benzyl-<<4-(S)-methyl-3(S)-(tert-butoxyformamido)-2-oxo-1-azetidinyl>oxy>acetate | 90849-37-9

• 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: benzyl-<<4-(S)-methyl-3(S)-(tert-butoxyformamido)-2-oxo-1-azetidinyl>oxy>acetate
• 英文别名: (3S-trans)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-methyl-1-[[(phenylmethoxy)carbonyl]methoxy]-2-azetidinone；benzyl 2-[(2S,3S)-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxoazetidin-1-yl]oxyacetate
• CAS: 90849-37-9
• 化学式: C₁₈H₂₄N₂O₆
• 分子量: 364.398
• InChiKey: CSNDUWYHWNLGGF-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl-<<4-(S)-methyl-3(S)-(tert-butoxyformamido)-2-oxo-1-azetidinyl>oxy>acetate 在 palladium on activated charcoal 氢气 、 potassium hydrogencarbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 6.5h， 生成 <<4(S)-methyl-3(S)-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic acid
  参考文献：
  名称：

  Synthesis and siderophore and antibacterial activity of N5-acetyl-N5-hydroxyl-L-ornithine derived siderophore-.beta.-lactam conjugates: iron transport mediated drug delivery

  摘要：

  N5-Acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithine, the functionally instrumental component of the albomycins and ferrichromes, has been incorporated as a ''carrier'' substructure into both carbacephalosporin and oxamazin type beta-lactam antibiotics. The previously synthesized protected version of this tripeptide (14) was coupled with various beta-lactam analogues 17, 19, 24, and 25 to give protected conjugates 21, 22, 26, and 27. Final deprotection by hydrogenolysis provided the deprotected siderophore-beta-lactam antibiotic conjugates 1-4. The growth-promoting ability of each has been evaluated using either the siderophore-deficient mutant Shigella flexneri SA 100 or S. flexneri SA240 (SA 100 iucD:Tn5). Measurement of the growth-promoting activity using two isogenic Escherichia coli strains differing only in the presence or absence of fhuA (hydroxamate ferrichrome receptor) suggests uptake by the hydroxamate iron-transport system. The antibacterial activity of these conjugates has been investigated, and the potential for use of the ferrichrome iron-transport system as a means of drug delivery is discussed.

  DOI：

  10.1021/jm00107a014
• 作为产物：
  描述：

  叔丁基((2S,3S)-1-羟基-2-甲基-4-氧代氮杂环丁烷-3-基)氨基甲酸酯 、 2-溴乙酸苄酯 、 三乙胺 在 乙酸乙酯 、 水 、 magnesium sulfate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以to yield 33.4g of the title compound as an oil的产率得到benzyl-<<4-(S)-methyl-3(S)-(tert-butoxyformamido)-2-oxo-1-azetidinyl>oxy>acetate
  参考文献：
  名称：

  2-oxoazetidin-1-yloxy acetic acids and analogs

  摘要：

  具有1-位置上的##STR1##取代基（及其类似物）和3-位置上的酰胺取代基的β-内酰胺类化合物具有抗生素活性。

  公开号：

  US04939253A1

文献信息

• 3-Acylamino-1-sulfonylaminocarbonylmethoxy-2-azetidinones
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04548747A1

  公开（公告）日：1985-10-22

  Antibacterial activity is exhibited by .beta.lactams having a 3-acylamino substituent and in the 1-position a group of the formula ##STR1## wherein R.sub.5 and R.sub.6 are the same or different and each is hydrogen, alkyl, alkenyl, alkynyl, phenyl, substituted phenyl, cycloalkyl or R.sub.c, or R.sub.5 and R.sub.6 together with the carbon atom to which they are attached are cycloalkyl or R.sub.c, or one of R.sub.5 and R.sub.6 is hydrogen and the other is azido, halomethyl, dihalomethyl, trihalomethyl, alkoxycarbonyl, alkenyl, alkynyl, 2-phenylethenyl, 2-phenylethynyl, carboxyl, --CH.sub.2 X.sub.1, --S--X.sub.2, --O--X.sub.2, or ##STR2## and R.sub.7 is alkyl, substituted alkyl, phenyl or substituted phenyl; and R.sub.c is 4,5,6 or 7-membered heterocycle.

  β-内酰胺具有3-酰氨基取代基并在1-位置具有公式##STR1##中的基团的抗菌活性，其中R.sub.5和R.sub.6相同或不同，每个都是氢、烷基、烯基、炔基、苯基、取代苯基、环烷基或R.sub.c，或R.sub.5和R.sub.6与它们连接的碳原子一起是环烷基或R.sub.c，或R.sub.5和R.sub.6中的一个是氢，另一个是叠氮基、卤代甲基、二卤代甲基、三卤代甲基、烷氧羰基、烯基、炔基、2-苯乙烯基、2-苯乙炔基、羧基、--CH.sub.2 X.sub.1、--S--X.sub.2、--O--X.sub.2或##STR2##，R.sub.7是烷基、取代烷基、苯基或取代苯基；而R.sub.c是4、5、6或7-成员杂环。
• US4548747A
  申请人：——

  公开号：US4548747A

  公开（公告）日：1985-10-22
• US4939253A
  申请人：——

  公开号：US4939253A

  公开（公告）日：1990-07-03
• Synthesis and siderophore and antibacterial activity of N5-acetyl-N5-hydroxyl-L-ornithine derived siderophore-.beta.-lactam conjugates: iron transport mediated drug delivery
  作者：E. Kurt Dolence、Albert A. Minnick、Chia En Lin、Marvin J. Miller、Shelley M. Payne

  DOI：10.1021/jm00107a014

  日期：1991.3

  N5-Acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithine, the functionally instrumental component of the albomycins and ferrichromes, has been incorporated as a ''carrier'' substructure into both carbacephalosporin and oxamazin type beta-lactam antibiotics. The previously synthesized protected version of this tripeptide (14) was coupled with various beta-lactam analogues 17, 19, 24, and 25 to give protected conjugates 21, 22, 26, and 27. Final deprotection by hydrogenolysis provided the deprotected siderophore-beta-lactam antibiotic conjugates 1-4. The growth-promoting ability of each has been evaluated using either the siderophore-deficient mutant Shigella flexneri SA 100 or S. flexneri SA240 (SA 100 iucD:Tn5). Measurement of the growth-promoting activity using two isogenic Escherichia coli strains differing only in the presence or absence of fhuA (hydroxamate ferrichrome receptor) suggests uptake by the hydroxamate iron-transport system. The antibacterial activity of these conjugates has been investigated, and the potential for use of the ferrichrome iron-transport system as a means of drug delivery is discussed.
• 2-oxoazetidin-1-yloxy acetic acids and analogs
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04939253A1

  公开（公告）日：1990-07-03

  Antibiotic activity is exhibited by .beta.-lactams having an ##STR1## substituent (and analogs thereof) in the 1-position and an acylamino substituent in the 3-position.

  具有1-位置上的##STR1##取代基（及其类似物）和3-位置上的酰胺取代基的β-内酰胺类化合物具有抗生素活性。