N-benzylmannofuranosylamine 2,3:5,6-diacetonide | 135902-07-7

• 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: N-benzylmannofuranosylamine 2,3:5,6-diacetonide
• 英文别名: 2,3:5,6-Di-O-isopropylidene-1-benzylamino-α-D-mannofuranose；5,6-di-O-isopropylidene-N-benzyl-D-mannosylamine；(3aS,6R,6aS)-N-benzyl-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-amine
• CAS: 135902-07-7
• 化学式: C₁₉H₂₇NO₅
• 分子量: 349.427
• InChiKey: MZDYMHBYBKBWMC-ILUDGRTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzylmannofuranosylamine 2,3:5,6-diacetonide 在 palladium on activated charcoal 、 potassium tert-butylate 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 (SSRR)-(3-acetamide-4-2.2-dimethyl-[1.3]dioxolan-4-yl)-2.2-dimethyl-2-oxo-2-phenyltetrahydro-2λ⁵-[1.2]oxaphosphinane
  参考文献：
  名称：

  SUGAR-ANALOG PHOSPHORUS-CONTAINING HETEROCYCLES HAVING AN ANTI-METASTATIC ACTIVITY

  摘要：

  使用在描述中定义的式（1）化合物，用于减少或预防患有癌症的患者出现转移的发生。还描述了用于人类或兽医药物的制剂，其中至少包含一种式（1）化合物。

  公开号：

  US20150376216A1
• 作为产物：
  描述：

  2,3,5,6-di-O-isopropylidene-D-mannofuranose 、 苄胺 在 magnesium sulfate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以58%的产率得到N-benzylmannofuranosylamine 2,3:5,6-diacetonide
  参考文献：
  名称：

  C-Glycoside Mimetics Inhibit Glioma Stem Cell Proliferation, Migration, and Invasion

  摘要：

  This paper reports the design and synthesis of C-glycoside mimetics (d-glycero-d-talo- and d-glycero-d-galactopyranose analogues), a subset of the recently published phostines, belonging to the [1,2]oxaphosphinane core. Eighteen new compounds were tested against 11 cancer cell types belonging to six categories of tumor tissues and three different species. The hit compound 5.3d inhibited invasion and migration of both GBM stem cells (Gli7 and Gli4) and GBM cancer cell lines (C6, SNB75) on fibronectin, vitronectin, and laminin. Ki values for Gli7 and Gli4 migration inhibition on fibronectin were16 and 31 nM respectively. Ki values for invasion inhibition in a 3D system were 46 nM for Gli7 and 290 nM for Gli4. These activities were associated with an antiproliferative effect on Gli4 (EC50 = 5.20 mu M) and Gli7 (EC50 = 2.33 mu M). In conclusion, the heptopyranose mimetic 5.3d, devoid of toxicity on astrocyte and cortical neuron cultures at concentrations below 100 mu M, opens new therapeutic perspectives against

  DOI：

  10.1021/jm500522y

文献信息

• Renin inhibitory pentols showing improved enteral bioavailability
  作者：Heinz Werner Kleemann、Holger Heitsch、Rainer Henning、Werner Kramer、Walter Kocher、Ulrich Lerch、Wolfgang Linz、Wolf Ulrich Nickel、Dieter Ruppert

  DOI：10.1021/jm00081a019

  日期：1992.2

  Incorporation of a C-terminal pentahydroxy functionality led to potent, low molecular weight hydrophilic renin inhibitors lacking the P1' side chain. As these compounds are easy to synthesize and have sufficient water solubility, they were chosen for further study. Compound 33 was transported across rabbit intestinal brush border membrane vesicles and yielded a hypotensive effect in sodium-depleted rhesus monkeys which lasted for 90 min when dosed at 2 mg/kg id.
• [EN] SUGAR-ANALOG PHOSPHORUS-CONTAINING HETEROCYCLES HAVING AN ANTI-METASTATIC ACTIVITY<br/>[FR] HÉTÉROCYCLES PHOSPHORÉS ANALOGUES DE SUCRES À ACTIVITÉ ANTIMÉTASTATIQUE
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2014128429A1

  公开（公告）日：2014-08-28

  L'invention concerne l'utilisation de composés de formule (1) telle que définie dans la présente description pour réduire ou prévenir l'apparition de métastases chez un patient atteint d'un cancer. L'invention fournit aussi des compositions pharmaceutiques pour une utilisation en médecine humaine ou vétérinaire, qui comprennent au moins un composé de formule (1).
• <i>C</i>-Glycoside Mimetics Inhibit Glioma Stem Cell Proliferation, Migration, and Invasion
  作者：Ludovic Clarion、Carine Jacquard、Odile Sainte-Catherine、Marc Decoux、Séverine Loiseau、Marc Rolland、Marc Lecouvey、Jean-Philippe Hugnot、Jean-Noël Volle、David Virieux、Jean-Luc Pirat、Norbert Bakalara

  DOI：10.1021/jm500522y

  日期：2014.10.23

  This paper reports the design and synthesis of C-glycoside mimetics (d-glycero-d-talo- and d-glycero-d-galactopyranose analogues), a subset of the recently published phostines, belonging to the [1,2]oxaphosphinane core. Eighteen new compounds were tested against 11 cancer cell types belonging to six categories of tumor tissues and three different species. The hit compound 5.3d inhibited invasion and migration of both GBM stem cells (Gli7 and Gli4) and GBM cancer cell lines (C6, SNB75) on fibronectin, vitronectin, and laminin. Ki values for Gli7 and Gli4 migration inhibition on fibronectin were16 and 31 nM respectively. Ki values for invasion inhibition in a 3D system were 46 nM for Gli7 and 290 nM for Gli4. These activities were associated with an antiproliferative effect on Gli4 (EC50 = 5.20 mu M) and Gli7 (EC50 = 2.33 mu M). In conclusion, the heptopyranose mimetic 5.3d, devoid of toxicity on astrocyte and cortical neuron cultures at concentrations below 100 mu M, opens new therapeutic perspectives against
• SUGAR-ANALOG PHOSPHORUS-CONTAINING HETEROCYCLES HAVING AN ANTI-METASTATIC ACTIVITY
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIRIQUE

  公开号：US20150376216A1

  公开（公告）日：2015-12-31

  The use of compounds of formula (1) as defined in the description, for reducing or preventing the onset of metastases in a patient suffering from cancer. Pharmaceutical compositions for using in human or veterinary medicine, including at least one compound of formula (1) are also described.

  使用在描述中定义的式（1）化合物，用于减少或预防患有癌症的患者出现转移的发生。还描述了用于人类或兽医药物的制剂，其中至少包含一种式（1）化合物。