(S)-2-(3,6,7-trimethoxy-phenanthren-9-ylmethyl)-pyrrolidine-2-carboxylic acid methyl ester | 1429481-89-9

• 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: (S)-2-(3,6,7-trimethoxy-phenanthren-9-ylmethyl)-pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S)-2-[(3,6,7-trimethoxyphenanthren-9-yl)methyl]pyrrolidine-2-carboxylate
• CAS: 1429481-89-9
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: KJMJGADZUXREDM-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-(3,6,7-trimethoxy-phenanthren-9-ylmethyl)-pyrrolidine-2-carboxylic acid methyl ester 在 盐酸 、 lithium aluminium tetrahydride 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (S)-2,3,6-trimethoxy-13a-methyl-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline
  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
• 作为产物：
  描述：

  (3S,7Ar)-3-三氯甲基-四氢吡咯[1,2-C]恶唑-1-酮 在 正丁基锂 、 乙酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 52.83h， 生成 (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

文献信息

• Enantioselective Approach to 13a-Methylphenanthroindolizidine Alkaloids
  作者：Bo Su、Chunlong Cai、Qingmin Wang

  DOI：10.1021/jo3012122

  日期：2012.9.21

  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.
• Design, synthesis, and evaluation of a water-soluble antofine analogue with high antiproliferative and antitumor activity
  作者：Yongseok Kwon、Jayoung Song、Boeun Lee、Jinkyung In、Hohyun Song、Hwa-Jin Chung、Sang Kook Lee、Sanghee Kim

  DOI：10.1016/j.bmc.2012.11.039

  日期：2013.2

  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.