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Volumn 64, Issue 9, 1999, Pages 3019-3025

Cyclic dipeptides. 3.1 Synthesis of methyl (R)-6-[(tert- butoxycarbonyl)amino]-4,5,6,7-tetrahydro-2-methyl-5-oxo-1,4-thiazepine-3- carboxylate and its hexahydro analogues: Elaboration of a novel dual ACE/NEP inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CYCLOPEPTIDE; DIPEPTIDE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; KETONE; MESYLIC ACID DERIVATIVE; PEPTIDE DERIVATIVE; SULFONIC ACID DERIVATIVE; THIAZEPINE DERIVATIVE; THIOL GROUP;

EID: 0033617331     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981425v     Document Type: Article
Times cited : (39)

References (72)
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    • Testa, B., Meyer, U. A., Eds.; Academic Press: San Diego, CA
    • (b) Lawton, G.; Paciorek, P. M.; Waterfall, J. F. In Advances in Drug Research; Testa, B., Meyer, U. A., Eds.; Academic Press: San Diego, CA, 1992; Vol. 23, pp 161-220.
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    • Lawton, G.1    Paciorek, P.M.2    Waterfall, J.F.3
  • 43
    • 85069129093 scopus 로고    scopus 로고
    • note
    • Prepared from 8a by reaction with potassium carbonate in refluxing chloroform (see the Supporting Information).
  • 44
    • 85069129912 scopus 로고    scopus 로고
    • note
    • For molecular mechanics calculations on the four possible stereoisomers of 2, see ref 14.
  • 45
    • 85069135417 scopus 로고    scopus 로고
    • We thank one of the reviewers for highlighting this point
    • We thank one of the reviewers for highlighting this point.
  • 53
    • 85069136782 scopus 로고    scopus 로고
    • note
    • No attempt has been made yet to assess the actual mechanism of this cyclization reaction.
  • 54
    • 85069141430 scopus 로고    scopus 로고
    • note
    • 3 as described for the synthesis of 2 were unsuccessful, giving complex reaction mixtures in which thiazepine 3 was never detected.
  • 55
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    • For a recent review on vinyl and aryl triflates, see: Ritter, K. Synthesis 1993, 735-761.
    • (1993) Synthesis , pp. 735-761
    • Ritter, K.1
  • 59
    • 0001454958 scopus 로고
    • They also suggested that the formation of allenylazetidinones would occur through a mechanism of the E1cb type. See also: (a) Hansen, R. L. J. Org. Chem. 1965, 30, 4322-4324. (b) Streitwieser, A., Jr.; Wilkins, C. L.; Kiehlmann, E. J. Am. Chem. Soc. 1968, 90, 1598-1601.
    • (1965) J. Org. Chem. , vol.30 , pp. 4322-4324
    • Hansen, R.L.1
  • 60
    • 0001152360 scopus 로고
    • They also suggested that the formation of allenylazetidinones would occur through a mechanism of the E1cb type. See also: (a) Hansen, R. L. J. Org. Chem. 1965, 30, 4322-4324. (b) Streitwieser, A., Jr.; Wilkins, C. L.; Kiehlmann, E. J. Am. Chem. Soc. 1968, 90, 1598-1601.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 1598-1601
    • Streitwieser A., Jr.1    Wilkins, C.L.2    Kiehlmann, E.3
  • 63
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    • Ph.D. Thesis, University of Siena
    • Crescenza, A. Ph.D. Thesis, University of Siena, 1998.
    • (1998)
    • Crescenza, A.1
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    • note
    • Compounds 16b and the corresponding sulfone exhibited in vitro cytotoxic activity in the MTT test at 50 μM concentration.
  • 71
    • 85069142609 scopus 로고    scopus 로고
    • note
    • SDP, Structure Determination Package, Enraf-Nonius, Delft, The Netherlands, 1982.
  • 72
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    • note
    • The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.