benzyl 6β-hydroxymethylpenicillanate | 76517-45-8

• 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: benzyl 6β-hydroxymethylpenicillanate
• 英文别名: benzyl (2S,5R,6R)-6-(hydroxymethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 76517-45-8
• 化学式: C₁₆H₁₉NO₄S
• 分子量: 321.397
• InChiKey: CDUPNEHRFHBCHY-MBNYWOFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 6β-hydroxymethylpenicillanate 生成 benzyl (2S,5R,6R)-3,3-dimethyl-6-(hydroxymethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide
  参考文献：
  名称：

  KELLOGG, M. S.

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl 6-beta-bromo-6-alpha-(hydroxymethyl)penicillanate 生成 benzyl 6β-hydroxymethylpenicillanate
  参考文献：
  名称：

  KELLOGG, M. S.

  摘要：

  DOI：

文献信息

• 6-.beta.-substituted penicillanic acid compound free of the
  申请人：Pfizer Inc.

  公开号：US04656263A1

  公开（公告）日：1987-04-07

  6-.beta.-Substituted penicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria, and 6-.beta.-substituted penicillanic acid derivatives wherein the carboxy group is protected by a conventional penicillin carboxy protecting group as useful intermediates leading to said synergistic agents. A process for converting 6,6-disubstituted penicillanic acid derivatives to the corresponding 6-.beta.-substituted penicillanic acid congeners.

  6-β-取代青霉烷酸及其衍生物作为增强多种β-内酰胺酶产生细菌对多种β-内酰胺类抗生素有效性的有用增效剂，以及6-β-取代青霉烷酸衍生物，其中羧基被传统的青霉素羧基保护基团所保护，作为导致所述协同作用剂的有用中间体。一种将6,6-二取代青霉烷酸衍生物转化为相应的6-β-取代青霉烷酸同系物的方法。
• Process for converting 6,6-disubstituted penicillanic acid derivatives
  申请人：Pfizer Inc.

  公开号：US04397783A1

  公开（公告）日：1983-08-09

  6-.beta.-Substituted penicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria, and 6-.beta.-substituted penicillanic acid derivatives wherein the carboxy group is protected by a conventional penicillin carboxy protecting group as useful intermediates leading to said synergistic agents. A process for converting 6,6-disubstituted penicillanic acid derivatives to the corresponding 6-.beta.-substituted penicillanic acid congeners.

  6-β-取代青霉烷酸及其衍生物作为增强多种β-内酰胺酶产生细菌对多种β-内酰胺类抗生素有效性的有用增效剂，以及6-β-取代青霉烷酸衍生物，其中羧基被传统的青霉素羧基保护基团所保护，作为导致所述协同作用剂的有用中间体。一种将6,6-二取代青霉烷酸衍生物转化为相应的6-β-取代青霉烷酸同系物的方法。
• Derivatives of 6.beta.-hydroxyalkylpenicillanic acids as
  申请人：Pfizer Inc.

  公开号：US04287181A1

  公开（公告）日：1981-09-01

  6.beta.-Hydroxyalkylpenicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria, and 6.beta.-substituted penicillanic acid benzyl ester derivatives as useful intermediates leading to said agents which enhance the effectiveness of .beta.-lactam antibiotics.

  6-β-羟基烷基青霉酸及其衍生物作为多种β-内酰胺类抗生素对许多产β-内酰胺酶细菌的有效增效剂，以及6-β-取代青霉酸苄酯衍生物作为有用的中间体，可用于增强β-内酰胺类抗生素的有效性。
• Penicillin derivatives as anti-inflammatory and antidegenerative agents
  申请人：Merck & Co., Inc.

  公开号：EP0170192A1

  公开（公告）日：1986-02-05

  Derivatives of Penicillin, their sulfoxides and sulfones of the structural formula: wherein q is 0, 1 or 2; A is, e.g., CH3 or CH2O(CO)CH3; R, is, e.g., R'NR. wherein R. is H or C1-6alkyl and R' is, e.g., hydrogen or where R represents: (i) hydrogen; (ii) C1-6alkyl; (iii) trifluoromethyl or methoxymethyl; (iv) thienyl; (v) phenyl; or (vi) mono- and disubstituted phenyl and thienyl wherein the substituents are selected from the group consisting of chloro, bromo, fluoro, nitro, loweralkyl, and loweralkoxy; n is 0 or 1; B is, e.g., hydrogen or alkyl and R is, e.g., H or halo; are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.

  青霉素的衍生物、其结构式为硫醚和砜的衍生物： 其中 q 是 0、1 或 2； A 是 CH3 或 CH2O(CO)CH3 等； 其中 R. 是 H 或 C1-6 烷基，R'是氢或 C1-6 烷基。 其中 R 代表 (i) 氢 (ii) C1-6 烷基 (iii) 三氟甲基或甲氧基甲基 (iv) 噻吩基 (v) 苯基；或 (vi) 单取代和二取代苯基和噻吩基，其中取代基选自由氯、溴、氟、硝基、低级烷基和低级烷氧基组成的组； n 为 0 或 1； B 是氢或烷基，以及 R 是氢或卤素； 是有效的弹性蛋白酶抑制剂，因此是有用的抗炎/抗变性制剂。
• 6-(Aminoacyloxymethyl) penicillanic acid 1, 1-dioxides as beta-lactamase inhibitors
  申请人：PFIZER INC.

  公开号：EP0154444A1

  公开（公告）日：1985-09-11

  beta-Lactamase inhibitors which are aminoacid esters of 6-alpha- and 6-beta-(hydroxymethyl)pencillanic acid 1,1-dioxides; pharmaceutically-acceptable salts thereof; conventional esters thereof which are hydrolyzable in vivo; bis-methanediol esters thereof; or mixed methanediol esters with said beta-lactamase inhibitors and sulbactam. Pharmaceutical compositions comprising said beta-lactamase inhibitors and a conventional beta-lactam antibiotic, said compositions useful in the treatment of bacterial infections. Compounds useful as intermediates in the synthesis of said beta-lactamase inhibitors. Antibacterial mixed bis-methanediol esters of said aminoacyloxymethyl penicillanic acid 1.1-dioxides and ampicillin or amoxicillin, also useful in the treatment of bacterial infections; and intermediates therefor.

  β-内酰胺酶抑制剂，其为 6-α-和 6-β-（羟甲基）青霉烷酸 1,1-二氧 化物的氨基酸酯；其药学上可接受的盐；其可在体内水解的常规酯；其双甲二醇酯； 或与所述β-内酰胺酶抑制剂和舒巴坦的混合甲二醇酯。包含所述β-内酰胺酶抑制剂和常规β-内酰胺类抗生素的药物组合物，所述组合物可用于治疗细菌感染。可用作合成所述β-内酰胺酶抑制剂的中间体的化合物。上述氨基乙酰氧甲基青霉烷酸 1.1-二氧化物和氨苄西林或阿莫西林的抗菌混合双甲二醇酯，也可用于治疗细菌感染；及其中间体。