tert-butyl N-but-2-enyl-N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-N'-[8-[4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-1,3,5-triazacyclotridec-4-en-1-yl]octyl]carbamimidoyl]carbamate | 1187422-83-8

• 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: tert-butyl N-but-2-enyl-N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-N'-[8-[4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-1,3,5-triazacyclotridec-4-en-1-yl]octyl]carbamimidoyl]carbamate
• CAS: 1187422-83-8
• 化学式: C₃₈H₆₉N₇O₇
• 分子量: 736.009
• InChiKey: SYGHCWANCYUPEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.27
• 重原子数：
  52.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  163.26
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-but-2-enyl-N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-N'-[8-[4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-1,3,5-triazacyclotridec-4-en-1-yl]octyl]carbamimidoyl]carbamate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis of linear and cyclic guazatine derivatives endowed with antibacterial activity

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.09.081
• 作为产物：
  描述：

  N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine 在 偶氮二甲酸二异丙酯 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 生成 tert-butyl N-but-2-enyl-N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-N'-[8-[4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-1,3,5-triazacyclotridec-4-en-1-yl]octyl]carbamimidoyl]carbamate
  参考文献：
  名称：

  Synthesis of linear and cyclic guazatine derivatives endowed with antibacterial activity

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.09.081

文献信息

• Synthesis of New Linear Guanidines and Macrocyclic Amidinourea Derivatives Endowed with High Antifungal Activity against <i>Candida</i> spp. and <i>Aspergillus</i> spp.
  作者：Fabrizio Manetti、Daniele Castagnolo、Francesco Raffi、Alessandra T. Zizzari、Suvi Rajamäki、Silvia D’Arezzo、Paolo Visca、Alessandra Cona、Maria Enrica Fracasso、Denise Doria、Brunella Posteraro、Maurizio Sanguinetti、Giovanni Fadda、Maurizio Botta

  DOI：10.1021/jm900760k

  日期：2009.12.10

  New linear and Cyclic guanidines were synthesized and tested in vitro for their antifungal activity toward clinically relevant strains of Candida species, in comparison to fluconazole. Macrocyclic Compounds showed a minimum inhibitory concentration ill the micromolar range and a biological activity profile ill some cases better than that of fluconazole. One macrocyclic derivative was also tested against Aspergillus species and showed high antifungal activity comparable to that of amphotericin B and itraconazole.