6-azido-2,3,4-tri-O-benzoyl-6-deoxy-α-D-mannopyranose-1-O-trichloroacetimidate | 863915-11-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-α-D-mannopyranose-1-O-trichloroacetimidate
• 英文别名: [(2R,3R,4S,5S,6R)-2-(azidomethyl)-4,5-dibenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 863915-11-1
• 化学式: C₂₉H₂₃Cl₃N₄O₈
• 分子量: 661.883
• InChiKey: NPNDNSLXOKGVJH-ZDTQQCKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-azido-2,3,4-tri-O-benzoyl-6-deoxy-α-D-mannopyranose-1-O-trichloroacetimidate 、 (S)-(+)-1,2-异亚丙基甘油 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以83%的产率得到3-O-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-α-D-mannopyranosyl)-1,2-isopropylidene-sn-glycerol
  参考文献：
  名称：

  Synthesis and antiviral evaluation of 6′-acylamido-6′-deoxy-α-d-mannoglycerolipids

  摘要：

  Eight new aminomannoglycerolipids (2a-h) with linear, branched, or aromatic acyl chains were synthesized and evaluated for their anti-influenza A virus (IAV) activity. By comparing six mannosyl donors with different protecting and leaving groups, the critical glycosylation reaction employed mannosyl trichloroacetimidate with 2-O-benzoyl protecting group as the donor to give the glycoside with absolute alpha-anomeric selectivity. The bioactivity results showed that the branched compound 2g could effectively inhibit IAV multiplication in MDCK cells with IC50 69.9 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.010
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-α-D-mannopyranose 在 甲醇 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 水 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 17.0h， 生成 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-α-D-mannopyranose-1-O-trichloroacetimidate
  参考文献：
  名称：

  Synthesis and antiviral evaluation of 6′-acylamido-6′-deoxy-α-d-mannoglycerolipids

  摘要：

  Eight new aminomannoglycerolipids (2a-h) with linear, branched, or aromatic acyl chains were synthesized and evaluated for their anti-influenza A virus (IAV) activity. By comparing six mannosyl donors with different protecting and leaving groups, the critical glycosylation reaction employed mannosyl trichloroacetimidate with 2-O-benzoyl protecting group as the donor to give the glycoside with absolute alpha-anomeric selectivity. The bioactivity results showed that the branched compound 2g could effectively inhibit IAV multiplication in MDCK cells with IC50 69.9 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.010

文献信息

• Synthesis of Functionalized 2-(4-Hydroxyphenyl)-3-methylbenzofuran Allosteric Modulators of Hsp90 Activity
  作者：Sara Sattin、Matteo Panza、Francesca Vasile、Francesca Berni、Giulio Goti、Jiahui Tao、Elisabetta Moroni、David Agard、Giorgio Colombo、Anna Bernardi

  DOI：10.1002/ejoc.201600420

  日期：2016.7

  Hsp90 is a molecular chaperone that plays a pivotal role in the cell life cycle. ATP-regulated internal dynamics are critical to Hsp90 function and we recently demonstrated that these dynamics can be modulated in an allosteric fashion; the protein C-terminal domain (CTD) can be effectively targeted with a family of 2-phenyl-benzofuran derivatives. Here we describe the expansion of the initial library

  Hsp90 是一种分子伴侣，在细胞生命周期中起着举足轻重的作用。ATP 调节的内部动力学对 Hsp90 功能至关重要，我们最近证明这些动力学可以以变构方式进行调节；2-苯基-苯并呋喃衍生物家族可以有效靶向蛋白质 C 端结构域 (CTD)。在这里，我们描述了初始库的扩展，报告了 28 种新衍生物，它们探索了苯并呋喃支架两端的化学空间。化合物与全长蛋白质同系物的相互作用通过饱和转移差异 (STD) NMR 光谱进行了探索。在这种情况下，我们还报告了 Novobiocin，一种已知的 CTD 抑制剂的相互作用表位。
• [EN] SULFATED OLIGOSACCHARIDE DERIVATIVES<br/>[FR] DERIVES D'OLIGOSACCHARIDES SULFATES
  申请人：PROGEN IND LTD

  公开号：WO2005085264A1

  公开（公告）日：2005-09-15

  The invention relates to compounds which are polysufated oligosaccharide derivatives having activity as inhibitors of heparan sulfate-binding proteins and inhibitors of the enzyme heparanase; methods for the preparation of the compounds; compositions comprising the compounds, and use of the compounds and compositions thereof for the antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic treatment, lowering of blood triglyceride levels and inhibition of cardiovascular disease of a mammalian subject.

  该发明涉及一类多硫代寡糖衍生物化合物，具有抑制肝素硫酸盐结合蛋白和抑制肝素酶酶活性的作用；该发明还涉及这些化合物的制备方法；包含这些化合物的组合物；以及这些化合物和组合物在哺乳动物主体中用于抗血管生成、抗转移、抗炎、抗微生物、抗凝血和/或抗血栓治疗、降低血液甘油三酯水平以及抑制心血管疾病的用途。
• Sulfated oligosaccharide derivatives
  申请人：Ferro Vito

  公开号：US20070185037A1

  公开（公告）日：2007-08-09

  The invention relates to compounds which are polysulfated oligosaccharide derivatives having activity as inhibitors of heparan sulfate-binding proteins and inhibitors of the enzyme heparanase; methods for the preparation of the compounds; compositions comprising the compounds, and use of the compounds and compositions thereof for the antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic treatment, lowering of blood triglyceride levels and inhibition of cardiovascular disease of a mammalian subject.

  该发明涉及一种多硫酸寡糖衍生物化合物，其具有作为肝素硫酸结合蛋白抑制剂和肝素酶抑制剂的活性；制备该化合物的方法；包含该化合物的组合物；以及使用该化合物和其组合物进行抗血管生成、抗转移、抗炎、抗微生物、抗凝血和/或抗血栓治疗、降低哺乳动物受试者的血甘油三酯水平和抑制心血管疾病的方法。
• SULFATED OLIGOSACCHARIDE DERIVATIVES
  申请人：Ferro Vito

  公开号：US20110130354A1

  公开（公告）日：2011-06-02

  The invention relates to compounds which are polysulfated oligosaccharide derivatives having activity as inhibitors of heparan sulfate-binding proteins and inhibitors of the enzyme heparanase; methods for the preparation of the compounds; compositions comprising the compounds, and use of the compounds and compositions thereof for the antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic treatment, lowering of blood triglyceride levels and inhibition of cardiovascular disease of a mammalian subject.

  本发明涉及化合物，这些化合物是聚硫酸化的寡糖衍生物，具有作为肝素硫酸结合蛋白抑制剂和肝素酶抑制剂的活性；制备这些化合物的方法；包含这些化合物的组合物；以及使用这些化合物和其组合物进行抗血管生成、抗转移、抗炎、抗微生物、抗凝血和/或抗血栓治疗、降低哺乳动物体内的血甘油三酯水平和抑制心血管疾病的方法。
• EP1720889A4
  申请人：——

  公开号：EP1720889A4

  公开（公告）日：2008-03-19