N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,4-dimethoxybenzylidene)rhodanine | 65562-18-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,4-dimethoxybenzylidene)rhodanine
• 英文别名: N-(Tetraacetyl-β-D-glucopyranosyl)-5-benzylidenrhodanin；5-benzylidene-3-(tetra-O-acetyl-β-D-glucopyranosyl)-2-thioxo-thiazolidin-4-one；N-(2,3,4,6-Tetra-O-acetyl-beta-D glucopyranosyl)-5-benzylidenerhodanine；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(5-benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)oxan-2-yl]methyl acetate
• CAS: 65562-18-7
• 化学式: C₂₄H₂₅NO₁₀S₂
• 分子量: 551.595
• InChiKey: LDZMLSWJYIOGHW-OXUVVOBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  192
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,4-dimethoxybenzylidene)rhodanine 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 (5Z)-5-benzylidene-2-sulfanylidene-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,3-thiazolidin-4-one
  参考文献：
  名称：

  N-Glucopyranosyl-5-aralkylidenerhodanines：合成以及抗菌和抗病毒活性。

  摘要：

  合成了一系列的N-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-5-芳烷基亚乙基金丹宁，并且除去了乙酰基基团，得到了N-β-D-吡喃葡萄糖基-5-芳烷基亚芳基但不通过酸水解裂解若丹宁环。在甲醇中用氨水进行碱水解会裂解为N-葡萄糖基硫脲，为N-糖苷的形成提供了证据。许多若丹宁衍生物，特别是在芳族环中具有硝基或氯基的那些，均显示出抗菌活性。N-β-D-Glucopyranosyl-5-（4-硝基亚苄基）若丹宁通过抑制病毒RNA合成表现出抗病毒活性。几种罗丹宁对血糖水平也有一定影响。

  DOI：

  10.1002/jps.2600661126
• 作为产物：
  描述：

  5-benzylidenerhodanine sodium 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 生成 N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,4-dimethoxybenzylidene)rhodanine
  参考文献：
  名称：

  N-糖基硫脲，N-糖基罗丹宁和N-糖基-2-氨基噻唑的合成及其抗菌活性。

  摘要：

  在N-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-5-芳烷基亚乙基内酯的氨解中发现了一种获得N-β-D-吡喃葡萄糖基硫脲的方法。尽管使用吗啉和羟胺获得了N-（2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖基）硫脲，但是三乙酰化或三苯甲酰化的核糖基罗丹宁的氨解通常不会产生核糖基硫脲，但会导致糖苷裂解。用溴丙酮酸乙酯对N-β-D-吡喃葡萄糖基硫脲进行环封闭，得到2-（N-β-D-吡喃葡萄糖基）氨基噻唑-4-羧酸乙酯，并且氨解反应产生相应的4-羧酰胺。对五种微生物的抗菌素筛选表明，N-（2,3,5-三-O-乙酰基-β-D-呋喃呋喃糖基）罗丹宁和葡糖基氨基噻唑-4-羧酸酯具有最广谱的抑制活性，

  DOI：

  10.1002/jps.2600700924

文献信息

• N-Sugar compounds, compositions and uses thereof
  申请人：——

  公开号：US04367226A1

  公开（公告）日：1983-01-04

  Novel, water-soluble antimicrobial compounds are provided which contain a sugar moiety linked to a nitrogen atom of substituted thiourea or a thiazole. The compounds have the general formula: ##STR1## and the pharmaceutically acceptable salts thereof wherein Su is a sugar moiety, i.e., mono- or polysaccharide and preferably glucosyl or acylated (i.e. C.sub.2 to C.sub.6 alkanoyl e.g. acetyl, propionyl, butyroyl etc. or aroyl e.g. benzoyl or C.sub.1 to C.sub.4 alkyl or alkoxy substituted benzoyl) ribosyl; and in Formula I, R.sub.1 and R.sub.2 are independently hydrogen, C.sub.1 to C.sub.8 alkyl or alkoxy; C.sub.1 to C.sub.8 .omega.-phenyl-(or substituted phenyl)-substituted C.sub.1 to C.sub.8 alkyl; C.sub.3 to C.sub.8 alkene, preferably allyl; ##STR2## wherein R.sub.3 and R.sub.4 are independently hydrogen or C.sub.1 to C.sub.8 alkyl, or the atoms to form a 5- or 6-membered heterocyclic [which may contain C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo (e.g., chloro, bromo or iodo), hydroxy, carboxamido, sulfonamido and the like] such as piperazino, methyl piperazino, pyrimidino, piperidino, morpholino, thiamorpholino, pyrrolyl, pyrrolidinyl, furyl, tetrahydrofuryl and the like, but only one of R.sub.1 and R.sub.2 is hydrogen, and in Formula II, R.sub.5 is oxy(C.sub.1 to C.sub.8)alkyl or substituted alkyl, phenyl or substituted phenyl or NR.sub.6 R.sub.7 wherein R.sub.6 and R.sub.7 are independently selected similarly as R.sub.1 and R.sub.2. The compounds are particularly useful in aqueous systems especially in cosmetic formulations for maintaining same in a septic state. Methods for making compounds of Formula I and II are also disclosed.

  提供了一种新型的水溶性抗菌化合物，其含有与硫脲或噻唑的氮原子相连的糖基。该化合物具有以下通式：##STR1##和其药学上可接受的盐，其中Su是糖基，即单糖或多糖，优选为葡萄糖基或酰化基（即C.sub.2到C.sub.6的脂肪酰基，例如乙酰基、丙酰基、丁酰基等或芳酰基，例如苯甲酰基或C.sub.1到C.sub.4烷基或烷氧基取代的苯甲酰基）核糖基；在式I中，R.sub.1和R.sub.2分别是氢、C.sub.1到C.sub.8烷基或烷氧基；C.sub.1到C.sub.8.ω.-苯基-(或取代苯基)-取代C.sub.1到C.sub.8烷基；C.sub.3到C.sub.8烯烃，优选为烯丙基；##STR2##其中R.sub.3和R.sub.4分别是氢或C.sub.1到C.sub.8烷基，或原子形成5或6元杂环[可以含有C.sub.1到C.sub.4烷基、C.sub.1到C.sub.4烷氧基、卤素（例如氯、溴或碘）、羟基、羧酰胺、磺酰胺等]，例如哌嗪、甲基哌嗪、嘧啶、吡啶、吗啉、噻吗啉、吡咯基、吡咯烷基、呋喃基、四氢呋喃基等，但R.sub.1和R.sub.2中仅有一个是氢，在式II中，R.sub.5是氧（C.sub.1到C.sub.8）烷基或取代烷基、苯基或取代苯基或NR.sub.6R.sub.7，其中R.sub.6和R.sub.7与R.sub.1和R.sub.2类似地独立选择。该化合物在水溶性系统中特别有用，尤其是在化妆品配方中，以维持其无菌状态。还公开了制备式I和II化合物的方法。
• Synthesis of n-glycosylthioureas, N-glycosylrhodanines, and N-glycosyl-2-aminothiazoles and their Antimicrobial Activity
  作者：William O. Foye、Seung Ho An

  DOI：10.1002/jps.2600700924

  日期：1981.9

  2-(N-beta-D-glucopyranosyl)aminothiazole-4-carboxylate, and ammonolysis led to the corresponding 4-carboxamide. Antimicrobial screening against five microorganisms showed that N-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)rhodanine and the glucosylaminothiazole-4-carboxylate had the broadest spectrum of inhibitory activity, although the thioureas usually showed inhibition of some organisms.

  在N-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-5-芳烷基亚乙基内酯的氨解中发现了一种获得N-β-D-吡喃葡萄糖基硫脲的方法。尽管使用吗啉和羟胺获得了N-（2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖基）硫脲，但是三乙酰化或三苯甲酰化的核糖基罗丹宁的氨解通常不会产生核糖基硫脲，但会导致糖苷裂解。用溴丙酮酸乙酯对N-β-D-吡喃葡萄糖基硫脲进行环封闭，得到2-（N-β-D-吡喃葡萄糖基）氨基噻唑-4-羧酸乙酯，并且氨解反应产生相应的4-羧酰胺。对五种微生物的抗菌素筛选表明，N-（2,3,5-三-O-乙酰基-β-D-呋喃呋喃糖基）罗丹宁和葡糖基氨基噻唑-4-羧酸酯具有最广谱的抑制活性，
• N-Glucopyranosyl-5-aralkylidenerhodanines: Synthesis and Antibacterial and Antiviral Activities
  作者：William O. Foye、Phichai Tovivich

  DOI：10.1002/jps.2600661126

  日期：1977.11

  N-glycoside formation. A number of the rhodanine derivatives, especially those with nitro or chloro groups in the aromatic ring, showed antibacterial activity. N-beta-D-Glucopyranosyl-5-(4-nitrobenzylidene) rhodanine showed antiviral activity by inhibition of viral RNA synthesis. Some effect on blood sugar levels also was observed with several rhodanines.

  合成了一系列的N-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-5-芳烷基亚乙基金丹宁，并且除去了乙酰基基团，得到了N-β-D-吡喃葡萄糖基-5-芳烷基亚芳基但不通过酸水解裂解若丹宁环。在甲醇中用氨水进行碱水解会裂解为N-葡萄糖基硫脲，为N-糖苷的形成提供了证据。许多若丹宁衍生物，特别是在芳族环中具有硝基或氯基的那些，均显示出抗菌活性。N-β-D-Glucopyranosyl-5-（4-硝基亚苄基）若丹宁通过抑制病毒RNA合成表现出抗病毒活性。几种罗丹宁对血糖水平也有一定影响。