t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate 1β-oxide | 95570-71-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate 1β-oxide
• 英文别名: tert-butyl (5S,6R,7S)-3-(acetyloxymethyl)-7-methoxy-5,8-dioxo-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；tert-butyl (5S,6R,7S)-3-(acetyloxymethyl)-7-methoxy-5,8-dioxo-5λ4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 95570-71-1
• 化学式: C₁₅H₂₁NO₇S
• 分子量: 359.4
• InChiKey: NNIUGIKAJGEYIP-UDWROGOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate 1β-oxide 在 palladium on activated charcoal tin(II) iodide 、 氢气 、 盐酸二甲胺 、 苯甲醚 、 乙酰氯 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 97.5h， 生成 p-carboxymethyl-3-acetoxymethyl-7α-methoxy-2α-methyl-3-cephem-4-carboxylate 1,1-dioxide
  参考文献：
  名称：

  Inhibition de l'élastase leucocytaire humaine: inhibition par des céphalosporines sulfones substituées sur le C-2

  摘要：

  DOI：

  10.1016/0223-5234(89)90027-5
• 作为产物：
  描述：

  tert-butyl (6R)-3-(acetyloxymethyl)-7-bromo-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 在 ammonium acetate 、 间氯过氧苯甲酸 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate 1β-oxide
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 1. Inhibition by C-7-substituted cephalosporin tert-butyl esters

  摘要：

  Time-dependent inhibitors of the enzyme human leukocyte elastase have been developed based on the cephem nucleus. A series of cephalosporin tert-butyl esters has been examined, and the activity of these compounds has been found to be very sensitive to C-7 substituents, with small, alpha-oriented, electron-withdrawing groups showing greatest activity. Additionally, the oxidation state of the sulfur atom has been found to play a role in potency, with sulfones showing considerably greater activity than the corresponding sulfides or beta-sulfoxides. The alpha-sulfoxides were inactive.

  DOI：

  10.1021/jm00171a028

文献信息

• HAGMANN, WILLIAM K.;OGRADY, LAURA A.;ASHE, BONNIE M.;DAHLGREN, M. ELLEN;W+, EUR. J. MED. CHEM., 24,(1989) N, C. 599-604
  作者：HAGMANN, WILLIAM K.、OGRADY, LAURA A.、ASHE, BONNIE M.、DAHLGREN, M. ELLEN、W+

  DOI：——

  日期：——
• Inhibition of human leukocyte elastase. 1. Inhibition by C-7-substituted cephalosporin tert-butyl esters
  作者：James B. Doherty、Bonnie M. Ashe、Peter L. Barker、Thomas J. Blacklock、John W. Butcher、Gilbert O. Chandler、M. Ellen Dahlgren、Philip Davies、Conrad P. Dorn

  DOI：10.1021/jm00171a028

  日期：1990.9

  Time-dependent inhibitors of the enzyme human leukocyte elastase have been developed based on the cephem nucleus. A series of cephalosporin tert-butyl esters has been examined, and the activity of these compounds has been found to be very sensitive to C-7 substituents, with small, alpha-oriented, electron-withdrawing groups showing greatest activity. Additionally, the oxidation state of the sulfur atom has been found to play a role in potency, with sulfones showing considerably greater activity than the corresponding sulfides or beta-sulfoxides. The alpha-sulfoxides were inactive.
• Inhibition de l'élastase leucocytaire humaine: inhibition par des céphalosporines sulfones substituées sur le C-2
  作者：W Hagmann

  DOI：10.1016/0223-5234(89)90027-5

  日期：1989.12