N-tert-butyloxycarbonyl-L-tert-butylglycyl-L-leucinol | 210492-83-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-tert-butyloxycarbonyl-L-tert-butylglycyl-L-leucinol
• 英文别名: tert-butyl N-[(2S)-1-[[(2S)-1-hydroxy-4-methylpentan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]carbamate
• CAS: 210492-83-4
• 化学式: C₁₇H₃₄N₂O₄
• 分子量: 330.468
• InChiKey: MUOSRQDRZGMMNO-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-L-tert-butylglycyl-L-leucinol 在 sodium hydroxide 、 三乙胺 、 三苯基膦 、 palladium dichloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 tert-butyl N-[(2S)-3,3-dimethyl-1-[[(2S)-4-methyl-1-(4-oxoazetidin-2-yl)sulfanylpentan-2-yl]amino]-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Inhibition of human cytomegalovirus protease N o with monocyclic β-lactams

  摘要：

  Monocyclic beta-lactams have been identified as potent and selective inhibitors of the human cytomegalovirus protease (HCMV) N-o. Two series of these inhibitors are described, a peptidyl series of compounds and non-peptidic molecules featuring lower molecular weights. The SAR work that lead to the discovery of these inhibitors, together with their synthesis is also disclosed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00240-6
• 作为产物：
  描述：

  L-亮氨醇 、 N-Boc-L-叔亮氨酸 在 N-甲基吗啉 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 以80%的产率得到N-tert-butyloxycarbonyl-L-tert-butylglycyl-L-leucinol
  参考文献：
  名称：

  Inhibition of human cytomegalovirus protease N o with monocyclic β-lactams

  摘要：

  Monocyclic beta-lactams have been identified as potent and selective inhibitors of the human cytomegalovirus protease (HCMV) N-o. Two series of these inhibitors are described, a peptidyl series of compounds and non-peptidic molecules featuring lower molecular weights. The SAR work that lead to the discovery of these inhibitors, together with their synthesis is also disclosed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00240-6

文献信息

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

  公开号：US06239125B1

  公开（公告）日：2001-05-29

  A compound of formula 1: wherein Y is S or O; R1 is C1-6 alkyl; (C0-6 alkyl)aryl; (C0-6 alkyl)Het; or R1 is an amino acid analog or dipeptide analog of the formula: wherein R2 is H, C1-10 alkyl; or an amide or ester group; A is C6-10 aryl, Het or CH—R3 wherein R3 is C1-6 alkyl or (C0-4 alkyl)aryl; and Z is H, C1-6 alkyl, or an acyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy, or benzyloxy; and R5 is alkyl, cycloalkyl, carboxyl group; an aryl; 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 phenyl or C(O)OCH2-phenyl, said phenyl ring optionally mono- or di-substituted with among others C(O)OR7 wherein R7 is lower alkyl or phenyl(lower alkyl); or a therapeutically acceptable acid addition salt thereof which compounds are useful in the treatment of HCMV infections.

  化合物的化学式为1：其中Y为S或O；R1为C1-6烷基；(C0-6烷基)芳基；(C0-6烷基)杂环基；或R1为以下式子的氨基酸类似物或二肽类似物：其中R2为H，C1-10烷基；或酰胺或酯基；A为C6-10芳基，杂环基或CH-R3，其中R3为C1-6烷基或(C0-4烷基)芳基；并且Z为H，C1-6烷基或酰基；R4为氢，低烷基，甲氧基，乙氧基或苄氧基；以及R5为烷基，环烷基，羧基；芳基，杂环基或Het(低烷基)；或R4和R5与它们连接的氮原子一起形成含氮环，该环可选择地被苯基或C(O)OCH2-苯基取代，所述苯环可选择地单取代或双取代，其中包括C(O)OR7，其中R7为低烷基或苯基(低烷基)；或其治疗上可接受的酸盐，该化合物在HCMV感染的治疗中有用。
• Inhibition of human cytomegalovirus protease N o with monocyclic β-lactams
  作者：R. Déziel、E. Malenfant

  DOI：10.1016/s0960-894x(98)00240-6

  日期：1998.6

  Monocyclic beta-lactams have been identified as potent and selective inhibitors of the human cytomegalovirus protease (HCMV) N-o. Two series of these inhibitors are described, a peptidyl series of compounds and non-peptidic molecules featuring lower molecular weights. The SAR work that lead to the discovery of these inhibitors, together with their synthesis is also disclosed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.