(4S,5R)-anti-aza-muricatacin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4S,5R)-anti-aza-muricatacin
• 英文别名: (5S)-5-[(1R)-1-hydroxytridecyl]pyrrolidin-2-one；(5S,6R)-aza-muricatacin；(5S)-5-(1-((R)-hydroxy)tridecyl)pyrrolidin-2-one
• 化学式: C₁₇H₃₃NO₂
• 分子量: 283.455
• InChiKey: PUNQCVLHLWRVBJ-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  L-焦谷氨酸 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (4S,5R)-anti-aza-muricatacin
  参考文献：
  名称：

  氮杂-muricatacin的合成：生物活性的muricatacin的类似物，番荔枝科的产原素

  摘要：

  Muricatacin是从muricata Annona中提取的羟基丁醇，具有细胞毒性。所述苏型和赤氮杂类似物，即羟基吡咯烷酮已通过两种不同的路线合成。

  DOI：

  10.1016/s0040-4039(97)00292-x

文献信息

• Enantioselective Henry Addition of Methyl 4-Nitrobutyrate to Aldehydes. Chiral Building Blocks for 2-Pyrrolidinones and Other Derivatives
  作者：Gonzalo Blay、Víctor Hernández-Olmos、José R. Pedro

  DOI：10.1021/ol1010888

  日期：2010.7.2

  enantioselective Henry addition of methyl 4-nitrobutyrate to aldehydes using a Cu(II)−amino pyridine complex as catalyst is described. The products resulting from this reaction constitute a new, highly versatile family of chiral building blocks as a result of the presence of three different functional groups on the molecule. These products have been transformed into nonracemic chiral γ-lactams, 5-hydroxy-5-substituted

  描述了使用Cu（II）-氨基吡啶络合物作为催化剂，将4-硝基丁酸甲酯对醛进行催化的高对映选择性亨利加成反应。该反应产生的产物由于分子上存在三个不同的官能团而构成了一种新的，高度通用的手性构建基家族。这些产物已被转化为非外消旋的手性γ-内酰胺，5-羟基-5-取代的乙酰丙酸衍生物和δ-内酯。
• Konno, Hiroyuki; Hiura, Naoki; Yanaru, Moegi, Heterocycles, 2002, vol. 57, # 10, p. 1793 - 1798
  作者：Konno, Hiroyuki、Hiura, Naoki、Yanaru, Moegi

  DOI：——

  日期：——
• Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues
  作者：A Cavé、C Chaboche、B Figadère、J.C. Harmange、A Laurens、J.F. Peyrat、M Pichon、M Szlosek、J Cotte-Lafitte、A.M. Quéro

  DOI：10.1016/s0223-5234(97)83287-4

  日期：1997.7

  A study of the structure-cytotoxic activity of the acetogenin of Annonaceae, muricatacin 1, is reported. Indeed, muricatacin 1 has shown promising antitumoral activity. Therefore several 5-hydroxy-4-alkanolides were prepared and then tested against KB and VERO cell lines. A few other analogues were synthesized and tested against both cell lines. Thus this work allowed us to better determine the pharmacophore of the molecule and to propose muricatacin 1 instead of a more complicated acetogenin of Annonaceae as a lead compound in the search for new antineoplastic agents.
• Stereoselective synthesis of (5S,6S)- and (5S,6R)-aza-muricatacin from an l-glutamic acid derivative
  作者：José M. Andrés、Noemı́ de Elena、Rafael Pedrosa、Alfonso Pérez-Encabo

  DOI：10.1016/s0957-4166(01)00251-8

  日期：2001.6

  A stereodivergent synthesis of threo and erythro aza-muricatacin. a non-natural aza-analogue of the bioactive annonaceous acetogenin muricatacin, is presented. The configuration of the C(5) stereocenter is controlled by diastereoselective alkylation of alpha -dibenzylamino aldehyde I or diastercoselective reduction of alpha -dibenzylamino ketone 3. (C) 2001 Elsevier Science Ltd. All rights reserved.