N-β-D-glucopyranosylthiourea | 76822-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-β-D-glucopyranosylthiourea
• 英文别名: β-D-glucopyranosylthiourea；Glucopyranosyl-thioharnstoff；β-D-glucopyranosyl-thiourea；β-D-Glucopyranosyl-thioharnstoff；N-β-D-Glucopyranosyl-thioharnstoff；β-D-Glucosylthioharnstoff；Thiourea, beta-D-glucopyranosyl-；[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]thiourea
• CAS: 76822-35-0
• 化学式: C₇H₁₄N₂O₅S
• 分子量: 238.265
• InChiKey: NFLXFOWCDDYFIR-VFUOTHLCSA-N

物化性质

• 熔点：
  207-210 °C (decomp)
• 沸点：
  511.3±60.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  160
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-β-D-glucopyranosylthiourea 在 溴乙烷 、 乙醇 、 水 作用下， 生成 N-[N-(D-glucitol-1-ylidene-carbamimidoyl)-glycyl]-glycine
  参考文献：
  名称：

  Micheel; Berlenbach, Chemische Berichte, 1952, vol. 85, p. 189,190

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate 在 甲醇 、 氨 作用下， 生成 N-β-D-glucopyranosylthiourea
  参考文献：
  名称：

  Mueller; Wilhelms, Chemische Berichte, 1941, vol. 74, p. 698,700

  摘要：

  DOI：

文献信息

• 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-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微生物化合物，其包含与替代硫脲或噻唑的氮原子相连的糖基团。该化合物具有以下一般式：##STR1##以及其药学上可接受的盐，其中Su是糖基团，即单糖或多糖，最好是葡萄糖基或酰化基（即C.sub.2至C.sub.6烷酰基，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至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独立地表示氢、C.sub.1至C.sub.8烷基或烷氧基；C.sub.1至C.sub.8.ω.-苯基（或取代苯基）取代的C.sub.1至C.sub.8烷基；C.sub.3至C.sub.8烯烃，最好是烯丙基；##STR2##其中R.sub.3和R.sub.4独立地表示氢或C.sub.1至C.sub.8烷基，或原子形成5或6元杂环[可以包含C.sub.1至C.sub.4烷基、C.sub.1至C.sub.4烷氧基、卤素（例如氯、溴或碘）、羟基、羧酰胺、磺酰胺等]，如哌嗪基、甲基哌嗪基、嘧啶基、吡啶基、吗啉基、噻吗啉基、吡咯基、吡咯烷基、呋喃基、四氢呋喃基等，但只有R.sub.1和R.sub.2中的一个是氢，在式II中，R.sub.5是氧（C.sub.1至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。这些化合物在水系统中特别有用，特别是在化妆品配方中，以维持其无菌状态。还公开了制备式I和II化合物的方法。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• Pill, Thomas; Beck, Wolfgang, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1993, vol. 48, # 11, p. 1461 - 1469
  作者：Pill, Thomas、Beck, Wolfgang

  DOI：——

  日期：——
• Westphal, Guenter; Kroh, Lothar; Koeppel, Hubert, Zeitschrift fur Chemie, 1982, vol. 22, # 4, p. 139 - 140
  作者：Westphal, Guenter、Kroh, Lothar、Koeppel, Hubert

  DOI：——

  日期：——