p-Nitrobenzyl (5R,6S)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

• 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: p-Nitrobenzyl (5R,6S)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• 英文别名: p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidovinylthio>-6-<(S)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate；p-Nitrobenzyl (5R,6S)-3-[(E)-2-acetamidoethenylthio]-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate；p-Nitrobenzyl (5R,6S)-3-[E-2-acetamidoethenylthio]-6-[(S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylate；(4-nitrophenyl)methyl (5R,6S)-3-[(E)-2-acetamidoethenyl]sulfanyl-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• 化学式: C₂₀H₂₁N₃O₇S
• 分子量: 447.469
• InChiKey: IJFZFEDXRGAAMV-JPJHXQKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  167
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-Nitrobenzyl (5R,6S)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 在 迭氮酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以61%的产率得到p-Nitrobenzyl (5R,6S)-3-<(E)-2-acetamidovinylthio>-6-<(R)-1-azidoethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Corbett, David F.; Coulton, Steven; Southgate, Robert, Journal of the Chemical Society. Perkin transactions I, 1982, # 12, p. 3011 - 3016

  摘要：

  DOI：

文献信息

• .beta.-Lactam antibiotics, their preparation and use
  申请人：Beecham Group p.l.c.

  公开号：US04410533A1

  公开（公告）日：1983-10-18

  The present invention provides a compound of the formula (I): ##STR1## or a pharmaceutically acceptable salt or in-vivo hydrolyzable ester thereof wherein R.sup.1 is a hydrogen atom, an .alpha.-sulphonato-oxyethyl group, an .alpha.-sulphonato-oxypropyl group or is a group CR.sup.3 R.sup.4 R.sup.5 wherein R.sup.3 is a hydrogen atom or a hydroxy group; R.sup.4 is a hydrogen atom or a C.sub.1-6 alkyl group; and R.sup.5 is a hydrogen atom or a C.sub.1-6 alkyl group, a benzyl group, a phenyl group or is joined to R.sup.4 to form together with the carbon atom to which they are joined a carbocyclic ring of 5 to 7 carbon atoms; R.sup.2 is a pyrimidinyl group substituted by one two or three groups selected from nitro, halo, amino or substituted amino, and in addition may be optionally substituted by one or two C.sub.1-6 alkyl groups as the degree of substitution permits; and x is zero or one. These compounds are antibacterial agents. Their preparation and use are described.

  本发明提供了式(I)的化合物：##STR1##或其药学上可接受的盐或体内水解酯，其中R.sup.1是氢原子，α-磺酸氧乙基基团，α-磺酸氧丙基基团或是CR.sup.3 R.sup.4 R.sup.5基团，其中R.sup.3是氢原子或羟基；R.sup.4是氢原子或C.sub.1-6烷基基团；R.sup.5是氢原子或C.sub.1-6烷基基团，苄基，苯基或与R.sup.4连接以与它们连接的碳原子一起形成5至7个碳原子的碳环的基团；R.sup.2是嘧啶基，其被从硝基，卤素，氨基或取代氨基中选择的一个、两个或三个基团取代，并且还可以根据取代程度选择性地被一个或两个C.sub.1-6烷基基团取代；x为零或一。这些化合物是抗菌剂。其制备和用途已经描述。
• Carbapenum derivatives, a process for their preparation and their use in
  申请人：Beecham Group Limited

  公开号：US04278686A1

  公开（公告）日：1981-07-14

  The present invention provides antibiotic compounds of the formula: ##STR1## and salts and cleavable esters thereof wherein X is a SCH.sub.2 CH.sub.2 NH.sub.2 or YNH-COCH.sub.3 group where Y is a SCH.sub.2 CH.sub.2, trans --SO--CH.dbd.-- or cis or trans --S--CH.dbd.CH-- group and R is a lower alkyl, aryl, aralkyl, lower alkenyl, or substituted lower alkyl.

  本发明提供了化合物的抗生素，其化学式为：##STR1##和其盐和可水解酯，其中X是SCH.sub.2 CH.sub.2 NH.sub.2或YNH-COCH.sub.3基团，其中Y是SCH.sub.2 CH.sub.2，trans -SO-CH.dbd.-或cis或trans -S-CH.dbd.CH-基团，R是较低的烷基，芳基，芳基烷基，较低的烯基或取代较低的烷基。
• Reaction of olivanic acids with hypobromous acid: the preparation and use of a versatile intermediate, the C-3 thiol
  作者：David F. Corbett

  DOI：10.1039/c39810000803

  日期：——

  The 3-(E)-2-acetamidoethenylthio-substituent of olivanic acid derivatives reacts with hypobromous acid to afford a C-3 thiol which undergoes alkylation reactions and addition to propiolates.

  橄榄酸衍生物的3-（E）-2-乙酰氨基乙烯基硫基取代基与次溴酸反应，得到C-3硫醇，其经过烷基化反应并加成丙酸酯。
• BASKER, MICHAEL J.;CORBETT, DAVID F.;COULTON, STEVEN;SOUTHGATE, ROBERT, J. ANTIBIOTICS, 43,(1990) N, C. 847-857
  作者：BASKER, MICHAEL J.、CORBETT, DAVID F.、COULTON, STEVEN、SOUTHGATE, ROBERT

  DOI：——

  日期：——
• CORBETT, D. F.;COULTON, S.;SOUTHGATE, R.
  作者：CORBETT, D. F.、COULTON, S.、SOUTHGATE, R.

  DOI：——

  日期：——