(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-3-(tritylamino)-2-azetidinone | 113599-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-3-(tritylamino)-2-azetidinone
• 英文别名: (3S,4S)-4-t-butyldimethylsilyloxymethyl-3-tritylaminoazetidin-2-one；(3S,4S)-4-t-Butyldimethylsilyloxymethyl-3-tritylaminoazetidinone；(3S,4S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(tritylamino)azetidin-2-one
• CAS: 113599-61-4
• 化学式: C₂₉H₃₆N₂O₂Si
• 分子量: 472.703
• InChiKey: YJPYTJJEVRWNEN-FTJBHMTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-3-(tritylamino)-2-azetidinone 在 氢氧化钾 、 四丁基溴化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxopropanoate
  参考文献：
  名称：

  An examination of O-2-isocephems as orally absorbable antibiotics

  摘要：

  The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.

  DOI：

  10.1021/jm00401a020
• 作为产物：
  描述：

  (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone 在 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 10.0h， 生成 (3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-3-(tritylamino)-2-azetidinone
  参考文献：
  名称：

  Design, synthesis and antibacterial activities of a series of new 2-oxaisocephems

  摘要：

  A series of 2-oxaisocephems with a thio-substituted methyl group at the 3-position and a [2-(5-amino-1,2,4-thiadizol-3-yl)-2-(Z)-alkoxyimino]acetamido moiety at 7-position were synthesized and tested for their antibacterial activities. The analogs 17c and 17f have well-balanced potency and significantly enhanced activity as compared with the reference compound ceftazidime. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.040

文献信息

• 2-isocephem and oxacephem derivatives, and use as antibacterial agents
  申请人：Pfizer, Inc.

  公开号：US05578591A1

  公开（公告）日：1996-11-26

  Compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group, in particular that of an antibacterially active cephalosporin; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a readily removable carboxy promoting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group; R.sup.4 represents hydrogen or up to four substituents, which my be present on any of the carbon atoms in the ring system shown, selected from alkyl, alkenyl, alkynyl, alkoxy, hydroxy, halogen, amino, alkylamino, acylamino, dialkylamino, CO.sub.2 R, CONR.sub.2, SO.sub.2 NR.sub.2 where R is hydrogen or alkyl, aryl and heterocyclyl, which may be the same or different and wherein any R.sup.4 aryl substituent is optionally substituted by one or more substituents selected from the list from which R.sup.4 is selected Y is O, S, SO or SO.sub.2 ; n is 0 or 1; and m is 1 or 2; for use in the treatment of bacterial infections in humans and animals.

  该公式的化合物为：##STR1## 其中 R.sup.1 是氢、甲氧基或甲酰胺基；R.sup.2 是酰基，特别是抗菌活性头孢菌素的酰基；CO.sub.2 R.sup.3 是羧基或羧酸盐阴离子，或者 R.sup.3 是易于去除的羧基促进基团或药用可接受的盐形成基团或体内水解的酯基团；R.sup.4 代表氢或最多四个取代基，这些取代基可以存在于所示环系的任何碳原子上，从烷基、烯基、炔基、烷氧基、羟基、卤素、氨基、烷基氨基、酰基氨基、二烷基氨基、CO.sub.2 R、CONR.sub.2、SO.sub.2 NR.sub.2 中选择，其中 R 为氢或烷基、芳基和杂环基，这些基团可以相同也可以不同，其中任何 R.sup.4 芳基取代基可选择性地由列表中 R.sup.4 所选取的一个或多个取代基取代，Y 为 O、S、SO 或 SO.sub.2；n 为 0 或 1；m 为 1 或 2；用于治疗人类和动物的细菌感染。
• A general enantioselective O-2-isocephem synthesis
  作者：Harold Mastalerz、Vivianne Vinet

  DOI：10.1039/c39870001283

  日期：——

  A simple procedure for the conversion of the readily available chiral azetidinone (2) into the O-2-isocephem (5) is described.

  描述了用于将容易获得的手性氮杂环丁酮（2）转化为O-2-异头孢烯（5）的简单程序。
• 2-isocephem and oxacephem derivatives and use as antibacterial agents
  申请人：Pfizer Inc.

  公开号：US06080855A1

  公开（公告）日：2000-06-27

  Compounds of formula (I) or salts thereof: ##STR1## wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a carboxy protecting group, pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group; R.sup.4 represents hydrogen or up to four substituents; X is O, S, SO or SO.sub.2 ; Y is O, S, SO or SO.sub.2 ; n is 0 or 1; and m is 1 or 2. The compounds have antibacterial activity. Methods of synthesis of, and pharmaceutical formulations containing, compounds (I) are also described.

  式(I)的化合物或其盐：##STR1## 其中R.sup.1是氢、甲氧基或甲酰胺基；R.sup.2是酰基；CO.sub.2R.sup.3是羧基或羧酸盐阴离子，或R.sup.3是羧基保护基、药学上可接受的盐形成基或体内水解酯基；R.sup.4代表氢或高达四个取代基；X是O、S、SO或SO.sub.2；Y是O、S、SO或SO.sub.2；n为0或1；m为1或2。这些化合物具有抗菌活性。还描述了合成方法和含有化合物(I)的药物配方。
• MASTALERZ, HAROLD;VINET, VIVIANNE, J. CHEM. SOC. CHEM. COMMUN.,(1987) N 17, 1283-1284
  作者：MASTALERZ, HAROLD、VINET, VIVIANNE

  DOI：——

  日期：——
• MASTALERZ, HAROLD;MENARD, MARCEL;VINET, VIVIANNE;DESIDERIO, JAMES;FUNG-TO+, J. MED. CHEM., 31,(1988) N 6, 1190-1196
  作者：MASTALERZ, HAROLD、MENARD, MARCEL、VINET, VIVIANNE、DESIDERIO, JAMES、FUNG-TO+

  DOI：——

  日期：——