BIOLOGICALLY ORIENTED ORGANIC SULFUR CHEMISTRY .21. HYDRODISULFIDE OF A PENICILLAMINE DERIVATIVE AND RELATED-COMPOUNDS
BIOLOGICALLY ORIENTED ORGANIC SULFUR CHEMISTRY .21. HYDRODISULFIDE OF A PENICILLAMINE DERIVATIVE AND RELATED-COMPOUNDS
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DOI：
10.1021/jo00320a030
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发表时间：
1981-01-01
影响因子：
3.6
通讯作者：
NEAL, RA
中科院分区：
文献类型：
--
作者：
HEIMER, NE;FIELD, L;NEAL, RA
为了研究氨基酸衍生的二硫化氢化合物（10，Me 2C（SR）CH（NHAc）CO2 Me，R = SH）的化学性质，开发了药物N-乙酰基-DL-青霉胺的二硫化氢衍生物的合成路线。10的氯仿溶液在室温下6天和55 ℃下1天后没有变化。C，然后消耗预期量的I。用碳酸氢盐洗涤导致立即分解;纯10在-10 ℃储存期间完全分解。10在盐酸-甲醇中的半衰期约为12 h。10与氰离子反应生成硫氰酸根离子，与2，4-二硝基氯苯反应生成二硝基苯基衍生物[13，R = 2，4-（NO2）2C 6 H3 S]。
For study of the chemistry of an amino acid derived hydrodisulfide (10, Me2C(SR)CH(NHAc)CO2Me, R = SH), a synthetic route to a hydrodisulfide derivative of the drug N-acetyl-DL-penicillamine was developed. Solutions of 10 in chloroform were unchanged after 6 days at room temperature and 1 day at 55.degree. C and then consumed the expected amount of I. Washing with bicarbonate led to immediate decomposition; neat 10 completely decomposed during storage at -10.degree. C for 36 h, and the half-life of 10 in HCl-methanol was about 12 h. Treatment of 10 with cyanide ion gave thiocyanate ion, and treatment with 2,4-dinitrochlorobenzene gave a dinitrophenyl derivative [13, R = 2,4-(NO2)2C6H3S].