tert-butyl (S)-4-((3-hydroxyphenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate | 1239586-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl (S)-4-((3-hydroxyphenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS: 1239586-96-9
• 化学式: C₁₇H₂₅NO₅
• 分子量: 323.389
• InChiKey: INZDUTQRANUMFR-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  亚磷酸二苄酯 、 tert-butyl (S)-4-((3-hydroxyphenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate 在 四溴化碳 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以76%的产率得到tert-butyl (S)-4-((3-(bis-(benzyloxy)phosphoryloxy)phenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and In Vitro evaluation on glucosamine-6P synthase of aromatic analogs of 2-Aminohexitols-6P

  摘要：

  The aminosugars are very important structural components of bacterial and fungi cell walls. Glucosamine-6-phosphate synthase (GlmS), which catalyses the first step of the aminosugar biosynthetic pathway i.e. the formation of D-glucosamine-6-phosphate from D-fructose-6-phosphate, is therefore an interesting target in the fight against microorganisms. In this work is described the synthesis of aromatic analogs of 2-amino-2-deoxy-D-glucitol-6-phosphate (ADGP) and its epimer 2-amino-2-deoxy-D-manitol-6-phosphate (ADMP), two important inhibitors of GlmS. The aromatic analogs displayed modest inhibitory activity against GlmS, with IC50 in the mmol L-1 range.

  DOI：

  10.1590/s0103-50532010000400014
• 作为产物：
  描述：

  (S)-(-)-3-BOC-4-甲氧羰基-2,2-二甲基-1,3-恶唑烷 在 锂硼氢 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 tert-butyl (S)-4-((3-hydroxyphenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Discovery of cytotoxic and pro-apoptotic compounds against leukemia cells: Tert-butyl-4-[(3-nitrophenoxy) methyl]-2,2-dimethyloxazolidine-3-carboxylate

  摘要：

  Aims: We evaluated biological activity in leukemia cells lines of R and S enantiomers of tert-butyl 4-[(3-nitrophenoxy)-methyl]-2,2-dimethyloxazolidine-3-carboxylate (BNDC).Main methods: Cytotoxic activity was assessed by MTT assay. Flow cytometry assays were used to determined DNA fragmentation (Propidium Iodide-PI staining) and phosphatidylserine exposure (Annexin-V and PI staining). DNA condensation was evaluated by fluorescence microscopy using double-staining in leukemia cells (Hoechst and PI). Caspase activities were measured using Z-VAD-FMK, a non-selective caspase inhibitor, by flow cytometry and Z-DEVD-AMC, a selective caspase-3 substrate, by fluorescence spectrometry.Key findings: Both enantiomers displayed cytotoxic activity against leukemia cell lines (HL60, HL60.Bcl-2, HL60.Bcl-XL and Jurkat) with low toxicity against human peripheral blood mononuclear cell - PBMC based on IC50 values. In HL60 cell lines, compounds induce exposure of phosphatidylserine and DNA fragmentation, which could be blocked by pretreatment of cells with Z-VAD-FMK. Confirming this observation, both enantiomers induced caspase-3 activation. Additional analysis revealed an increased percentage of apoptotic cells (defined as those with fragmented nuclei and condensed chromatin) after treatment with compounds.Significance: Taken together, the results indicate that BNDC compounds exhibited cytotoxic and pro-apoptotic activities and have a potential for developing a new class of anticancer drugs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2011.09.012