N-methylgirinimbine | 26870-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-methylgirinimbine
• 英文别名: 3',3',3,9-tetramethylpyrano[3,2-a]carbazole；N-Methylgirinimbin；3,3,5,11-tetramethyl-3,11-dihydro-pyrano[3,2-a]carbazole；3,3,5,11-Tetramethylpyrano[3,2-a]carbazole
• CAS: 26870-53-1
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: ZNLNSESDUHAKCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methylgirinimbine 以 苯 为溶剂， 反应 6.0h， 以65%的产率得到5,9,18-trimethyl-7-oxa-18-azatetracyclo[9.7.0.02,8.012,17]octadeca-1(11),2(8),4,9,12,14,16-heptaene
  参考文献：
  名称：

  Photochemical rearrangements of pyranocarbazole alkaloids: Part-I

  摘要：

  DOI：

  10.1016/s0040-4039(00)82414-4
• 作为产物：
  描述：

  3-甲基-9H-咔唑-2-醇 在 titanium(IV) isopropylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 25.5h， 生成 N-methylgirinimbine
  参考文献：
  名称：

  Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo

  摘要：

  A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.084

文献信息

• On the structures of girinimbine, mahanimbine, isomahanimbine, koenimbidine and murrayacine
  作者：B.S. Joshi、V.N. Kamat、D.H. Gawad

  DOI：10.1016/s0040-4020(01)92976-x

  日期：1970.1

  Murraya koenigii Spreng. is reported. Spectroscopic and degradative evidence has been presented supporting structures for girinimbine (3), mahanimbine (4), isomahanimbine (13), koenimbidine (17) and murrayacine (12).

  从Murraya koenigii Spreng的叶子和根中分离出马哈宁宾，吉利比滨和两种新的咔唑生物碱异马哈宁滨和科尼安定。被报道。已经提出了光谱学和降解性证据，证实了吉利尼滨（3），马哈宁（4），异马尼滨（13），可尼苯丁（17）和莫拉西碱（12）的支持结构。
• CHAKRABARTI, AMIT;CHAKRABORTY, D. P., TETRAHEDRON, 45,(1989) N2, C. 7007-7012
  作者：CHAKRABARTI, AMIT、CHAKRABORTY, D. P.

  DOI：——

  日期：——
• CHAKRABARTI, AMIT;CHAKRABORTY, D. P., TETRAHEDRON LETT., 29,(1988) N 50, C. 6625-6628
  作者：CHAKRABARTI, AMIT、CHAKRABORTY, D. P.

  DOI：——

  日期：——
• A novel access to bis-carbazole alkaloids: substituent effect on the efficiency and regioselectivity in BF3-Et2O mediated intermolecular coupling of pyranocarbazole alkaloids
  作者：Amit Chakrabarti、D.P. Chakraborty

  DOI：10.1016/s0040-4020(01)89168-7

  日期：——
• Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo
  作者：Yingda Zang、Xiuyun Song、Chuangjun Li、Jie Ma、Shifeng Chu、Dandan Liu、Qian Ren、Yan Li、Naihong Chen、Dongming Zhang

  DOI：10.1016/j.ejmech.2017.11.084

  日期：2018.1

  A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke. (C) 2017 Elsevier Masson SAS. All rights reserved.