1-iodo-9-methoxynonane | 634585-77-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-iodo-9-methoxynonane
• CAS: 634585-77-6
• 化学式: C₁₀H₂₁IO
• 分子量: 284.181
• InChiKey: CHKBCTMAIFBQCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  12
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-iodo-9-methoxynonane 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 以88%的产率得到1-azido-9-methoxynonane
  参考文献：
  名称：

  Exploiting angled thin film vortex microfluidics for expeditious syntheses of iminosugars

  摘要：

  氨基糖是碳水化合物治疗领域的重要化合物。涡流薄膜微流体反应器可有效合成此类化合物。

  DOI：

  10.1039/d2ra04409a
• 作为产物：
  描述：

  9-bromo-1-methoxynonane 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 72.0h， 生成 1-iodo-9-methoxynonane
  参考文献：
  名称：

  由异恶唑-5(2H)-酮合成一些手性2-氨基烷基恶唑-4-羧酸盐

  摘要：

  在碳二亚胺存在下，4-甲基-5-氧代-2,5-二氢异恶唑-3-甲酸乙酯可以被许多天然和合成的邻苯二甲酰亚胺基氨基酸N-酰化。N-酰化产物在丙酮中以 300 nm 照射时顺利形成相应的恶唑。然后去除邻苯二甲酰亚胺保护基团以良好的总产率得到 2-氨基烷基恶唑-4-羧酸酯，并且在任何步骤中都没有显着的外消旋化。

  DOI：

  10.1071/ch03052

文献信息

• GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME
  申请人：Pinto M. Brian

  公开号：US20070244184A1

  公开（公告）日：2007-10-18

  The compounds of the present invention relate to chain-extended and chain-modified analogues of salacinol, including embodiments where the sulfate moiety has been substituted with a carboxylate or phosphate moiety. In other embodiments the sulfate moiety has been shifted by one carbon atom in the zwitterionic structure. In another embodiment the polyhydroxylated side chain may be replaced with a lipophilic alkyl chain and a suitable counterion. The invention also encompasses methods for synthesizing the salacinol analogues and using the analogues for enzyme inhibition applications.

  本发明的化合物涉及与salacinol的链延伸和链修饰类似物，包括其中硫酸酯基团已被羧酸酯基团或磷酸酯基团取代的实施例。在其他实施例中，硫酸酯基团在带电离结构中已被向一碳原子移位。在另一实施例中，多羟基侧链可以被脂溶性烷基链和适当的对离子取代。本发明还涵盖了合成salacinol类似物的方法以及将这些类似物用于酶抑制应用的方法。
• <i>N</i>-Substituted <scp>l</scp>-Iminosugars for the Treatment of Sanfilippo Type B Syndrome
  作者：Valeria De Pasquale、Anna Esposito、Gianluca Scerra、Melania Scarcella、Mariangela Ciampa、Antonietta Luongo、Daniele D’Alonzo、Annalisa Guaragna、Massimo D’Agostino、Luigi Michele Pavone

  DOI：10.1021/acs.jmedchem.2c01617

  日期：2023.2.9

  Sanfilippo syndrome comprises a group of four genetic diseases due to the lack or decreased activity of enzymes involved in heparan sulfate (HS) catabolism. HS accumulation in lysosomes and other cellular compartments results in tissue and organ dysfunctions, leading to a wide range of clinical symptoms including severe neurodegeneration. To date, no approved treatments for Sanfilippo disease exist

  由于参与硫酸乙酰肝素 (HS) 分解代谢的酶缺乏或活性降低，Sanfilippo 综合征包括一组四种遗传病。H2S 在溶酶体和其他细胞区室中的积累导致组织和器官功能障碍，导致广泛的临床症状，包括严重的神经变性。迄今为止，尚无批准的 Sanfilippo 病治疗方法。在这里，我们报告了N-取代的l-亚氨基糖显着减少 Sanfilippo 成纤维细胞和 Sanfilippo B 亚型神经元细胞模型中的底物储存和溶酶体功能障碍的能力。特别是，我们发现它们增加了有缺陷的 α- N的水平-乙酰氨基葡萄糖苷酶并纠正其向溶酶体室的正确分类。此外，l-亚氨基糖通过下调外泌体糖基转移酶的蛋白质水平来减少 HS 积累。这些结果突出了这些糖模拟物在 Sanfilippo 综合征中的有趣药理学潜力，为开发治疗此类不治之症的新型治疗方法铺平了道路。
• Synthesis of S-alkylated sulfonium-ions and their glucosidase inhibitory activities against recombinant human maltase glucoamylase
  作者：Sankar Mohan、Lyann Sim、David R. Rose、B. Mario Pinto

  DOI：10.1016/j.carres.2007.01.018

  日期：2007.5

  The syntheses of nine S-alkylated, cyclic sulfonium-ions with varying alkyl chain lengths, as mimics of N-alkylated imino sugars, and their glucosidase inhibitory activities are described. The target compounds were synthesized by alkylation of 2,3,5-tri-O-benzyl-1,4-anhydro-4-thio-D-arabinitol at the ring sulfur atom using various alkyl halides, followed by deprotection using boron trichloride. Enzyme inhibitory assays against recombinant human maltase glucoamylase (NIGA), a critical enzyme in the small intestine involved in the breakdown of glucose oligosaccharides into glucose itself, shows that they are effective inhibitors of MGA with K-i values ranging from 6 to 75 mu M. (c) 2007 Elsevier Ltd. All rights reserved.
• [EN] THERAPEUTIC COMPOSITIONS WITH IMINO SUGARS FOR THE TREATMENT OF DISEASES WITH ACCUMULATION OF HEPARAN SULFATE<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES AVEC DES IMINOSUCRES POUR LE TRAITEMENT DE MALADIES D'ACCUMULATION DU SULFATE D'HÉPARANE
  申请人：[en]PAVONE, Luigi Michele

  公开号：WO2023203004A1

  公开（公告）日：2023-10-26

  Compositions herein disclosed are conceived for the treatment and prevention of diseases caused by accumulation of heparan sulfate including mucopolysaccharidosis, Alzheimer's disease and cancers. These compositions include as active ingredient an iminosugar belonging to L-steric series and derivatives thereof. The L-iminosugars of this invention are able to reduce the levels of heparan sulfate in cells of patients affected by mucopolysaccharidosis and cancer, and to reduce the accumulation of amyloid plaques in a model of neurodegenerative disease. Therefore, the use of these compounds prevents the onset of symptoms associated with these diseases, thus improving the quality and length of life of patients suffering from diseases characterized by accumulation of heparan sulfate.