16-碘十六烷-1-醇 | 824404-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 16-碘十六烷-1-醇
• 英文名称: 16-iodohexadecanol
• 英文别名: 16-iodohexadecan-1-ol；16-Iodohexadecan-1-ol
• CAS: 824404-39-9
• 化学式: C₁₆H₃₃IO
• 分子量: 368.342
• InChiKey: FAFIDRZIPNQMKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  18
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  16-碘十六烷-1-醇 在 二乙胺基三氟化硫 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到1-fluoro-16-iodohexadecane
  参考文献：
  名称：

  Conformationally-locked N-glycosides: Exploiting long-range non-glycone interactions in the design of pharmacological chaperones for Gaucher disease

  摘要：

  Pyranoid-type glycomimetics having a cis-1,2-fused glucopyranose-2-alkylsulfany1-1,3-oxazoline (Glc-PSO) structure exhibit an unprecedented specificity as inhibitors of mammalian beta-glucosidase. Notably, their inhibitory potency against human beta-glucocerebrosidase (GCase) was found to be strongly dependent on the nature of aglycone-type moieties attached at the sulfur atom. In the particular case of omega-substituted hexadecyl chains, an amazing influence of the terminal group was observed. A comparative study on a series of Glc-PSO derivatives suggests that hydrogen bond acceptor functionalities, e.g. fluoro or methyloxycarbonyl, significantly stabilize the Glc-PSO:GCase complex. The S-(16-fluorohexadecyl)-PSO glycomimetic turned out to be a more potent GCase competitive inhibitor than ambroxol, a non glycomimetic drug currently in pilot trials as a pharmacological chaperone for Gaucher disease. Moreover, the inhibition constant increased by one order of magnitude when shifting from neutral (pH 7) to acidic (pH 5) media, a favorable characteristic for a chaperone candidate. Indeed, the fluoro-PSO derivative also proved superior to ambroxol in mutant GCase activity enhancement assays in N370S/N370S Gaucher fibroblasts. The results presented here represent a proof of concept of the potential of exploiting long-range non-glycone interactions for the optimization of glycosidase inhibitors with chaperone activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.002
• 作为产物：
  描述：

  16-溴-1-十六烷醇 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以98%的产率得到16-碘十六烷-1-醇
  参考文献：
  名称：

  Conformationally-locked N-glycosides: Exploiting long-range non-glycone interactions in the design of pharmacological chaperones for Gaucher disease

  摘要：

  Pyranoid-type glycomimetics having a cis-1,2-fused glucopyranose-2-alkylsulfany1-1,3-oxazoline (Glc-PSO) structure exhibit an unprecedented specificity as inhibitors of mammalian beta-glucosidase. Notably, their inhibitory potency against human beta-glucocerebrosidase (GCase) was found to be strongly dependent on the nature of aglycone-type moieties attached at the sulfur atom. In the particular case of omega-substituted hexadecyl chains, an amazing influence of the terminal group was observed. A comparative study on a series of Glc-PSO derivatives suggests that hydrogen bond acceptor functionalities, e.g. fluoro or methyloxycarbonyl, significantly stabilize the Glc-PSO:GCase complex. The S-(16-fluorohexadecyl)-PSO glycomimetic turned out to be a more potent GCase competitive inhibitor than ambroxol, a non glycomimetic drug currently in pilot trials as a pharmacological chaperone for Gaucher disease. Moreover, the inhibition constant increased by one order of magnitude when shifting from neutral (pH 7) to acidic (pH 5) media, a favorable characteristic for a chaperone candidate. Indeed, the fluoro-PSO derivative also proved superior to ambroxol in mutant GCase activity enhancement assays in N370S/N370S Gaucher fibroblasts. The results presented here represent a proof of concept of the potential of exploiting long-range non-glycone interactions for the optimization of glycosidase inhibitors with chaperone activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.002

文献信息

• Regio- and Chemoselective One-Step 3-O-Alkylenation of Unprotected Ascorbic Acid Using ω-Iodoalkanols
  作者：Bang Luu、Thierry Muller、Paul Heuschling

  DOI：10.1055/s-0028-1087662

  日期：——

  A regio- and chemoselective alkylenation employing unprotected ascorbic acid and a series of unprotected iodoalkanols in the presence of sodium hydrogen carbonate in dimethyl sulfoxide is described. This atom economic high yielding procedure delivers the corresponding 3-O-alkylene ethers in a single step without prior protection. Specific 3-O-etherification was also observed with ­unprotected 16-iodohexadecanoic acid and with 2-(10-iododecyl)isoindole-1,3-dione. Furthermore, an 2-O-alkylene derivative was obtained when 3-O-benzyl ascorbic acid was reacted with unprotected 10-iododecanol under slightly modified conditions. Finally, the antioxidative activity of all compounds was determined and compared to vitamin C and E.

  描述了一种使用未保护的抗坏血酸和一系列未保护的碘烷醇，在碳酸氢钠存在下于二甲基亚砜中进行的区域和化学选择性烷基化。这种原子经济、高产率的程序在无需事先保护的情况下，单步合成了相应的3-O-烷基醚。同时，未保护的16-碘十六酸和2-(10-碘十烷基)异吲哚-1,3-二酮也观察到了特定的3-O-醚化。此外，当3-O-苄基抗坏血酸与未保护的10-碘癸醇在稍微修改的条件下反应时，获得了一个2-O-烷基衍生物。最后，所有化合物的抗氧化活性被测定并与维生素C和E进行了比较。
• Tocopherol long chain fatty alcohols decrease the production of TNF-α and NO radicals by activated microglial cells
  作者：Thierry Muller、Luc Grandbarbe、Eleonora Morga、Paul Heuschling、Bang Luu

  DOI：10.1016/j.bmcl.2004.09.078

  日期：2004.12

  The synthesis of a series of Tocopherol long chain Fatty Alcohols (TEA) and their biological activities on the modulation of microglial activation are described. Specifically, the 2-(12-hydroxy-dodecyl)-2,5,7,8-tetramethyl-chroman-6-ol, the TEA bearing 12 carbon atoms on the side chain (n = 12), shows the most potent inhibition of secretion on nitric oxide (NO) and tumour necrosis factor-alpha (TNF-alpha) by lipopolysaccharide (LPS)-activated microglia. (C) 2004 Elsevier Ltd. All rights reserved.
• DRUG DELIVERY FROM IMPLANTS USING SELF-ASSEMBLED MONOLAYERS-THERAPEUTIC SAMS
  申请人：Agrawal C. Mauli

  公开号：US20090123516A1

  公开（公告）日：2009-05-14

  Disclosed are medical devices comprising one or more surfaces, one or more SAM molecules attached to the one or more surfaces of the medical device, and one or more therapeutic agents attached to the one or more self-assembled monolayer molecules. Also disclosed are medical devices comprising one or more surfaces, one or more self-assembled monolayer molecules attached to the one or more surfaces of the medical device, one or more linkers comprising a first functional group and a second functional group, the first functional group attached to the self-assembled monolayer molecule and a therapeutic agent attached to the second functional group. The therapeutic agent may be attached to the SAM molecule via a linker. The present invention also concerns methods of administering a therapeutic agent to a subject, comprising contacting the subject with one of the medical devices set forth herein.
• [EN] DRUG DELIVERY FROM IMPLANTS USING SELF-ASSEMBLED MONOLAYERS - THERAPEUTIC SAMS<br/>[FR] LIBERATION DE MEDICAMENTS PAR DES IMPLANTS COMPRENANT DES MONOCOUCHES AUTO-ASSEMBLEES (SAM) SAM THERAPEUTIQUES
  申请人：UNIV TEXAS

  公开号：WO2007019478A2

  公开（公告）日：2007-02-15

  [EN] Disclosed are medical devices comprising one or more surfaces, one or more SAM molecules attached to the one or more surfaces of the medical device, and one or more therapeutic agents attached to the one or more self-assembled monolayer molecules. Also disclosed are medical devices comprising one or more surfaces, one or more self-assembled monolayer molecules attached to the one or more surfaces of the medical device, one or more linkers comprising a first functional group and a second functional group, the first functional group attached to the self-assembled monolayer molecule and a therapeutic agent attached to the second functional group. The therapeutic agent may be attached to the SAM molecule via a linker. The present invention also concerns methods of administering a therapeutic agent to a subject, comprising contacting the subject with one of the medical devices set forth herein.
  [FR] L'invention concerne des dispositifs médicaux comprenant une ou plusieurs surfaces, une ou plusieurs molécules SAM attachées à une ou plusieurs surfaces du dispositif médical, et un ou plusieurs agents thérapeutiques fixés sur les molécules de la ou des monocouches auto-assemblées. L'invention concerne en outre des dispositifs médicaux comprenant une ou plusieurs surfaces, une ou plusieurs molécules de monocouche auto-assemblée fixées à la surface ou aux surfaces du dispositif médical, un ou plusieurs lieurs comprenant un premier groupe fonctionnel et un second groupe fonctionnel, le premier groupe fonctionnel étant attaché à la molécule de la monocouche auto-assemblée, et un agent thérapeutique attaché au second groupe fonctionnel. L'agent thérapeutique peut être fixé sur la molécule SAMS par l'intermédiaire d'un lieur. L'invention porte également sur des procédés d'administration d'un agent thérapeutique à un sujet consistant appliquer un dispositif médical du type décrit à un sujet.