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Volumn 64, Issue 7, 1999, Pages 2219-2231

Solid-phase synthesis of 3,5-disubstituted 2,3-dihydro-1,5- benzothiazepin-4(5H)-ones

Author keywords

[No Author keywords available]

Indexed keywords

1,5 BENZOTHIAZEPINE 4 ONE; BENZOTHIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033515461     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981567p     Document Type: Article
Times cited : (71)

References (49)
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    • For a recent review, see: Lévai, A. Trends Heterocycl. Chem. 1995, 4, 51. See also: Wünsch, K.-H.; Ehlers, A. Z. Chem. 1970, 10, 361
    • (1995) Trends Heterocycl. Chem. , vol.4 , pp. 51
    • Lévai, A.1
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    • For a recent review, see: Lévai, A. Trends Heterocycl. Chem. 1995, 4, 51. See also: Wünsch, K.-H.; Ehlers, A. Z. Chem. 1970, 10, 361
    • (1970) Z. Chem. , vol.10 , pp. 361
    • Wünsch, K.-H.1    Ehlers, A.2
  • 24
    • 0032511925 scopus 로고    scopus 로고
    • A synopsis of all results obtained was presented at the 2nd Canadian Conference of Combinatorial Chemistry, Montreal, Canada, Oct. 6 and 7, 1997. Described were solid-phase syntheses of 1,5-benzothiazepin-4-ones, 1,6-benzothiazocin-5-ones, 1,5-benzodiazepin-2-ones, 4-alkoxy-1,4-thiazin-3-ones, quinoxalin-2-ones, and of a thieno-thiazepine
    • Schwarz, M. K.; Tumelty, D.; Gallop, M. A. Tetrahedron Lett. 1998, 39, 8397. A synopsis of all results obtained was presented at the 2nd Canadian Conference of Combinatorial Chemistry, Montreal, Canada, Oct. 6 and 7, 1997. Described were solid-phase syntheses of 1,5-benzothiazepin-4-ones, 1,6-benzothiazocin-5-ones, 1,5-benzodiazepin-2-ones, 4-alkoxy-1,4-thiazin-3-ones, quinoxalin-2-ones, and of a thieno-thiazepine.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8397
    • Schwarz, M.K.1    Tumelty, D.2    Gallop, M.A.3
  • 25
    • 0344677399 scopus 로고    scopus 로고
    • Loading: 0.33 mmol/g
    • Loading: 0.33 mmol/g.
  • 27
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    • See for example: (a) ref 11
    • See for example: (a) ref 11.
  • 30
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    • 2 (see Experimental Section)
    • 2 (see Experimental Section).
  • 31
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    • 2) to liberate the products for the purpose of analysis. After thorough evaporation of the solvent and gravimetric estimation of the crude yields, the residues were routinely analyzed by HPLC (UV detection at 220/280 nm) and ESI-MS
    • 2) to liberate the products for the purpose of analysis. After thorough evaporation of the solvent and gravimetric estimation of the crude yields, the residues were routinely analyzed by HPLC (UV detection at 220/280 nm) and ESI-MS.
  • 43
    • 0344245915 scopus 로고
    • Amide-formation, deprotection, and disulfide formation in peptide synthesis
    • Gutte, B., Ed.; Academic Press: San Diego, New York, Boston, London, Sydney, Tokyo, Toronto
    • Kiso, Y.; Yajima, H. Amide-Formation, Deprotection, and Disulfide Formation in Peptide Synthesis. In Peptides: Synthesis, Structures, and Applications; Gutte, B., Ed.; Academic Press: San Diego, New York, Boston, London, Sydney, Tokyo, Toronto, 1995; pp 40-93.
    • (1995) Peptides: Synthesis, Structures, and Applications , pp. 40-93
    • Kiso, Y.1    Yajima, H.2
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    • The importance of solvent choice with regard to limiting the extent of N-acylureas formation has long been appreciated: Sheehan, J. C.; Goodman, M.; Hess, G. P. J. Am. Chem. Soc. 1958, 78, 1367.
    • (1958) J. Am. Chem. Soc. , vol.78 , pp. 1367
    • Sheehan, J.C.1    Goodman, M.2    Hess, G.P.3
  • 45
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    • See Experimental Section
    • See Experimental Section.
  • 46
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    • note
    • Terminology based on the absolute configuration at C(3). Compound 38c was not synthesized.
  • 49
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    • Fmoc removal from the latter furnished the starting resin 42
    • 2 (loading: 0.41 mmol/g) was differentiated using a 9:1 molar ratio of Fmoc-Cl and Alloc-Cl and, following Fmoc deprotection, coupled with the Rink-type, acid-labile linker p-[(R,S)-[1-(9H-fluoren-9-yl)-methoxyformamido]-2,4-dimethoxybenzyl]- phenoxyacetic acid (Bernatowicz, M. S.; Daniels, S. B.; Köster, H. Tetrahedron Lett. 1989, 30, 4645). Fmoc removal from the latter furnished the starting resin 42.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4645
    • Bernatowicz, M.S.1    Daniels, S.B.2    Köster, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.