discovery 6 (2007) 126
13. Pasteris R.J. New Discoveries in Agrochemicals. ACS Symp. Ser. 892 Vol. 892 (2005), American Chemical Society, Washington, DC 109
14. Lindell S.D., and Scherkenbeck J. Comb. Chem. High Throughput Screening 8 (2005) 555
15. Scherkenbeck J., and Lindell S. Comb. Chem. High Throughput Screening 8 (2005) 563
16. Smith S.C., Delaney J.S., Robinson M.P., and Rice M.J. Comb. Chem. High Throughput Screening 8 (2005) 577
17. Tietjen K., Drewes M., and Stenzel K. Comb. Chem. High Throughput Screening 8 (2005) 589
18. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Delivery Rev. 23 (1997) 3
19. Briggs, G. G. Predicting Uptake and Movement of Agrochemicals from Physical Properties, Presentation at SCI Meeting: Uptake of Agrochemicals and Pharmaceuticals, Belgrave Square, London, England, 9th December 1997.
20. Abraham M.H., Chadha H.S., Whiting G.S., and Mitchell R.C. J. Pharm. Sci. 83 (1994) 1085
21. Briggs G.G. J. Agric. Food Chem. 29 (1981) 1050
22. Hartley G.S., and Graham-Bryce I.J. Physical Principles of Pesticide Behaviour: The dynamics of applied pesticides in the local environment in relation to biological response Vol. 2 (1980), Academic Press, London, New York
23. Oprea T.I., Davis A.M., Teague S.J., and Leeson P.D. J. Chem. Inf. Comput., Sci. 41 (2001) 1308
24. Proudfoot J. Biorg. Med. Chem. Lett. 12 (2002) 1647
25. Clarke E.D., and Delaney J.S. Chimia 57 (2003) 731
26. Clarke, E. Bioavailability: An Agrochemical Research Perspective, Presentation at QSAR and Chemoinformatics Group Meeting, Jealotts Hill, Bracknell, England, 25th April 2001. See http://www.iainm.demon.co.uk/ukqsar/meetings/2001-04-25.html.
27. Tice C.M. Pestic. Manag. Sci. 57 (2001) 3
28. Tice C.M. Pestic. Manag. Sci. 58 (2002) 219
29. Genix, P.; Lachaise, H., Bayer CropScience AG, unpublished results. The HTS F-tests refer to high throughput cell tests conducted on plant pathogenic fungi.
30. Briggs, G. G; Desbordes, P.; Genix, P. Are There Limits to the Physical Properties of Fungicides? Poster Presentation at 10th IUPAC Int. Congress on the Chemistry of Crop Protection, Basel, Switzerland, 4-9th August 2002.
31. Ertl P., Rohde B., and Selzer P. J. Med. Chem. 43 (2000) 3714
32. Haaf K. Comb. Chem. High Throughput Screening 8 (2005) 637
33. Bae S., Hahn H.-G., and Nam K.D. J. Comb. Chem. 7 (2005) 7
34. Es-Sayed M., Beck M., Bräse S., de Meijere A., Funke C., Kather K., Limbach M., Lormann C., Paulitz C., Wroblowsky H., and Zimmermann V. New Discoveries in Agrochemicals. ACS Symp. Ser. 892 Vol. 892 (2005), American Chemical Society, Washington, DC 74-86
35. Dietrich H., Giencke W., and Klein R. Comb. Chem. High Throughput Screening 8 (2005) 623
36. Dietrich, H.; Giencke, W.; Lindell, S.; Tiebes, J. Lead Discovery Using High Throughput Chemistry, Poster Presentation at 11th IUPAC Int. Congress on the Chemistry of Crop Protection, Kobe, Japan, 6-10th August 2006.
37. Carreras I., Scherkenbeck J., and Paulitz C. Comb. Chem. High Throughput Screening 8 (2005) 643
38. Martinez-Teipel B., Teixidó J., Pascual R., Mora M., Pujalà J., Fujimoto T., Borrell J.I., and Michelotti E.L. J. Comb. Chem. 7 (2005) 436
39. Ren X.L., Li H.B., Wu C., and Yang H.Z. ARKIVOC xv (2005) 59
40. Weber L. Drug Discovery Today 7 (2002) 143
41. Cottrell K., Holyoke C.W., Klein M., Lee K.C., Nassirpour M.R., Pasteris R.J., and Shah S. Comb. Chem. High Throughput Screening 8 (2005) 617
42. Benting J., Leonhardt M., Lindell S.D., and Tiebes J. Comb. Chem. High Throughput Screening 8 (2005) 649
43. Paduraru P.M., Popoff R.T.W., Nair R., Gries R., Gries G., and Plettner E. J. Comb. Chem. 10 (2008) 123
44. Cordier C., Morton D., Murrison S., Nelson A., and O'Leary-Steele C. Nat. Prod. Rep. 25 (2008) 719
45. and. Mentel M., and Breinbauer R. Top. Curr. Chem. 287 (2007) 209
46. Evans B.E., Rittle K.E., Bock M.G., DiPrado R.M., Freidinger R.M., Whitter W.L., Lundell G.F., Veber D.F., Anderson P.S., Chang R.S.L., Lotti V.J., Cerino D.J., Chen T.B., Kling P.J., Kunkel K.A., Springer J.P., and Hirshfield J. J. Med. Chem. 31 (1988) 2235
47. For reviews on privileged structures see:. Duarte C.D., Barreiro E.J., and Fraga C.A. Mini-Rev. Med. Chem. 7 (2007) 1108
48. Costantino L., and Barlocco D. Curr. Med. Chem. 13 (2006) 65
49. DeSimone R.W., Currie K.S., Mitchell S.A., Darrow J.W., and Pippin D.A. Comb. Chem. High Throughput Screening 7 (2004) 473 456
50. Arve L., Voigt T., and Waldmann H. QSAR Comb. Sci. 25 (2006) 449
51. Noren-Muller A., Reis-Correa I., Prinz H., Rosenbaum C., Saxena K., Schwalbe H.J., Vestweber D., Cagna G., Schunk S., Schwarz O., Schiewe H., and Waldmann H. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 10606
52. Smith S.C., James D.R., Abelman M.M., and Sexton G.J. Comb. Chem. High Throughput Screening 8 (2005) 607
53. Ruiz J.M., and Lorsbach B.A. New Discoveries in Agrochemicals. ACS Symp. Ser. 892 Vol. 892 (2005), American Chemical Society, Washington, DC 99-108
54. Cox R.J., and O'Hagan D. J. Chem. Soc., Perkin Trans. 1 (1991) 2537
55. Rigby J., and Balasurbramanian N. J. Org. Chem. 54 (1989) 224
56. Comins D.L., and Nolan J.M. Org. Lett. 3 (2001) 4255
57. In: Tomlin C.D.S. (Ed). The Pesticide Manual. 14th ed. (2006), BCPC
58. Turner J.A., Dick M.R., Bargar T.M., Garvin G.M., and Siddall T.L. New Discoveries in Agrochemicals. ACS Symp. Ser. 892 Vol. 892 (2005), American Chemical Society, Washington, DC 119-129
59. Shi S., Zhu S., Gerritz S., Esposito K., Padmanabha R., Li W., Herbst J., Wong H., Zhong Shu Y., Lam K., and Sofia M. Bioorg. Med. Chem. Lett. 15 (2005) 4151
60. Babu K.S., Li X.-C., Jacob M.R., Zhang Q., Khan S.I., Ferreira D., and Clark A.M. J. Med. Chem. 49 (2006) 7877
61. Serrano P., Casas J., Llebaria A., Zucco M., Emeric G., and Delgado A. J. Comb. Chem. 9 (2007) 635
62. Al-Obeidi F., Austin R.E., Okonya J.F., and Bond D.R.S. Mini-Rev. Med. Chem. 3 (2003) 449
63. Nuechter M., and Ondruschka B. Mol. Divers. 7 (2003) 253
64. Swamy K.M.K., Yeh W.-B., Lin M.-J., and Sun C.-H. Curr. Med. Chem. 10 (2003) 2403
65. Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 6250
66. Lange T., and Lindell S. Comb. Chem. High Throughput Screening 8 (2005) 595
67. Kappe C.O., and Matloobi M. Comb. Chem. High Throughput Screening 10 (2007) 735
68. Zhou Z.-Z., and Yang G.-F. Bioorg. Med. Chem. 14 (2006) 8666
69. Schnur D.M., Tebben A.J., and Cavallaro C.L. In: Mason J. (Ed). Comp. Med. Chem. II Vol. 4 (2007), Elsevier Ltd, Oxford, UK 307-336
70. Schnur D.M. Curr. Opin. Drug Discovery Dev. 11 (2008) 375
71. Waszkowycz B. Drug Discovery Today 13 (2008) 219
72. Erlanson D.A., McDowell R.S., and O'Brien T. J. Med. Chem. 47 (2004) 1
73. Camper D.L., and Parker M.H. ACS Symp. Ser. 948 Vol. 948 (2007), American Chemical Society, Washington, DC 105-117
74. Tempest P.A., and Armstrong R.W. J. Am. Chem. Soc. 119 (1997) 7607
75. Sauer W.H.B., and Schwarz M.K. Chimia 57 (2003) 276
76. Bleicher K.H., Boehm H.-J., Mueller K., and Alanine A.I. Nat. Rev. Drug Discovery 2 (2003) 369
77. Burke M.D., and Schreiber S.L. Angew. Chem., Int. Ed. 43 (2004) 46
78. Lindell, S. D. Can More Intelligent Virtual Library Design Help Save Combinatorial Chemistry, Presentation at IQPC Meeting, 4th International Conference Compound Libraries 2008, Maritim Hotel, Düsseldorf, Germany, 7-8th October 2008. The author would like to thank R. Klein for molecular modeling support and M. Leonhardt for technical assistance.
79. Siehl D.L., Subramanian M.V., Walters E.W., Blanding J.H., Niderman T., and Weinmann C. Weed Sci. 45 (1997) 628
80. The Research Collaboratory for Structural Bioinformatics (RCSB) Protein Data Bank. See http://www.rcsb.org/pdb. The Salmonella typhimurium enzyme structure (1ilq.pdb) was used in the modeling studies.
81. Rarey M., and Lengauer T. Perspect. Drug Discovery Des. 20 (2000) 63
82. Kontoyianni M., McClellan L.M., and Sokul G.S. J. Med. Chem. 47 (2004) 558
83. Cummings M.D., DesJarlais R.L., Gibbs A.C., Mohan V., and Jaeger E.P. J. Med. Chem. 48 (2005) 962
84. Warren G.L., Andrews C.W., Capelli A.-M., Clarke B., LaLonde J., Lambert M.H., Lindvall M., Nevins N., Semus S.F., Senger S., Tedesco G., Wall I.D., Woolven J.M., Preishoff C.E., and Head M.S. J. Med. Chem. 49 (2006) 5912
85. Chen H., Lyne P.D., Giordanetto F., Lovell T., and Li J. J. Chem. Inf. Model 46 (2006) 401
86. Zhou Z., Felts A.K., Friesner R.A., and Levy R.M. J. Chem. Inf. Model 47 (2007) 1599
87. Teramoto R., and Fukunishi H. J. Chem. Inf. Model 48 (2008) 288
88. Claussen H., Buning C., Rarey M., and Lengauer T. J. Mol. Biol. 308 (2001) 377
89. Sherman W., Day T., Jacobson M.P., Friesner R.A., and Farid R. J. Med. Chem. 49 (2006) 534
90. May A., Sieker F., and Zacharias M. Curr. Comput. Aided Drug Des. 4 (2008) 143
91. Kokh D.B., and Wenzel W. J. Med. Chem. 51 (2008) 5919
92. Kellogg G.E., Burnett J.C., and Abraham D.J. J. Comput.-Aided Mol. Des. 15 (2001) 381
93. Friesner R.A., Murphy R.B., Repasky M.P., Frye L.L., Greenwood J.R., Halgren T.A., Sanschagrin P.C., and Mainz D.T. J. Med. Chem. 49 (2006) 6177
94. Spyrakis F., Kellog G.E., Amadasi A., and Cozzini P. Front. Drug Des. Discovery 3 (2007) 317
95. Reulencke I., Lange G., Albrecht J., Klein R., and Rarey M. ChemMedChem 3 (2008) 885