[(2,2-dimethylmalonyl)oxy]methyl penicillanate sulfone | 87353-21-7

• 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: [(2,2-dimethylmalonyl)oxy]methyl penicillanate sulfone
• 英文别名: 3-[[(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethoxy]-2,2-dimethyl-3-oxopropanoic acid；3-[[(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethoxy]-2,2-dimethyl-3-oxopropanoic acid
• CAS: 87353-21-7
• 化学式: C₁₄H₁₉NO₉S
• 分子量: 377.372
• InChiKey: WTYSNKMSQIOTJU-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2,2-dimethylmalonyl)oxy]methyl penicillanate sulfone 在 sodium 2-ethylhexanoic acid 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以98%的产率得到Sodium; 2-((2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyloxymethoxycarbonyl)-2-methyl-propionate
  参考文献：
  名称：

  Orally effective acid prodrugs of the .beta.-lactamase inhibitor sulbactam

  摘要：

  Sulbactam (1) is a beta-lactamase inhibitor with limited oral bioavailability. Lipophilic double-ester prodrug sulbactam pivoxil (2) significantly improves the oral absorption of sulbactam, as does the mutual prodrug double ester sultamicillin (3). We have found that double-ester prodrugs of sulbactam terminating in a carboxyl group (8) also were effective oral-delivery vehicles in rats. Carboxyl-terminated double esters have several potential advantages over their nonionizable lipophilic counterparts, including water solubility, crystallinity, choice of salts for dosage forms, and formation of innocuous byproducts on hydrolysis.

  DOI：

  10.1021/jm00163a055
• 作为产物：
  描述：

  <<3-(benzyloxy)-2,2-dimethylmalonyl>oxy>methyl penicillanate sulfone 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以90%的产率得到[(2,2-dimethylmalonyl)oxy]methyl penicillanate sulfone
  参考文献：
  名称：

  Orally effective acid prodrugs of the .beta.-lactamase inhibitor sulbactam

  摘要：

  Sulbactam (1) is a beta-lactamase inhibitor with limited oral bioavailability. Lipophilic double-ester prodrug sulbactam pivoxil (2) significantly improves the oral absorption of sulbactam, as does the mutual prodrug double ester sultamicillin (3). We have found that double-ester prodrugs of sulbactam terminating in a carboxyl group (8) also were effective oral-delivery vehicles in rats. Carboxyl-terminated double esters have several potential advantages over their nonionizable lipophilic counterparts, including water solubility, crystallinity, choice of salts for dosage forms, and formation of innocuous byproducts on hydrolysis.

  DOI：

  10.1021/jm00163a055

文献信息

• 1,1-Alkanediol dicarboxylate linked antibacterial agents
  申请人：PFIZER INC.

  公开号：EP0083484A1

  公开（公告）日：1983-07-13

  Useful antibacterial agents in which a penicillin and/or a beta-lactamase inhibitor are linked via 1,1-alkanediol dicarboxylates are of the formula where A is the residue of certain dicarboxyic acids, R3 is H or (C1-C3)alkyl, n is zero or 1 such that when n is zero R is P or B and R1 'is the residue of certain esters, H or a salt thereof; and when n is 1, one of R and R1 is P and the other is B, and P is where R2 is H or certain acyl groups, and B is the residue of a beta-lactamase inhibiting carboxylic acid; a method for their use, pharmaceutical compositions thereof and intermediates useful in their production.

  通过 1,1-烷二醇二羧酸盐连接青霉素和/或 β-内酰胺酶抑制剂的有用抗菌剂的结构式为 其中 A 是某些二羧酸的残基，R3 是 H 或 (C1-C3)烷基，n 是零或 1，当 n 为零时，R 是 P 或 B，R1 '是某些酯的残基、H 或其盐；当 n 为 1 时，R 和 R1 中的一个是 P，另一个是 B，且 P 是 其中 R2 是 H 或某些酰基，B 是抑制 beta-内酰胺酶的羧酸的残基；它们的使用方法、它们的药物组合物和生产它们的中间体。
• Bis-esters of dicarboxylic acids with amoxicillin and certain hydroxymethylpenicillanate 1,1-dioxides
  申请人：PFIZER INC.

  公开号：EP0121383A1

  公开（公告）日：1984-10-10

  Antibacterial agents of the formula:- and Z is 1,4-cyclohexylene or alkylene having from 1 to 6 carbon atoms; their pharmaceutically acceptable salts, and certain amino-protected intermediates therefore.

  配方中的抗菌剂：- 和 Z 是 1，4-环己烯或具有 1 至 6 个碳原子的亚烷基；它们的药学上可接受的盐，以及某些氨基保护的中间体。
• ENGLISH, ARTHUR R.;GIRARD, DENNIS;JASYS, V. JOHN;MARTINGANO, ROBERT J.;KE+, J. MED. CHEM., 33,(1990) N, C. 344-347
  作者：ENGLISH, ARTHUR R.、GIRARD, DENNIS、JASYS, V. JOHN、MARTINGANO, ROBERT J.、KE+

  DOI：——

  日期：——
• US4457924A
  申请人：——

  公开号：US4457924A

  公开（公告）日：1984-07-03
• US4462934A
  申请人：——

  公开号：US4462934A

  公开（公告）日：1984-07-31