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Volumn 7, Issue 10, 1997, Pages 1359-1364

Rational design, synthesis, and serine protease inhibitory activity of novel P1-argininoyl heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; BLOOD CLOTTING FACTOR 10A; DIPEPTIDE; PLASMIN; PROTHROMBIN A; SERINE PROTEINASE; SERINE PROTEINASE INHIBITOR; THROMBIN;

EID: 0031579958     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00227-8     Document Type: Article
Times cited : (23)

References (34)
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    • All new compounds were characterized by full spectroscopic (NMR, IR, low/high-resolution MS) data. Yields refer to spectroscopically and chromatographically homogeneous (≥95% by 1H NMR, HPLC, TLC) materials
    • All new compounds were characterized by full spectroscopic (NMR, IR, low/high-resolution MS) data. Yields refer to spectroscopically and chromatographically homogeneous (≥95% by 1H NMR, HPLC, TLC) materials.
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    • Attempts to convert t-butylacetyl-dPhePro-nitroargininal cyanohydrin to the corresponding peptidoyl benzoxazole via the imidate employing the standard protocol were unsuccessful in our laboratory
    • Attempts to convert t-butylacetyl-dPhePro-nitroargininal cyanohydrin to the corresponding peptidoyl benzoxazole via the imidate employing the standard protocol were unsuccessful in our laboratory.
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    • Boc Ng-nitroargininal 5 was prepared according to a modified procedure of Goel et al. NMR and HPLC analyses indicate that 5 exists as a mixture of the two cyclic hemiaminal forms and the free aldehyde
    • Boc Ng-nitroargininal 5 was prepared according to a modified procedure of Goel et al. NMR and HPLC analyses indicate that 5 exists as a mixture of the two cyclic hemiaminal forms and the free aldehyde.
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    • This mixture of stereosiomers was carried forward through the synthesis. The stereochemistry becomes irrelevant due to the loss of the stereocenter during the oxidation to the ketone at the last step
    • This mixture of stereosiomers was carried forward through the synthesis. The stereochemistry becomes irrelevant due to the loss of the stereocenter during the oxidation to the ketone at the last step.
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    • For a detailed experimental procedure describing the preparation of compound 8, see US Patent 5,371,072
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    • For a detailed experimental procedure describing the preparation of compound 8, see Webb, T.R.; Miller, T.A.; Vlasuk, G.P. US Patent 5,371,072, 1994; Chem. Abstr. 1997, 126, 199831.
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    • Mono-Boc phenylene diamine was prepared by the treatment of phenylenediamine, dihydrochloride salt, with one equiv Boc anhydride and three equiv sodium bicarbonate in aqueous dioxane. Recrystallization of the crude product from ethyl acetate/hexanes provided the desired product, which was spectroscopically and chromatographically homogeneous (≥95% by 1H NMR, and TLC)
    • Mono-Boc phenylene diamine was prepared by the treatment of phenylenediamine, dihydrochloride salt, with one equiv Boc anhydride and three equiv sodium bicarbonate in aqueous dioxane. Recrystallization of the crude product from ethyl acetate/hexanes provided the desired product, which was spectroscopically and chromatographically homogeneous (≥95% by 1H NMR, and TLC).
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    • t-Butylacetyl-dPheProOH and Ac-dPheProOH, prepared using standard solution phase peptide coupling techniques, were spectroscopically and chromatographically homogeneous (≥95% by 1H NMR, and TLC)
    • t-Butylacetyl-dPheProOH and Ac-dPheProOH, prepared using standard solution phase peptide coupling techniques, were spectroscopically and chromatographically homogeneous (≥95% by 1H NMR, and TLC).
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    • The crystal structure of PPACK-thrombin was elucidated by and was used with the computer programs Insight II and Discover (MSI, San Diego, CA) to model and display the inhibitors
    • The crystal structure of PPACK-thrombin was elucidated by Vijayalakshmi, J.; Padmanabhan, K.P.; Mann, K.G.; Tulinsky, A. Protein Sci. 1994, 3, 2254, and was used with the computer programs Insight II and Discover (MSI, San Diego, CA) to model and display the inhibitors.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.