1-(N1,N2-bis(tert-butoxycarbonyl)guanidine)-17-(N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)guanidine)-9-azaheptadecane | 1176238-49-5

• 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: 1-(N1,N2-bis(tert-butoxycarbonyl)guanidine)-17-(N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)guanidine)-9-azaheptadecane
• 英文别名: tert-butyl N-[N'-[8-[8-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]octylamino]octyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-N-(cyclopropylmethyl)carbamate
• CAS: 1176238-49-5
• 化学式: C₄₂H₇₉N₇O₈
• 分子量: 810.131
• InChiKey: LTFZHHPHURFHQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  57
• 可旋转键数：
  32
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  181
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(N1,N2-bis(tert-butoxycarbonyl)guanidine)-17-(N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)guanidine)-9-azaheptadecane 、 tert-butyl N-[N'-[8-[8-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]octyl-carbonochloridoylamino]octyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-N-(cyclopropylmethyl)carbamate 在 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  [EN] LINEAR GUANIDINE DERIVATIVES, METHODS OF PREPARATION AND USES THEREOF
  [FR] DÉRIVÉS DE GUANIDINE LINÉAIRES, PROCÉDÉS DE PRÉPARATION ET UTILISATIONS DE CEUX-CI

  摘要：

  本发明涉及线性胍基衍生物，其制备方法，用途和药物组合物。公式1或2的化合物对革兰氏阳性和革兰氏阴性细菌表现出高抗菌活性。

  公开号：

  WO2016055644A1
• 作为产物：
  描述：

  1,8-辛二胺 在 cesiumhydroxide monohydrate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 49.0h， 生成 1-(N1,N2-bis(tert-butoxycarbonyl)guanidine)-17-(N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)guanidine)-9-azaheptadecane
  参考文献：
  名称：

  [EN] LINEAR GUANIDINE DERIVATIVES, METHODS OF PREPARATION AND USES THEREOF
  [FR] DÉRIVÉS DE GUANIDINE LINÉAIRES, PROCÉDÉS DE PRÉPARATION ET UTILISATIONS DE CEUX-CI

  摘要：

  本发明涉及线性胍基衍生物，其制备方法，用途和药物组合物。公式1或2的化合物对革兰氏阳性和革兰氏阴性细菌表现出高抗菌活性。

  公开号：

  WO2016055644A1

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.
• 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.
• Synthesis and Biological Evaluation of Guanidino Compounds Endowed with Subnanomolar Affinity as Competitive Inhibitors of Maize Polyamine Oxidase
  作者：Fabrizio Manetti、Alessandra Cona、Lucilla Angeli、Claudia Mugnaini、Francesco Raffi、Caterina Capone、Elena Dreassi、Alessandra Tania Zizzari、Alessandra Tisi、Rodolfo Federico、Maurizio Botta

  DOI：10.1021/jm900371z

  日期：2009.8.13

  Previous studies on agmatine and its derivatives suggested that the presence of hydrophobic groups on the guanidine moiety was a crucial key for inhibitory activity of maize polyamine oxidase. Accordingly, new lipophilic agmatine and iminoctadine derivatives were synthesized and tested for their ability to inhibit this enzyme. Several compounds showed an affinity in the nanomolar range, while a cyclopropylmethyl derivative of iminoctadine was found to be the most potent inhibitor of maize polyamine oxidase reported so far (K-i = 0.08 nM).
• [EN] LINEAR GUANIDINE DERIVATIVES, METHODS OF PREPARATION AND USES THEREOF<br/>[FR] DÉRIVÉS DE GUANIDINE LINÉAIRES, PROCÉDÉS DE PRÉPARATION ET UTILISATIONS DE CEUX-CI
  申请人：LEAD DISCOVERY SIENA S R L

  公开号：WO2016055644A1

  公开（公告）日：2016-04-14

  The present invention relates to linear guanidine derivatives, methods of preparation, uses and pharmaceutical compositions thereof. The compounds of Formulas 1 or 2 exhibit high antimicrobial activity against Gram positive and Gram negative bacteria.

  本发明涉及线性胍基衍生物，其制备方法，用途和药物组合物。公式1或2的化合物对革兰氏阳性和革兰氏阴性细菌表现出高抗菌活性。