7-O-β-D-吡喃葡萄糖基-Alpha-后莫野尻霉素 | 104343-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 7-O-β-D-吡喃葡萄糖基-Alpha-后莫野尻霉素
• 中文别名: 7-O-β-D-吡喃葡萄糖基-α-后莫野尻霉素
• 英文名称: 2,6-dideoxy-7-O-(β-D-glucopyranosyl) 2,6-imino-D-glycero-L-gulo-heptitol
• 英文别名: 7-O-β-D-glucopyranosyl α-homonojirimycin；7-O-β-D-glucopyranosyl-α-homonojirimycin；7-O-β-glucopyranosyl-α-homonojirimycin；MDL 25637；(2R,3R,4S,5S,6R)-2-(hydroxymethyl)-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)methyl)piperidine-3,4,5-triol；2,6-imino-2,6-dideoxy-7-O-(β-D-glucopyranosyl)-D-glycero-L-gulo-heptitol；(2R,3R,4S,5S,6R)-2-(hydroxymethyl)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]piperidine-3,4,5-triol
• CAS: 104343-33-1
• 化学式: C₁₃H₂₅NO₁₀
• 分子量: 355.342
• InChiKey: VCIPQQCYKMORDY-KBYFLBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  192
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 7-O-β-D-吡喃葡萄糖基-Alpha-后莫野尻霉素 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以49 mg的产率得到N-butyl-7-O-β-D-glucopyranosyl-α-homonojirimycin
  参考文献：
  名称：

  α-Glucosidase-inhibitory iminosugars from the leaves of Suregada glomerulata

  摘要：

  A water extract of the leaves of Suregada glomerulata (Euphorbiaceae) was found to inhibit rat small intestinal alpha-glucosidase. An examination of the extract afforded 20 iminosugars including one pyrrolidine and 19 piperidines. The structures of the 10 new compounds (11-20) were determined by NMR, and MS spectroscopic data analyses, and chemical correlations. The novelty of the identified compounds mainly stems from the loss of a hydroxy at C-4 and the presence of an 8-hydroxyoctyl side chain. Nine N-alkyl derivatives including N-methyl (1a, 8a, and 13a), N-butyl (1b, 2b, and 9b) and N,N-dimethyl (1c, 2c, and 9c) were synthesized. The compounds were tested for rat small intestinal a-glucosidase inhibitory activity. In total, 15 compounds, including compounds 11, 12, 15, and 19 and the three derivatives 8a, 9b, and 13a, showed inhibitory activity with IC50 values less than 40 mu M. In vivo results showed that total alkaloids of S. glomerulata (10 mg/kg) and four major iminosugars 1, 2, 3, and 9 (10 mg/kg) can lower the postprandial blood glucose level after sucrose and starch load in healthy male ICR mice. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.048
• 作为产物：
  描述：

  2,6-dideoxy-2,6-<<(phenylmethoxy)carbonyl>imino>-7-O-<2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-glucopyranosyl>-1,3,4,5-tetrakis-O-(phenylmethyl)-D-glycero-L-gulo-hepitol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 72.0h， 以74%的产率得到7-O-β-D-吡喃葡萄糖基-Alpha-后莫野尻霉素
  参考文献：
  名称：

  Total synthesis of 2,6-dideoxy-2,6-imino-7-O-(.beta.-D-glucopyranosyl)-D-glycero-L-gulo-heptitol hydrochloride. A potent inhibitor of .alpha.-glucosidases

  摘要：

  DOI：

  10.1021/jo00230a012

文献信息

• PYRIDONE GPR119 G PROTEIN-COUPLED RECEPTOR AGONISTS
  申请人：Wacker Dean A.

  公开号：US20090023702A1

  公开（公告）日：2009-01-22

  Novel compounds are provided which are GPR119 G protein-coupled receptor modulators. GPR119 G protein-coupled receptor modulators are useful in treating, preventing, or slowing the progression of diseases requiring GPR 119 G protein-coupled receptor modulator therapy. These novel compounds have the structure Formula I or Formula IA.

  提供了一些新的化合物，它们是GPR119 G蛋白偶联受体调节剂。GPR119 G蛋白偶联受体调节剂在治疗、预防或减缓需要GPR 119 G蛋白偶联受体调节剂疗法的疾病方面非常有用。这些新的化合物具有结构式I或结构式IA。
• PYRIMIDINYLPIPERIDINYLOXYPYRIDINONE ANALOGUES AS GPR119 MODULATORS
  申请人：Wacker Dean

  公开号：US20110251221A1

  公开（公告）日：2011-10-13

  Novel compounds of structure Formula I: or an enantiomer, a diastereomer, or a pharmaceutically acceptable salt thereof, wherein n 1 , R 1 , R 2 , R 3 and R 4 are defined herein, are provided which are GPR119 G protein-coupled receptor modulators. GPR119 G protein-coupled receptor modulators are useful in treating, preventing, or slowing the progression of diseases requiring GPR119 G protein-coupled receptor modulator therapy. Thus, the disclosure also concerns compositions comprising these novel compounds and methods of treating diseases or conditions related to the activity of the GPR119 G protein-coupled receptor by using any of these novel compounds or a composition comprising any of such novel compounds.

  结构式I的新化合物：或其对映体、非对映体异构体或药用可接受盐，其中n1、R1、R2、R3和R4在此处定义，这些化合物是GPR119 G蛋白偶联受体调节剂。GPR119 G蛋白偶联受体调节剂在治疗、预防或减缓需要GPR119 G蛋白偶联受体调节剂治疗的疾病方面是有用的。因此，该公开还涉及包含这些新化合物的组合物以及使用任何这些新化合物或包含任何这些新化合物的组合物治疗与GPR119 G蛋白偶联受体活性相关的疾病或症状的方法。
• [EN] ISOTOPICALLY LABELED TRIAZOLOPYRIDINE 11-BETA HYDROXYSTEROID DEHYDROGENASE TYPE I INHIBITORS<br/>[FR] INHIBITEURS DE TRIAZOLOPYRIDINE 11-BÊTA HYDROXYSTÉROÏDE DÉSHYDROGÉNASE DE TYPE 1 À MARQUAGE ISOTOPIQUE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015061272A1

  公开（公告）日：2015-04-30

  Novel compounds are provided which are 11-beta-hydroxysteroid dehydrogenase type I inhibitors. 11-beta-hydroxysteroid dehydrogenase type I inhibitors are useful in treating, preventing, or slowing the progression of diseases requiring 11-beta-hydroxysteroid dehydrogenase type I inhibitor therapy. These novel compounds of formula I: or stereoisomers or pharmaceutically acceptable salts thereof, wherein R* is an isotopically labeled hydroxypropyl moiety.

  提供了新的化合物，它们是11-beta-羟基类固醇脱氢酶I型抑制剂。11-beta-羟基类固醇脱氢酶I型抑制剂在治疗、预防或减缓需要11-beta-羟基类固醇脱氢酶I型抑制剂治疗的疾病方面非常有用。这些新的化合物的化学式为I：或其立体异构体或药学上可接受的盐，其中R*是同位素标记的羟丙基基团。
• [6,5]-BICYCLIC GPR119 G PROTEIN-COUPLED RECEPTOR AGONISTS
  申请人：Fevig John M.

  公开号：US20090018055A1

  公开（公告）日：2009-01-15

  Novel compounds are provided which are GPR119 G protein-coupled receptor modulators. GPR119 G protein-coupled receptor modulators are useful in treating, preventing, or slowing the progression of diseases requiring GPR119 G protein-coupled receptor modulator therapy. These novel compounds have the structure: or stereoisomers or prodrugs or pharmaceutically acceptable salts thereof, wherein n 2 , n 3 , n 4 , A, B, D, E, G, J, Y, R 1 and R 2 are defined herein.

  提供了一种新型化合物，它们是GPR119 G蛋白偶联受体调节剂。GPR119 G蛋白偶联受体调节剂在治疗、预防或减缓需要GPR119 G蛋白偶联受体调节剂治疗的疾病方面非常有用。这些新型化合物的结构为：或其立体异构体、前药或药物可接受的盐，其中n2、n3、n4、A、B、D、E、G、J、Y、R1和R2在此定义。
• METHOD FOR MODULATING GPR119 G PROTEIN-COUPLED RECEPTOR AND SELECTED COMPOUNDS
  申请人：Wacker Dean A.

  公开号：US20090042919A1

  公开（公告）日：2009-02-12

  A method of modulating the activity of the GPR119 G protein-coupled receptor comprising administering to a mammalian patient in need thereof a therapeutically effective amount of at least one compound of Formula I or Formula IA and, optionally, an additional therapeutic agent.

  一种调节GPR119 G蛋白偶联受体活性的方法，包括向需要治疗的哺乳动物患者施用至少一种公式I或公式IA化合物的治疗有效量，以及可选的其他治疗剂。