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Volumn 7, Issue 8, 1997, Pages 1021-1026

Synthesis and creatine kinase inhibitory activity of nonhydrolyzable analogs of phosphocreatine

Author keywords

[No Author keywords available]

Indexed keywords

AMIDINE; CREATINE KINASE; CREATINE PHOSPHATE; ENZYME INHIBITOR; PHOSPHONIC ACID DERIVATIVE;

EID: 0030934347     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00161-3     Document Type: Article
Times cited : (5)

References (26)
  • 17
    • 0343997098 scopus 로고    scopus 로고
    • note
    • In a typical experimental procedure: Diethyl N-(carboxymethyl)amidinomethylphospnonate (5): 1.0165 g (2.90 mmol) of 4 was added to a stirred mixture of 0.2213 g (2.95 mmol) of glycine, 1.0 mL of dichloromethane and 2.0 mL of pyridine. The mixture was stirred overnight and then filtered to remove solids. After rinsing with dichloromethane, hexanes was added to the filtrate until it was persistently cloudy, and the mixture was placed in a 5 °C refrigerator overnight. The solid was removed by filtration and air dried on the filter after thorough rinsing with cold dichloromethane. The white solid weighs 0.5897 g (44.3%).
  • 18
    • 0343560875 scopus 로고    scopus 로고
    • note
    • In a typical experimental procedure: N-(Carboxymethyl)amidinomethylphosphonic acid, disodium salt (1): Bromotrimethylsilane (1.5 equiv.) was added to diethyl N-(carboxymethyl)amidinomethyl-phosphonate (1.0 equiv.) and the mixture was stirred at room temperature overnight. The excess TMSBr was evaporated under vacuum. The residue was redissolved in of water and stirred at room temperature for 4 h. The mixture was then lyophilized to dryness. The solid was redissolved in water, loaded onto an anion exchange column (Dowex 1×8-200, HCO3-form) (18 mm × 9.4 cm) and eluted with a linear gradient from 100% water to 1 M TBK (TBK = triethylammonium bicarbonate, prepared by mixing 139 mL of triethylamine in 1 L of water and bubbling CO2 into the mixture until the pH reaches 8.6). The fractions with product were identified by spotting them on a silica plate and staining with ninhydrin. The ones which had material that stained more darkly than triethylamine and ran with TBK were combined and lyophilized to dryness. The solid was lyophilized twice more from 2 mL of water each time to ensure that no TBK remained. The solid was dissolved in water, loaded onto a cation exchange column (Dowex 50×8-100, Na+ form) (10 mm × 9 cm) and eluted with water. Fractions containing product were identified as before, combined and lyophilized to dryness.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.