3-bromopropyl tetra-O-acetyl-α-D-mannopyranoside | 258283-46-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-bromopropyl tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: 3'-bromopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside；(2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(3-bromopropoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-(3-bromopropoxy)oxan-2-yl]methyl acetate
• CAS: 258283-46-4
• 化学式: C₁₇H₂₅BrO₁₀
• 分子量: 469.284
• InChiKey: XKZPAGAQQQLHEH-NRKLIOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-bromopropyl tetra-O-acetyl-α-D-mannopyranoside 在 palladium on activated charcoal sodium azide 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 3-aminopropyl-α-D-mannopyranoside
  参考文献：
  名称：

  一锅法合成多价甘露糖单糖和二糖阵列

  摘要：

  描述了多种甘露糖单糖和二糖多价阵列的合成，其可能用作抗肠杆菌感染的抗感染剂。

  DOI：

  10.1016/j.tet.2003.08.011
• 作为产物：
  描述：

  1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 氢溴酸 、 一溴化碘 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 生成 3-bromopropyl tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Novel multivalent mannose compounds and their inhibition of the adhesion of type 1 fimbriated uropathogenic E. coli

  摘要：

  A series of multivalent mannose containing compounds were prepared varying in size from small divalent, to 16-valent glycodenrimers and 21-valent glycopolymers. The molecules were approached via a common mannose building block. As scaffolds dendrimers and dendrons based on the 3,5-di-(2-aminoethoxy)-benzoic acid branching unit were used along with commercially available PAMAM dendrimers. To include larger structures, linear glycopolymers with varying amounts of mannose were prepared via radical polymerization. The compounds were tested for their biological activity using a newly developed ELISA based inhibition assay, for their ability to inhibit the binding of recombinant type I fimbriated E. coli to a monolayer of T24 cell line derived from human urinary bladder epithelium. All compounds showed enhanced affinity as compared to mannose with IC50's down to the low micromolar range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.014

文献信息

• Towards an unprotected self-activating glycosyl donor system: Bromobutyl glycosides
  作者：Benjamin G Davis、Steven D Wood、Michael AT Maughan

  DOI：10.1139/v02-029

  日期：2002.6.1

  Bromobutyl mannopyranosides have been successfully used as both protected and unprotected glycosyl donors both with and without the use of an external activator.Key words: glycosylation, unprotected glycosyl donors, oligosaccharides.

  溴丁基甘露聚糖已成功用作受保护和未受保护的糖基供体，无论是否使用外部活化剂。关键词：糖基化，未受保护的糖基供体，寡糖。
• [EN] MACROPHAGE TARGETING DRUG CONJUGATES<br/>[FR] CONJUGUÉS DE MÉDICAMENT CIBLANT DES MACROPHAGES
  申请人：P I F ENTREPRENEURS LTD

  公开号：WO2022034582A1

  公开（公告）日：2022-02-17

  Described herein are novel, macrophage targeting drug conjugates. The macrophage targeting drug conjugates comprise a drug moiety, a mannose moiety, and a linker connecting the drug moiety and the mannose moiety. The linker may comprise a hydrazone group or an oxime group.

  本文描述了一种新颖的巨噬细胞靶向药物共轭物。这些巨噬细胞靶向药物共轭物包括药物部分、甘露糖部分和连接药物部分与甘露糖部分的连接物。连接物可能包括肼酮基团或肟基团。
• Synthesis of Neoglycopolymers by a Combination of “Click Chemistry” and Living Radical Polymerization
  作者：Vincent Ladmiral、Giuseppe Mantovani、Guy J. Clarkson、Solene Cauet、Jacob L. Irwin、David M. Haddleton

  DOI：10.1021/ja058364k

  日期：2006.4.1

  an anomeric azide (alpha or beta) onto these polymers by Cu(I)-catalyzed "click chemistry", providing a simple and efficient route to synthetic glycopolymers. The strategy provides an extremely powerful tool for the synthesis of libraries of materials that differ only in the nature of the sugar moiety presented on a well-defined polymer scaffold. A library of multivalent ligands were then prepared

  描述了通过活性自由基聚合合成具有窄分子量分布 (PDI = 1.09-1.17) 的新型明确定义的炔侧链功能聚合物。通过 Cu(I) 催化的“点击化学”，通过 C-6 或异头叠氮化物（α 或β）将受保护和未受保护的碳水化合物接枝到这些聚合物上，为合成糖聚合物提供了一种简单有效的途径。该策略为合成材料库提供了极其强大的工具，这些材料库仅在定义明确的聚合物支架上呈现的糖部分的性质有所不同。然后按照“coclicking”合成方案制备多价配体库，以及这些糖聚合物在伴刀豆球蛋白 A 和蓖麻凝集素存在下的反应性，
• Mannose-conjugated platinum complexes reveals effective tumor targeting mediated by glucose transporter 1
  作者：Ran Liu、Hong Li、Xiangqian Gao、Qian Mi、Hongxia Zhao、Qingzhi Gao

  DOI：10.1016/j.bbrc.2017.04.004

  日期：2017.5

  Despite numerous studies that report the glucose derived glycoconjugates as antitumor candidates, using mannose as sugar motif for specific tumor targeting remains less studied. In this research, two novel mannose-conjugated platinum complexes 4a and 4b that target the Warburg effect were designed, synthesized and evaluated for their antitumor activities in vitro and in vivo. Compared with oxaliplatin

  尽管有大量研究报道葡萄糖衍生的糖缀合物作为抗肿瘤候选物，但使用甘露糖作为糖作为特定肿瘤靶向的基序仍然较少研究。在这项研究中，设计，合成和评估了两种靶向Warburg效应的新型甘露糖共轭铂复合物4a和4b的体外和体内抗肿瘤活性。与奥沙利铂相比，两种复合物在六种人类癌细胞系中均显示出水溶性的显着增强以及优异或相当的细胞毒性。对葡萄糖转运蛋白1（GLUT1）下调或过度表达的细胞的细胞毒性评估以及铂的积累研究表明，化合物4a的细胞摄取受GLUT1调节。特别是4a通过抑制Bcl-2和Bcl-XL的表达诱导HT29细胞凋亡，初步解释了抗肿瘤作用的机制起源。正如其最大耐受剂量测定法和体内抗癌活性所表明的那样，化合物4a比奥沙利铂具有更好的安全性和功效。这项研究的结果表明，将甘露糖缀合的铂络合物作为先导化合物进行进一步的临床前评估的可能性。
• Synthesis and cytotoxic evaluation of glycosyl derivatives of icaritin
  作者：Chunyong Wei、Xun Sun、Lei Zhang

  DOI：10.1080/14786419.2024.2334333

  日期：——

  A series of glycosyl alkyl/triazol-linked icaritin derivatives have been designed and synthesised. The target glycosyl derivatives were evaluated for their anticancer activity against three human c...

  设计并合成了一系列糖基烷基/三唑连接的淫羊藿素衍生物。评估了目标糖基衍生物对三种人类癌症的抗癌活性。