(2R,3S)-3-氨基-2-甲基-4-氧代-1-吖丁啶磺酸 | 80582-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: (2R,3S)-3-氨基-2-甲基-4-氧代-1-吖丁啶磺酸
• 中文别名: N-[[双[4-(二甲基氨基)苯基]氨基]羰基]甘氨酸单钠盐
• 英文名称: (3S)-cis-3-amino-4-metyl-2-oxoazetidine-1-sulfonic acid
• 英文别名: (3S)-cis-3-amino-4-methyl-2-oxoazetidine-1-sulfonic acid；(3S,4R) 3-ammonio-4-methyl-2-oxoazetidine-1-sulfonate；(2R,3S)-3-amino-2-methyl-4-oxo-1-azetidinesulfonic acid；(2R-cis)-3-amino-2-methyl-4-oxo-1-azetidine-sulfonic acid；2R-[2α,3α]-3-amino-2-methyl-4-oxo-1-sulfo-azetidine；(3S-cis)-3-amino-4-methyl-2-oxo-1-azetidinesulfonic acid；(3S,4R) 3-amino-4-methyl-2-oxoazetidin-1 sulfonic acid；(2R,3S)-3-azaniumyl-2-methyl-4-oxoazetidine-1-sulfonate
• CAS: 80582-09-8
• 化学式: C₄H₈N₂O₄S
• 分子量: 180.185
• InChiKey: ISUIVWNWEDIHJD-GBXIJSLDSA-N

物化性质

• 溶解度：
  溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

制备方法与用途

用途
这是一种在制备β-内酰胺类化合物时的有用中间体。

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-氨基-2-甲基-4-氧代-1-吖丁啶磺酸 、 苯氧乙酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,4R) tetra-n-butylammonium 4-methyl-2-oxo-3-(phenoxyacetylamino)azetidine-1-sulfonate
  参考文献：
  名称：

  通过手性3-羟基酯的亲电胺化反应合成顺式单bactams的对映体和非对映选择性

  摘要：

  据报道，从β-羟基酯开始新的有效进入顺式单bactams的方法。该制备基于β-羟基酯二价阴离子的立体选择性“亲电胺化”和β-内酰胺核的米勒仿生合成。通过这种途径，制备了用于制备具有药理学意义的顺式氨曲南2和卡鲁米南3的关键中间体。

  DOI：

  10.1016/s0040-4020(01)89308-x
• 作为产物：
  描述：

  (3S)-cis-3-<(tert-butoxycarbonyl)amino>-4-methyl-2-oxoazetidine-1-sulfonic acid tetra-n-butylammonium salt 在 氮气 、 二氯甲烷 作用下， 以 甲酸 为溶剂， 反应 20.0h， 以to yield 982 mg of the title compound的产率得到(2R,3S)-3-氨基-2-甲基-4-氧代-1-吖丁啶磺酸
  参考文献：
  名称：

  Process for preparing a 2-oxo-1-azetidinesulfonic acid salt

  摘要：

  (R)-3-(乙酰氨基)-3-甲氧基-2-氧代-1-氮杂丁磺酸的药用可接受盐，可以通过在含有可同化碳水化合物和氮源的水性营养培养基上，在大约25℃的条件下，以浸没式好氧条件下培养紫色单胞菌Chromobacterium violaceum ATCC No.31532来制备。

  公开号：

  US04529698A1

文献信息

• [EN] METHODS OF SYNTHESIZING AZTREONAM DERIVATIVES<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE DÉRIVÉS D'AZTRÉONAM
  申请人：ARIXA PHARMACEUTICALS INC

  公开号：WO2020219258A1

  公开（公告）日：2020-10-29

  Disclosed herein are aztreonam derivatives, therapeutic methods of using the aztreonam derivatives, and methods of synthesizing aztreonam derivatives. The aztreonam derivatives can be administered orally to provide orally bioavailable aztreonam.

  本文揭示了阿特雷侬酮衍生物、使用阿特雷侬酮衍生物的治疗方法，以及合成阿特雷侬酮衍生物的方法。这些阿特雷侬酮衍生物可以经口服给药，从而提供口服可利用的阿特雷侬酮。
• Sulfamated amino acid amides
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04386034A1

  公开（公告）日：1983-05-31

  The process of this invention provides for the conversion of amino acid amides having the formula ##STR1## to 3-amino-2-oxo-1-azetidinesulfonic acid salts having the formula ##STR2## wherein one of R.sub.2 and R.sub.3 is hydrogen and the other is hydrogen, alkyl, cycloalkyl, phenyl or substituted phenyl and M.sup..sym. is hydrogen or a cation.

  该发明的过程提供了将具有以下化学式的氨基酸酰胺转化为具有以下化学式的3-氨基-2-氧代-1-氮杂环丙磺酸盐的方法：其中R.sub.2和R.sub.3中的一个是氢，另一个是氢，烷基，环烷基，苯基或取代苯基，M.sup..sym. 是氢或阳离子。
• 2-oxo-1-azetidinesulfonic acid salts
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04775670A1

  公开（公告）日：1988-10-04

  Antibacterial activity is exhibited by .beta.-lactams having a sulfonic acid salt substituent in the 1-position and an amino or acylamino substituent in the 3-position.

  具有磺酸盐取代基在1-位和氨基或酰胺基取代基在3-位的β-内酰胺类化合物表现出抗菌活性。
• Process for preparing (s)-3-amino-2-oxo-1-azetidinesulfonic acid salts
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04625022A1

  公开（公告）日：1986-11-25

  The process of this invention provides for the conversion of amino acid amides having the formula ##STR1## to 3-amino-2-oxo-1-azetidinesulfonic acid salts having the formula ##STR2## wherein one of R.sub.2 and R.sub.3 is hydrogen and the other is hydrogen, alkyl, cycloalkyl, phenyl or substituted phenyl and M.sup..sym. is hydrogen or a cation.

  这项发明的过程提供了将具有以下公式的氨基酸酰胺转化为具有以下公式的3-氨基-2-氧代-1-氮杂环戊烷磺酸盐的方法： 其中R.sub.2和R.sub.3中的一个是氢，另一个是氢、烷基、环烷基、苯基或取代苯基，M.sup..sym.是氢或阳离子。
• Antimicrobial effects of novel siderophores linked to β-lactam antibiotics
  作者：T Kline、M Fromhold、T.E McKennon、S Cai、J Treiberg、N Ihle、D Sherman、W Schwan、M.J Hickey、P Warrener、P.R Witte、L.L Brody、L Goltry、L.M Barker、S.U Anderson、S.K Tanaka、R.M Shawar、L.Y Nguyen、M Langhorne、A Bigelow、L Embuscado、E Naeemi

  DOI：10.1016/s0968-0896(99)00261-8

  日期：2000.1

  As a strategy to increase the penetration of antibiotic drugs through the outer membrane of Gram-negative pathogens, facilitated transport through siderophore receptors has been frequently exploited. Hydroxamic acids, catechols, or very close isosteres of catechols, which are mimics of naturally occurring siderophores, have been used successfully as covalently linked escorting moieties, but a much wider diversity of iron binding motifs exists. This observation, coupled to the relative lack of specificity of siderophore receptors, prompted us to initiate a program to identify novel, noncatechol siderophoric structures. We screened over 300 compounds for their ability to (1) support growth in low iron medium of a Pseudomonas aeruginosa siderophore biosynthesis deletion mutant, or (2) compete with a bactericidal siderophore-antibiotic conjugate for siderophore receptor access. From these assays we identified a set of small molecules that fulfilled one or both of these criteria. We then synthesized these compounds with functional groups suitable for attachment to both monobactam and cephalosporin core structures. Siderophore-P-lactam conjugates then were tested against a panel of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains. Although several of the resultant chimeric compounds had antimicrobial activity approaching that of ceftazidime, and most compounds demonstrated very potent activity against their cellular targets, only a single compound was obtained that had enhanced, siderophore-mediated antibacterial activity. Results with tonB mutants frequently showed increased rather than decreased susceptibilities, suggesting that multiple factors influenced the intracellular concentration of the drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.