Synthesis and synthetic applications of 2-amino-3-halo-1-oxypropanes

Tetrahedron

Volumn 64, Issue 15, 2008, Pages 3275-3285

  D'hooghe, Matthias ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

2 Amino 3 halo 1 oxypropanes; Aziridines; Epichlorohydrin; l Serine

Indexed keywords

2 AMINO 3 HALO 1 OXYPROPANE DERIVATIVE; ALLYL ALCOHOL; AMINE; AZIRIDINE; EPICHLOROHYDRIN; OXAZOLIDINE DERIVATIVE; PROPANE; SERINE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ANTIOXIDANT ACTIVITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NONHUMAN; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

EID: 39749128325     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.048     Document Type: Review

References (95)

1. A few recent examples:
2. Holloway G.A., Baell J.B., Fairlamb A.H., Novello P.M., Parisot J.P., Richardson J., Watson K.G., and Street I.P. Bioorg. Med. Chem. Lett. 17 (2007) 1422
3. Mendez-Andino J.L., Colson A.-O., Meyers K.M., Mitchell M.C., Hodge K., Howard J.M., Kim N., Ackley D.C., Holbert J.K., Mittelstadt S.W., Dowty M.E., Obringer C.M., Suchanek P., Reizes O., Hu X.E., and Wos J.A. Bioorg. Med. Chem. 15 (2007) 2092
4. Marinescu S.C., Agapie T., Day M.W., and Bercaw J.E. Organometallics 26 (2007) 1178
5. Fang Y.-Q., Karisch R., and Lautens M. J. Org. Chem. 72 (2007) 1341
6. Rhee H.-K., Park H.J., Lee S.K., Lee C.-O., and Choo H.-Y.P. Bioorg. Med. Chem. 15 (2007) 1651
7. Couty F., David O., Larmanjat B., and Marrot J. J. Org. Chem. 72 (2007) 1058
8. May B.C.H., Zorn J.A., Witkop J., Sherrill J., Wallace A.C., Legname G., Prusiner S.B., and Cohen F.E. J. Med. Chem. 50 (2007) 65
9. Behforouz M., Cai W., Mohammadi F., Stocksdale M.G., Gu Z., Ahmadian M., Baty D.E., Etling M.R., Al-Anzi C.H., Swiftney T.M., Tanzer L.R., Merriman R.L., and Behforouz N.C. Bioorg. Med. Chem. 15 (2007) 495
10. D'hooghe M., Vervisch K., and De Kimpe N. J. Org. Chem. 72 (2007) 7329
11. Whittaker S.J., and Foss F.M. Cancer Treat. Rev. 33 (2007) 146
12. Denny W.A. Curr. Med. Chem. 8 (2001) 533
13. Narimatsu S., Arai T., Watanabe T., Masubuchi Y., Horie T., Suzuki T., Ishikawa T., Tsutsui M., Kumagai Y., and Cho A.K. Chem. Res. Toxicol. 10 (1997) 289
14. Bair K.W., Tuttle R.L., Knick V.C., Cory M., and McKee D.D. J. Med. Chem. 33 (1990) 2385
15. Bair K.W., Andrews C.W., Tuttle R.L., Knick V.C., Cory M., and McKee D.D. J. Med. Chem. 34 (1991) 1983
16. Mamedova P.S., Gamzayeva S.A., Kuliyev F.A., Gayeva E.A.A., and Soltanova Z.K. Izv. Vuz. Khim. Kh. Tekh. 48 (2005) 41
17. Chem. Abstr. 145 (2006) 213876
18. Sehgal R.K., Almassian B., Rosenbaum D.P., Zadrozny R., and Sengupta S.K. J. Med. Chem. 30 (1987) 1626
19. Selivanova A.S., Molodykh Z.V., Lisenkova A.N., Dzhundubaev K.D., Yarmukhametova D.K., Kudryavtsev B.V., and Barabanov V.I. Med. Parazitologiya i Parazitarnye Bolezni 44 (1975) 484
20. Chem. Abstr. 84 (1976) 124
21. Ge, P.; Horvath, R. F.; Zhang, L. Y.; Yamaguchi, Y.; Kaiser, B.; Zhang, X.; Zhang, S.; Zhao, H.; John, S.; Moorcroft, N.; Shutske, G. PCT Int. Appl. WO 2005023806 A2, 2005;
22. Chem. Abstr. 142 (2005) 316863
23. Annis, G. D.; Chiang, G. C. -S.; Forney, D. R.; Patel, K. M.; Rorer, M. P.; Smith, W. F., III; Stevenson, T. M.; Sun, K.-M.; Tseng, C.-P. PCT Int. Appl. WO 2000043377 A1, 2000;
24. Chem. Abstr. 133 (2000) 135313
25. Takeda, K.; Terashima, N.; Nakano, J.; Minami, H.; Kobayashi, T.; Furuhata, K.; Takakura, T.; Takata, M.; Kawafuchi, H.; Hiraiwa, T. PCT Int. Appl. WO 9410158 A1, 1994;
26. Chem. Abstr. 122 (1995) 214056
27. Eldred, C. D.; Pennell, A. M. K. PCT Int. Appl. WO 9924451 A2, 1999;
28. Chem. Abstr. 130 (1999) 325350
29. More then 200 references were found in SciFinder. A few selected examples:
30. Sabitha G., Babu R.S., Reddy M.S.K., and Yadav J.S. Synthesis (2002) 2254
31. Cepanec I., Litvic M., Mikuldas H., Bartolincic A., and Vinkovic V. Tetrahedron 59 (2003) 2435
32. Chakraborti A.K., and Kondaskar A. Tetrahedron Lett. 44 (2003) 8315
33. Rodriguez J.R., and Navarro A. Tetrahedron Lett. 45 (2004) 7495
34. Chakraborti A.K., Kondaskar A., and Rudrawar S. Tetrahedron 60 (2004) 9085
35. Kamal A., Ramu R., Azhar M.A., and Khanna G.B.R. Tetrahedron Lett. 46 (2005) 2675
36. Shivani, Pujala B., and Chakraborti A.K. J. Org. Chem. 72 (2007) 3713
37. Magerramov A.M., Abdinbekova R.T., Kurbanova M.M., Zamanova A.V., and Allakhverdiev M.A. Russ. J. Appl. Chem. 77 (2004) 1667
38. Kurbanova M.M., Akhmedova K.T., Allachverdiyev M.A., and Magerramov A.M. Izv. Vuz. Khim. Kh. Tekh. 47 (2004) 95
39. Chem. Abstr. 144 (2005) 434757
40. Marquerramov A.M., Abdinbekova R.T., Kurbanova M.M., Zamanova A.V., and Allachverdiyev M.A. Neft Kim. Neft E'mali Pros. (2003) 50
41. Chem. Abstr. 144 (2005) 6492
42. Pacchioni M., Cornia A., Fabretti A.C., Zobbi L., Bonacchi D., Caneschi A., Chastanet G., Gatteschi D., and Sessoli R. Chem. Commun. (2004) 2604
43. Puterova Z., Vegh D., Gottasova R., and Vegh Z. ARKIVOC xii (2005) 36
44. Morisaki Y., Ishida T., and Chujo Y. Org. Lett. 8 (2006) 1029
45. Capeller R.V., Griot R., Häring M., and Wagner-Jauregg T. Helv. Chim. Acta 40 (1957) 1652
46. De Kimpe N., Jolie R., and De Smaele D. J. Chem. Soc., Chem. Commun. (1994) 1221
47. De Kimpe N., De Smaele D., and Szakonyi Z. J. Org. Chem. 62 (1997) 2448
48. D'hooghe M., Waterinckx A., and De Kimpe N. J. Org. Chem. 70 (2005) 227
49. D'hooghe M., Rottiers M., Jolie R., and De Kimpe N. Synlett (2005) 931
50. D'hooghe M., and De Kimpe N. Synlett (2006) 2089
51. Qiu X.L., Meng W.D., and Qing F.L. Tetrahedron 60 (2004) 6711
52. Sutherland A., and Willis C.L. Nat. Prod. Rep. 17 (2000) 621
53. Wu G., Schumacher D.P., Tormos W., Clark J.E., and Murphy B.L. J. Org. Chem. 62 (1997) 2996
54. Markov V.I., Doroshenko V.A., Klimenko O.I., and Sachko G.P. Zh. Org. Khim. 8 (1972) 1717
55. Chem. Abstr. 77 (1972) 139853
56. Ho M., Chung J.K.K., and Tang N. Tetrahedron Lett. 34 (1993) 6513
57. Brands K.M.J., and Pandit U.K. Heterocycles 30 (1990) 257
58. Brands K.M.J., Meekel A.A.P., and Pandit U.K. Tetrahedron 47 (1991) 2005
59. Garner P., and Park J.M. Org. Synth. 70 (1992) 18
60. Dondoni A., and Perrone D. Synthesis (1997) 527
61. Pavé G., Usse-Versluys S., Viaud-Massuard M.-C., and Guillaumet G. Org. Lett. 5 (2003) 4253
62. Paul R., Williams R.P., and Cohen E. J. Org. Chem. 40 (1975) 1653
63. Beger J., Günther K., and Vogel J. J. Prakt. Chem. 311 (1969) 15
64. Paul R., Williams R.P., and Cohen E. Contraception 9 (1974) 451
65. Hansen J.F., and Cooper C.S. J. Org. Chem. 41 (1976) 3219
66. Aït-Haddou H., Hoarau O., Cramailére D., Pezet F., Daran J.-C., and Balavoine G.G.A. Chem.-Eur. J. 10 (2004) 699
67. Xi Z., Cheng X.-F., Chen W.-B., and Cao L.-Q. Tetrahedron Lett. 47 (2006) 3337
68. McKillop A., Taylor R.J.K., Watson R.J., and Lewis N. Synthesis (1994) 31
69. Kenworthy M.N., Kilburn J.P., and Taylor R.J.K. Org. Lett. 6 (2004) 19
70. Barfoot C.W., Harvey J.E., Kenworthy M.N., Kilburn J.P., Ahmed M., and Taylor R.J.K. Tetrahedron 61 (2005) 3403
71. Harvey J.E., Kenworthy M.N., and Taylor R.J.K. Tetrahedron Lett. 45 (2004) 2467
72. Jose Maria E., Da Silva A.D., Fourrey J.-L., Machado A.S., and Robert-Géro M. Tetrahedron Lett. 35 (1994) 3301
73. Iwasa S., Nakamura H., and Nishiyama H. Heterocycles 52 (2000) 939
74. Cook G.R., and Pararajasingham K. Tetrahedron Lett. 43 (2002) 9027
75. Ohno H., Anzai M., Toda A., Ohishi S., Fujii N., Tanaka T., Takemoto Y., and Ibuka T. J. Org. Chem. 66 (2001) 4904
76. Bravo P., Cavicchio G., Crucianelli M., Poggiali A., and Zanda M. Tetrahedron: Asymmetry 8 (1997) 2811
77. Engman L. J. Org. Chem. 58 (1993) 2394
78. Okada T., Tsuji T., Tsushima T., Yoshida T., and Matsuura S. J. Heterocycl. Chem. 28 (1991) 1061
79. Khripak S.M., Plesha M.V., Slivka M.V., Yakubets V.I., and Krivovyaz A.A. Russ. J. Org. Chem. 40 (2004) 1705
80. Eastwood F.W., Perlmutter P., and Yang Q. J. Chem. Soc., Perkin Trans. 1 (1997) 35
81. Foster A.B., Jarman M., Kinas R.W., Van Maanen J.M.S., Taylor G.N., Gaston J.L., Parkin A., and Richardson A.C. J. Med. Chem. 24 (1981) 1399
82. Lown J.W., and Joshua A.V. Can. J. Chem. 55 (1977) 131
83. Lown J.W., and Joshua A.V. Can. J. Chem. 55 (1977) 508
84. Diner U.E., Worsley M., and Lown J.W. J. Chem. Soc. (1971) 3131
85. Higashiura K., and Ienaga K. J. Chem. Res., Synop. (1992) 250
86. Higashiura, K.; Kurohashi, M. Jpn. Kokai Tokkyo Koho JP 04077466 A, 1992;
87. Chem. Abstr. 117 (1992) 70336
88. Cardillo G., Orena M., Porzi G., and Sandri S. J. Chem. Soc., Chem. Commun. (1982) 1309
89. Newsholme G., and Tipping A.E. J. Fluorine Chem. 68 (1994) 93
90. Ziyatdinov R.N., Il'yasov A.V., and Morozov V.I. Izv. Vuz. Khim. Kh. Tekh. 34 (1991) 37
91. Chem. Abstr. 116 (1992) 150921
92. Zaagsma J. J. Med. Chem. 22 (1979) 441
93. Cockayne G.A., and Taylor P.J. J. Chem. Soc., Perkin Trans. 2 (1972) 2173
94. Todo Y., Takagi H., Iino F., Fukuoka Y., Takahata M., Okamoto S., Saikawa I., and Narita H. Chem. Pharm. Bull. 42 (1994) 2569
95. Mikhel'son M.Y., and Shelkovnikov S.A. Gen. Pharmacol. 11 (1980) 75