(Sp,S,S,S,R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[4-methoxypheny]l-2-oxo-2λ5-[1,2]oxaphosphinane | 1359860-02-8

• 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: (Sp,S,S,S,R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[4-methoxypheny]l-2-oxo-2λ5-[1,2]oxaphosphinane
• 英文别名: (2S,3S,4S,5S,6R)-3-azido-2-phenyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-1,2lambda5-oxaphosphinane 2-oxide；(2S,3S,4S,5S,6R)-3-azido-2-phenyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-1,2λ5-oxaphosphinane 2-oxide
• CAS: 1359860-02-8
• 化学式: C₃₂H₃₂N₃O₅P
• 分子量: 569.597
• InChiKey: NBFWMJRCAJCJEF-ZXPFLCMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Sp,S,S,S,R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[4-methoxypheny]l-2-oxo-2λ5-[1,2]oxaphosphinane 在 polymer-bound triphenylphosphine 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以0.074 g的产率得到(Sp,S,S,S,R)-3-amino-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane
  参考文献：
  名称：

  Oxaphosphinanes: New Therapeutic Perspectives for Glioblastoma

  摘要：

  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.

  DOI：

  10.1021/jm201428a
• 作为产物：
  描述：

  在 叠氮基三甲基硅烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (Sp,S,S,S,R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[4-methoxypheny]l-2-oxo-2λ5-[1,2]oxaphosphinane 、 (Sp,R,S,S,R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[4-methoxypheny]l-2-oxo-2λ5-[1,2]oxaphosphinane
  参考文献：
  名称：

  Oxaphosphinanes: New Therapeutic Perspectives for Glioblastoma

  摘要：

  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.

  DOI：

  10.1021/jm201428a