(S)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid | 69126-85-8

• 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: (S)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• 英文别名: (5R,S)-2-Penem-3-carboxylic acid；(5S)-7-Oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• CAS: 69126-85-8
• 化学式: C₆H₅NO₃S
• 分子量: 171.177
• InChiKey: DUNKKIRUWZSMPT-YFKPBYRVSA-N

物化性质

• 沸点：
  472.9±45.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5S)-acetonyl penem-3-carboxylate 生成 (S)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Thia-aza compounds with a .beta.-lactam ring

  摘要：

  公式为##STR1##的2-青霉素-3-羧酸化合物，其中R.sub.1代表氢，由碳原子与环碳原子结合的有机基团或醚化巯基团，R.sub.2代表羟基或与羰基团--C(.dbd.O)--一起形成保护羧基的基团R.sub.2.sup.A，其1-氧化物，以及具有形成盐的盐基团的这种化合物的盐，以拉克米和光学活性形式存在，它们的制备方法，含有这种化合物的药物组合物，以及它们作为抗生素的用途，以及在生产公式I化合物中有用的中间体及其制备方法。

  公开号：

  US04331676A1

文献信息

• Penem derivatives and antimicrobial agents containing the same
  申请人：SUNTORY LIMITED

  公开号：EP0774465A1

  公开（公告）日：1997-05-21

  Penem derivatives represented by the following Formula (I): wherein Z represents a hydroxyl group or a fluorine atom, R1 represents a substituted or unsubstituted alkyl, alkenyl, aralkyl group, aryl group, heterocyclic, or acyl group, or a hydrogen atom, and R2 represents a hydrogen atom or a carboxyl-protecting group; and pharmacologically acceptable salts thereof are antibacterial agents effective against, inter alia, methicillin-resistant Staphylococcus aureus. The derivatives and salts are novel except when R1 is ethyl and Z is hydroxyl. The analogous compounds in which R2 is a carboxyl-protecting group and any hydroxyl group represented by Z is protected are novel process intermediates.

  Penem衍生物由以下公式（I）表示：其中Z代表一个羟基团或氟原子，R1代表一个取代或未取代的烷基，烯基，芳基甲基，芳基，杂环基或酰基，或氢原子，R2代表一个氢原子或羧基保护基；及其药理学上可接受的盐是有效的抗菌剂，可用于治疗耐甲氧西林金黄色葡萄球菌等感染。这些衍生物和盐是新颖的，除非R1是乙基且Z是羟基。其中R2是羧基保护基且Z代表的任何羟基被保护的类似化合物是新颖的工艺中间体。
• BETA-LACTAMASE INHIBITORS
  申请人：SUTTON Larry

  公开号：US20100261700A1

  公开（公告）日：2010-10-14

  Broad spectrum beta-lactamase inhibitors. Certain inhibitors also exhibit potent antibiotic activity in addition to beta-lactamase inhibition. Compounds of the invention are designed such that on cleavage of the beta-lactam ring reactive moieties are generated which can inactivate beta-lactamase. Also provided are methods of making beta-lactamase inhibitors and beta-lactam antibiotics exhibiting such inhibition. Additionally provided are pharmaceutical compositions for treatment or prevention of bacterial infections and methods of treatment of such infections.

  广谱β-内酰胺酶抑制剂。某些抑制剂除了抑制β-内酰胺酶外，还表现出强效的抗生素活性。本发明的化合物设计成在β-内酰胺环裂解时生成可以灭活β-内酰胺酶的反应性基团。还提供了制备β-内酰胺酶抑制剂和表现出这种抑制作用的β-内酰胺类抗生素的方法。此外还提供了用于治疗或预防细菌感染的药物组合物和治疗此类感染的方法。
• [EN] beta -METHYLCARBAPENEM DERIVATIVES, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING SAME<br/>[FR] DERIVES DU beta -METHYLCARBAPENEM, PROCEDE DE FABRICATION DESDITS DERIVES, ET COMPOSITION PHARMACEUTIQUE LES CONTENANT
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY

  公开号：WO1997020844A1

  公开（公告）日：1997-06-12

  (EN) A $g(b)-methylcarbapenem compound of formula (I), a salt or an ester thereof, a process for the preparation thereof and a pharmaceutical composition containing same, wherein R1 is a C1-16 alkyl, C1-16 alkenyl, cycloalkyl, aryl or heterocyclic aryl group.(FR) Composé du $g(b)-méthylcarbapenem de formule (I), un de ses sels ou de ses esters, procédé de préparation associé, et composition pharmaceutique les contenant, où R1 est C1-C6 alkyle, C1-C6 alkényle, cycloalkyle, aryle ou un groupe aryle hétérocyclique.

  一个公式为(I)的$g(b)-甲基碳青霉烯化合物，其盐或酯，其制备方法以及含有该化合物的药物组合物，其中R1是C1-16烷基，C1-16烯基，环烷基，芳基或杂环芳基。
• Carbapenem derivatives having antibiotic activity, their preparation and their use
  申请人：Sankyo Company Limited

  公开号：EP0443883A1

  公开（公告）日：1991-08-28

  Carbapenem compounds of formula (I) : [in which : A is a fully saturated heterocyclic group, of which at least one ring atom is nitrogen ; R1 is hydrogen or methyl ; R2 is hydrogen or alkyl ; R3 is hydrogen or a negative ion; Q is: (i) -B-N+R8R9R10, where R8, R9 and R10 are alkenyl, alkynyl or optionally substituted alkyl, and B is alkylene or alkylidene ; (ii) a heterocyclic group of which one ring atom is a >N+R11R12, where R11 and R12 are alkenyl, alkynyl or optionally substituted alkyl ; (iii) alkyl substituted by a heterocyclic group as defined in (ii) above ; or (iv) alkyl substituted by an aromatic heterocyclic group, of which one ring atom is or R2 and Q, and the nitrogen to which they are attached, form a group of formula (II) : where m and n are 1, 2 or 3 ; R6 is optionally substituted alkyl ; and R7 is alkenyl, alkynyl or optionally substituted alkyl] and pharmaceutically acceptable salts and esters thereof have valuable antibacterial activity with enhanced resistance to dehydropeptidase I and β-lactamase. Methods of preparing and using the compounds are also provided.

  式(I)的碳青霉烯化合物：[其中：A是完全饱和的杂环基团，其中至少一个环原子是氮；R1是氢或甲基；R2是氢或烷基；R3是氢或负离子；Q是：(i)-B-N+R8R9R10，其中R8、R9和R10是烯基、炔基或可选取代的烷基，B是烷基或烷基亚甲基；(ii)杂环基团，其中一个环原子是>N+R11R12，其中R11和R12是烯基、炔基或可选取代的烷基；(iii)由(ii)中定义的杂环基团取代的烷基；或(iv)由一个芳香杂环基团取代的烷基，其中一个环原子是R2或Q，它们附着的氮形成式(II)的基团：其中m和n为1、2或3；R6是可选取代的烷基；R7是烯基、炔基或可选取代的烷基。其药学上可接受的盐和酯具有有价值的抗菌活性，并具有对脱氢肽酶I和β-内酰胺酶的增强抗性。还提供了制备和使用这些化合物的方法。
• Penem derivatives and antimicrobial agent containing the same
  申请人：Ishiguro Masaji

  公开号：US20050004092A1

  公开（公告）日：2005-01-06

  A penem derivative represented by the following formula (I): wherein R 1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkenylthio group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic thio group, a substituted or unsubstituted acylthio group, a mercapto group or a hydrogen atom, and R 2 represents a hydrogen atom or a carboxyl-protecting group; or a pharmacologically acceptable salt thereof. The compound (I) exhibits strong antibacterial activities, and especially, shows strong activities against MRSA. It is therefore useful not only as a general antibacterial agent but also as an antibacterial agent for MRSA against which no general antibacterial agents are recognized to be-effective.

  以下是公式（I）所代表的一种青霉烷衍生物： 其中，R1代表取代或未取代的烷基、取代或未取代的烯基、取代或未取代的芳基烷基、取代或未取代的芳基、取代或未取代的烷基硫基、取代或未取代的烯基硫基、取代或未取代的芳基烷基硫基、取代或未取代的芳基硫基、取代或未取代的杂环基、取代或未取代的杂环硫基、取代或未取代的酰基硫基、巯基或氢原子，R2代表氢原子或羧酸保护基；或其药学上可接受的盐。该化合物（I）表现出强大的抗菌活性，特别是对MRSA表现出强大的活性。因此，它不仅有用作一般抗菌剂，还有用作抗MRSA的抗菌剂，对于这种细菌，一般的抗菌剂被认为无效。