Relative rates of Michael reactions of 2′-(phenethyl)thiol with vinyl sulfones, vinyl sulfonate esters, and vinyl sulfonamides relevant to vinyl sulfonyl cysteine protease inhibitors
Relative rates of Michael reactions of 2′-(phenethyl)thiol with vinyl sulfones, vinyl sulfonate esters, and vinyl sulfonamides relevant to vinyl sulfonyl cysteine protease inhibitors
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DOI：
10.1021/ol034555l
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发表时间：
2003-05-29
期刊：
影响因子：
5.2
通讯作者：
Roush, WR
中科院分区：
文献类型：
--
作者：
Reddick, JJ;Cheng, JM;Roush, WR
测量2 '-（苯乙基）硫醇与代表性乙烯基磺酰基迈克尔受体的迈克尔加成的相对速率。迈克尔受体上的磺酰基R取代基的性质的反应性的依赖性进行了测定，以评估这些取代基上的α-取代的乙烯基磺酰基半胱氨酸蛋白酶抑制剂的失活动力学的影响。这些迈克尔加成的速率变化超过3个数量级，其中苯基乙烯基磺酸酯（R = OPh）约为1.5。3000-比N-苄基乙烯基磺酰胺（R = NHBn）的反应活性高1倍。
[GRAPHIC]The relative rates of Michael additions of 2'-(phenethyl)thiol to representative vinyl sulfonyl Michael acceptors were measured. The dependence of the reactivity of the Michael acceptor on the nature of the sulfonyl R substituent was determined in order to evaluate the effect of these substituents on the inactivation kinetics of comparably substituted vinyl sulfonyl cysteine protease inhibitors. The rates of these Michael additions vary over 3 orders of magnitude, with phenyl vinyl sulfonate esters (R = OPh) being ca. 3000-fold more reactive than N-benzyl vinyl sulfonamides (R = NHBn).