tert-butyl allyl{[(tert-butoxycarbonyl)imino](1H-pyrazol-1-yl)methyl}carbamate | 220652-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl allyl{[(tert-butoxycarbonyl)imino](1H-pyrazol-1-yl)methyl}carbamate
• CAS: 220652-06-2
• 化学式: C₁₇H₂₆N₄O₄
• 分子量: 350.418
• InChiKey: KKRAJNADGFVTFK-UHFFFAOYSA-N

物化性质

• 沸点：
  412.5±38.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  86.02
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl allyl{[(tert-butoxycarbonyl)imino](1H-pyrazol-1-yl)methyl}carbamate 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 24.0h， 生成 (S)-2-amino-4-(N'-allylguanidino)butanoic acid
  参考文献：
  名称：

  Selective Substrate-Based Inhibitors of Mammalian Dimethylarginine Dimethylaminohydrolase

  摘要：

  The enzyme DDAH metabolizes methylarginines that are inhibitors of nitric oxide synthase (NOS). Substrate-based inhibitors of mammalian DDAH have been synthesized, with optimization to give selective inhibition of DDAH with no significant direct effect on NOSs. These are the first examples of reversible DDAH inhibitors with significant activity and selectivity. In vivo administration increases plasma ADMA levels, giving proof of concept that these inhibitors can be used to probe the physiological effects of DDAH inhibition, with potential for pharmaceutical use of DDAH inhibitors in diseases where excess NO production is implicated.

  DOI：

  10.1021/jm050187a
• 作为产物：
  描述：

  烯丙醇 、 N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到tert-butyl allyl{[(tert-butoxycarbonyl)imino](1H-pyrazol-1-yl)methyl}carbamate
  参考文献：
  名称：

  A Convenient Synthesis of Disubstituted Guanidines via the Mitsunobu Protocol

  摘要：

  描述了一种高效的合成二取代胍的制备方法。初级和次级醇在 Mitsunobu 条件下与胍化试剂反应，随后与胺的反应生成二取代胍。

  DOI：

  10.1055/s-1999-2584

文献信息

• Synthesis of linear and cyclic guazatine derivatives endowed with antibacterial activity
  作者：Giorgio Maccari、Stefania Sanfilippo、Filomena De Luca、Davide Deodato、Alexandru Casian、Maria Chiara Dasso Lang、Claudio Zamperini、Elena Dreassi、Gian Maria Rossolini、Jean-Denis Docquier、Maurizio Botta

  DOI：10.1016/j.bmcl.2014.09.081

  日期：2014.12

  Antibiotic resistance has reached alarming levels in many clinically-relevant human pathogens, and there is an increasing clinical need for new antibiotics active on drug-resistant Gram-negative pathogens who rapidly evolve towards pandrug resistance phenotypes. Here, we report on two related classes of guanidinic compounds endowed with antibacterial activity. The two best compounds (9a and 13d) exhibited the most potent antibacterial activity with MIC values ranging 0.12-8 mu g/ml with most tested pathogens, including both Gram-positive and Gram-negative bacteria. Interestingly, MIC values were not affected (1-8 mu g/ml) when measured using recent clinical isolates with various antibiotic resistance determinants. The results reported herein identify guazatine derivatives as an interesting starting point for the optimization of a potentially novel class of antibacterial agents. (C) 2014 Elsevier Ltd. All rights reserved.
• An Efficient Route to N-Monosubstituted Guanidino-Lactams
  作者：Matteo Zanda、Sara Tommasi、Chiara Zanato、Rey Carabeo、Arduino Mangoni、Sergio Dall’Angelo

  DOI：10.1055/s-0034-1378845

  日期：——

  A small library of guanidino-lactams were synthesized in four steps and good overall yields by following the routes: preparation of guanylating agents, synthesis of protected guanidino-acids, cyclization to fully protected guanidino-lactams, and deprotection to the target compounds. The guanidino-lactams were assayed as antimicrobials on E. coli showing no significant antibiotic activity.