6-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole | 67396-94-5

• 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: 6-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
• 英文别名: 6-methyl-4,9-dihydro-3H-β-carboline；6-Methyl-4,9-dihydro-3H-beta-carboline
• CAS: 67396-94-5
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: ARDYRRRGELAPTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole 、 水杨酰氯 生成 10-methyl-7,8,13,13b-tetrahydro-5H-benzo[5',6'][1,3]oxazino[3',2':1,2]pyrido[3,4-b]indol-5-one
  参考文献：
  名称：

  Kametani,T. et al., Heterocycles, 1978, vol. 9, p. 673 - 676

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲基色胺 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 6-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
  参考文献：
  名称：

  生物活性指导的合成加速了吴茱萸碱衍生物作为强效杀虫剂候选者的发现

  摘要：

  害虫通过降低作物产量和损害其质量来威胁全球粮食安全。基于天然产物的分子设计和结构优化一直是创新农药以实现昆虫综合治理的最有效方法之一。为了继续我们先前对发现杀虫铅的研究，我们设计、合成了一系列吴茱萸碱衍生物，并对其杀虫活性进行了评估。生物测定结果表明，化合物Ian和Iao在 2.5 mg/L 时对Mythimna separata的杀虫活性分别为 90% 和 80%，优于吴茱萸碱（10%，10 mg/L）、苦参碱（45%，600 mg/L）。 L) 和鱼藤酮 (30% at 200 mg/L)。化合物Ian-Iap对小菜蛾的杀虫活性为 1.0 mg/L，远高于吴茱萸碱、苦参碱和鱼藤酮。化合物Ian在5.0 mg/L时对棉铃虫的杀虫活性为60% ，而吴茱萸碱、苦参碱和鱼藤酮的杀虫活性很差。通过钙成像实验对杀虫作用机制的研究表明，昆虫兰尼碱受体（RyRs）可能是Ian的潜在靶点。此外，分子对接

  DOI：

  10.1021/acs.jafc.1c08297

文献信息

• Catalyst-free synthesis of novel dimeric β-carboline derivatives via an unexpected [2 + 2 + 2] annulation
  作者：Hai-Lei Cui、Jing-Fang Wang、Hai-Lin Zhou、Xiao-Lin You、Xiao-Jie Jiang

  DOI：10.1039/c7ob00689f

  日期：——

  We report here an unexpected catalyst-free [2 + 2 + 2] annulation reaction which allows access to novel complex dimeric β-carboline derivatives in a single step. Various substituted ynones could react with dihydro-β-carboline imines to deliver interesting [2 + 2 + 2] annulation products in moderate to good yields. Alkynoates can also be tolerated in this system.

  我们在这里报告了出乎意料的无催化剂[2 + 2 + 2]环化反应，该反应可在单个步骤中获得新型复杂的二聚β-咔啉衍生物。各种取代的炔酮可以与二氢-β-咔啉亚胺反应，以中等至良好的产率提供有趣的[2 + 2 + 2]环化产物。炔酸也可以在该系统中耐受。
• Novel Evodiamine-Based Sulfonamide Derivatives as Potent Insecticide Candidates Targeting Insect Ryanodine Receptors
  作者：Jingbo Liu、Bingyan Guo、Siying Zhong、Yabing Shi、Zhengping Li、Zhenwu Yu、Zesheng Hao、Li Zhang、Fengyun Li、Yuanhong Wang、Yuxin Li

  DOI：10.1021/acs.jafc.3c05680

  日期：2024.1.17

  global food security. On the basis of our prior research focused on identifying insecticidal leads targeting insect ryanodine receptors (RyRs), we aimed to identify evodiamine scaffold-based novel insecticides. Thus, a variety of evodiamine-based derivatives were designed, synthesized, and assessed for their insecticidal activity against the larvae of Mythimna separata (M. separata) and Plutella xylostella

  害虫是高效农业生产的重要障碍，并对全球粮食安全构成威胁。在我们之前专注于识别针对昆虫兰尼碱受体（RyRs）的杀虫先导化合物的研究基础上，我们的目标是识别基于吴茱萸碱支架的新型杀虫剂。因此，设计、合成了多种基于吴茱萸碱的衍生物，并评估了它们对粘虫（ M. separata ）和小菜蛾（ P. xylostella ）幼虫的杀虫活性。初步生物测定结果表明，与吴茱萸碱、苦参碱和鱼藤酮相比，超过一半的目标化合物对M. separata表现出优异的活性。其中，化合物21m显示出最有效的杀幼虫效率，在2.5 mg/L时死亡率高达93.3%，比吴茱萸碱（10 mg/L时为10.0%）、苦参碱（200 mg/L时为10.0%）有显着改善。 ）和鱼藤酮（200 mg/L 时为 30.0%）。对于小菜蛾，化合物21m和21o显示出较高的杀幼虫活性，其LC 50值分别为9.37 × 10 –2和0.13 mg/L，超过了吴茱萸碱（13
• New Tricks for an Old Natural Product: Discovery of Highly Potent Evodiamine Derivatives as Novel Antitumor Agents by Systemic Structure–Activity Relationship Analysis and Biological Evaluations
  作者：Guoqiang Dong、Shengzheng Wang、Zhenyuan Miao、Jianzhong Yao、Yongqiang Zhang、Zizhao Guo、Wannian Zhang、Chunquan Sheng

  DOI：10.1021/jm300605m

  日期：2012.9.13

  Evodiamine is a quinazolinocarboline alkaloid isolated from the fruits of traditional Chinese herb Evodiae fructus. Previously, we identified N13-substituted evodiamine derivatives as potent topoisomerase I inhibitors by structure-based virtual screening and lead optimization. Herein, a library of novel evodiamine derivatives bearing various substitutions or modified scaffold were synthesized. Among them, a number of evodiamine derivatives showed substantial increase of the antitumor activity, with GI(50) values lower than 3 nM. Moreover, these highly potent compounds can effectively induce the apoptosis of A549 cells. Interestingly, further computational target prediction calculations in combination with biological assays confirmed that the evodiamine derivatives acted by dual inhibition of topoisomerases I and II. Moreover, several hydroxyl derivatives, such as 10-hydroxyl evodiamine (10j) and 3-amino-10-hydroxyl evodiamine (18g), also showed good in vivo antitumor efficacy and low toxicity at the dose of 1 mg/kg or 2 mg/kg. They represent promising candidates for the development of novel antitumor agents.
• An A-ring substituted evodiamine derivative with potent anticancer activity against human non-small cell lung cancer cells by targeting heat shock protein 70
  作者：Hye-Young Min、Yijae Lim、Hyukjin Kwon、Hye-Jin Boo、Seung Yeob Hyun、Junhwa Hong、Suckchang Hong、Ho-Young Lee

  DOI：10.1016/j.bcp.2023.115507

  日期：2023.5
• CN116332930
  申请人：——

  公开号：——

  公开（公告）日：——