(2S,3S,4R,5S)-1-butyl-3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]piperidine | 441061-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4R,5S)-1-butyl-3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]piperidine
• 英文别名: (2S,3S,4R,5S)-1-butyl-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)piperidine
• CAS: 441061-42-3
• 化学式: C₃₈H₄₅NO₄
• 分子量: 579.78
• InChiKey: DZPAABGOOAWABR-IZBQCXFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S)-1-butyl-3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]piperidine 在 氢气 、 palladium dichloride 作用下， 以 甲醇 为溶剂， 以70%的产率得到(2S,3S,4R,5S)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol
  参考文献：
  名称：

  Pharmaceutically active piperidine derivatives

  摘要：

  式(I)的化合物：其中R代表各种取代基团，可用作葡糖基硫脂合成酶的抑制剂。

  公开号：

  US09199935B2
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-galactitol 在 吡啶 作用下， 反应 120.0h， 生成 (2S,3S,4R,5S)-1-butyl-3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]piperidine
  参考文献：
  名称：

  Pharmaceutically active piperidine derivatives

  摘要：

  式(I)的化合物：其中R代表各种取代基团，可用作葡糖基硫脂合成酶的抑制剂。

  公开号：

  US09199935B2

文献信息

• Pharmaceutically active piperidine derivatives
  申请人：Butters Terence D.

  公开号：US09199935B2

  公开（公告）日：2015-12-01

  Compounds of formula (I): wherein R represents various substituent groups, are useful as inhibitors of glucosylceramide synthase.

  式(I)的化合物：其中R代表各种取代基团，可用作葡糖基硫脂合成酶的抑制剂。
• Dual-Action Lipophilic Iminosugar Improves Glycemic Control in Obese Rodents by Reduction of Visceral Glycosphingolipids and Buffering of Carbohydrate Assimilation
  作者：Tom Wennekes、Alfred J. Meijer、Albert K. Groen、Rolf G. Boot、Johanna E. Groener、Marco van Eijk、Roelof Ottenhoff、Nora Bijl、Karen Ghauharali、Hang Song、Tom J. O’Shea、Hanlan Liu、Nelson Yew、Diane Copeland、Richard J. van den Berg、Gijsbert A. van der Marel、Herman S. Overkleeft、Johannes M. Aerts

  DOI：10.1021/jm901281m

  日期：2010.1.28

  The lipophilic iminosugar N-[5-(adamantan-1-ylmethoxy)pentyl]-1-deoxynojirimycin (2, AMP-DNM) potently controls hyperglycemia in obese rodent models of insulin resistance. The reduction of visceral glycosphingolipids by 2 is thought to underlie its beneficial action. It cannot, however, be excluded that concomitant inhibition of intestinal glycosidases and associated buffering of carbohydrate assimilation add to this. To firmly establish the mode of action or 2, we developed a panel of lipophilic iminosugars varying in configuration at C-4/C-5 and N-substitution of the iminosugar. From these we identified the L-ido derivative of 2, L-ido-AMP-DNM (4), as a selective inhibitor of glycosphingolipid synthesis. Compound 4 lowered visceral glycosphingolipids in ob/ob mice and ZDF rats on a par with 2. In contrast to 2, 4 did not inhibit sucrase activity or sucrose assimilation. Treatment with 4 was significantly less effective in reducing blood glucose and HbAlc. We conclude that the combination of reduction of glycosphingolipids in tissue and buffering of carbohydrate assimilation by 2 produces a superior glucose homeostasis.