8-bromoharmane | 144434-73-1

• 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: 8-bromoharmane
• 英文别名: 8-bromo-1-methyl-9H-pyrido[3,4-b]indole
• CAS: 144434-73-1
• 化学式: C₁₂H₉BrN₂
• 分子量: 261.121
• InChiKey: AMRXMWSCZQEHEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吲哚 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 硫酸 、 palladium on activated charcoal 、 ammonium acetate 、 顺丁烯二酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 36.5h， 生成 6-溴-1-甲基-9h-吡啶并[3,4-b]吲哚 、 8-bromoharmane
  参考文献：
  名称：

  ß-CARBOLINE, DIHYDRO-ß-CARBOLINE AND TETRAHYDRO-ß-CARBOLINE ALKALOID DERIVATIVES AND PREPARATION METHODS SAME AND USE IN ASPECTS OF PREVENTING AND TREATING PLANT VIRUSES, FUNGICIDES AND INSECTICIDES

  摘要：

  本发明涉及β-咔啉、二氢β-咔啉和四氢β-咔啉生物碱衍生物(I)，以及其制备方法和在预防和治疗植物病毒、杀菌剂和杀虫剂方面的用途。本发明中的β-咔啉、二氢β-咔啉和四氢β-咔啉生物碱衍生物显示出特别出色的抗植物病毒活性，同时还具有杀菌和杀虫活性。

  公开号：

  US20160326166A1

文献信息

• A new method for bromination of carbazoles, β-carbolines and iminodibenzyls by use of N-bromosuccinimide and silica gel
  作者：Keith Smith、D.Martin James、Anil G. Mistry、Martin R. Bye、D.John Faulkner

  DOI：10.1016/s0040-4020(01)90362-x

  日期：1992.9

  in high yields at ambient temperature in dichloromethane by use of the appropriate quantity of N-bromosuccinimide in the presence of silica gel. By contrast, the brominations of the β-carbolines, harmane and norharman, are less selective and give mixtures of products, some of which have unusual substitution patterns.

  咔唑，N-乙基咔唑，亚氨基二苄基（10,11-二氢-5H-二苯并[b，f] a庚因），N-乙基亚氨基二苄基和丙咪嗪在环境温度下很容易在二氯甲烷中以高收率单溴，二溴或多溴化在硅胶存在下适量的N-溴琥珀酰亚胺。相比之下，β-咔啉，harmane和Norharman的溴化选择性较低，并产生产物混合物，其中一些具有不同寻常的取代模式。
• Synthesis and isolation of bromo-β-carbolines obtained by bromination of β-carboline alkaloids
  作者：María A. Ponce、Rosa Erra-Balsells

  DOI：10.1002/jhet.5570380512

  日期：2001.9

  2c, 2d, 2e are reported (mp, Rf, 1H-nmr, 13C-nmr and ms) together with the preparation, isolation and charaterization, for the first time, of the bromoderivatives obtained from harmine (3a-3e), harmol (4a, 4b) and 7-acetylharmol (5a-5c). As brominating reagent N-bromosuccinimide and N-bromosuccinimide-silica gel in dichloromethane and in chloroform as well as the β-carboline - N-bomosuccinimide solid

  在不同的实验条件下，β-咔啉（1-5）会被N-溴代琥珀酰亚胺进行亲电芳香取代。尽管前段时间通过溴化正六烷（1）溴化获得的6-溴-正六烷（1a）已被分离并完全表征，但正六烷（1b-1e）和harmane（2a-2e）的其他溴代衍生物部分被描述为反应混合物的一部分。报告了1b，1c，1d，1e，2a，2b，2c，2d，2e的制备以及随后的分离，纯化和完整表征（mp，R f，1 H-nmr，13C-nmr和ms）以及从harmine（3a-3e），harmol（4a，4b）和7-乙酰基harmol （5a-5c）获得的溴代衍生物的首次制备，分离和表征。作为溴化剂Ñ溴代琥珀酰亚胺和Ñ溴代琥珀酰亚胺硅胶在二氯甲烷和氯仿中，以及在β咔啉- ñ -bomosuccinimide固体混合物已被用于和其用途进行了比较。进行了半经验的AMI和PM3计算，以便根据HOMO的能量，HOMO-LUMO的差异以及β-
• [EN] Β-CARBOLINE, DIHYDRO-Β-CARBOLINE AND TETRAHYDRO-Β-CARBOLINE ALKALOID DERIVATIVES AND METHOD FOR PREPARING SAME AND USE IN ASPECTS OF PREVENTING AND TREATING PLANT VIRUSES, FUNGICIDES AND INSECTICIDES<br/>[FR] DÉRIVÉS ALCALOÏDES DE LA Β-CARBOLINE, DIHYDRO-Β-CARBOLINE ET TÉTRAHYDRO-Β-CARBOLINE ET PROCÉDÉ POUR LES PRÉPARER ET UTILISATION DANS LES ASPECTS DE PRÉVENTION ET DE TRAITEMENT CONTRE LES VIRUS DES PLANTES, FONGICIDES ET INSECTICIDES<br/>[ZH] β-咔啉，二氢-β-咔啉和四氢-β-咔啉生物碱衍生物及其制备方法和在防治植物病毒、杀菌、杀虫方面的应用
  申请人：UNIV NANKAI

  公开号：WO2015101206A1

  公开（公告）日：2015-07-09

  本发明涉及β-咔啉，二氢-β-咔啉和四氢-β-咔啉生物碱衍生物(I)及其制备方法和在防治植物病毒、杀虫、杀菌方面的应用，式中各基团的意义见说明书。本发明的β-咔啉，二氢-β-咔啉和四氢-β-咔啉生物碱衍生物表现出特别优异的抗植物病毒活性，还具有杀菌活性和杀虫活性。
• Synthesis and Antiviral and Fungicidal Activity Evaluation of β-Carboline, Dihydro-β-carboline, Tetrahydro-β-carboline Alkaloids, and Their Derivatives
  作者：Hongjian Song、Yongxian Liu、Yuxiu Liu、Lizhong Wang、Qingmin Wang

  DOI：10.1021/jf404840x

  日期：2014.2.5

  Six known beta-carboline, dihydro-beta-carboline, and tetrahydro-beta-carboline alkaloids and a series of their derivatives were designed, synthesized, and evaluated for their anti-tobacco mosaic virus (TMV) and fungicidal activities for the first time. All of the alkaloids and some of their derivatives (compounds 3, 4, 14, and 19) exhibited higher anti-TMV activity than the commercial antiviral agent Ribavirin both in vitro and in vivo. Especially, the inactivation, curative, and protection activities of alkaloids Harmalan (62.3, 55.1, and 60.3% at 500 mu g/mL) and tetrahydroharmane (64.2, 57.2, and 59.5% at 500 mu g/mL) in vivo were much higher than those of Ribavirin (37.4, 36.2, and 38.5% at 500 mu g/mL). A new derivative, 14, with optimized physicochemical properties, obviously exhibited higher activities in vivo (50.4, 43.9, and 47.9% at 500 mu g/mL) than Ribavirin and other derivatives; therefore, 14 can be used as a new lead structure for the development of anti-TMV drugs. Moreover, most of these compounds exhibited good fungicidal activity against 14 kinds of fungi, especially compounds 4, 7, and 11.
• ß-CARBOLINE, DIHYDRO-ß-CARBOLINE AND TETRAHYDRO-ß-CARBOLINE ALKALOID DERIVATIVES AND PREPARATION METHODS SAME AND USE IN ASPECTS OF PREVENTING AND TREATING PLANT VIRUSES, FUNGICIDES AND INSECTICIDES
  申请人：NANKAI UNIVERSITY

  公开号：US20160326166A1

  公开（公告）日：2016-11-10

  The present invention relates to β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives (I) and a method for preparing same and the use in the aspects of preventing and treating plant viruses, fungicides and insecticides. For the meaning of each group in formula (I) see the description. The β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives of the present invention show a particularly ourstanding anti-plant virus activity, and also have fungicidal and insecticidal activities.

  本发明涉及β-咔啉、二氢β-咔啉和四氢β-咔啉生物碱衍生物(I)，以及其制备方法和在预防和治疗植物病毒、杀菌剂和杀虫剂方面的用途。本发明中的β-咔啉、二氢β-咔啉和四氢β-咔啉生物碱衍生物显示出特别出色的抗植物病毒活性，同时还具有杀菌和杀虫活性。