(R)-(2,3,6-Trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo-[f,h]pyrrolo[1,2-b]isoquinolin-13a-yl)methanol | 1397943-66-6

• 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: (R)-(2,3,6-Trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo-[f,h]pyrrolo[1,2-b]isoquinolin-13a-yl)methanol
• 英文别名: [(13aR)-2,3,6-trimethoxy-11,12,13,14-tetrahydro-9H-phenanthro[9,10-f]indolizin-13a-yl]methanol
• CAS: 1397943-66-6
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: KSSDYLDWAFPPIT-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(2,3,6-Trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo-[f,h]pyrrolo[1,2-b]isoquinolin-13a-yl)methanol 在 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (-)-antofine
  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：

  (R)-2-(3,6,7-trimethoxy-phenanthren-9-ylmethyl)-pyrrolidine-2-carboxylic acid methyl ester 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (R)-(2,3,6-Trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo-[f,h]pyrrolo[1,2-b]isoquinolin-13a-yl)methanol
  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

• 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.