bis(3-azido-3-deoxy-β-D-galactopyranosyl)sulfane | 1193784-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis(3-azido-3-deoxy-β-D-galactopyranosyl)sulfane
• 英文别名: Bis-(3-azido-3-deoxy-beta-D-galactopyranosyl)-sulfane；(2S,3R,4S,5R,6R)-4-azido-2-[(2S,3R,4S,5R,6R)-4-azido-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl-6-(hydroxymethyl)oxane-3,5-diol
• CAS: 1193784-39-2
• 化学式: C₁₂H₂₀N₆O₈S
• 分子量: 408.392
• InChiKey: AZZIBGKZSLGNAF-ZFDCCPEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  194
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  bis(3-azido-3-deoxy-β-D-galactopyranosyl)sulfane 在 盐酸 、 D(+)-10-樟脑磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1,1'-sulfanediyl-bis{3-deoxy-3-[4-(3-fluorophenyl)-1H-1,2-pyrazol-1-yl]-β-D-galactopyranoside}
  参考文献：
  名称：

  [EN] NOVEL GALACTOSIDE INHIBITOR OF GALECTINS
  [FR] NOUVEL INHIBITEUR DE GALECTINES À BASE DE GALACTOSIDE

  摘要：

  The present invention relates to a D-galactopyranose compound of formula (1) wherein the pyranose ring is beta-D-galactopyranose, and these compounds are high affinity galectin-1 and/or 3 inhibitors for use in treatment of inflammation; fibrosis, such as pulmonary fibrosis, liver fibrosis, kidney fibrosis, ophthalmological fibrosis and fibrosis of the skin and heart; scarring; keloid formation; aberrant scar formation; surgical adhesions; scleroderma; systemic sclerosis; septic shock; cancer, such as carcinomas, sarcomas, leukemias and lymphomas, such as T-cell lymphomas; metastasising cancers; autoimmune diseases, such as psoriasis, rheumatoid arthritis, Crohn's disease, ulcerative colitis, intestinal fibrosis, ankylosing spondylitis, systemic lupus erythematosus; metabolic disorders; heart disease; heart failure; aortic stenosis, atherosclerosis, pathological angiogenesis, such as ocular angiogenesis or a disease or condition associated with ocular angiogenesis, e.g. neovascularization related to cancer; and eye diseases, such as age-related macular degeneration and comeal neovascularization; atherosclerosis; metabolic diseases such as diabetes; type 2 diabetes; insulin resistance; obesity; Diastolic HF; asthma and other interstitial lung diseases, including Hermansky-Pudlak syndrome, pulmonary arterial hypertension, RA- ILD, SSc-ILD, Lung disease with fibrosis such as COPD and asthma. Otosclerosis, mesothelioma; liver disorders, such as non-alcoholic steatohepatitis or non-alcoholic fatty liver disease, Liver cirrhosis of various origins, such as alcoholic and non-alcoholic, autoimmune cirrhosis such as primary biliary cirrhosis and sclerosing cholangitis, virally induced cirrhosis, cirrhosis induced by genetic disease. Liver cancer, cholangiocarcinoma, biliary tract cancer; neurodegenerative disorders such as Parkinsons disease, Alzheimers disease, cognitive impairment, cerebrovascular diseases such as stroke, traumatic brain injury, Huntington's disease, amyotrophic lateral sclerosis, multiple sclerosis, peripheral nephropathy.

  公开号：

  WO2022171561A1
• 作为产物：
  描述：

  phenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-galactopyranoside 在 溴 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 bis(3-azido-3-deoxy-β-D-galactopyranosyl)sulfane
  参考文献：
  名称：

  [EN] METHODS, COMPOSITIONS AND KITS FOR TREATING, MODULATING, OR PREVENTING OCULAR ANGIOGENESIS OR FIBROSIS IN A SUBJECT USING A GALECTIN PROTEIN INHIBITOR
  [FR] MÉTHODES, COMPOSITIONS ET KITS DE TRAITEMENT, DE MODULATION OU DE PRÉVENTION DE L'ANGIOGENÈSE OU DE LA FIBROSE OCULAIRE CHEZ UN SUJET UTILISANT UN INHIBITEUR DE GALECTINE

  摘要：

  本文提供了用于抑制眼部血管生成或纤维化的制药组合物的方法和试剂盒，该组合物包括一种药用合适载体或稀释剂和足以抑制血管生成或纤维化的抑制剂组合物的数量，通过抑制表达和/或活性的低聚半乳糖蛋白或其部分来抑制血管生成或纤维化。

  公开号：

  WO2014078655A1

文献信息

• Galectin-3-Binding Glycomimetics that Strongly Reduce Bleomycin-Induced Lung Fibrosis and Modulate Intracellular Glycan Recognition
  作者：Tamara Delaine、Patrick Collins、Alison MacKinnon、G. Sharma、John Stegmayr、Vishal K. Rajput、Santanu Mandal、Ian Cumpstey、Amaia Larumbe、Bader A. Salameh、Barbro Kahl-Knutsson、Hilde van Hattum、Monique van Scherpenzeel、Roland J. Pieters、Tariq Sethi、Hans Schambye、Stina Oredsson、Hakon Leffler、Helen Blanchard、Ulf J. Nilsson

  DOI：10.1002/cbic.201600285

  日期：2016.9.15

  synthesis, optimization, and structural analysis of doubly C3‐aryltriazolyl‐substituted thiodigalactosides. The synthetic ligands efficiently inhibit intracellular galectin‐3 accumulation in dots on damaged vesicles and attenuate experimentally induced lung fibrosis.

  去点：通过双C3-芳基三唑基取代的硫代二半乳糖苷的合成、优化和结构分析，发现了高效的半乳凝素-1和-3拮抗剂。合成配体可有效抑制受损囊泡上点状细胞内半乳糖凝集素-3的积累，并减轻实验诱导的肺纤维化。
• [EN] METHODS, COMPOSITIONS AND KITS FOR TREATING, MODULATING, OR PREVENTING OCULAR ANGIOGENESIS OR FIBROSIS IN A SUBJECT USING A GALECTIN PROTEIN INHIBITOR<br/>[FR] MÉTHODES, COMPOSITIONS ET KITS DE TRAITEMENT, DE MODULATION OU DE PRÉVENTION DE L'ANGIOGENÈSE OU DE LA FIBROSE OCULAIRE CHEZ UN SUJET UTILISANT UN INHIBITEUR DE GALECTINE
  申请人：UNIV TUFTS

  公开号：WO2014078655A1

  公开（公告）日：2014-05-22

  Methods and kits using a pharmaceutical composition for use in inhibiting ocular angiogenesis or fibrosis are provided herein, such that composition includes a pharmaceutically suitable carrier or diluent and an amount of the inhibitor composition effective to inhibit the angiogenesis or the fibrosis by inhibiting expression and/or activity of a galectin protein or a portion thereof.

  本文提供了用于抑制眼部血管生成或纤维化的制药组合物的方法和试剂盒，该组合物包括一种药用合适载体或稀释剂和足以抑制血管生成或纤维化的抑制剂组合物的数量，通过抑制表达和/或活性的低聚半乳糖蛋白或其部分来抑制血管生成或纤维化。
• Novel galactoside inhibitor of galectins
  申请人：GALECTO BIOTECH AB

  公开号：US20160096861A1

  公开（公告）日：2016-04-07

  Provided is a compound of the general formula (I): The compound of formula (I) is suitable for treating pulmonary fibrosis, such as Idiopathic pulmonary fibrosis in a mammal. Also provided is a method for treatment of pulmonary fibrosis, such as Idiopathic pulmonary fibrosis in a human subject having a galectin-3 level indicative of pulmonary fibrosis or exacerbation of symptoms as well as a method for making said compound.

  提供的是通式（I）的化合物：公式（I）的化合物适用于治疗哺乳动物的肺纤维化，如特发性肺纤维化。还提供了一种治疗肺纤维化的方法，例如对于人类患有表明肺纤维化或症状加剧的半乳糖凝集素-3水平的特发性肺纤维化患者，以及制备该化合物的方法。
• NOVEL SYNTHESIS OF GALACTOSIDE INHIBITORS
  申请人：Nilsson Ulf

  公开号：US20110130553A1

  公开（公告）日：2011-06-02

  Novel synthesis routes for preparation of thiodigalactosides and intermediates are presented. The method includes the use of a 3-azido-galactosyl thiouronium salt derivative, which is activated to the corresponding thiol in situ, which in turn is directly reacted with a 3-azido-galactosyl bromide resulting in the 3,3′-di-azido-thio-di-galactoside before the thiol has a chance to reduce the azido 10 group. Hence, in situ formation of the 3-azido-galactosyl thiol from the thiouronium salt is essential in the synthesis procedure, because any other method that generate the thiol separately results in extensive unwanted azide reduction.

  提出了用于制备硫代半乳糖苷和中间体的新型合成路线。该方法包括使用3-偶氮基-半乳糖基硫脲盐衍生物，该衍生物在原位激活为相应的巯基，然后直接与3-偶氮基-半乳糖基溴反应，形成3,3'-二偶氮基硫代二半乳糖苷，此时巯基还没有机会还原偶氮基。因此，在合成过程中原位形成3-偶氮基-半乳糖基巯基是必要的，因为任何其他单独生成巯基的方法都会导致大量不需要的偶氮基还原。
• Galactoside Inhibitor of Galectin-3 and its use for Treating Pulmonary Fibrosis
  申请人：GALECTO BIOTECH AB

  公开号：US20150274764A1

  公开（公告）日：2015-10-01

  The present invention relates to a compound of the general formula (I) for pulmonary administration. The compound of formula (I) is suitable for treating pulmonary fibrosis, such as Idiopathic pulmonary fibrosis in a mammal. Furthermore the present invention concerns a method for treatment of pulmonary fibrosis, such as Idiopathic pulmonary fibrosis in a human subject.

  本发明涉及一种适用于肺部给药的通式(I)化合物。通式(I)的化合物适用于治疗哺乳动物的肺纤维化，例如特发性肺纤维化。此外，本发明还涉及一种用于治疗肺纤维化的方法，例如用于治疗人体主体的特发性肺纤维化。