N-dodecyl-β-D-glucopyranosylamine | 3676-73-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-dodecyl-β-D-glucopyranosylamine
• 英文别名: N-dodecyl-β-D-glucosylamine；N-dodecyl glucosylamine；n-dodecylglucosylamine；N-dodecylglucosamine；DoGPA；DoGA；(2R,3R,4S,5S,6R)-2-(dodecylamino)-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol；(2R,3R,4S,5S,6R)-2-(dodecylamino)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 3676-73-1
• 化学式: C₁₈H₃₇NO₅
• 分子量: 347.495
• InChiKey: CGRNGAJCQIWCRM-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-dodecyl-β-D-glucopyranosylamine 在 重水 作用下， 反应 168.0h， 生成
  参考文献：
  名称：

  Synthesis ofN-Alkyl-β-d-glucosylamines and Their Antimicrobial Activity againstFusarium proliferatum,Salmonellatyphimurium, andListeria innocua

  摘要：

  In this study, different N-alkyl-beta-D-glucosylamines were evaluated for both antifungal and antibacterial activity against Fusarium proliferatum (INRA, MUCL 1807.7), Listeria innocua (ISTAB, Universite Bordeaux 1), and Salmonella typhimurium (Institut Pasteur 5858). The tested glucosylamines were beta-D-glucosylamine (GPA), N-ethyl-beta-D-glucosylamine (EtGPA), N-butyl-beta-D-glucosylamine (BuGPA), N-hexyl-beta-D-glucosylamine (HeGPA), N-octyl-beta-D-glucosylamine (OcGPA), N-dodecyl-beta-D-glucosylamine (DoGPA), N-(2-hydroxyethyl)-beta-D-glucosylamine (HEtGPA), N,N-di(2-hydroxyethyl)-beta-D-glucosylamine (DHEtGPA) and N,N-diethyl-beta-D-glucosylamine (DEtGPA). The effectiveness of N-alkyl length, N-substitution, and N-hydroxyalkyl groups on both antibacterial and antifungal activity were evaluated. Results indicated that these compounds exhibited different biological activities and their effectiveness was highly increased from short to long N-alkyl chains. DoGPA exhibited more potent biological activity against all target strains than other N-alkyl glucosylamines tested. Using a radial growth method, we demonstrated that this compound completely inhibited fungal growth at 0.5 x 10(-4) mol mL(-1), while OcGPA and HeGPA lead to 71% and 43% fungal inhibition, respectively. Using the coating method, we demonstrated that DoGPA completely inhibited bacterial growth at 0.025 x 10(-4) and 0.05 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively, while at the same concentrations, OcGPA exhibited weaker antibacterial activity of 12% and 27%, respectively, for L. innocua and S. typhimurium. The hole plate method enabled us to estimate the minimum inhibitory concentration (MIC) of DoGPA found to be 0.02 x 10(-4) and 0.025 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively. Glucosylamines with N-hydroxyalkyl and short N-alkyl chains varying from C-2 to C-4 exhibited weaker antimicrobial activity.

  DOI：

  10.1021/jf9016114
• 作为产物：
  描述：

  十二烷基伯胺 、 葡萄糖 以 甲醇 为溶剂， 反应 24.0h， 以85%的产率得到N-dodecyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  设计的双功能糖基表面活性剂：胶束催化水中C–X偶联反应

  摘要：

  一种双功能糖基表面活性剂ALA14被设计为配体和胶束构造剂，并被证明能促进水中铜的C-X偶联反应。用CMC，DLS和TEM研究了由糖基表面活性剂形成的胶束的性质，从而验证了胶束中底物的包封和聚集。另外，通过1 H-NMR分析发现底物的富集位置在亲脂性烷基链中。最后，在这项工作中获得了中等至极高的目标产品收率。这种非常简单的策略扩大了水中C–X偶联反应的范围。最值得注意的是，水和ALA14都可以回收再利用。

  DOI：

  10.1039/c9gc00964g

文献信息

• N-glycosylated carboxamide derivatives as growth-promoters in livestock
  申请人：Bayer Aktiengesellschaft

  公开号：US04680287A1

  公开（公告）日：1987-07-14

  Growth of animals is promoted by inclusion in their feed of compounds of the formula ##STR1## in which Z is a glycosyl radical bonded via the anomeric carbon atom, R.sub.1 is hydrogen or an optionally substituted hydrocarbon radical having up to 30 Carbon atoms optionally interrupted by O, N or S, and R.sub.2 is hydrogen or an alkyl or aralkyl radical having up to 30 Carbon atoms optionally interrupted by O or substituted by groups containing oxygen or by halogen, with the proviso that COR.sub.1 is not an acyl group having 1-5 Carbon atoms when R.sub.2 is an alkyl group having 10-20 Carbon atoms.

  动物生长可以通过在其饲料中添加以下化合物的形式得到促进：其中Z是通过异头碳原子连接的糖基自由基，R1是氢或者是一个最多含有30个碳原子，可以选择性地被O、N或S原子隔断的，也可以选择性地被取代的烃基团，而R2是氢或者是一个最多含有30个碳原子的烷基或芳烷基团，可以选择性地被O原子隔断或被含氧基团或卤素取代，条件是当R2是一个含有10-20个碳原子的烷基团时，COR1不能是一个含有1-5个碳原子的酰基团。
• N-glycosylated carboxamide derivatives and their use for influencing the
  申请人：Bayer Aktiengesellschaft

  公开号：US04683222A1

  公开（公告）日：1987-07-28

  The invention relates to N-glycosylated carboxamide derivatives of Formula I which are useful for influencing the body's inherent defenses, e.g. for increasing immune system antibodies. Also included in the invention are compositions containing said N-glycosylated carboxamide derivative of Formula I as active ingredients and methods for the use of said compounds and compositions.

  本发明涉及式I的N-糖基化羧酰胺衍生物，它们可用于影响机体的固有防御，例如用于增加免疫系统的抗体。发明还包括含有式I的N-糖基化羧酰胺衍生物作为活性成分的组合物，以及使用所述化合物和组合物的方法。
• N-glycosylated carboxylic acid derivatives as agents for combating
  申请人：Troponwerke GmbH & Co., KG

  公开号：US04710491A1

  公开（公告）日：1987-12-01

  A method of combating rheumatic diseases which comprises administering to a patient afflicted therewith an amount effective to combat such disease of a compound of the formula ##STR1## in which Z is a glycosyl radical bonded via the anomeric carbon atom, R.sub.1 is hydrogen or an optionally substituted hydrocarbon radical with up to 30 C atoms, which hydrocarbon radical is optionally interrupted by O, N or S, and R.sub.2 is hydrogen or an alkyl or aralkyl radical with up to 30 C atoms, which is optionally interrupted by O, N or S or substituted by an oxygen-containing group or halogen, with the proviso that COR.sub.1 is not an acyl group with 1-5 C atoms if R.sub.2 is alkyl with 10-20 C atoms.

  一种治疗风湿病的方法，包括给患者施用有效治疗该疾病的量的以下化合物的公式：##STR1## 其中Z是通过异构碳原子连接的糖基自由基，R1是氢或最多有30个碳原子的可选取代的烃基，该烃基可被O、N或S隔断，R2是氢或最多有30个碳原子的烷基或芳烷基，该基团可被O、N或S隔断或被含氧基团或卤素取代，条件是如果R2是10-20个碳原子的烷基，则COR1不是1-5个碳原子的酰基。
• Efficient synthesis of glycosylamines in solventless conditions promoted by mechanical milling
  作者：Cédric Epoune Lingome、Gwladys Pourceau、Virginie Gobert-Deveaux、Anne Wadouachi

  DOI：10.1039/c4ra04321a

  日期：——

  A mecanosynthesis of glycosylamines under solventless conditions was established. This environmentally friendly approach optimized with L-rhamnose, was investigated using a variety of amines and other carbohydrates. High reaction yields and simple work-up allow the clean and fast synthesis of a variety of glycosylamines and glycosyl-(di)-amines.

  建立了在无溶剂条件下糖基胺的机械合成。使用多种胺类和其他碳水化合物对这种以L-鼠李糖优化的环保方法进行了研究。高反应产率和简单的后处理使得各种糖基胺和糖基-（二）-胺的清洁和快速合成成为可能。
• NOVEL METHOD FOR SYNTHESIZING N-ALKYL-GLYCOSYL(DI)AMINE DERIVATIVES AND USES OF SAME AGAINST PHYTOPATHOGENS
  申请人：UNIVERSITE DE PICARDIE JULES VERNE

  公开号：US20160102115A1

  公开（公告）日：2016-04-14

  The present invention relates to a novel method for synthesising, without a solvent, N-alkyl-glycosyl(di)amine derivatives represented by the following general formula (I): The invention also concerns the use of N-alkyl-glycosyl(di)amine derivatives represented by the general formula (I), and N-alkyl-glycosyl(di)ammonium quaternary salts represented by the general formula (II) and N-alkyl-glycamine derivatives represented by the general formula (III) obtained from N-alkyl-glycosyl(di)amine derivatives represented by the general formula (I), as antibacterial and/or antifungal agents against phytopathogens.

  本发明涉及一种新型方法，用于合成以下一般式(I)所代表的无溶剂N-烷基-糖基（二）胺衍生物。本发明还涉及使用由一般式(I)所代表的N-烷基-糖基（二）胺衍生物、一般式(II)所代表的N-烷基-糖基（二）胺盐和由一般式(I)所代表的N-烷基-糖基（二）胺衍生物所得到的一般式(III)所代表的N-烷基-糖胺衍生物作为抗菌和/或抗真菌剂，用于对抗植物病原体。