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Volumn 5, Issue 3, 2008, Pages 178-181

Synthesis and antimalarial activity of novel hydroxyethylamines, potential aspartyl protease inhibitors

Author keywords

Antimalarial; Hydroxyethylamine; Protease inhibitors

Indexed keywords

ASPARTIC PROTEINASE INHIBITOR; ETHYLAMINE;

EID: 42149154871     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018008784083938     Document Type: Article
Times cited : (15)

References (22)
  • 9
    • 0003658456 scopus 로고    scopus 로고
    • Ogden R.C, Flexner, C.W, Eds, Marcel Dekker Inc, New York
    • Ogden R.C., Flexner, C.W. (Eds.), Protease Inhibitors in AIDS Therapy; Marcel Dekker Inc., New York, 2001.
    • (2001) Protease Inhibitors in AIDS Therapy
  • 18
    • 42149087367 scopus 로고    scopus 로고
    • General Procedure for preparation of compounds 6a-k: To a mixture of the amine 4 (1 mmol) in ethyl acetate (15 ml) was added triethylamine (1.1 mmol) and DMF (3 drops) followed by the addition of the benzoyl chloride (1.1 mmol) in ethyl acetate (5 ml) at room temperature. The reaction mixture was warmed to 50°C and stirred for 4 hours. The organic extract was washed with saturated aqueous NaCl solution, dried (Mg2SO4, filtered and evaporated. Flash chromatography on silica gel using mixture of ethyl acetate and hexane as eluent, provided the target compound 6a-k as solid. Preparation of unavailable benzoyl chlorides for preparation of compounds 6f, 6g, 6h, 6i, 6j, 6k, Excess of thionyl chloride was added to corresponding benzoic acid and the resulting mixture was stirred at 50oC for 4 hours. Thionyl chloride was removed by distillation under reduced pressure and residue dried under vacuum
    • 4), filtered and evaporated. Flash chromatography on silica gel using mixture of ethyl acetate and hexane as eluent, provided the target compound 6a-k as solid. Preparation of unavailable benzoyl chlorides (for preparation of compounds 6f, 6g, 6h, 6i, 6j, 6k): Excess of thionyl chloride was added to corresponding benzoic acid and the resulting mixture was stirred at 50oC for 4 hours. Thionyl chloride was removed by distillation under reduced pressure and residue dried under vacuum.
  • 19
    • 42149196308 scopus 로고    scopus 로고
    • Selected data for compound 6i: Yield, 65, m.p. 99-102°C. 1H NMR (500 MHz, MeOD, 7.33 (d, 2H, J, 7.0 Hz, 7.22 (m, 3H, 7.13 (m, 2H, 6.79 (d, 1H, J, 8.0 Hz, 5.98 (dd, 2H, J, 3.0 Hz, 2J, 1.0 Hz, 4.44 (dt, 1H, J, 10.5 Hz, 2J, 4.0 Hz, 3.99 (m, 1H, 3.14 (dd, 1H, J, 11.5 Hz, 2J, 2.5 Hz, 3.05 (m, 2H, 2.69 (dd, 1H, J, 12.5 Hz, 2J, 8.0 Hz, 2.62 (dd, 1H, J, 11.0 Hz, 2J, 3.0 Hz, 2.19 (m, 2H, 2.09 (dd, 1H, J, 24.5 Hz, 2J, 13.0 Hz, 1.96 (m, 1H, 1.81 (m, 1H, 1.74 (m, 1H, 1.66 (m, 1H, 1.57 (m, 2H, 1.49 (dd, 1H, J, 13.5 Hz, 2J, 3.5 Hz, 1.43 (t, 2H, J, 7.0 Hz, 2J, 3.5 Hz, 1.37 (m, 1H, 1.26 (s, 9H, 13C NMR 100 MHz, MeOD, 176.2; 167.1; 149.3; 140.6; 136.5; 133.2; 132.9; 130.5; 129.9; 129.3; 127.2; 125.7; 71.6; 71.4; 60
    • 13C NMR (100 MHz, MeOD): 176.2; 167.1; 149.3; 140.6; 136.5; 133.2; 132.9; 130.5; 129.9; 129.3; 127.2; 125.7; 71.6; 71.4; 60.3; 60.2; 57.2; 51.9; 37.7; 36.1; 35.2; 32.2; 31.7; 28.8; 27.6; 27.3; 21.9.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.