2,3,4-tri-O-acetyl-L-fucosyl fluoride | 194790-60-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-L-fucosyl fluoride
• 英文别名: (3S,4R,5R,6S)-2-fluoro-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate；(2,3,4-tri-O-acetyl)-L-fucopyranosyl fluoride；[(2S,3R,4R,5S)-4,5-diacetyloxy-6-fluoro-2-methyloxan-3-yl] acetate
• CAS: 194790-60-8
• 化学式: C₁₂H₁₇FO₇
• 分子量: 292.261
• InChiKey: SAOYKKJFCIMXDB-PFFKSSDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-L-fucosyl fluoride 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 tin(ll) chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.5h， 生成 -L-glutamic acid 1-methylamide 5-benzyl ester
  参考文献：
  名称：

  Studies on Selectin Blockers. 7. Structure−Activity Relationships of Sialyl Lewis X Mimetics Based on Modified Ser-Glu Dipeptides

  摘要：

  We have previously found that heterochiral fucodipeptides, L-Ser-D-Glu (3a) and D-Ser-L-Glu (3b), exhibited up to 20-100 times more potency than a sialyl Lewis X (sLe(x), 1) and a 3'-sulfated Lewis X analogue (2) toward E-selectin binding and have also proposed, from molecular dynamics calculation, that their strong activities would depend on a possible formation of the type II and/or type II' beta-turn of compounds 3a,b (Tsukida, T.; Hiramatsu, Y.; Tsujishita, H.; Kiyoi, T.; Yoshida, M.; Kurokawa, K.; Moriyama, H.; Ohmoto, H.; Wada, Y.; Saito, T.; Kondo, H. J. Med. Chem. 1997, 40, 3534-3541). To clarify our hypothesis, we synthesized several analogues of compounds 3a,b and investigated their structure-activity relationships. As a result, it was indicated that the type II and/or type II' beta-turn conformation would be a comparatively tight form and would play important roles in favorable binding to E-selectin. These findings indicate that sLe(x) mimetics with type II and type II'-beta-turn dipeptides could be a useful methodology for the design of an active selectin blocker.

  DOI：

  10.1021/jm980267x
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-L-fucopyranose 在 trans-4,4'-diaminostilbene-2,2'-disulfonic acid 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,4-tri-O-acetyl-L-fucosyl fluoride
  参考文献：
  名称：

  Fucose derivatives, drugs containing the same as active ingredient, and

  摘要：

  化合物的公式（I）：##STR1##其中X.sup.1是以下公式之一的基团（1）、（2）和（3）：##STR2##R.sup.1是支链长链烷基基团，R.sup.2是--CONHR.sup.3、羧基或氢原子，n是0、1或2的整数，R.sup.3是较低的烷基基团或苯基，或其药学上可接受的盐，用作选择素抑制剂，可用于预防或治疗各种炎症性疾病，如炎症性皮炎（例如特应性皮炎、接触性过敏、光敏性皮炎等）、自身免疫慢性疾病（例如类风湿关节炎、慢性甲状腺炎等）和缺血再灌注损伤。

  公开号：

  US05919769A1

文献信息

• FUCOSE DERIVATIVES, DRUGS CONTAINING THE SAME AS ACTIVE INGREDIENT, AND INTERMEDIATES FOR PRODUCING THE SAME
  申请人：KANEBO, LTD.

  公开号：EP0859005A1

  公开（公告）日：1998-08-19

  A compound of the formula (I): wherein X1 is a group of one of the following formulae (1), (2) and (3): R1 is a branched long chain alkyl group, R2 is ―CONHR3, a carboxyl group or a hydrogen atom, n is an integer of 0, 1 or 2, and R3 is a lower alkyl group or a phenyl group, or a pharmaceutically acceptable salt thereof, which is useful as a selectin inhibitor, and can be used in the prophylaxis or treatment of various inflammatory diseases such as inflammatory dermatitis (e.g., atopic dermatitis, contact hypersensitivity, photodermatosis, etc.), autoimmune chronic diseases (e.g. rheumatoid arthritis, chronic thyroiditis, etc.), and ischemia-reperfusion injury.

  式 (I) 的化合物： 其中 X1 是下式（1）、（2）和（3）之一的基团： R1是支链长链烷基，R2是-CONHR3、羧基或氢原子，n是0、1或2的整数，R3是低级烷基或苯基，或其药学上可接受的盐，可作为选择素抑制剂，用于预防或治疗各种炎症性疾病，如炎症性皮炎（如、特应性皮炎、接触性过敏、光敏性皮肤病等）、自身免疫性慢性疾病（如类风湿性关节炎、慢性甲状腺炎等）以及缺血再灌注损伤。
• Senolytic compositions and uses thereof
  申请人：Rubedo Life Sciences, Inc.

  公开号：US11026963B2

  公开（公告）日：2021-06-08

  Provided herein are senolytic agents for selectively killing senescent cells that are associated with numerous pathologies and diseases, including age-related pathologies and diseases. As disclosed herein, senescent cell-associated diseases and disorders may be treated or prevented by administering at least one senolytic agent or pharmaceutical compositions thereof. The senescent cell-associated diseases or disorders treated or prevented by the methods described herein include, but are not limited to, cardiovascular diseases or disorders, cardiovascular diseases and disorders associated with arteriosclerosis, such as atherosclerosis, idiopathic pulmonary fibrosis (IPF), chronic obstructive pulmonary disease (COPD), osteoarthritis, inflammatory diseases or disorders, autoimmune diseases or disorders, pulmonary diseases or disorders, neurological diseases or disorders, dermatological diseases or disorders, chemotherapeutic side effects, radiotherapy side effects, metastasis and metabolic diseases.

  本文提供了用于选择性杀死衰老细胞的衰老剂，衰老细胞与多种病理和疾病有关，包括与年龄有关的病理和疾病。如本文所述，衰老细胞相关疾病可通过施用至少一种衰老分解剂或其药物组合物来治疗或预防。本文所述方法可治疗或预防的衰老细胞相关疾病或紊乱包括但不限于心血管疾病或紊乱、与动脉硬化相关的心血管疾病和紊乱，如动脉粥样硬化、特发性肺纤维化（IPF）、慢性阻塞性肺病（COPD）、骨关节炎、炎症性疾病或紊乱、自身免疫性疾病或紊乱、肺部疾病或紊乱、神经系统疾病或紊乱、皮肤病或紊乱、化疗副作用、放疗副作用、转移和代谢性疾病。
• WO2020014409A5
  申请人：——

  公开号：WO2020014409A5

  公开（公告）日：2022-07-19
• High Affinity Glycodendrimers for the Lectin LecB from Pseudomonas aeruginosa
  作者：Nathalie Berthet、Baptiste Thomas、Isabelle Bossu、Emilie Dufour、Emilie Gillon、Julian Garcia、Nicolas Spinelli、Anne Imberty、Pascal Dumy、Olivier Renaudet

  DOI：10.1021/bc400239m

  日期：2013.9.18

  Following an iterative oxime ligation procedure, cyclopeptide (R) and lysine-based dendron (D) were combined in all possible arrangements and successively functionalized with alpha-fucose and beta-fucose to provide a new series of hexadecavalent glycosylated scaffolds (i.e., scaffolds RD16, RR16, DR16 and DD16). These compounds and smaller analogs (tetra- and hexavalent scaffolds R-4 and R-6) were used to evaluate the influence of the ligand valency and architecture, and of the anomer configuration in the binding to the alpha Fuc-specific lectin LecB from Pseudomonas aeruginosa. Competitive enzyme-linked lectin assays (ELLA) revealed that only the RD16 architecture displaying alpha Fuc (9A) reaches strong binding improvement (IC50 of 0.6 nM) over alpha MeFuc, and increases the alpha-selectivity of LecB. Dissociation constant of 28 nM was measured by isothermal titration micorcalorimetry (ITC) for 9A, which represents the highest affinity ligand ever reported for LecB. ITC and molecular modeling suggested that the high affinity observed might be due to an aggregative chelate binding involving four sugar head groups and two lectins. Interestingly, unprecedented binding effects were observed with beta-fucosylated conjugates, albeit being less active than the corresponding ligands of the alpha Fuc series. In particular, the more flexible lysine-based dendritic structures (15B and 18B) showed a slight inhibitory enhancement in comparison with those having cyclopeptide core.
• SENOLYTIC COMPOSITIONS AND USES THEREOF
  申请人：Rubedo Life Sciences, Inc.

  公开号：EP3790861A1

  公开（公告）日：2021-03-17