tert-butyl N-(cyclopropylmethyl)-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 | 1448321-50-3

• 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-(cyclopropylmethyl)-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: 1448321-50-3
• 化学式: C₃₈H₆₉N₇O₇
• 分子量: 736.009
• InChiKey: JILNXUYWTXHBAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  163
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(cyclopropylmethyl)-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 1-[8-(4-amino-2-oxo-1,3,5-triazacyclotridec-4-en-1-yl)octyl]-2-(cyclopropylmethyl)guanidine;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Novel Macrocyclic Amidinoureas: Potent Non-Azole Antifungals Active against Wild-Type and Resistant Candida Species

  摘要：

  Novel macrocyclic amidinourea derivatives 11, 18, and 25 were synthesized and evaluated as antifungal agents against wild-type and fluconazole resistant Candida species. Macrocyclic compounds 11 and 18 were synthesized through a convergent approach using as a key step a ring-closing metathesis macrocyclization reaction, whereas compounds 25 were obtained by our previously reported synthetic pathway. All the macrocyclic amidinoureas showed antifungal activity toward different Candida species higher or comparable to fluconazole and resulted highly active against fluconazole resistant Candida strains showing in many cases minimum inhibitory concentration values lower than voriconazole.

  DOI：

  10.1021/ml400187w
• 作为产物：
  描述：

  8-氨基辛酸 在 palladium 10% on activated carbon 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 tert-butyl N-(cyclopropylmethyl)-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：

  Novel Macrocyclic Amidinoureas: Potent Non-Azole Antifungals Active against Wild-Type and Resistant Candida Species

  摘要：

  Novel macrocyclic amidinourea derivatives 11, 18, and 25 were synthesized and evaluated as antifungal agents against wild-type and fluconazole resistant Candida species. Macrocyclic compounds 11 and 18 were synthesized through a convergent approach using as a key step a ring-closing metathesis macrocyclization reaction, whereas compounds 25 were obtained by our previously reported synthetic pathway. All the macrocyclic amidinoureas showed antifungal activity toward different Candida species higher or comparable to fluconazole and resulted highly active against fluconazole resistant Candida strains showing in many cases minimum inhibitory concentration values lower than voriconazole.

  DOI：

  10.1021/ml400187w

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.
• Novel Macrocyclic Amidinoureas: Potent Non-Azole Antifungals Active against Wild-Type and Resistant Candida Species
  作者：Maurizio Sanguinetti、Stefania Sanfilippo、Daniele Castagnolo、Dominique Sanglard、Brunella Posteraro、Giovanni Donzellini、Maurizio Botta

  DOI：10.1021/ml400187w

  日期：2013.9.12

  Novel macrocyclic amidinourea derivatives 11, 18, and 25 were synthesized and evaluated as antifungal agents against wild-type and fluconazole resistant Candida species. Macrocyclic compounds 11 and 18 were synthesized through a convergent approach using as a key step a ring-closing metathesis macrocyclization reaction, whereas compounds 25 were obtained by our previously reported synthetic pathway. All the macrocyclic amidinoureas showed antifungal activity toward different Candida species higher or comparable to fluconazole and resulted highly active against fluconazole resistant Candida strains showing in many cases minimum inhibitory concentration values lower than voriconazole.