1,3,2’,6’-tetrazido-5,6-O-cyclohexylidene neamine | 688744-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,2’,6’-tetrazido-5,6-O-cyclohexylidene neamine
• 英文别名: 1,3,2',6'-tetraazido-5,6-O-cyclohexylideneneamine；1,3,2',6'-tetrazido-5,6-O-cyclohexylideneneamine；(2R,3S,4R,5R,6R)-6-[(3aS,4R,5S,7R,7aS)-5,7-diazidospiro[3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-2,1'-cyclohexane]-4-yl]oxy-5-azido-2-(azidomethyl)oxane-3,4-diol
• CAS: 688744-65-2
• 化学式: C₁₈H₂₆N₁₂O₆
• 分子量: 506.481
• InChiKey: WYXRGKQVDPERPU-YAUPXBKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1,3,2’,6’-tetrazido-5,6-O-cyclohexylidene neamine 在 4-二甲氨基吡啶 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 5,6-di-O-acetyl-3',4'-di-O-benzyl-1,3,2',3'-tetraazidoneamine
  参考文献：
  名称：

  Tuning the Regioselectivity of the Staudinger Reaction for the Facile Synthesis of Kanamycin and Neomycin Class Antibiotics with N-1 Modification

  摘要：

  A novel method for achieving the desired regioselective reduction of the N-1 azido group on a tetraazidoneamine has been developed that leads to the synthesis of both kanamycin and neomycin class antibiotics bearing N-1 modification. Both classes of aminoglycosides are active against aminoglycoside-resistant bacteria carrying APH(3')-I and AAC(6')/APH(2").

  DOI：

  10.1021/ol051045d
• 作为产物：
  描述：

  neamine tetrahydrochloride 在 triflic azide 、 对甲苯磺酸 、 copper(II) sulfate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 1,3,2’,6’-tetrazido-5,6-O-cyclohexylidene neamine
  参考文献：
  名称：

  Application of Glycodiversification:  Expedient Synthesis and Antibacterial Evaluation of a Library of Kanamycin B Analogues

  摘要：

  The expedient synthesis of a library of kanamycin B analogues is reported. The revealed SAR will guide future designs in developing kanamycin-type aminoglycoside antibiotics against drug-resistant bacteria.

  DOI：

  10.1021/ol0497685

文献信息

• miRNA PROCESSING INHIBITOR EFFICACY ASSAYS AND SUBSTANCES
  申请人：Arenz Christoph

  公开号：US20090092980A1

  公开（公告）日：2009-04-09

  The invention relates to assays for assessing miRNA maturation effector (preferably: inhibitor) efficacy, and to substances useful for influencing, particularly for inhibiting, maturation of miRNA. According to the invention there is provided assay of miRNA processing inhibitor efficacy, comprising the steps of: a) providing a target miRNA precursor, b) providing a potential inhibitor of one or more processing steps of the target miRNA precursor, c) bringing together of the target miRNA precursor and the potential inhibitor under miRNA maturation conditions, and d) determining inhibition efficiency. The assay of the present invention allows for a very fast and easy assessment of the efficacy of a potential inhibitor in inhibiting processing of a miRNA precursor into miRNA.

  该发明涉及用于评估miRNA成熟效应子（优选：抑制剂）效力的检测方法，以及用于影响miRNA成熟的物质，特别是用于抑制miRNA成熟的物质。根据该发明提供了miRNA处理抑制剂效力的检测方法，包括以下步骤：a）提供目标miRNA前体，b）提供一个或多个目标miRNA前体处理步骤的潜在抑制剂，c）在miRNA成熟条件下将目标miRNA前体和潜在抑制剂结合在一起，d）确定抑制效率。本发明的检测方法允许非常快速和简便地评估潜在抑制剂在抑制miRNA前体转化为miRNA的处理过程中的效力。
• Short and Efficient Synthesis of Alkyne-Modified Amino Glycoside Building Blocks
  作者：Claudine M. Klemm、Arne Berthelmann、Saskia Neubacher、Christoph Arenz

  DOI：10.1002/ejoc.200900076

  日期：2009.6

  In the light of recent progress in RNA biology, the need for molecules that bind to RNA and thus may be suited to manipulating RNA-mediated processes is steadily increasing. We present a very short and efficient synthetic route to alkyne-modified neamine and 2-deoxystreptamine derivatives on a half-gram scale. These derivatives are suitable for constructing a library of potential divalent RNA binders

  鉴于 RNA 生物学的最新进展，对与 RNA 结合并因此可能适合操纵 RNA 介导过程的分子的需求正在稳步增加。我们提出了一种非常短且有效的合成路线，以半克规模合成炔烃改性的新胺和 2-脱氧链霉胺衍生物。这些衍生物适用于通过铜催化的 1,3-偶极环加成与二叠氮化物（“点击化学”）构建潜在二价 RNA 结合剂库。由此形成的缀合物二聚体抑制 Dicer 介导的微 RNA 成熟，IC50 值介于 0.6 和 15 μM 之间。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2009）
• Synthesis of 4′-deoxy-4′-fluoro neamine and 4′-deoxy-4′-fluoro 4′-<i>epi</i>neamine
  作者：Stephen Hanessian、Oscar M. Saavedra、Miguel A. Vilchis-Reyes、Ana M. Llaguno-Rueda

  DOI：10.1039/c4md00072b

  日期：——

  The syntheses of 4′-deoxy-4′-fluoro neamine and 4′-deoxy-4′-fluoro 4′-epineamine from the readily available neamine and paromamine are described.

  描述了从易得的neamine和paromamine合成4'-去氧-4'-氟奈胺和4'-去氧-4'-氟4'-epi奈胺的方法。
• Novel anti bacterial compounds
  申请人：Chang Tom Cheng-Wei

  公开号：US20060234961A1

  公开（公告）日：2006-10-19

  The invention relates to novel paranmycin compounds that have activity against gram positive and gram negative bacteria, preferably bacteria that are resistant to other antibiotics. Paranmycins are of the general formula

  本发明涉及新型的帕拉霉素化合物，其具有对革兰氏阳性和革兰氏阴性细菌的活性，更好地对抗其他抗生素耐药的细菌。帕拉霉素的一般化学式为：
• Structure–Activity Relationships for Antibacterial to Antifungal Conversion of Kanamycin to Amphiphilic Analogues
  作者：Marina Fosso、Madher N. AlFindee、Qian Zhang、Vincent de Paul Nzuwah Nziko、Yukie Kawasaki、Sanjib K. Shrestha、Jeremiah Bearss、Rylee Gregory、Jon Y. Takemoto、Cheng-Wei Tom Chang

  DOI：10.1021/acs.joc.5b00248

  日期：2015.5.1

  Novel fungicides are urgently needed. It was recently reported that the attachment of an octyl group at the O-4 '' position of kanamycin B converts this antibacterial aminoglycoside into a novel antifungal agent. To elucidate the structure-activity relationship (SAR) for this phenomenon, a lead compound FG03 with a hydroxyl group replacing the 3 ''-NH2 group of kanamycin B was synthesized. FG03's antifungal activity and Synthetic scheme inspired the synthesis of a library of kanamycin B analogues alkylated at various hydroxyl groups. SAR. studies of the library revealed that for antifungal activity the O-4 '' position is the optimal site for attaching a linear alkyl chain and that the 3 ''-NH2 and 6 ''-OH groups of the kanamycin B parent molecule are not essential for antifungal activity. The discovery of lead compound, FG03, is an example of reviving clinically obsolete drugs like kanamycin by simple chemical modification and an alternative strategy for discovering novel antimicrobials.