The enantiospecific synthesis of an isoxazoline. A RGD mimic platelet GPIIb/IIIa antagonist

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2466-2470

  Zhang, Lin Hua ^a   Chung, J C ^a   Costello, T D ^a   Valvis, I ^a   Ma, P ^a   Kauffman, S ^a   Ward, R ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 [[[3 [4 (AMINOIMINOMETHYL)PHENYL] 4,5 DIHYDRO 5 ISOXAZOLYL]ACETYL]AMINO] N (BUTOXYCARBONYL)ALANINE ACETIC ACID METHYL ESTER; FIBRINOGEN RECEPTOR ANTAGONIST; ISOXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030962376     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9612537     Document Type: Article

References (46)

1. (a) Zhang, L.-H.; Ma, P. Tetrahedron Lett. 1994, 35, 8387.
2. (b) Gould, R. J.; Polokoff, M. A.; Friedman, P. A.; Huang, T.-F.; Holt, J. C.; Cook, J. J. Niewiarowski, S. Proc. Soc. Exp. Biol. Med. 1990, 195, 168.
3. (c) Semanen, J.; Ali, F.; Romoff, T.; Calvo, R.; Sorenson, E.; Vasko, J.; Storer, B.; Berry, D.; Bennett, D.; Strohsacker, M.; Powers, D.; Stadel, J.; Nichols, A. J. Med. Chem. 1991, 34, 3114.
4. Bach, A. C.; Eyermann, C. J.; Gross, J. D.; Bower, M. J.; Harlow, R. L.; Weber, P. C.; Degrade, W. F. J. Am. Chem. Soc. 1994, 116, 3207.
5. Wolff, M. E. Burgers Medicinal Chemistry and Drug Discovery, 5th ed. 1995.
6. (a) Olson, R. E.; Wityak, J.; Xue, C.; Sielecki, T.; Cain, G.; Mousa, S.; Thoolen, M.; Racanelli, A.; Hausner, E.; Reilly, T.; Degrado, W.; Wexler, R. 211th New Orleans, LA, Mar 24-28, 1996; American Chemical Society: Washington, DC, 1996; #250.
7. (h) Wityak, J.; Pinto, D. J.; Wang, S.; Sze, J. Y.; Mousa, S. A.; Olson, R. E.; Wexler, R. R. 211th New Orleans, LA, Mar 24-28, 1996; American Chemical Society: Washington, DC, 1996; #131.
8. (c) Xue, C. B.; Wityak, J.; Sielecki, T. M.; Cain, G. A.; Liu, J.; Bostrom, L. L.; DiMeo, S. V.; Higley, C. A.; Lalka, G. K.; Tobin, A. E.; Frietze, W. E.; Emmett, G.; Mousa, S. A.; Sze, J. Y.; Thoolen, M. J.; Reilly, T.; DeGrado, W. F.; Olson, R. E.; Wexler, R. R. 211th National Meeting of the American Chemical Society, #132. March 24-28, 1996.
9. (d) Wityak, J.; Sielecki, T. M.; Pinto, D. J.; Emmett, G.; Sze, J. Y.; Liu, J.; Tobin, E.; Wang, S.; Jiang, B.; Ma, P.; Mousa, S. A.; Wexler, R. R.; Olson, R. E. J. Med. Chem. 1997, 40, 50.
10. Zhang, L.-H.; Anzalone, L.; Ma, P.; Kauffman, G. S.; Storace, L.; Ward, R. Tetrahedron Lett. 1996, 37, 4455.
11. (a) Adams, R.; Johnson, J. L. J. Am. Chem. Soc. 1949, 71, 705. Malathi, K.; Padmanaban, G.; Padubidri, S. Ind. J. Biochem. 1968, 5, 184. Dugenett, P.; Yaouanc, J. J.; Sturtz, G. Synthesis 1902, 781. Hettinger, T. P.; Craig, L. C. Biochemistry 1970, 3, 1224. Mokotoff, M.; Logue, L. W. J. Med. Chem. Soc. 1981, 24, 554. Ikegami, F.; Murakoshi, I. Phytochemistry 1994, 35, 1089.
12. (a) Adams, R.; Johnson, J. L. J. Am. Chem. Soc. 1949, 71, 705. Malathi, K.; Padmanaban, G.; Padubidri, S. Ind. J. Biochem. 1968, 5, 184. Dugenett, P.; Yaouanc, J. J.; Sturtz, G. Synthesis 1902, 781. Hettinger, T. P.; Craig, L. C. Biochemistry 1970, 3, 1224. Mokotoff, M.; Logue, L. W. J. Med. Chem. Soc. 1981, 24, 554. Ikegami, F.; Murakoshi, I. Phytochemistry 1994, 35, 1089.
13. (a) Adams, R.; Johnson, J. L. J. Am. Chem. Soc. 1949, 71, 705. Malathi, K.; Padmanaban, G.; Padubidri, S. Ind. J. Biochem. 1968, 5, 184. Dugenett, P.; Yaouanc, J. J.; Sturtz, G. Synthesis 1902, 781. Hettinger, T. P.; Craig, L. C. Biochemistry 1970, 3, 1224. Mokotoff, M.; Logue, L. W. J. Med. Chem. Soc. 1981, 24, 554. Ikegami, F.; Murakoshi, I. Phytochemistry 1994, 35, 1089.
14. (a) Adams, R.; Johnson, J. L. J. Am. Chem. Soc. 1949, 71, 705. Malathi, K.; Padmanaban, G.; Padubidri, S. Ind. J. Biochem. 1968, 5, 184. Dugenett, P.; Yaouanc, J. J.; Sturtz, G. Synthesis 1902, 781. Hettinger, T. P.; Craig, L. C. Biochemistry 1970, 3, 1224. Mokotoff, M.; Logue, L. W. J. Med. Chem. Soc. 1981, 24, 554. Ikegami, F.; Murakoshi, I. Phytochemistry 1994, 35, 1089.
15. (a) Adams, R.; Johnson, J. L. J. Am. Chem. Soc. 1949, 71, 705. Malathi, K.; Padmanaban, G.; Padubidri, S. Ind. J. Biochem. 1968, 5, 184. Dugenett, P.; Yaouanc, J. J.; Sturtz, G. Synthesis 1902, 781. Hettinger, T. P.; Craig, L. C. Biochemistry 1970, 3, 1224. Mokotoff, M.; Logue, L. W. J. Med. Chem. Soc. 1981, 24, 554. Ikegami, F.; Murakoshi, I. Phytochemistry 1994, 35, 1089.
16. (a) Adams, R.; Johnson, J. L. J. Am. Chem. Soc. 1949, 71, 705. Malathi, K.; Padmanaban, G.; Padubidri, S. Ind. J. Biochem. 1968, 5, 184. Dugenett, P.; Yaouanc, J. J.; Sturtz, G. Synthesis 1902, 781. Hettinger, T. P.; Craig, L. C. Biochemistry 1970, 3, 1224. Mokotoff, M.; Logue, L. W. J. Med. Chem. Soc. 1981, 24, 554. Ikegami, F.; Murakoshi, I. Phytochemistry 1994, 35, 1089.
17. (b) Golding, B. T.; Howes, C. J. Chem. Res., Miniprint 1984, 1, 1. Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605. Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105. Kucharczyk, N.; Badet, B.; Goffic, F. Le. Synth. Commun. 1989, 19, 1603.
18. (b) Golding, B. T.; Howes, C. J. Chem. Res., Miniprint 1984, 1, 1. Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605. Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105. Kucharczyk, N.; Badet, B.; Goffic, F. Le. Synth. Commun. 1989, 19, 1603.
19. (b) Golding, B. T.; Howes, C. J. Chem. Res., Miniprint 1984, 1, 1. Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605. Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105. Kucharczyk, N.; Badet, B.; Goffic, F. Le. Synth. Commun. 1989, 19, 1603.
20. (b) Golding, B. T.; Howes, C. J. Chem. Res., Miniprint 1984, 1, 1. Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605. Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105. Kucharczyk, N.; Badet, B.; Goffic, F. Le. Synth. Commun. 1989, 19, 1603.
21. (c) Teshima, T.; Nomoto, S.; Wakamiya, T.; Shiba, T. Bull. Chem. Soc. Jpn. 1977, 50, 3372. Rao, S. L. N. Biochemistry 1975, 14, 5218.
22. (c) Teshima, T.; Nomoto, S.; Wakamiya, T.; Shiba, T. Bull. Chem. Soc. Jpn. 1977, 50, 3372. Rao, S. L. N. Biochemistry 1975, 14, 5218.
23. (d) The material was purchased from Bachem.
24. (a) Otsuka, M.; Kittaka, A.; Iimori, T.; Yamashita, H.; Kobayashi, S., Ohno, M. Chem. Pharm. Bull. 1985, 33, 509.
25. (b) Sy, A. O.; Raksis, J. W. Tetrahedron Lett. 1980, 21, 2223.
26. Senanayake, C. H.; Fredenburgh, L. E.; Reamer, R. A.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Am. Chem. Soc. 1994, 116, 7947.
27. Staskun, B. J. Org. Chem. 1988, 53, 5287.
28. (a) Waki, M.; Kitajima, Y.; Izumiya, N. Synthesis. 1981, 266.
29. (b) Pavlidis, V. H.; Chan, E. D.; Pennington, L.; McParland, M.; Whitehead, M. Synth. Commun. 1988, 18, 1615.
30. (c) Kanaoka, Y.; Okajima, H.; Hatanaka, Y. J. Org. Chem. 1979, 44, 1751.
31. (d) Tamura, M.; Jacyno, J.; Stammer, C. H. Tetrahedron Lett. 1986, 27, 5435. Boutin, R. H.; Loudon, G. M. J. Org. Chem. 1984, 49, 4277.
32. (d) Tamura, M.; Jacyno, J.; Stammer, C. H. Tetrahedron Lett. 1986, 27, 5435. Boutin, R. H.; Loudon, G. M. J. Org. Chem. 1984, 49, 4277.
33. Willgerodt, C. Ber. 1892, 25, 3495. Sharefkin, J. G.; Saltzman, H. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 660.
34. Willgerodt, C. Ber. 1892, 25, 3495. Sharefkin, J. G.; Saltzman, H. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 660.
35. (a) Huisgen, R. Angew. Chem. 1963, 75, 604.
36. (b) Pedwa, A. Comp. Org. Synth. 1991, 4, 1069.
37. (b) Wade, P. A. Comp. Org. Synth. 1991, 4, 1111.
38. (c) Kim, Y.; Kim, S.; Park, D. Tetrahedron Lett. 1993, 34, 6063.
39. (d) Gothelf, K. V.; Thomsen, I.; Jorgensen, K. A. J. Am. Chem. Soc. 1996, 118, 59.
40. (e) Gilbertson, S. R.; Dawson, D. P.; Lopez, O. D.; Marshall, K. L. J. Am. Chem. Soc. 1995, 117, 4431.
41. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH: Weinheim, 1995.
42. (a) Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205.
43. (b) Rivero, A.; Somanathan, R.; Helberg, L. H. Synth. Commun. 1995, 25, 2185.
44. (c) Dudash, J. J.; Jiang, J.; Mayer, S. C.; Joullie, M. M. Synth. Commun. 1993, 23, 349.
45. Rousselet, G.; Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1993, 34, 6395.
46. Allen, R.; Schumann, E.; Day, W.; Campen, M. J. Am. Chem. Soc. 1958, 80, 591.