(4''R)-isopropyl-2''-oxazolidino-N-(3',4'-methylenedioxy) phenylacetate | 1004760-66-0

• 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: (4''R)-isopropyl-2''-oxazolidino-N-(3',4'-methylenedioxy) phenylacetate
• 英文别名: (4R)-3-[2-(1,3-benzodioxol-5-yl)acetyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 1004760-66-0
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: FMSFZXVKCBKZRP-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 (4''R)-isopropyl-2''-oxazolidino-N-(3',4'-methylenedioxy) phenylacetate 、 (4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 在 三乙胺 、 magnesium chloride 作用下， 以 乙酸乙酯 为溶剂， 反应 12.17h， 以90%的产率得到(4''R,2S,3R,4R,5S)-4''-isopropyl-2''-oxazolidino-N-[2-(3',4'-methylenedioxy)phenyl-3-trimethylsilyloxy-4,5-isopropylidenedioxy-6-tert-butyldimethylsilyloxy] hexanoate
  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：

  (R)-(+)-4-异丙基-2-恶唑啉酮 、 2-(3,4-Methylenedioxyphenyl)acetic pivalic anhydride 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 (4''R)-isopropyl-2''-oxazolidino-N-(3',4'-methylenedioxy) phenylacetate
  参考文献：
  名称：

  不寻常的氯化镁催化可烯醇化 L-苏糖衍生物的非埃文桑蒂-羟醛反应

  摘要：

  乙酸苯酯衍生的恶唑烷酮的氯化镁催化的抗羟醛反应容易与可烯醇化的 L-苏糖衍生物 8 进行，以高产率和非常高的非对映选择性提供抗羟醛加合物。该反应对芳香醛也有效，并提供稍低的非对映选择性。这个扩展

  DOI：

  10.1002/ejoc.200700854

文献信息

• Unusual Magnesium Chloride Catalyzed Non-Evansanti-Aldol Reactions of an EnolizableL-Threose Derivative
  作者：James McNulty、Jerald J. Nair、Marcin Sliwinski、Laura E. Harrington、Siyaram Pandey

  DOI：10.1002/ejoc.200700854

  日期：2007.12

  The magnesium chloride catalyzed anti-aldol reaction of phenyl acetate derived oxazolidinones proceeds readily with enolizable L-threose derivative 8 to provide anti-aldol adducts in high yields and with very high diastereoselectivities. The reaction is also efficient with aromatic aldehydes and provides slightly lower diastereoselectivities. This extension

  乙酸苯酯衍生的恶唑烷酮的氯化镁催化的抗羟醛反应容易与可烯醇化的 L-苏糖衍生物 8 进行，以高产率和非常高的非对映选择性提供抗羟醛加合物。该反应对芳香醛也有效，并提供稍低的非对映选择性。这个扩展
• 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.
• 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.
• Potent and selective inhibition of human cytochrome P450 3A4 by seco-pancratistatin structural analogs
  作者：James McNulty、Jerald J. Nair、Mohini Singh、Denis J. Crankshaw、Alison C. Holloway

  DOI：10.1016/j.bmcl.2010.01.157

  日期：2010.4

  seco-Derivatives of the anticancer agent pancratistatin bearing the 2S,3S,4S,5S configuration were accessed via a novel, highly diastereoselective anti-aldol reaction. Structure-activity relationships reveal important insights into the seco-pancratistatin pharmacophore as a potent and selective inhibitor of human cytochrome P450 3A4 (CYP3A4), and highlight features of concern in advancing a potent, selective anticancer agent in the pancratistatin series. (C) 2010 Elsevier Ltd. All rights reserved.