[(2R,3R,4S,5S)-2-(3',4'-methylenedioxy)phenyl-3-hydroxy-4,5-isopropylidenedioxy-6-tert-butyldimethylsilyloxy]hexyl benzamide | 1010821-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: [(2R,3R,4S,5S)-2-(3',4'-methylenedioxy)phenyl-3-hydroxy-4,5-isopropylidenedioxy-6-tert-butyldimethylsilyloxy]hexyl benzamide
• 英文别名: N-((2R,3R)-2-(benzo[d][1,3]dioxol-5-yl)-3-((4S,5S)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropyl)benzamide；N-[(2R,3R)-2-(1,3-benzodioxol-5-yl)-3-[(4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropyl]benzamide
• CAS: 1010821-36-9
• 化学式: C₂₉H₄₁NO₇Si
• 分子量: 543.733
• InChiKey: HZWJSPQRTMLPAY-DTGGKOQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S)-2-(3',4'-methylenedioxy)phenyl-3-hydroxy-4,5-isopropylidenedioxy-6-tert-butyldimethylsilyloxy]hexyl benzamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到[(2R,3R,4S,5S)-2-(3',4'-methylenedioxy)phenyl-3,6-dihydroxy-4,5-isopropylidenedioxy-6-tert-butyldimethylsilyloxy]hexyl benzamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Fully Functionalized seco-Pancratistatin Analogues

  摘要：

  The total synthesis of fully functionalized polyhydroxyamide B,C-seco-analogues of the anticancer compound pancratistatin (PST) (1) is reported. Key steps include an Evans' MgCl2-promoted anti-aldol reaction between a functionalized L-threose derivative and (R)-(+)-oxazolidinone to stereoselectively form the C-1/C-10b bond and a regiospecific radical-mediated oxidative fragmentation of a 1,3-benzylidene. The B,C-seco compounds 25 and 26 exhibited low activity (ED50 > 30 yg/mL) for inducing apoptosis in human cancer cells.

  DOI：

  10.1021/np0705460
• 作为产物：
  描述：

  [(2R,3R,4S,5S)-1-azido-2-(3',4'-methylenedioxy)phenyl-3-(O)-benzoyl-4,5-isopropylidenedioxy-6-tert-butyldimethylsilyloxy]hexane 在 10% Pd/C 、 氢气 作用下， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以94%的产率得到[(2R,3R,4S,5S)-2-(3',4'-methylenedioxy)phenyl-3-hydroxy-4,5-isopropylidenedioxy-6-tert-butyldimethylsilyloxy]hexyl benzamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Fully Functionalized seco-Pancratistatin Analogues

  摘要：

  The total synthesis of fully functionalized polyhydroxyamide B,C-seco-analogues of the anticancer compound pancratistatin (PST) (1) is reported. Key steps include an Evans' MgCl2-promoted anti-aldol reaction between a functionalized L-threose derivative and (R)-(+)-oxazolidinone to stereoselectively form the C-1/C-10b bond and a regiospecific radical-mediated oxidative fragmentation of a 1,3-benzylidene. The B,C-seco compounds 25 and 26 exhibited low activity (ED50 > 30 yg/mL) for inducing apoptosis in human cancer cells.

  DOI：

  10.1021/np0705460

文献信息

• Synthesis and Biological Evaluation of Fully Functionalized <i>seco</i>-Pancratistatin Analogues
  作者：James McNulty、Jerald J. Nair、Carly Griffin、Siyaram Pandey

  DOI：10.1021/np0705460

  日期：2008.3.1

  The total synthesis of fully functionalized polyhydroxyamide B,C-seco-analogues of the anticancer compound pancratistatin (PST) (1) is reported. Key steps include an Evans' MgCl2-promoted anti-aldol reaction between a functionalized L-threose derivative and (R)-(+)-oxazolidinone to stereoselectively form the C-1/C-10b bond and a regiospecific radical-mediated oxidative fragmentation of a 1,3-benzylidene. The B,C-seco compounds 25 and 26 exhibited low activity (ED50 > 30 yg/mL) for inducing apoptosis in human cancer cells.
• Structure–activity studies on seco-pancratistatin analogs: Potent inhibitors of human cytochrome P450 3A4
  作者：James McNulty、Jerald J. Nair、Mohini Singh、Denis J. Crankshaw、Alison C. Holloway

  DOI：10.1016/j.bmcl.2009.08.032

  日期：2009.10

  Two total syntheses of fully functionalized seco-analogs of the anticancer compound pancratistatin are reported. Structure-activity relationship (SAR) studies identified potent and selective inhibitors of human cytochrome P450 3A4 (CYP3A4) and revealed several core pharmacophoric elements. These studies identify potential roadblocks and will guide the further development of a viable selective clinical pancratistatin derivative. (C) 2009 Elsevier Ltd. All rights reserved.