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Volumn 5, Issue 13, 2003, Pages 2343-2346

Efficient synthesis of 3-aminocyclobut-2-en-1-ones: Squaramide surrogates as potent VLA-4 antagonists

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; CD29 ANTIGEN; CD29 ANTIGEN ANTAGONIST; CHLORIDE; CYCLOBUTANONE DERIVATIVE; PHENYLALANINE; REAGENT; RECEPTOR BLOCKING AGENT; SODIUM CHLORIDE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0141853175     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034701n     Document Type: Article
Times cited : (19)

References (24)
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    • Seiffge, J. J. Rheumatol. 1996, 23, 2086. Gordon, F. H.; Lai, C. W. Y.; Hamilton, M. I.; Pounder, R. E. Gastroenterology 2001, 121, 268. Borchers, M. T.; Crosby, J.; Farmer, S. Am. J. Physiol. 2001, 280, 813.
    • (2001) Am. J. Physiol. , vol.280 , pp. 813
    • Borchers, M.T.1    Crosby, J.2    Farmer, S.3
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    • (2000) IDrugs , vol.3 , pp. 788
    • Porter, J.R.1
  • 13
    • 0000831564 scopus 로고
    • Wasserman, Martin, and Moore have each reported the synthesis of a single example of the title compound using this approach, the latter within the context of the preparation of an amino-substituted naphthol, see: (a) Wasserman, H. H.; Piper, J. U.; Dehmlow, E. V. J. Org. Chem. 1973, 38, 1451. (b) Hasek, R. H.; Gott, P. G.; Martin, J. C. J. Org. Chem. 1964, 29, 2510. (c) Turnbull, P.; Moore, H. W. J. Org. Chem. 1995, 60, 644.
    • (1973) J. Org. Chem. , vol.38 , pp. 1451
    • Wasserman, H.H.1    Piper, J.U.2    Dehmlow, E.V.3
  • 14
    • 0141438785 scopus 로고
    • Wasserman, Martin, and Moore have each reported the synthesis of a single example of the title compound using this approach, the latter within the context of the preparation of an amino-substituted naphthol, see: (a) Wasserman, H. H.; Piper, J. U.; Dehmlow, E. V. J. Org. Chem. 1973, 38, 1451. (b) Hasek, R. H.; Gott, P. G.; Martin, J. C. J. Org. Chem. 1964, 29, 2510. (c) Turnbull, P.; Moore, H. W. J. Org. Chem. 1995, 60, 644.
    • (1964) J. Org. Chem. , vol.29 , pp. 2510
    • Hasek, R.H.1    Gott, P.G.2    Martin, J.C.3
  • 15
    • 0001029204 scopus 로고
    • Wasserman, Martin, and Moore have each reported the synthesis of a single example of the title compound using this approach, the latter within the context of the preparation of an amino-substituted naphthol, see: (a) Wasserman, H. H.; Piper, J. U.; Dehmlow, E. V. J. Org. Chem. 1973, 38, 1451. (b) Hasek, R. H.; Gott, P. G.; Martin, J. C. J. Org. Chem. 1964, 29, 2510. (c) Turnbull, P.; Moore, H. W. J. Org. Chem. 1995, 60, 644.
    • (1995) J. Org. Chem. , vol.60 , pp. 644
    • Turnbull, P.1    Moore, H.W.2
  • 16
    • 0005941701 scopus 로고
    • Raphael, R. A., Taylor, E. C., Ed.; Interscience Publishers: New York
    • Arens, J. F. Advances in Organic Chemistry Methods and Results; Raphael, R. A., Taylor, E. C., Ed.; Interscience Publishers: New York, 1960; Vol. 2, pp 117-212. Martin, J. C. U.S. Patent 3 288 854, 1966.
    • (1960) Advances in Organic Chemistry Methods and Results , vol.2 , pp. 117-212
    • Arens, J.F.1
  • 17
    • 0141773631 scopus 로고    scopus 로고
    • U.S. Patent 3 288 854, 1966
    • Arens, J. F. Advances in Organic Chemistry Methods and Results; Raphael, R. A., Taylor, E. C., Ed.; Interscience Publishers: New York, 1960; Vol. 2, pp 117-212. Martin, J. C. U.S. Patent 3 288 854, 1966.
    • Martin, J.C.1
  • 18
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    • note
    • Ethoxyacetylene was purchased from Lancaster Chemical Co. as an approximately 50%w/w solution in hexanes. Yields 7a-1 were calculated based upon the amount of acid chloride used.
  • 19
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    • 9a and 9b were prepared in 99% and 92% yields, respectively
    • Pons, J.-M.; Kocienski, P. Tetrahedron Lett. 1989, 30, 1833. 9a and 9b were prepared in 99% and 92% yields, respectively.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 1833
    • Pons, J.-M.1    Kocienski, P.2
  • 21
    • 0141661694 scopus 로고    scopus 로고
    • note
    • Contrastingly, the reaction of 4 with cyclopenta-1,3-dione required several days for completion under these conditions.
  • 24
    • 0141773632 scopus 로고    scopus 로고
    • U.S. Patent 4 387 158, 1983
    • 1-Methyltetrazole-5-sulfenyl chloride has been previously prepared by chlorination of the mercaptan with chlorine. See: Postle, S. R. U.S. Patent 4 387 158, 1983.
    • Postle, S.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.