(3S,7aS)-3-(trichloromethyl)-7a-((3,6,7-trimethoxyphenanthren-9-yl)methyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one | 1397943-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (3S,7aS)-3-(trichloromethyl)-7a-((3,6,7-trimethoxyphenanthren-9-yl)methyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one
• 英文别名: (3S,7aS)-3-trichloromethyl-7a-(3,6,7-trimethoxy-phenanthren-9-ylmethyl)-tetrahydro-pyrrolo[1,2-c]oxazol-1-one；(3S,7aS)-3-(trichloromethyl)-7a-[(3,6,7-trimethoxyphenanthren-9-yl)methyl]-3,5,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazol-1-one
• CAS: 1397943-56-4
• 化学式: C₂₅H₂₄Cl₃NO₅
• 分子量: 524.828
• InChiKey: URTUYRFKAJKHTK-UPVQGACJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,7aS)-3-(trichloromethyl)-7a-((3,6,7-trimethoxyphenanthren-9-yl)methyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以73%的产率得到(S)-2-(3,6,7-trimethoxy-phenanthren-9-ylmethyl)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis, and evaluation of a water-soluble antofine analogue with high antiproliferative and antitumor activity

  摘要：

  New water soluble antofine C-13a analogues were designed, synthesized, and evaluated for antiproliferative activity against cancer cells. Particularly, (-)-(R)-13a-hydroxymethylantofine ((-)-(R)-4b) demonstrated notable growth inhibition against a panel of human cancer cell lines. This growth inhibition was associated with the arrest of the cell cycle in the G0/G1 phases and suppression of mTOR signaling in human lung A549 cancer cells. Compound (-)-(R)-4b also overcame paclitaxel-resistance in human lung cancer cells (A549-Pa) by suppressing P-glycoprotein expression. Furthermore, compound (-)-(R)-4b significantly inhibited the tumor growth of A549 and A549-Pa xenografts in a nude mouse model, which suggests it is a promising novel antitumor agent with sufficient aqueous solubility. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.039
• 作为产物：
  描述：

  D-脯氨酸 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 4.33h， 生成 (3S,7aS)-3-(trichloromethyl)-7a-((3,6,7-trimethoxyphenanthren-9-yl)methyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one
  参考文献：
  名称：

  Enantioselective Approach to 13a-Methylphenanthroindolizidine Alkaloids

  摘要：

  The first enantioselective approach to 13a-methylphenanthroindolizidine alkaloids is reported, featuring an efficient stereoselective Seebach's alkylation and Pictet-Spengler cyclization. The proposed and other three most probable structures were ruled out, indicating hypoestestatin 1 needs further assignment.

  DOI：

  10.1021/jo3012122

文献信息

• Spatial Configuration and Three-Dimensional Conformation Directed Design, Synthesis, Antiviral Activity, and Structure–Activity Relationships of Phenanthroindolizidine Analogues
  作者：Bo Su、Chunlong Cai、Meng Deng、Qingmin Wang

  DOI：10.1021/acs.jafc.5b06112

  日期：2016.3.16

  conformation of the molecules on their anti-TMV activities and related structure–activity relationship (SAR), a series of D-ring opened derivatives 3, 4, 5a–5j, 6, and 7, chiral 13a- and/or 14-substituted phenanthroindolizidine analogues 10–12 and 18–20, and their enantiomers ent-10–ent-12 and ent-18–ent-20 were synthesized and evaluated for their anti-TMV activities. Bioassay results showed that most of the

  我们最近对菲咯啉吲哚啶生物碱类似物的抗烟草花叶病毒（TMV）活性的研究初步表明，与分子的空间排列密切相关的分子C13a位置的基本骨架和取代模式具有很大的作用。对生物活性的影响。为了进一步研究的空间配置和其抗TMV活动分子和相关的结构-活性关系（SAR）的三维（3D）构象的深入影响，一系列d形环的开衍生物3，4，5a – 5j，6和7，手性13a和/或14取代的菲咯啉吲哚并烷类似物合成了10 – 12和18 – 20以及它们的对映体ent-10 – ent-12和ent-18 – ent-20，并评估了它们的抗TMV活性。生物测定结果显示，大多数手性菲咯啉吲哚并咪唑具有良好的体内抗TMV活性。在这些化合物中，ent-11与宁南霉素（最成功的商业抗病毒药物之一）相比，它具有更强的活性，因此逐渐成为植物病毒的潜在抑制剂。在手性情况下，还首次讨论了其他SAR，这表明分子的空间构型和3D构象对于保持高抗TMV活性至关重要。