benzyl (S,Z)-1-amino-1-(hydroxyimino)propan-2-ylcarbamate | 1058149-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (S,Z)-1-amino-1-(hydroxyimino)propan-2-ylcarbamate
• 英文别名: benzyl N-[(2S)-1-amino-1-hydroxyiminopropan-2-yl]carbamate
• CAS: 1058149-19-1
• 化学式: C₁₁H₁₅N₃O₃
• 分子量: 237.258
• InChiKey: GFRCMTMMYQWWLY-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (S,Z)-1-amino-1-(hydroxyimino)propan-2-ylcarbamate 、 4-正辛基苯甲酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以1.6 mmol的产率得到benzyl (R,Z)-1-amino-1-(4-octylbenzoyloxyimino)propan-2-ylcarbamate
  参考文献：
  名称：

  Discovery, Biological Evaluation, and Structure−Activity Relationship of Amidine Based Sphingosine Kinase Inhibitors

  摘要：

  Sphingosine 1-phosphate (S1P), a potent phospholipid growth and trophic factor, is synthesized in vivo by two sphingosine kinases. Thus these kinases have been proposed as important drug targets for treatment of hyperproliferative diseases and inflammation. We report here a new class of amidine-based sphingosine analogues that are competitive inhibitors of sphingosine kinases exhibiting varying degrees of enzyme selectivity. These inhibitors display K(I) values in the submicromolar range for both sphingosine kinases and, in cultured vascular smooth muscle cells, decrease S1P levels and initiate growth arrest.

  DOI：

  10.1021/jm901860h
• 作为产物：
  描述：

  N-[(1S)-1-氰基乙基]氨基甲酸苯甲酯 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以2.3 mmol的产率得到benzyl (S,Z)-1-amino-1-(hydroxyimino)propan-2-ylcarbamate
  参考文献：
  名称：

  Discovery, Biological Evaluation, and Structure−Activity Relationship of Amidine Based Sphingosine Kinase Inhibitors

  摘要：

  Sphingosine 1-phosphate (S1P), a potent phospholipid growth and trophic factor, is synthesized in vivo by two sphingosine kinases. Thus these kinases have been proposed as important drug targets for treatment of hyperproliferative diseases and inflammation. We report here a new class of amidine-based sphingosine analogues that are competitive inhibitors of sphingosine kinases exhibiting varying degrees of enzyme selectivity. These inhibitors display K(I) values in the submicromolar range for both sphingosine kinases and, in cultured vascular smooth muscle cells, decrease S1P levels and initiate growth arrest.

  DOI：

  10.1021/jm901860h

文献信息

• A fast and efficient one-pot microwave assisted synthesis of variously di-substituted 1,2,4-oxadiazoles
  作者：Andrea Porcheddu、Roberta Cadoni、Lidia De Luca

  DOI：10.1039/c1ob06055d

  日期：——

  A one-pot two-step microwave assisted synthesis of variously disubstituted 1,2,4-oxadiazoles from carboxylic acids and amidoximes is reported. This methodology is characterized by short reaction times, is versatile, robust and high-yielding and allows for the preparation of heterocycles with a stereocenter with 100% enantiomeric purity.

  据报道，由一锅两步微波辅助从羧酸和a胺肟合成各种二取代的1,2,4-恶二唑。该方法的特点是反应时间短，用途广泛，稳定可靠且产率高，并且可以制备具有100％对映体纯度的立体中心的杂环。
• Synthesis of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics
  作者：Vommina V. Sureshbabu、Hosahalli P. Hemantha、Shankar A. Naik

  DOI：10.1016/j.tetlet.2008.06.091

  日期：2008.8

  The synthesis of a new class of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics is described. The protocol employs a reaction between an N-protected amino acyl fluoride and an amino acid-derived amidoxime. All the three commonly employed urethanes have been used in this protocol for N-protection. The course of the reaction was found to be high yielding and all new compounds were well characterized by NMR and mass spectroscopy. The C-acyl amidoxime intermediate has also been isolated as a stable solid. (C) 2008 Elsevier Ltd. All rights reserved.