6-(D-α-aminophenyl-acetylamino)-penicillanic acid

• 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: 6-(D-α-aminophenyl-acetylamino)-penicillanic acid
• 英文别名: 6-(alpha-aminophenylacetamido)penicillanic acid；(2S,5R)-6-[[2-(2-aminophenyl)acetyl]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: WQLYKNDWIGWOMC-VBVNFKHJSA-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 、 6-(D-α-aminophenyl-acetylamino)-penicillanic acid 、 4-(2-imidazolinyl)-phenylacetic acid chloride-hydrochloride 生成 penicillin G
  参考文献：
  名称：

  Acylaminopenicillanic acids and process for preparing them

  摘要：

  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。

  公开号：

  US04018933A1

文献信息

• A penicillin salt, process for its preparation and pharmaceutical compositions containing it
  申请人：BEECHAM GROUP PLC

  公开号：EP0004740A2

  公开（公告）日：1979-10-17

  Ampicillin phthalidyl ester naphthalene-2-sulphonate, its preparation, and its use in pharmaceutical compositions to treat infections.

  氨苄西林酞酰酯萘-2-磺酸盐、其制备方法及其在治疗感染的药物组合物中的用途。
• Improved process for the preparation of penicillanic acid esters
  申请人：PFIZER INC.

  公开号：EP0061284A1

  公开（公告）日：1982-09-29

  A process for the preparation of chloromethyl esters of penicillanic acids, using iodochloromethane or bromochloromethane and a tetraalkylammonium salt of the penicillanic acid, and their use in processes for the synthesis of penicillanic acid esters, using a halomethyl ester and the tetraalkylammonium salt of the penicillanic acid, which readily hydrolyze in vivo to antibacterial penicillins and the beta-lactamase inhibitor penicillanic acid sulfone.

  一种利用碘氯甲烷或溴氯甲烷和青霉烷酸的四烷基铵盐制备青霉烷酸氯甲酯的工艺，及其在利用卤代甲酯和青霉烷酸的四烷基铵盐合成青霉烷酸酯工艺中的应用，这种青霉烷酸酯在体内容易水解为抗菌青霉烷酸酯和β-内酰胺酶抑制剂青霉烷酸砜。
• N,N'-carboxyl-bis-(4-ethyl-2,3-dioxo)-piperazine, process for the preparation thereof and use thereof
  申请人：GEMA S.A.

  公开号：EP0317484A2

  公开（公告）日：1989-05-24

  A new compound called N,N'-carbonyl-bis-(4-ethyl-2,3-dioxo)-piperazine of Formula I A process for the preparation thereof based on the reaction of 4-ethyl-2,3-dioxo-piperazine or a trimethylsilyl derivative thereof with carbonyl chloride or a derivative thereof. The use of the compound of Formula I as an intermediate in the preparation of compounds of Formula II where R is a radical, substituted in alpha position, of a molecule of an acid selected from the group formed by phenylacetic acid, p-hydroxy phenylacetic acid, a 6-(phenylacetamido)-penicillanic acid and a 7-(phenylacetamido)-cephalosporanic acid.

  一种名为 N,N'-羰基-双-(4-乙基-2,3-二氧代)-哌嗪的新化合物，其式为 I 一种基于 4-乙基-2,3-二氧代哌嗪或其三甲硅基衍生物与羰酰氯或其衍生物反应的制备方法。 使用式 I 化合物作为制备式 II 化合物的中间体 其中 R 是选自苯乙酸、对羟基苯乙酸、6-(苯乙酰氨基)-青霉烷酸和 7-(苯乙酰氨基)-头孢烷酸所组成的组中的酸分子的α位取代基。
• Process for the preparation of 3-chloro-cefem compounds
  申请人：ANTIBIOTICOS, S.A.

  公开号：EP0377958A2

  公开（公告）日：1990-07-18

  The process comprises a series of stages essentially comprising the protection of the functional groups of the side chain of Ampicillin, esterification of the acid group, oxidation to sulphoxide, expansion of the thiazole ring to a thiazine ring, ozonolysis of the exomethylene cefam derivative obtained, substitution of the hydroxyl group by chlorine and de-protection of the functional groups, in which the order of some stages can be varied without affecting the final result.

  该工艺包括一系列阶段，主要包括保护氨苄西林侧链的官能团、酯化酸基、氧化成亚砜、噻唑环扩展成噻嗪环、臭氧分解得到的外亚甲基头孢酰胺衍生物、用氯取代羟基和去保护官能团，其中某些阶段的顺序可以改变而不影响最终结果。
• Improved process for preparing penicillins and cephalosporins
  申请人：RECORDATI S.A. CHEMICAL and PHARMACEUTICAL COMPANY

  公开号：EP0473008A2

  公开（公告）日：1992-03-04

  Improved process for preparing penicillins and cephalosporins by reacting 6-amino-penicillanic acid, 7-amino-cephalosporanic acid, 7-amino-3-deacetoxy-cephalosporanic acid or their derivatives with derivatives of α-aminoacids in the presence of a properly immobilised penicillin acylase enzyme, at a temperature ranging from -5°C to +20°C. The process minimises the production of by-products and ensures industrially advantageous yields.

  改进的青霉素和头孢菌素制备工艺，在-5°C 至 +20°C的温度范围内，在适当固定的青霉素酰化酶存在下，使 6-氨基青霉烷酸、7-氨基头孢烷酸、7-氨基-3-脱乙酰氧基头孢烷酸或其衍生物与 α-氨基酸的衍生物发生反应。该工艺最大程度地减少了副产品的产生，并确保了具有工业优势的产量。