Herdewijn P, Claes P J, Vanderhaeghe H
J Med Chem. 1986 May;29(5):661-4. doi: 10.1021/jm00155a013.
The total synthesis of (+/-)-1-methylene-2,2- dimethyl-7-amino-1-carbacephem-4-carboxylic acid (1) is described. The reaction scheme was essentially that described by Christensen et al. for the synthesis of (+/-)-1-carbacephems. In vitro antibacterial activities of the 7-phenoxyacetyl and 7-D-alpha-phenylglycyl derivatives of 1 were compared with those of 7-(phenoxyacetamido)desacetoxycephalosporanic acid and cefalexin. Derivatives of 1 were 2-4 times less active against most of the sensitive organisms than the corresponding 7-aminodesacetoxycephalosporanic acid analogues. The activity of the 7-D-alpha-phenylglycyl derivative of 1 however was about 20 times lower than that of cefalexin when measured against Staphylococcus aureus ATCC 6538P.
描述了（±）-1-亚甲基-2,2-二甲基-7-氨基-1-碳头孢烯-4-羧酸（1）的全合成。反应方案基本上是克里斯滕森等人描述的用于合成（±）-1-碳头孢烯的方案。将1的7-苯氧乙酰基和7-D-α-苯甘氨酰衍生物的体外抗菌活性与7-（苯氧乙酰胺基）去乙酰氧基头孢烷酸和头孢氨苄的抗菌活性进行了比较。1的衍生物对大多数敏感菌的活性比相应的7-氨基去乙酰氧基头孢烷酸类似物低2-4倍。然而，当针对金黄色葡萄球菌ATCC 6538P进行测定时，1的7-D-α-苯甘氨酰衍生物的活性比头孢氨苄低约20倍。
