D-6-(2-amino-2-phenyl-acetamido)penicillanic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: D-6-(2-amino-2-phenyl-acetamido)penicillanic acid
• 英文别名: ampicillin；6-(D-2-amino-2-phenylacetamido)penicillanic acid；6-(2-amino-2-phenylacetamido)penicillanic acid；AMP；6-(D-(-)-α-amino-α-phenylacetamido)penicillanic acid；6-(D-α-aminophenylacetylamino)-penicillanic acid；(2S,5R)-6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 化学式: C₁₆H₁₉N₃O₄S
• 分子量: 349.411
• InChiKey: AVKUERGKIZMTKX-YXLKDIQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-6-(2-amino-2-phenyl-acetamido)penicillanic acid 、 氯甲酸对硝基苄酯 以82%的产率得到6-(2-[4-Nitrobenzyloxycarbonylamino]-2-phenylacetamido)penicillanic Acid
  参考文献：
  名称：

  Bis-esters of methanediol with penicillins and penicillanic acid

  摘要：

  6'-酰胺基青霉烷酸氧甲基酯是一种有用的抗菌剂。6'-氨基青霉烷酸氧甲基酯、卤代甲基酯、烷基磺酰氧甲基酯和芳基磺酰氧甲基酯是上述抗菌剂的有用中间体。

  公开号：

  US04244951A1

文献信息

• Bis-esters of methanediol with penicillins and penicillanic acid
  申请人：Pfizer Inc.

  公开号：US04244951A1

  公开（公告）日：1981-01-13

  6'-Acylaminopenicillanoyloxymethyl esters of penicillanic acid 1,1-dioxide are useful as antibacterial agents. The 6'-aminopenicillanoyloxymethyl ester, halomethyl esters, alkylsulfonyloxymethyl esters and arylsulfonyloxymethyl esters of penicillanic acid 1,1-dioxide are all useful intermediates for the aforesaid antibacterial agents.

  6'-酰胺基青霉烷酸氧甲基酯是一种有用的抗菌剂。6'-氨基青霉烷酸氧甲基酯、卤代甲基酯、烷基磺酰氧甲基酯和芳基磺酰氧甲基酯是上述抗菌剂的有用中间体。
• Acylaminopenicillanic acids and process for preparing them
  申请人：Hoechst Aktiengesellschaft

  公开号：US04018933A1

  公开（公告）日：1977-04-19

  Acylaminopenicillanic acids of the general formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 represent hydrogen or lower alkyl which may be substituted, and in which the radicals R.sup.1 and R.sup.2 or R.sup.2 and R.sup.3 may form together an alkylene radical which may be substituted, R.sup.4 and R.sup.5 represent hydrogen or lower alkyl, R.sup.6 represents phenyl which may be substituted, a monocyclic aromatic heterocycle which may be substituted, or dihydrophenyl, A represents a benzene or thiophene ring which may be substituted, and X represents oxygen or a single bond, a process for preparing them and pharmaceutical compositions active against bacterial infections containing these compounds.

  通用公式为##STR1##的酰胺青霉酸，其中R.sup.1、R.sup.2和R.sup.3代表氢或可以被取代的较低烷基，且基团R.sup.1和R.sup.2或R.sup.2和R.sup.3可以共同形成一个可以被取代的烷基基团，R.sup.4和R.sup.5代表氢或较低烷基，R.sup.6代表可以被取代的苯基、可以被取代的单环芳香杂环或二氢苯基，A代表可以被取代的苯环或噻吩环，X代表氧或单键，一种制备它们的方法以及含有这些化合物的对抗细菌感染活性的药物组合物。
• 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。
• Beta-lactamase inhibiting 2-beta-substituted-2-alpha-methyl-(5R) penam-3-alpha-carboxylic acid 1,1-dioxides and intermediates therefor
  申请人：PFIZER INC.

  公开号：EP0074783A1

  公开（公告）日：1983-03-23

  Beta-lactamase inhibiting 2-beta-substituted-2-alphamethyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxides and esters thereof, wherein the 2-beta-substituent is cyano, acetyl, alkoxycarbonyl, omegahydroxyalkoxycarbonyl, car- balkoxymethoxycarbonyl or dialkylaminocarbonyl; intermediates therefor wherein the 2-beta-substituent is carboxy, chlorocarbonyl or aminocarbonyl; methods for their preparation and use as beta-lactamase inhibitors.

  抑制β-内酰胺酶的2-beta-取代基-2-樟脑甲基-(5R)戊-3-α-羧酸1,1-二氧化物及其酯类，其中2-beta-取代基为氰基、乙酰基、烷氧基羰基、ω-羟基烷氧基羰基、car- balkoxymoxycarbonyl或二烷基氨基羰基；其中2-beta-取代基为羧基、氯羰基或氨基羰基的中间体；其制备方法和作为β-内酰胺酶抑制剂的用途。
• Bis-hydroxymethyl carbonate bridged antibacterial agents
  申请人：PFIZER INC.

  公开号：EP0082666A1

  公开（公告）日：1983-06-29

  Antibacterial agents in which a pencillin and a beta-lactamase inhibitor are linked by means of a bis- hydroxymethyl carbonate bridge are of the formula and pharmaceutically acceptable acid addition salts thereof, wherein R1 is hydrogen, hydroxy, certain acyloxy or certain alkoxycarbonyloxy groups, a method for their use, pharmaceutical compositions thereof, and intermediates useful in their production.

  通过双羟甲基碳酸酯桥连接青霉素和β-内酰胺酶抑制剂的抗菌剂及其药学上可接受的酸加成盐（其中 R1 为氢、羟基、某些酰氧基或某些烷氧基羰氧基）、其使用方法、其药物组合物以及用于生产它们的中间体。