|
【结 构 式】 
|
【药物名称】Cefminox sodium, MT-141, Alteporina, Tencef, Meicelin 【化学名称】7beta-[2-[2(S)-Amino-2-carboxyethylthio]acetamido]-7alpha-methoxy-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid sodium salt 【CA登记号】88641-36-5 【 分 子 式 】C16H20N7NaO7S3 【 分 子 量 】541.5623 |
【开发单位】Bristol-Myers Squibb (Originator), Meiji Seika (Originator), Alter (Licensee) 【药理作用】Cephalosporins |
合成路线1
A new method for the synthesis of MT-141 has been reported: By condensation of 7-bromoacetamido-7alpha-methoxy-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (I) with D-cysteine (II) in aqueous NaHCO3.
| 【1】 Ogino, H.; Omoto, S.; Tsuruoka, T.; Miyauchi, K.; Niida, T.; Inouye, S.; Mizutani, K.; Iwamatsu, K.; Watanabe, T.; Synthesis and biological activity of 7beta-(2-amino-2-carboxy)-ethylthioacetamido-7alpha-methoxycephalosporin derivatives. J Antibiot 1983, 36, 3, 229-241. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 30738 | (6R,7S)-7-[(2-bromoacetyl)amino]-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C13H15BrN6O5S2 | 详情 | 详情 | |
| (II) | 25404 | D-cysteine; (S)-2-Amino-3-mercaptopropionic acid | 921-01-7 | C3H7NO2S | 详情 | 详情 |
合成路线2
The reaction of 7-beta-bromoacetamido-7-alphamethoxycephalosporanic acid (I) with D-cysteine (II) in water at pH 7 gives 7-(2-aminocarboxyethylthio)acetamido-7-alpha-methoxycephalosporanic acid (III), which is then condensed with 5-mercapto-1-methyl-1H-tetrazole (IV) in water at pH 6.5-7 and at 60 C.
| 【1】 Iwamatsu, K.; Inoue, S.; Miyauchi, K.; Kondo, S.; Seki, S.; Yamada, Y. (Meiji Seika Kaisha, Ltd.); 7alpha-Methoxycephalosporin derivatives. JP 55083791 . |
| 【2】 Blancafort, P.; Castaner, J.; Loren, J.G.; Serradell, M.N.; MT-141. Drugs Fut 1982, 7, 6, 395. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 31959 | (6R,7S)-3-[(acetoxy)methyl]-7-[(2-bromoacetyl)amino]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-beta-bromoacetamido-7-alphamethoxycephalosporanic acid | C13H15BrN2O7S | 详情 | 详情 | |
| (II) | 25404 | D-cysteine; (S)-2-Amino-3-mercaptopropionic acid | 921-01-7 | C3H7NO2S | 详情 | 详情 |
| (III) | 31960 | (6R,7S)-3-[(acetoxy)methyl]-7-[(2-[[(2S)-2-amino-2-carboxyethyl]sulfanyl]acetyl)amino]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-(2-aminocarboxyethyIthio)acetamido-7-alpha-methoxycephalosporanic acid | C16H21N3O9S2 | 详情 | 详情 | |
| (IV) | 28420 | 5-Mercapto-1-methyl-1H-tetrazole; 1-Methyl-1H-1,2,3,4-tetraazol-5-ylhydrosulfide | 13183-79-4 | C2H4N4S | 详情 | 详情 |