bis-{3-O-[(2H-chromen-2-one-3-yl)-methyl]-β-D-galactopyranosyl}sulfane | 1448725-30-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: bis-{3-O-[(2H-chromen-2-one-3-yl)-methyl]-β-D-galactopyranosyl}sulfane
• 英文别名: bis-{3-O-[(2H-1-benzopyran-2-on-3-yl)methyl]-β-D-galactopyranosyl} sulfane；3-[[(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2-oxochromen-3-yl)methoxy]oxan-2-yl]sulfanyl-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxymethyl]chromen-2-one
• CAS: 1448725-30-1
• 化学式: C₃₂H₃₄O₁₄S
• 分子量: 674.68
• InChiKey: NUVVBMDSAGKGGC-PBGHOUHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  236
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  3-甲基氧杂萘邻酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异戊腈 、 二正丁基氧化锡 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.0h， 生成 bis-{3-O-[(2H-chromen-2-one-3-yl)-methyl]-β-D-galactopyranosyl}sulfane
  参考文献：
  名称：

  未保护的硫代二糖半乳糖苷的区域选择性3-O取代：直接向半乳凝素抑制剂的途径。

  摘要：

  定制的生物活性碳水化合物的合成通常包括挑战性的（去保护）步骤，这降低了合成产量并增加了时间需求。我们在这里介绍在β- d-吡喃半乳糖基（1→1）-硫代-β- d的3-羟基上的苄基取代基的区域选择性单步引入γ-吡喃半乳糖苷（TDG）采用二丁基氧化锡，收率高。这些糖模拟物可充当半乳糖凝集素（人凝集素）的抑制剂，半乳糖凝集素是在医学上具有吸引力的靶标，可用于例如癌症的治疗抑制。在酶联免疫吸附（ELISA）型分析中研究了制备的糖模拟物对galectin-1和galectin-3的亲和力，并显示了它们在细胞表面抑制galectin结合的潜力。我们使用了原始的体内生物素化半乳糖凝集素构建体，以便通过流式细胞术轻松检测。将生物学实验的结果与两种半乳凝素的分子建模数据进行了比较。O替代。

  DOI：

  10.1002/chem.202002084

文献信息

• [EN] NOVEL GALACTOSIDE INHIBITORS OF GALECTINS<br/>[FR] NOUVEAUX INHIBITEURS GALACTOSIDES DE GALECTINES
  申请人：GALECTO BIOTECH AB

  公开号：WO2013110704A1

  公开（公告）日：2013-08-01

  The present invention relates to novel compounds prepared from readily accessible 3-O-propargyl-D-galactopyranoside derivatives and having an effect as i.a., galectin inhibitors, the use of said compounds as a medicament as well as for the manufacture of a medicament for treatment of disorders relating to the binding of galectin to ligandsin a mammal, wherein said galectin is preferably a galectin-3. The novel compounds are defined by the general formula (I).

  本发明涉及从易得到的3-O-丙炔基-D-半乳糖苷衍生物制备的新化合物，具有抑制住凝集素等作用，所述化合物的用途为药物，以及用于制造治疗哺乳动物中住凝集素与配体结合相关疾病的药物，其中所述住凝集素优选为住凝集素-3。新化合物由通式（I）定义。
• A Selective Galactose–Coumarin-Derived Galectin-3 Inhibitor Demonstrates Involvement of Galectin-3-glycan Interactions in a Pulmonary Fibrosis Model
  作者：Vishal K. Rajput、Alison MacKinnon、Santanu Mandal、Patrick Collins、Helen Blanchard、Hakon Leffler、Tariq Sethi、Hans Schambye、Balaram Mukhopadhyay、Ulf J. Nilsson

  DOI：10.1021/acs.jmedchem.6b00957

  日期：2016.9.8

  that the coumaryl substituents stack onto arginine side chains. One inhibitor displayed efficacy in a murine model of bleomycin-induced lung fibrosis similar to that of a known nonselective galectin-1/galectin-3 inhibitor, which strongly suggests that blocking galectin-3 glycan recognition is an important antifibrotic drug target.

  由双-3- O-炔丙基-硫代二半乳糖苷合成双 3 - O-香豆基甲基取代的硫代二半乳糖苷产生了高选择性和高亲和力的半乳凝素 3 抑制剂。突变体研究、结构分析和分子建模表明香豆基取代基堆积在精氨酸侧链上。一种抑制剂在博莱霉素诱导的肺纤维化小鼠模型中显示出与已知的非选择性半乳糖凝集素 1/半乳糖凝集素 3 抑制剂相似的功效，这强烈表明阻断半乳糖凝集素 3 聚糖识别是一个重要的抗纤维化药物靶点。
• Novel galactoside inhibitors of galectins
  申请人：Galecto Biotech AB

  公开号：EP2620443A1

  公开（公告）日：2013-07-31

  The present invention relates to novel compounds prepared from readily accessible 3-O-propargyl-D-galactopyranoside derivatives and having an effect as i.a., galectin inhibitors, the use of said compounds as a medicament as well as for the manufacture of a medicament for treatment of disorders relating to the binding of galectin to ligands in a mammal, wherein said galectin is preferably a galectin-3. The novel compounds being defined by the general formula (1).

  本发明涉及从易得到的3-O-丙炔基-D-半乳糖苷衍生物制备的新化合物，具有抑制住手套蛋白等作用，所述化合物作为药物的使用，以及制造治疗哺乳动物中住手套蛋白与配体结合相关疾病的药物，其中所述住手套蛋白优选为住手套蛋白-3。新化合物由通式（1）定义。
• NOVEL GALACTOSIDE INHIBITORS OF GALECTINS
  申请人：Galecto Biotech AB

  公开号：EP2807176B1

  公开（公告）日：2015-12-30
• Novel galectoside inhibitors of galectins
  申请人：GALECTO BIOTECH AB

  公开号：US20140336146A1

  公开（公告）日：2014-11-13

  The present invention relates to novel compounds prepared from readily accessible 3-O-propargyl-D-galactopyranoside derivatives and having an effect as i.a., galectin inhibitors, the use of said compounds as a medicament as well as for the manufacture of a medicament for treatment of disorders relating to the binding of galectin to ligands in a mammal, wherein said galectin is preferably a galectin-3. The novel compounds are defined by the general formula (I).