Parallel synthesis of a library of acylsemicarbazides using a solution-phase one-pot method and their evaluation as crop-protection agents

Synthesis

Volumn , Issue 14, 2005, Pages 2384-2392

  Grzyb, Justyna A ^a   Dekeyser, Mark A ^b   Batey, Robert A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b Crompton Co/Cie   (Canada)

Author keywords

1,3,4 oxadiazol 2 one; Acylsemicarbazides; Acylthiosemicarbazides; Crop protection; Library; Solution phase

Indexed keywords

PLANT CELL CULTURE; PRECIPITATION (CHEMICAL); PURIFICATION; SOLUTIONS; SYNTHESIS (CHEMICAL);

1,3,4-OXADIAZOL-2-ONE; ACYLSEMICARBAZIDES; ACYLTHIOSEMICARBAZIDES; CROP PROTECTION; LIBRARY; SOLUTION PHASE;

AMINES;

1,3,4 OXADIAZOLE 2 ONE; 3,4 DIHYDRO 1H ISOQUINOLINE 2 CARBOXYLIC ACID N' (3 BROMOBENZOYL)HYDRAZIDE; 3,4 DIHYDRO 1H ISOQUINOLINE 2 CARBOXYLIC ACID N' (5 CHLOROTHIOPHENE 2 CARBONYL)HYDRAZIDE; 4 PHENYLPIPERAZINE 1 CARBOXYLIC ACID N' (5 CHLOROTHIOPHENE 2 CARBONYL)HYDRAZIDE; 4,4 DIETHYL 1 (THIOPHENE 2 CARBONYL)SEMICARBAZIDE; AMIDE; HYDRAZIDE DERIVATIVE; MORPHOLINE 4 CARBOXYLIC ACID N' (THIOPHENE 2 CARBONYL)HYDRAZIDE; OXADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CROP PROTECTION; FILTRATION; FUNGICIDE APPLICATION; HERBICIDAL ACTIVITY; PHASE TRANSITION; PLANT GROWTH; SYNTHESIS;

EID: 24944486793     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-870020     Document Type: Article

References (80)

1. (a) Gante, J. Synthesis 1989, 405.
2. (b) Gibson, C.; Goodman, S. L.; Hahn, D.; Hölzemann, G.; Kassler, H. J. Org. Chem. 1999, 64, 7388.
3. (c) Weber, D.; Berger, C.; Eickelmann, P.; Antel, J.; Kessler, H. J. Med. Chem. 2003, 46, 1918.
4. Andurkar, S. V.; Béguin, C.; Stables, J. P.; Kohn, H. J. Med. Chem. 2001, 44, 1475.
5. (a) Wing, K. D. Science 1988, 241, 467.
6. (b) Wing, K. D.; Slawecki, R. A.; Carlson, G. R. Science 1988, 241, 470.
7. (a) Nakagawa, Y.; Smagghe, G.; Kugimiya, S.; Hattori, K.; Ueno, T.; Tirry, L.; Fujita, T. Pestic. Sci. 1999, 55, 909.
8. (b) Mulvihill, M. J.; Shaber, S. H.; MacDougall, B. S.; Ajello, C.; Martinez-Teipel, B.; Joseph, R.; Nguyen, D. V.; Weaver, D. G.; Chung, K.-H.; Gusev, A.; Wierenga, J. M.; Mathis, W. D. Synthesis 2002, 53.
9. Wang, Q.; Huang, R. Tetrahedron Lett. 2001, 42, 8881.
10. For reviews on solid-phase organic synthesis, see: (a) Krchnák, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61.
11. (b) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549.
12. (c) Kobayashi, S. Chem. Soc. Rev. 1999, 28, 1.
13. (d) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817.
14. (e) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293.
15. (f) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449.
16. (g) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
17. For reviews on liquid-phase organic synthesis, see: (a) Sun, C.-M. Comb. Chem. High Throughput Screening 1999, 2, 299.
18. (b) Wentworth, P. Jr. Trends Biotechnol. 1999, 17, 448.
19. (c) Wentworth, P. Jr.; Janda, K. D. Chem. Commun. 1999, 1917.
20. (d) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
21. For reviews on solution-phase organic synthesis, see: (a) An, H.; Cook, P. D. Chem. Rev. 2000, 100, 3311.
22. (b) Merritt, A. T. Comb. Chem. High Throughput Screening 1998, 1, 57.
23. (c) Boger, D. L.; Goldberg, J. J. Comb. Chem. 2000, 303.
24. (d) Coe, D. M.; Storer, R. Mol. Diversity 1999, 4, 31.
25. (a) Peng, S. X.; Henson, C.; Strojnowski, M. J.; Golebiowski, A.; Klopfenstein, S. R. Anal. Chem. 2000, 72, 261.
26. (b) Chen, Y.; Bilban, M.; Foster, C. A.; Boger, D. L. J. Am. Chem. Soc. 2002, 124, 5431.
27. (a) Curran, D. P. Angew. Chem. Int. Ed. Engl. 1998, 37, 1174.
28. (b) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531.
29. (c) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480.
30. (d) Studer, A.; Curran, D. P. Tetrahedron 1997, 53, 6681.
31. (e) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
32. (f) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714.
33. (a) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320.
34. (b) Song, C. E.; Le, S.-G. Chem. Rev. 2002, 102, 3495.
35. (c) Ley, S. V.; Baxendale, I. R.; Brusotti, G.; Caldarelli, M.; Massi, A.; Nesi, M. II Farmaco 2002, 57, 321.
36. (d) 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.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815.
37. (e) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18.
38. (f) Weller, H. N. Mol. Diversity 1999, 4, 47.
39. (a) Shuttleworth, S. J.; Quimpére, M.; Lee, N.; DeLuca, J. Mol. Diversity 1998, 4, 183.
40. (b) Kang, K. H.; Pae, A. N.; Choi, K. I.; Cho, Y. S.; Chung, B. Y.; Lee, J. E.; Jung, S. H.; Koh, H. Y.; Lee, H.-Y. Tetrahedron Lett. 2001, 42, 1057.
41. (c) Tietze, L. F.; Evers, H.; Töpken, E. Helv. Chim. Acta 2002, 85, 4200.
42. (d) Tietze, L. F.; Evers, H.; Töpken, E. Angew. Chem. Int. Ed. 2001, 40, 903.
43. (e) Beaulieu, P. L.; Haché, B.; von Moos, E. Synthesis 2003, 1683.
44. (f) Lee, H.-K.; Chui, W.-K. Bioorg. Med. Chem. 1999, 7, 1255.
45. (g) Pirrung, M. C.; Sarma, K. D. J. Am. Chem. Soc. 2004, 126, 444.
46. (a) Honigfort, M. E.; Brittain, W. J.; Bosanac, T.; Wilcox, C. S. Macromolecules 2002, 35, 4849.
47. (b) Bosanac, T.; Wilcox, C. S. J. Am. Chem. Soc. 2002, 124, 4194.
48. (c) Bosanac, T.; Yang, J.; Wilcox, C. S. Angew. Chem. Int. Ed. 2001, 40, 1875.
49. (a) Ahn, J.-M.; Wentworth, P. Jr.; Janda, K. D. Chem. Commun. 2003, 480.
50. (b) Sieber, F.; Wentworth, P. Jr.; Janda, K. D. J. Comb. Chem. 1999, 1, 540.
51. (c) Zhao, X.-Y.; Metz, W. A.; Sieber, F.; Janda, K. D. Tetrahedron Lett. 1998, 39, 8433.
52. (d) Huang, K.-T.; Sun, C.-M. Bioorg. Med. Chem. Lett. 2002, 12, 1001.
53. (e) Huang, K.-T.; Sun, C.-M. Bioorg. Med. Chem. Lett. 2001, 11, 271.
54. (f) Sun, C.-M.; Shey, J.-Y. J. Comb. Chem. 1999, 1, 361.
55. (g) Shey, J.-Y.; Sun, C.-M. Bioorg. Med. Chem. Lett. 1999, 9, 519.
56. (h) Ho, K.-C.; Sun, C.-M. Bioorg. Med. Chem. Lett. 1999, 9, 1517.
57. (a) Davidson, J. S. Monatsh. Chem. 1988, 119, 1027.
58. (b) Novikov, M. S.; Khlebnikov, A. F.; Stepanov, A. A.; Kostikov, R. R. Synthesis 1994, 782.
59. (a) Stillings, M. R.; Freeman, S.; Myers, P. L.; Readhead, M. J.; Welbourn, A. P.; Ranee, M. J.; Atkinson, D. C. J. Med. Chem. 1985, 28, 225.
60. (b) Yale, H. L.; Losee, K. A.; Perry, F. M.; Bernstein, J. J. Am. Chem. Soc. 1954, 76, 2208.
61. (a) Batey, R. A.; Santhakumar, V.; Yoshina-Ishii, C.; Taylor, S. D. Tetrahedron Lett. 1998, 39, 6267.
62. (b) Batey, R. A.; Yoshina-Ishii, C.; Taylor, S. D.; Santhakumar, V. A. Tetrahedron Lett. 1999, 40, 2669.
63. (c) Grzyb, J. A.; Batey, R. A. Tetrahedron Lett. 2003, 44, 7485.
64. For examples of the use of CDI in parallel synthesis, see: (a) Acharya, A. N.; Ostresh, J. M.; Houghten, R. A. Tetrahedron 2002, 58, 2095.
65. (b) Nefzi, A.; Giulianotti, M.; Truong, L.; Rattan, S.; Ostresh, J. M.; Houghten, R. A. J. Comb. Chem. 2002, 4, 175.
66. (c) Nefzi, A.; Ostresh, J. M.; Giulianotti, M.; Houghten, R. A. J. Comb. Chem. 1999, 7, 195.
67. (d) Deegan, T. L.; Nitz, T. J.; Cebzanov, D.; Pufko, D. E.; Porco, J. A. Jr. Bioorg. Med. Chem. Lett. 1999, 9, 6267.
68. (e) Nefzi, A.; Ostresh, J. M.; Meyer, J.-P.; Houghten, R. A. Tetrahedron Lett. 1997, 38, 931.
69. (a) Firoozi, F.; Javidnia, K.; Kamali, M.; Fooladi, A.; Foroumadi, A.; Shafiee, A. J. Heterocycl. Chem. 1995, 32, 123.
70. (b) Mullican, M. D.; Wilson, M. W.; Connor, D. T.; Kostlan, C. R.; Schrier, D. J.; Dyer, R. D. J. Med. Chem. 1993, 36, 1090.
71. (c) Davidson, J. S. Monatsh. Chem. 1984, 115, 565.
72. (d) Tihanyi, E.; Gál, M.; Dvortsák, P. Heterocycles 1983, 20, 571.
73. (a) Stempel, A.; Zelauskas, J.; Aeschlimann, J. A. J. Org. Chem. 1955, 20, 412.
74. (b) Saegusa, Y.; Harada, S.; Nakamura, S. J. Heterocycl. Chem. 1988, 25, 1337.
75. Chau, N.; Saegusa, Y.; Iwakura, Y. J. Heterocycl. Chem. 1982, 19, 541.
76. Kramer, J. B.; Boschelli, D. H.; Connor, D. T. J. Heterocycl. Chem. 1994, 31, 1439.
77. Pancechowska-Ksepko, D.; Foks, H.; Janowiec, M.; Zwolska-Kwiek, Z. Acta Pol. Pharm. 1993, 50, 259.
78. Other nucleophiles that are known to ring-open 1,3,4-oxadiazole-2-ones via nucleophilic attack include hydrazines and thiols, for example, see ref. 20 and: (a) Thompson, S. K.; Halbert, S. M.; DesJarlais, R. L.; Tomaszek, T. A.; Levy, M. A.; Tew, D. G.; Ijames, C. F.; Veber, D. F. Bioorg. Med. Chem. 1999, 7, 599.
79. (b) Kristinsson, H.; Winkler, T.; Mollenkopf, M. Helv. Chim. Acta 1986, 69, 333.
80. (c) Werbel, L. M.; McNamara, D. J.; Colbry, N. L.; Johnson, J. L.; Degnan, M. J.; Whitney, B. J. Heterocycl. Chem. 1979, 16, 881.