(3R,4S)-3-[(triethylsilyl)oxy]-4-(furan-2-yl)-3-methyl-azetidinone | 496918-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-3-[(triethylsilyl)oxy]-4-(furan-2-yl)-3-methyl-azetidinone
• 英文别名: (3R,4S)-4-(furan-2-yl)-3-triethylsilyloxy-3-methyl-azetidin-2-one；(3R,4S)-4-(furan-2-yl)-3-methyl-3-triethylsilyloxyazetidin-2-one
• CAS: 496918-70-8
• 化学式: C₁₄H₂₃NO₃Si
• 分子量: 281.427
• InChiKey: DGFXFLQHJUMZAU-GXTWGEPZSA-N

物化性质

• 沸点：
  374.6±42.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-[(triethylsilyl)oxy]-4-(furan-2-yl)-3-methyl-azetidinone 在 4-二甲氨基吡啶 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15R,16S)-4,12-diacetyloxy-15-[(2R,3S)-3-(furan-2-yl)-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-triethylsilyloxypropanoyl]oxy-10,14,20,20-tetramethyl-11,18-dioxo-9-triethylsilyloxy-6,17,19-trioxapentacyclo[11.6.1.01,16.03,10.04,7]icos-13-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2‘-Methyl Taxoids Derived from Baccatin III and 14β-OH-Baccatin III 1,14-Carbonate

  摘要：

  A series of 2'-methyl taxoids were synthesized and essayed for growth inhibition experiments conducted in human ovarian cancer cell line A2780wt and its counterparts A2780cis, A2780tax, and A2780adr, resistant to cisplatin, paclitaxel, and doxorubicin, respectively, to test the effect of this substituent on the antitumor activity. Additional experiments were performed on MCF-7 human breast cancer cell line and MCF7-R resistant to doxorubicin. In several cases these taxoids were more active than paclitaxel showing subnanomolar IC50 values.

  DOI：

  10.1021/jm034146v
• 作为产物：
  描述：

  (furan-2-ylmethylene)(trimethylsilanyl)amine 在 咪唑 、 六甲基磷酰三胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,4S)-3-[(triethylsilyl)oxy]-4-(furan-2-yl)-3-methyl-azetidinone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2‘-Methyl Taxoids Derived from Baccatin III and 14β-OH-Baccatin III 1,14-Carbonate

  摘要：

  A series of 2'-methyl taxoids were synthesized and essayed for growth inhibition experiments conducted in human ovarian cancer cell line A2780wt and its counterparts A2780cis, A2780tax, and A2780adr, resistant to cisplatin, paclitaxel, and doxorubicin, respectively, to test the effect of this substituent on the antitumor activity. Additional experiments were performed on MCF-7 human breast cancer cell line and MCF7-R resistant to doxorubicin. In several cases these taxoids were more active than paclitaxel showing subnanomolar IC50 values.

  DOI：

  10.1021/jm034146v

文献信息

• C-2' methylated derivatives of paclitaxel for use as antitumour agents
  申请人：——

  公开号：US20040242674A1

  公开（公告）日：2004-12-02

  Taxane derivatives of formula (I) in which: R is trifluoromethyl, phenyl, 2-furyl, 2-thienyl; R 1 is t-butoxycarbonyl or benzoyl; R 2 is hydroxy; R 3 is hydrogen or, together with R 2 , it forms the residue of a cyclic carbonate of formula: [I] with the proviso that when R3 is hydrogen, R is different from phenyl. Compounds of formula (I) have antitumor activity. 1

  公式（I）的紫杉烷衍生物，其中：R是三氟甲基，苯基，2-呋喃基，2-噻吩基; R1是叔丁氧羰基或苯甲酰基; R2是羟基; R3是氢或与R2一起形成公式的环状碳酸酯残基：[I]，但当R3为氢时，R与苯基不同。化合物公式（I）具有抗肿瘤活性。
• C-2′ methylated derivatives of paclitaxel for use as antitumour agents
  申请人：Indena S.p.A.

  公开号：US07153884B2

  公开（公告）日：2006-12-26

  Taxane derivatives of formula (I) in which: R is trifluoromethyl, phenyl, 2-furyl, 2-thienyl; R1 is t-butoxycarbonyl or benzoyl; R2 is hydroxy; R3 is hydrogen or, together with R2, it forms the residue of a cyclic carbonate of formula: II with the proviso that when R3 is hydrogen, R is different from phenyl. Compounds of formula (I) have antitumor activity

  公式（I）的紫杉烷衍生物：其中：R是三氟甲基，苯基，2-呋喃基，2-噻吩基；R1是t-丁氧羰基或苯甲酰基；R2是羟基；R3是氢或与R2一起形成公式II的环碳酸酯残基，但是当R3为氢时，R与苯基不同。公式（I）的化合物具有抗肿瘤活性。
• Synthesis and Biological Evaluation of 2‘-Methyl Taxoids Derived from Baccatin III and 14β-OH-Baccatin III 1,14-Carbonate
  作者：Arturo Battaglia、Ralph J. Bernacki、Carlo Bertucci、Ezio Bombardelli、Samanta Cimitan、Cristiano Ferlini、Gabriele Fontana、Andrea Guerrini、Antonella Riva

  DOI：10.1021/jm034146v

  日期：2003.11.1

  A series of 2'-methyl taxoids were synthesized and essayed for growth inhibition experiments conducted in human ovarian cancer cell line A2780wt and its counterparts A2780cis, A2780tax, and A2780adr, resistant to cisplatin, paclitaxel, and doxorubicin, respectively, to test the effect of this substituent on the antitumor activity. Additional experiments were performed on MCF-7 human breast cancer cell line and MCF7-R resistant to doxorubicin. In several cases these taxoids were more active than paclitaxel showing subnanomolar IC50 values.