4(S)-benzyl-1-(tert-butyldimethylsilyl)-3(S)-hydroxyazetidin-2-one | 211619-52-2

• 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: 4(S)-benzyl-1-(tert-butyldimethylsilyl)-3(S)-hydroxyazetidin-2-one
• 英文别名: (3S,4S)-4-benzyl-1-[tert-butyl(dimethyl)silyl]-3-hydroxyazetidin-2-one
• CAS: 211619-52-2
• 化学式: C₁₆H₂₅NO₂Si
• 分子量: 291.466
• InChiKey: VONUPNCGWDSYMQ-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4(S)-benzyl-1-(tert-butyldimethylsilyl)-3(S)-hydroxyazetidin-2-one 在 cesium fluoride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.5h， 生成 4(S)-benzyl-3(S)-methoxyazetidin-2-one
  参考文献：
  名称：

  β-Lactam Derivatives as Inhibitors of Human Cytomegalovirus Protease

  摘要：

  The development of novel monobactam inhibitors of HCMV protease incorporating a carbon side chain at C-4 and a urea function at N-1 is described. Substitution with small groups at the C-3 position of the beta-lactam ring gave an increase in enzymatic activity and in stability; however, a lack of selectivity against other serine proteases was noted. The use of both tri- and tetrasubstituted urea functionalities gave effective inhibitors of HCMV protease. Benzyl substitution of the urea moiety was beneficial, especially when strong electron-withdrawing groups where attached at the para position. Modest antiviral activity was found in a plaque reduction assay.

  DOI：

  10.1021/jm980131z
• 作为产物：
  描述：

  Z-Phe-O-COO-isoBu 在 palladium dihydroxide 氢气 、 氧气 、 silver benzoate 、 碳酸氢钠 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 、 三甲氧基磷 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 42.92h， 生成 4(S)-benzyl-1-(tert-butyldimethylsilyl)-3(S)-hydroxyazetidin-2-one
  参考文献：
  名称：

  β-Lactam Derivatives as Inhibitors of Human Cytomegalovirus Protease

  摘要：

  The development of novel monobactam inhibitors of HCMV protease incorporating a carbon side chain at C-4 and a urea function at N-1 is described. Substitution with small groups at the C-3 position of the beta-lactam ring gave an increase in enzymatic activity and in stability; however, a lack of selectivity against other serine proteases was noted. The use of both tri- and tetrasubstituted urea functionalities gave effective inhibitors of HCMV protease. Benzyl substitution of the urea moiety was beneficial, especially when strong electron-withdrawing groups where attached at the para position. Modest antiviral activity was found in a plaque reduction assay.

  DOI：

  10.1021/jm980131z

文献信息

• Azetidinone derivatives for the treatment of HCMV infections
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US06242439B1

  公开（公告）日：2001-06-05

  A compound of formula I wherein R1 is hydrogen, methyl, ethyl, methoxy or methylthio; R2 and R3 each independently is hydrogen or lower alkyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy or benzyloxy; R5 is lower alkyl, lower cycloalkyl, (CH2)mC(O)OR6 wherein m is the integer 1 or 2 and R6 is lower alkyl, phenyl optionally substituted; optionally Het or Het(lower alkyl); or R4 and R5 together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with C(O)O-benzyl or with phenyl optionally substituted with C(O)OR7 wherein R7 is lower alkyl or (lower alkyl)phenyl; and Z is lower alkyl or optionally substituted phenyl or Het; with the proviso that when Z is (CH2)p-(Het), then R2 and R3 each is hydrogen; or a therapeutically acceptable acid addition salt thereof which compound is useful in the treatment of HCMV infections.

  化合物I的化学式为：其中R1为氢、甲基、乙基、甲氧基或甲硫基；R2和R3各自独立地为氢或低碳基；R4为氢、低碳基、甲氧基、乙氧基或苄氧基；R5为低碳基、低环戊基、（CH2）mC（O）OR6，其中m为整数1或2，R6为低碳基、苯环可选择取代基；可选择为Het或Het（低碳基）；或者R4和R5与它们连接的氮原子一起形成含氮环，该环可选择取代为C（O）O-苄基或可选择取代为C（O）OR7的苯环，其中R7为低碳基或（低碳基）苯基；Z为低碳基或可选择取代的苯环或Het；但是当Z为（CH2）p-（Het）时，R2和R3各自为氢。该化合物或其治疗上可接受的酸盐在HCMV感染的治疗中有用。
• β-Lactam Derivatives as Inhibitors of Human Cytomegalovirus Protease
  作者：Christiane Yoakim、William W. Ogilvie、Dale R. Cameron、Catherine Chabot、Ingrid Guse、Bruno Haché、Julie Naud、Jeff A. O'Meara、Raymond Plante、Robert Déziel

  DOI：10.1021/jm980131z

  日期：1998.7.1

  The development of novel monobactam inhibitors of HCMV protease incorporating a carbon side chain at C-4 and a urea function at N-1 is described. Substitution with small groups at the C-3 position of the beta-lactam ring gave an increase in enzymatic activity and in stability; however, a lack of selectivity against other serine proteases was noted. The use of both tri- and tetrasubstituted urea functionalities gave effective inhibitors of HCMV protease. Benzyl substitution of the urea moiety was beneficial, especially when strong electron-withdrawing groups where attached at the para position. Modest antiviral activity was found in a plaque reduction assay.