2-乙酰氨基-2-脱氧-3,4,6-O-三乙酰基-beta-D-吡喃葡萄糖异硫氰酸酯 | 20590-45-8

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙酰氨基-2-脱氧-3,4,6-O-三乙酰基-beta-D-吡喃葡萄糖异硫氰酸酯
• 中文别名: 2-乙酰氨基-2-脱氧-3,4,6-O-三乙酰基-BETA-D-吡喃葡萄糖异硫氰酸酯；2-乙酰氨基-3,4,6-三-邻乙酰基-2-脱氧-beta-d-异硫氰酸吡喃葡萄糖酯
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl isothiocyanate
• 英文别名: 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl isothiocyanate；3,4,6-tri-O-acetyl-2-N-acetylamido-2-deoxy-β-D-glucopyranosyl isothiocyanate；2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosyl isothiocyanate；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-isothiocyanatooxan-2-yl]methyl acetate
• CAS: 20590-45-8
• 化学式: C₁₅H₂₀N₂O₈S
• 分子量: 388.398
• InChiKey: PNMDNJALVHCMOX-KJWHEZOQSA-N

物化性质

• 熔点：
  164-166 °C (decomp)
• 沸点：
  572.0±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-乙酰氨基-2-脱氧-3,4,6-O-三乙酰基-beta-D-吡喃葡萄糖异硫氰酸酯 在 N-甲基吡咯烷酮 、 sodium methylate 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis, Characterization, and Biological Evaluation of Some Novel Glycosyl 1,3,4-Thiadiazole Derivatives as Acetylcholinesterase Inhibitors

  摘要：

  The corresponding 4-substituted glycosyl thiosemicarbazide derivatives (6a-61) were obtained by the reaction of glycosyl isothiocyanate 4 with various hydrazides. Further cyclization with the system of p-TsCl/TEA led to the formation of N-glycosyl-5-substituted 1,3,4-thiadiazole-2-amine (7a-71). Subsequent removal of the acetyl groups were conducted using the system of NaOMe/MeOH. The chemical structures of all new products were confirmed by JR. H-1 NMR and ESI-HRMS. The acetylcholinesterase (AChE) inhibitory activities of those compounds were tested by Ellman's method. Among them, the compound 8h possessed the best acetylcholinesterase-inhibition activity with IC50 of 18.38 +/- 0.89 mu M.

  DOI：

  10.3987/com-14-13134
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖酰基叠氮化物 在 solid phase supported triphenylphosphine 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 25.5h， 生成 2-乙酰氨基-2-脱氧-3,4,6-O-三乙酰基-beta-D-吡喃葡萄糖异硫氰酸酯
  参考文献：
  名称：

  糖基芳基磺酰胺羧酸盐作为选择性和水溶性基质金属蛋白酶-12抑制剂

  摘要：

  基质金属蛋白酶-12（MMP-12）被认为是研究选择性抑制剂的有吸引力的靶标，这些抑制剂可用于开发针对肺和心血管疾病的新疗法。在这项研究中，一个新的系列芳基磺酰胺羧酸，具有增加的亲水性从得到的缀合与β- Ñ乙酰基d -葡糖胺部分，设计并作为MMP-12选择性抑制剂合成。使用荧光测定法评估了它们对人MMP的抑制活性，并进行了晶体学分析以表征其结合模式。在这些糖缀合物中，是一种水溶性增强的纳摩尔MMP-12抑制剂，化合物3 [（R）-2-（N-（2-（3-（2-乙酰胺基-2-脱氧-β-d-吡喃葡糖基）硫脲基）乙基）联苯-4-基磺酰胺基）-3-甲基丁酸]。

  DOI：

  10.1002/cmdc.201600235

文献信息

• Synthesis of a GlcNAcylated arginine building block for the solid phase synthesis of death domain glycopeptide fragments
  作者：Siyao Wang、Leo Corcilius、Phillip P. Sharp、Richard J. Payne

  DOI：10.1016/j.bmc.2017.03.012

  日期：2017.6

  describe the synthesis of glycopeptide fragments from the death domains of TRADD and FADD bearing the recently discovered Nω-GlcNAc-β-arginine post-translational modification. TRADD and FADD glycopeptides were accessed through the use of a suitably protected synthetic glycosylamino acid 'cassette' that could be directly incorporated into conventional solid phase peptide synthesis (SPPS) protocols.

  本文中，我们描述了从TRADD和FADD的死亡域携带最近发现的Nω-GlcNAc-β-精氨酸翻译后修饰中糖肽片段的合成。TRADD和FADD糖肽是通过使用适当保护的合成糖基氨基酸“盒式磁带”来访问的，该盒式磁带可直接并入常规固相肽合成（SPPS）方案中。
• Synthesis and biological evaluation of novel C1-glycosyl thiazole derivatives as acetylcholinesterase inhibitors
  作者：Long Yin、Feng–Chang Cheng、Qu–Xiang Li、Wei–Wei Liu、Xiu–Jian Liu、Zhi–Ling Cao、Da–Hua Shi

  DOI：10.3184/174751916x14711768865726

  日期：2016.9

  A new series of C1-glycosyl thiazole derivatives was synthesised by the reaction of 1-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranos-2-yl)thiourea with 2-bromoacetophenone derivatives. Subsequent removal of the acetyl groups were conducted using NaOMe–MeOH. The structures of all new products were confirmed by IR, 1H NMR and HRMS (ESI). The acetylcholinesterase inhibitory activities of these new compounds

  1-(1,3,4,6-四-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖-2-基)硫脲与2-基反应合成了一系列新的C1-糖基噻唑衍生物。溴苯乙酮衍生物。随后使用 NaOMe-MeOH 进行乙酰基的去除。所有新产品的结构均通过 IR、1H NMR 和 HRMS (ESI) 确认。测试了这些新化合物的乙酰胆碱酯酶抑制活性。其中，N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(4-nitrophenyl)-1,3-thiazole-2-amine显示出最佳活性，抑制率为 43.21%。
• New Sugar Mitomycin C Analogues: Preparation, Murine P388 Antitumor Activity, and Leukopenia Induction
  作者：Abdolhossen Talebian、Dianna Green、Charles F. Hammer、Eugene McPherson、Philip S. Schein

  DOI：10.1002/jps.2600791213

  日期：1990.12

  Four new sugar:mitomycin C derivatives were synthesized by coupling of N-1 of mitomycin C with tetra-O-acetylglucopyranosyl isothiocyanate and 3,4,6-tri-O-acetyl-2-(N-acetylamino)-2-deoxyglucopyranosyl isothiocyanate. Conversion of each derivative to its water-soluble analogue was achieved by deacetylation, using saturated NH3:CH3OH. Antitumor activity, assessed using the in vivo murine P388 ascitic

  通过将丝裂霉素C的N-1与四-O-乙酰基吡喃葡萄糖基异硫氰酸酯和3,4,6-三-O-乙酰基-2-（N-乙酰氨基）-2-脱氧葡糖基吡喃异氰酸酯偶联，合成了四种新的糖：丝裂霉素C衍生物。 。使用饱和的NH3：CH3OH通过脱乙酰作用将每种衍生物转化为其水溶性类似物。使用体内鼠P388腹水性白血病系统评估的抗肿瘤活性证明与母体丝裂霉素C相当。但是，与高度抑制骨髓的母体药物不同，仅产生有限的白细胞减少症的剂量可获得最佳的抗肿瘤活性。
• Synthesis of Glycosylamines from Glycosyl Isothiocyanates and Bis(tributyltin) Oxide
  作者：Joaquin Isac-García、Francisco G. Calvo-Flores、Fernando Hernández-Mateo、Francisco Santoyo-González

  DOI：10.1002/1099-0690(200101)2001:2<383::aid-ejoc383>3.0.co;2-n

  日期：2001.1

  The synthesis of glycopyranosylamines is described from the reaction of glycopyranosyl isothiocynates with bis(tributyltin) oxide. The method is simple and efficient allowing, under very mild conditions, the synthesis of N-acyl glycopyranosylamines in one pot. The reactions were performed using both 2-deoxy-2-iodo glycopyranosyl isothiocyanates and glycopyranosyl isothiocyanates derived from mono-

  吡喃糖基胺的合成是通过吡喃糖基异硫氰酸酯与双（三丁基锡）氧化物的反应来描述的。该方法简单有效，允许在非常温和的条件下在一锅中合成 N-酰基吡喃糖胺。使用衍生自单糖和二糖的 2-脱氧-2-碘吡喃糖基异硫氰酸酯和吡喃糖基异硫氰酸酯进行反应。当起始材料是 α-吡喃葡萄糖基衍生物时观察到异构化。该方法也已用于制备几种糖基氨基酸。
• Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives
  作者：You-Xian Wang、Shu-Hao Liu、Zhong-Bai Shao、Lian-Gong Cao、Kai-Jun Jiang、Xing Lu、Lei Wang、Wei-Wei Liu、Da-Hua Shi、Zhi-Ling Cao

  DOI：10.1177/1747519820948358

  日期：2021.5

  Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory

  通过糖基硫脲与3-溴乙酰基香豆素在乙醇中的环化和缩合反应，合成了11种糖基香豆基噻唑衍生物。优化了反应条件，并获得了良好的收率（80％–95％）。所有新产品的结构均通过IR，1 H和13 C NMR以及HRMS（电喷雾电离）确定。在体外乙酰胆碱酯酶抑制这些新化合物的活性由Ellman氏方法进行测试。其中，N-（2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β - D-吡喃吡喃糖基）-4-（6-硝基香豆基）-1,3-噻唑-2-胺在体外显示出最佳活性AChE抑制率为58％，IC 50值为12±0.38μg/ mL。