(2S_p,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-O-trifluoromethane sulfonyl-2-phenyl-2-oxo-2λ⁵-[1,2]-oxaphosphinane | 1359860-01-7

• 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: (2S_p,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-O-trifluoromethane sulfonyl-2-phenyl-2-oxo-2λ⁵-[1,2]-oxaphosphinane
• 英文别名: (Sp,R,S,S,R)-3-O-trifluoromethanesulfonyl-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane
• CAS: 1359860-01-7
• 化学式: C₃₃H₃₂F₃O₈PS
• 分子量: 676.647
• InChiKey: RQHWWYWQWFCCAS-AYDBBHOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S_p,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-O-trifluoromethane sulfonyl-2-phenyl-2-oxo-2λ⁵-[1,2]-oxaphosphinane 在 potassium fluoride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以41%的产率得到(2R_p,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ⁵-[1,2]oxa phosphine-3-ene
  参考文献：
  名称：

  α-Halogenated oxaphosphinanes: Synthesis, unexpected reactions and evaluation as inhibitors of cancer cell proliferation

  摘要：

  This paper describes the preparation and the biological evaluation of a-halogenated oxaphosphinanes. These halogen derivatives were synthetized from a short and stereoselective synthetic sequence starting by previously described hydroxy-precursors 1 and 2 with respectively a glucose and mannose-like configuration. The in vitro biological tests of these unnatural halogenated phosphinosugars, on several cell lines, highlighted, for some of them, their antiproliferative and anti migration and invasion properties at nanomolar concentration. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.027
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (3R)-hydroxy-(4S,5S)-bis-benzyloxy-(6R)-benzyloxymethyl-(2S)-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以44%的产率得到(2S_p,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-O-trifluoromethane sulfonyl-2-phenyl-2-oxo-2λ⁵-[1,2]-oxaphosphinane
  参考文献：
  名称：

  α-Halogenated oxaphosphinanes: Synthesis, unexpected reactions and evaluation as inhibitors of cancer cell proliferation

  摘要：

  This paper describes the preparation and the biological evaluation of a-halogenated oxaphosphinanes. These halogen derivatives were synthetized from a short and stereoselective synthetic sequence starting by previously described hydroxy-precursors 1 and 2 with respectively a glucose and mannose-like configuration. The in vitro biological tests of these unnatural halogenated phosphinosugars, on several cell lines, highlighted, for some of them, their antiproliferative and anti migration and invasion properties at nanomolar concentration. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.027

文献信息

• Oxaphosphinanes: New Therapeutic Perspectives for Glioblastoma
  作者：Ludovic Clarion、Carine Jacquard、Odile Sainte-Catherine、Séverine Loiseau、Damien Filippini、Marie-Hélène Hirlemann、Jean-Noël Volle、David Virieux、Marc Lecouvey、Jean-Luc Pirat、Norbert Bakalara

  DOI：10.1021/jm201428a

  日期：2012.3.8

  This paper reports the design and the synthesis of a new family of compounds, the phostines, belonging to the [1,2]oxaphosphinane family. Twenty-six compounds have been screened for their antiproliferative activity against a large panel of NCI cancer cell lines. Because of its easy synthesis and low EC50 value (500 nM against the C6 rat glioma cell line); compound 3.1a was selected for further biological study. Moreover, the specific biological effect of 3.1a on the glioblastoma phylogenetic cluster from the NCI is dependent on its stereochemistry. Within that cluster, 3.1a has a higher antiproliferative activity than Temozolomide and is more potent than paclitaxel for the SF295 and SNB75 cell lines. In constrast with paclitaxel and vincristine, 3.1a is devoid of astrocyte toxicity. The original activity spectrum of 3.1a on the NCI cancer cell line panel allows the development of this family for use in association with existing drugs, opening new therapeutic perspectives.