(R_P,3R,4S,5R,6R,4'R)-3-hydroxy-4-(2.2-dimethyl[1.3]dioxolan-4-yl)-2.2-dimethyl-2-oxo-2-phenyltetrahydro-2λ⁵-[1.2]oxaphosphinane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R_P,3R,4S,5R,6R,4'R)-3-hydroxy-4-(2.2-dimethyl[1.3]dioxolan-4-yl)-2.2-dimethyl-2-oxo-2-phenyltetrahydro-2λ⁵-[1.2]oxaphosphinane
• 英文别名: 4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-oxo-6-phenyl-tetrahydro-6λ⁵-[1,3]dioxolo[4,5-d][1,2]oxaphosphinin-7-ol；4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-2-oxo-2-phenyl-tetrahydro-6λ*5*-[1,3]dioxolo[4,5-d][1,2]oxaphosphinan-3-ol；(3aR,4R,6R,7R,7aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-oxo-6-phenyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-d]oxaphosphinin-7-ol
• 化学式: C₁₈H₂₅O₇P
• 分子量: 384.366
• InChiKey: MAKXAOVRUMEYMV-MSXRDDOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R_P,3R,4S,5R,6R,4'R)-3-hydroxy-4-(2.2-dimethyl[1.3]dioxolan-4-yl)-2.2-dimethyl-2-oxo-2-phenyltetrahydro-2λ⁵-[1.2]oxaphosphinane 在 Amberlyst(R) resin 作用下， 以 甲醇 为溶剂， 反应 120.0h， 生成 6-(1,2-dihydroxyethyl)-2-oxo-phenyl-2λ⁵-[1,2]oxaphosphinane-3,4,5-triol
  参考文献：
  名称：

  First synthesis of P-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides

  摘要：

  The synthesis and X-ray crystal structure of the first example of arylphosphinosugar are reported. The protected polyhydroxylated 1,2-oxaphosphinane is prepared by a two steps sequence (phenylphosphinate addition on protected mannofuranose followed by intramolecular transesterification) on gram scale. Deprotection of the di-isopropylidene derivative using acidic cation-exchange resin affords the free hydroxy organophosphorus heterocycle analogous to C-arylglycosides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.148
• 作为产物：
  描述：

  2,3,5,6-di-O-isopropylidene-D-mannofuranose 、 methyl phenylphosphinate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以39%的产率得到(R_P,3R,4S,5R,6R,4'R)-3-hydroxy-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：

  First synthesis of P-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides

  摘要：

  The synthesis and X-ray crystal structure of the first example of arylphosphinosugar are reported. The protected polyhydroxylated 1,2-oxaphosphinane is prepared by a two steps sequence (phenylphosphinate addition on protected mannofuranose followed by intramolecular transesterification) on gram scale. Deprotection of the di-isopropylidene derivative using acidic cation-exchange resin affords the free hydroxy organophosphorus heterocycle analogous to C-arylglycosides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.148

文献信息

• [EN] NEW PHOSPHORUS CONTAINING HETEROCYCLIC COMPOUNDS, SUGAR ANALOGUES, AND COMPOSITIONS HAVING ANTI-CANCER ACTIVITY CONTAINING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS HÉTÉROCYCLIQUES CONTENANT DU PHOSPHORE, ANALOGUES DE SUCRES, ET COMPOSITIONS AYANT UNE ACTIVITÉ ANTICANCÉREUSE LES CONTENANT
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2009004096A1

  公开（公告）日：2009-01-08

  The invention provides new anticancer compounds of formula (1) such as defined in the present description. The invention also provides pharmaceutical compositions to be used in human or veterinary medicine, comprising at least one compound of formula (1). The present invention further relates to a compound of formula (1) such as defined in the present description, for use as a drug. The invention further relates to the use of a compound of formula (1) for manufacturing a human or animal anticancer pharmaceutical composition.

  该发明提供了新的抗癌化合物，其化学式为（1），如本说明中所定义。该发明还提供了用于人类或兽医药物的制剂，包括至少一种化合物（1）。本发明进一步涉及一种化合物，其化学式为（1），如本说明中所定义，用作药物。该发明还涉及使用化合物（1）制造人类或动物抗癌药物组合物。
• <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
• First synthesis of P-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides
  作者：Henri-Jean Cristau、Jérôme Monbrun、Julie Schleiss、David Virieux、Jean-Luc Pirat

  DOI：10.1016/j.tetlet.2005.03.148

  日期：2005.5

  The synthesis and X-ray crystal structure of the first example of arylphosphinosugar are reported. The protected polyhydroxylated 1,2-oxaphosphinane is prepared by a two steps sequence (phenylphosphinate addition on protected mannofuranose followed by intramolecular transesterification) on gram scale. Deprotection of the di-isopropylidene derivative using acidic cation-exchange resin affords the free hydroxy organophosphorus heterocycle analogous to C-arylglycosides. (c) 2005 Elsevier Ltd. All rights reserved.