4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl thiopseudourea hydrobromide | 106571-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl thiopseudourea hydrobromide
• 英文别名: 2,3,4,6-terta-O-acetyl-β-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl isothiouronium bromide；[amino-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanylmethylidene]azanium;bromide
• CAS: 106571-26-0
• 化学式: BrH*C₂₇H₃₈N₂O₁₇S
• 分子量: 775.58
• InChiKey: NYPROWXURWCXMR-ZCNPANNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.58
• 重原子数：
  48
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  289
• 氢给体数：
  2
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl thiopseudourea hydrobromide 在 potassium pyrosulfite 、 potassium carbonate 作用下， 以 氯仿 、 丙酮 为溶剂， 生成 (5-nitro-2-pyridyl) per-O-acetyl-1-thio-β-D-lactoside
  参考文献：
  名称：

  Synthesis and antiviral activity of a novel glycosyl sulfoxide against classical swine fever virus

  摘要：

  A novel compound-2 '',3 '',4 '',6 ''-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 4)-2',3',6'-tri-O-acetyl-1-thio-beta-D-glucopyranosyl-(5-nitro-2-pyridyl) sulfoxide-designated GP6 was synthesized and assayed for cytotoxicity and in vitro antiviral properties against classical swine fever virus (CSFV) in this study. We showed that the examined compound effectively arrested CSFV growth in swine kidney cells (SK6) at a 50% inhibitory concentration (IC50) of 5 +/- 0.12 mu g/ml without significant toxicity for mammalian cells. Moreover, GP6 reduced the viral E2 and E-rns glycoproteins expression in a dose-dependent manner. We have excluded the possibility that the inhibitor acts at the replication step of virus life cycle as assessed by monitoring of RNA level in cells and culture medium of SK6 cells after single round of infection as a function of GP6 treatment. Using recombinant E-rns and E2 proteins of classical swine fever virus produced in baculovirus expression system we have demonstrated that GP6 did not influence glycoprotein production and maturation in insect cells. In contrast to mammalian glycosylation pathway, insect cells support only the ER-dependent early steps of this process. Therefore, we concluded that the late steps of glycosylation process are probably the main targets of GP6. Due to the observed antiviral effect accompanied by low cytotoxicity, this inhibitor represents potential candidate for the development of antiviral agents for anti-flavivirus therapy. Further experiments are needed for investigating whether this compound can be used as a safe antiviral agent against other viruses from unrelated groups. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.027
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 氢溴酸 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 生成 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl thiopseudourea hydrobromide
  参考文献：
  名称：

  Synthesis and antiviral activity of a novel glycosyl sulfoxide against classical swine fever virus

  摘要：

  A novel compound-2 '',3 '',4 '',6 ''-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 4)-2',3',6'-tri-O-acetyl-1-thio-beta-D-glucopyranosyl-(5-nitro-2-pyridyl) sulfoxide-designated GP6 was synthesized and assayed for cytotoxicity and in vitro antiviral properties against classical swine fever virus (CSFV) in this study. We showed that the examined compound effectively arrested CSFV growth in swine kidney cells (SK6) at a 50% inhibitory concentration (IC50) of 5 +/- 0.12 mu g/ml without significant toxicity for mammalian cells. Moreover, GP6 reduced the viral E2 and E-rns glycoproteins expression in a dose-dependent manner. We have excluded the possibility that the inhibitor acts at the replication step of virus life cycle as assessed by monitoring of RNA level in cells and culture medium of SK6 cells after single round of infection as a function of GP6 treatment. Using recombinant E-rns and E2 proteins of classical swine fever virus produced in baculovirus expression system we have demonstrated that GP6 did not influence glycoprotein production and maturation in insect cells. In contrast to mammalian glycosylation pathway, insect cells support only the ER-dependent early steps of this process. Therefore, we concluded that the late steps of glycosylation process are probably the main targets of GP6. Due to the observed antiviral effect accompanied by low cytotoxicity, this inhibitor represents potential candidate for the development of antiviral agents for anti-flavivirus therapy. Further experiments are needed for investigating whether this compound can be used as a safe antiviral agent against other viruses from unrelated groups. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.027

文献信息

• Synthesis of the methyl and 1-octyl glycosides of the P-antigen tetrasaccharide (globotetraose)
  作者：Karin Leontein、Marianne Nilsson、Thomas Norberg

  DOI：10.1016/s0008-6215(00)90671-2

  日期：1985.12

  The methyl and 1-octyl beta-glycosides of the P-antigen tetrasaccharide [globotetraose, beta-D-GalpNAc-(1----3)-alpha-D-Galp-(1----4)-beta-D-Galp-(1----4) -D-Glc] were synthesised from a tetrasaccharide precursor, prepared using methyl disaccharide 1-thioglycosides as intermediates. In the key glycosidation with silver triflate, HO-2 was used as an alpha-directing group in the glycosyl bromide.

  P-抗原四糖[globotetraose，beta-D-GalpNAc-（1 ---- 3）-alpha-D-Galp-（1 ---- 4）-beta-的甲基和1-辛基β-糖苷由四糖前体合成了D-Galp-（1 ---- 4）-D-Glc]，该前体是使用甲基二糖1-硫代糖苷为中间体制备的。在三氟甲磺酸银的关键糖苷化中，HO-2被用作糖基溴化物中的α-导向基团。
• Facile synthesis of 1-thio-β-lactoside clusters scaffolded onto p-methoxyphenyl, β-d-galactopyranoside, β-d-glucopyranoside, and lactoside
  作者：Xiang-Bao Meng、Lian-Dai Yang、Hui Li、Qing Li、Tie-Ming Cheng、Meng-Shen Cai、Zhong-Jun Li

  DOI：10.1016/s0008-6215(02)00094-0

  日期：2002.6

  -acetyl-1-thio-β- d -glucopyranose to the allyl ether functions of p -methoxyphenyl per- O -allyl- d -galactopyranoside, d -glucopyranoside, and lactoside provides a concise and effective route for synthesis of glycoside clusters, of use for exploring anti-metastatic activity.

  摘要2,3,4,6-四-O-乙酰基-β-d-半乳糖吡喃糖基-（1→4）-2,3,6-三-O-乙酰基-1-硫基-β的自由基加成反应-d-吡喃葡萄糖对p-甲氧基苯基的-O-烯丙基-d-吡喃半乳糖苷，d-吡喃葡萄糖苷和乳糖苷的烯丙基醚功能提供了用于合成糖苷簇的简洁有效的途径，用于探索抗转移活性。
• Synthesis of Interglycosidically <i>S</i>‐Linked 1‐Thio‐Oligosaccharides Under Microwave Irradiation
  作者：El Sayed H. El Ashry、Laila F. Awad、H. M. Abdel Hamid、Atta I. Atta

  DOI：10.1080/07328300500282540

  日期：2005.9.1

  Microwave irradiation (MWI) has accelerated the synthesis of S-(2,3,4,6-tetra- O-acetyl-beta-D-glucopyranosyl)thiouronium bromide (2a), whose reaction with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (1a) in the presence of Et3N afforded stereoselectively the acetylated beta,beta-1-thiotrehalose 4a. Similarly, the respective D-galactopyranosyl 4b and 2-acetylamino-2-deoxy-D-glucopyranosyl 4c analog as well as 4,4'-di-O-(2,3,4,6-tetra-O-acetyl-beta-D- galactopyranosyl) 4d and 4,4'-di-O-(2,3,4,6-tetra-O-acetyl-alpha-D- glucopyranosyl) 4e derivatives of 2,2',3,3',6,6'-hexa-O-acetyl beta,beta-1- thiotrehalose were prepared.
• Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds
  作者：S Saito、T Furumoto、M Ochiai、A Hosono、H Hoshino、U Haraguchi、R Ikeda、N Shimada

  DOI：10.1016/0223-5234(96)89163-x

  日期：1996.1

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.
• Transition metal-catalyzed syntheses of ‘rod-like’ thioglycoside dimers
  作者：Zhonghong Gan、René Roy

  DOI：10.1016/s0040-4039(99)02285-6

  日期：2000.2

  Using copper(I)-catalyzed Glaser reaction and palladium-catalyzed Sonogashira reaction, divalent 'rod-like' thiomanno-, gluco, galacto, and lactoside clusters were prepared in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.