(9H-β-carbolin-1-yl)-o-tolyl-methanone | 6912-99-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (9H-β-carbolin-1-yl)-o-tolyl-methanone
• 英文别名: 1-o-toluoyl-9H-β-carboline；1-o-Toluoyl-9H-β-carbolin；(2-methylphenyl)-(9H-pyrido[3,4-b]indol-1-yl)methanone
• CAS: 6912-99-8
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: RRUUYHPSLGWMNF-UHFFFAOYSA-N

物化性质

• 熔点：
  325 °C(Solv: methanol (67-56-1))
• 沸点：
  507.1±35.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (9H-β-carbolin-1-yl)-o-tolyl-methanone 在 氢氧化钾 、 戊醇 作用下， 生成 (9H-β-carbolin-1-yl)-o-tolyl-methanol
  参考文献：
  名称：

  祖尔·欣西宾斯（Zur Konstitution des Yohimbins）

  摘要：

  DOI：

  10.1002/hlca.193501801123
• 作为产物：
  描述：

  邻甲基苯乙酸 在 sodium dichromate 、 phosphorus pentoxide 、 钯 、 溶剂黄146 、 xylene 作用下， 180.0~190.0 ℃ 、3.33 kPa 条件下， 生成 (9H-β-carbolin-1-yl)-o-tolyl-methanone
  参考文献：
  名称：

  吲哚系列研究；育亨宾 合成了yobyrine，yobyrone和tetrahydroyobyrine。

  摘要：

  DOI：

  10.1021/ja01181a052

文献信息

• Über das Sempervirin
  作者：V. Prelog

  DOI：10.1002/hlca.19480310239

  日期：——

  Das Sempervirin C19H16N2, aus Gelsemium sempervirens, Ait., wurde durch Erhitzen rnit Selen in das Yobyrin (IT) übergefuhrt. Durch Kochen rnit Raney-Nickel in Xylol liefert das Sempervirin das „Tetrahydro-ycbyrin” (IV). Auf Grund seines chemischen Verhaltens und seines Absorptionsspektrums wird fur das Sempervirin die Formel 1 vorgeschlagen.

  通过与硒一起加热，将来自美国伊利诺伊州格森姆维尔森州的森巴韦林C 19 H 16 N 2转化为yobyrin（IT）。通过将阮内镍与二甲苯中的阮内醇一起沸腾，森伯韦林产生“四羟基拜林”（IV）。根据其化学行为和吸收光谱，建议使用sempervirin的式1。
• Witkop, Justus Liebigs Annalen der Chemie, 1943, vol. 554, p. 118
  作者：Witkop

  DOI：——

  日期：——
• Synthesis, in vitro anti-inflammatory and cytotoxic evaluation, and mechanism of action studies of 1-benzoyl-β-carboline and 1-benzoyl-3-carboxy-β-carboline derivatives
  作者：Mei-Lin Yang、Ping-Chung Kuo、Tsong-Long Hwang、Wen-Fei Chiou、Keduo Qian、Chin-Yu Lai、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmc.2011.01.034

  日期：2011.3

  In the present study, various 1-substituted and 1,3-disubstituted beta-carboline derivatives were synthesized by a modified single-step Pictet-Spengler reaction. The compounds were examined for cytotoxicity and anti-inflammatory activity, as measured by the inhibition of prostaglandin E-2 (PGE(2)) production and nitric oxide (NO) production. While only two compounds (28 and 31) showed marginal cytotoxicity against four human cancer cell lines, most of the tested compounds exhibited potent inhibitory activity of both NO and PGE(2) production. Moreover, compounds 6 and 16 significantly reduced the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX2), suggesting that beta-carboline analogs can inhibit NO and PGE(2) production at the translational level. In addition, several of the beta-carboline derivatives (1, 2, 48, 11, 13, 22, 25, 27, 31, and 41-43) displayed significant inhibitory activity of superoxide anion (O-2(center dot-)) generation or elastase release compared to the reference compound, with 6 being the most potent. N-Formyl-L-methionyl-phenylalanine (FMLP)-induced phosphorylation of c-Jun N-terminal kinase (JNK) and protein kinase B (AKT) were also inhibited by 6, suggesting that it suppresses human neutrophil functions by inhibiting the activation of JNK and AKT signaling pathways. Therefore, the synthetic 1-benzoyl-3-carboxy beta-carboline analogs may have great potential to be developed as anti-inflammatory agents. (C) 2011 Elsevier Ltd. All rights reserved.
• Chatterjee; Pakrashi, Journal of the Indian Chemical Society, 1954, vol. 31, p. 31
  作者：Chatterjee、Pakrashi

  DOI：——

  日期：——
• Studies in the Indole Series. X. Yohimbine (Part 2). The Synthesis of Yobyrine, Yobyrone and “Tetrahydroyobyrine”
  作者：Percy L. Julian、William J. Karpel、Arthur Magnani、Edwin W. Meyer

  DOI：10.1021/ja01181a052

  日期：1948.1