tert-butyl N-[({8-[(8-aminooctyl)amino]octyl}amino)({[(tert-butoxy)carbonyl]amino})methylidene]carbamate | 1000005-28-6

• 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-[({8-[(8-aminooctyl)amino]octyl}amino)({[(tert-butoxy)carbonyl]amino})methylidene]carbamate
• 英文别名: 1-amino-17-[N2,N3-bis(tert-butoxycarbonyl)guanidino]-9-azaheptadecane；tert-butyl N-[N'-[8-(8-aminooctylamino)octyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 1000005-28-6
• 化学式: C₂₇H₅₅N₅O₄
• 分子量: 513.765
• InChiKey: GFOOZESYGXQPKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[({8-[(8-aminooctyl)amino]octyl}amino)({[(tert-butoxy)carbonyl]amino})methylidene]carbamate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 36.0h， 生成 1-(guanidino)-17-(N1-(propargyl)guanidino)-9-azaheptadecane tris(trifluoroacetate)
  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：

  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 37.0h， 生成 tert-butyl N-[({8-[(8-aminooctyl)amino]octyl}amino)({[(tert-butoxy)carbonyl]amino})methylidene]carbamate
  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

• Efficient Synthesis of Iminoctadine, a Potent Antifungal Agent and Polyamine Oxidase Inhibitor (PAO)
  作者：Maurizio Botta、Francesco Raffi、Federico Corelli

  DOI：10.1055/s-2007-983898

  日期：2007.10

  Iminoctadine (1,17-diguanidino-9-azaheptadecane), isolated from a mixture of polyamines and guanidines known as guazatine that is used in agriculture as a fungicide, showed interesting activity as human antifungal agent and PAO inhibitor. In this paper, we propose a straightforward synthetic strategy for obtaining pure iminoctadine tris(trifluoroacetate) in high overall yield.

  亚胺辛他啶（1,17-二胍基-9-氮杂十七烷）是从一种被称为瓜扎汀的多胺和胍的混合物中分离出来的，该混合物在农业中被用作杀真菌剂，亚胺辛他啶作为人体抗真菌剂和 PAO 抑制剂显示出有趣的活性。在本文中，我们提出了一种直接的合成策略，可以高产率地获得纯的亚氨基辛二胺三(三氟乙酸)。
• Linear and cyclic guanidine derivatives, method of preparation and uses thereof
  申请人：Botta Maurizio

  公开号：US08685953B2

  公开（公告）日：2014-04-01

  The present invention relates to linear and cyclic guanidine derivatives, method of preparation and uses thereof, pharmaceutical compositions to be used as antifungal agents, in particular against Candida species.

  本发明涉及线性和环状胍衍生物，其制备方法和用途，制备的药物组合物可用作抗真菌剂，特别针对白色念珠菌属。
• LINEAR AND CYCLIC GUANIDINE DERIVATIVES, METHOD OF PREPARATION AND USES THEREOF
  申请人：Botta Maurizio

  公开号：US20110039854A1

  公开（公告）日：2011-02-17

  The present invention relates to linear and cyclic guanidine derivatives, method of preparation and uses thereof, pharmaceutical compositions to be used as antifungal agents, in particular against Candida species.

  本发明涉及线性和环状胍衍生物，其制备方法及其用途，药物组合物可用作抗真菌剂，特别是对抗念珠菌属菌株。
• Linear guanidine derivatives, methods of preparation and uses thereof
  申请人：LEAD DISCOVERY SIENA S.R.L.

  公开号：US10004702B2

  公开（公告）日：2018-06-26

  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.

  本发明涉及线性胍衍生物及其制备方法、用途和药物组合物。 式 1 或式 2 的化合物对革兰氏阳性菌和革兰氏阴性菌具有很高的抗菌活性。
• Alkyl-guanidine Compounds as Potent Broad-Spectrum Antibacterial Agents: Chemical Library Extension and Biological Characterization
  作者：Carolina Pasero、Ilaria D’Agostino、Filomena De Luca、Claudio Zamperini、Davide Deodato、Giuseppina I. Truglio、Filomena Sannio、Rosita Del Prete、Teresa Ferraro、Daniela Visaggio、Arianna Mancini、Mario B. Guglielmi、Paolo Visca、Jean-Denis Docquier、Maurizio Botta

  DOI：10.1021/acs.jmedchem.8b00619

  日期：2018.10.25

  Nowadays, the increasing of multidrug-resistant pathogenic bacteria represents a serious threat to public health, and the lack of new antibiotics is becoming a global emergency. Therefore, research in antibacterial fields is urgently needed to expand the currently available arsenal of drugs. We have recently reported an alkyl-guanidine derivative (2), characterized by a symmetrical dimeric structure, as a good candidate for further developments, with a high antibacterial activity against both Gram-positive and Gram-negative strains. In this study, starting from its chemical scaffold, we synthesized a small library of analogues. Moreover, biological and in vitro pharmacokinetic characterizations were conducted on some selected derivatives, revealing notable properties: broad-spectrum profile, activity against resistant clinical isolates, and appreciable aqueous solubility. Interestingly, 2 seems neither to select for resistant strains nor to macroscopically alter the membranes, but further studies are required to determine the mode of action.