2-benzyl-7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole | 57032-15-2

• 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: 2-benzyl-7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 英文别名: 2-Benzyl-7-methoxy-1-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indole；2-benzyl-7-methoxy-1-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 57032-15-2
• 化学式: C₂₀H₂₂N₂O
• 分子量: 306.407
• InChiKey: RZVGTFQFEHTTDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzyl-7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 在 palladium on activated charcoal 、 氢气 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以80%的产率得到四氢骆驼蓬碱
  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
• 作为产物：
  描述：

  2-benzyl-7-methoxy-1-methyl-9H-β-carbolinium; chloride 在 甲醇 、 sodium tetrahydroborate 作用下， 生成 2-benzyl-7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Jachontow; Rubzow, Zhurnal Obshchei Khimii, 1958, vol. 28, p. 3108,3111; engl. Ausg. S. 3139, 3141

  摘要：

  DOI：

文献信息

• 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。
• β-carboline, dihydro-β-carboline and tetrahydro-β-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：US10208033B2

  公开（公告）日：2019-02-19

  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)及其制备方法，以及在预防和治疗植物病毒、杀真菌剂和杀虫剂方面的用途。式（I）中各基团的含义见说明。本发明的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突出的抗植物病毒活性，同时还具有杀菌和杀虫活性。
• [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。
• Wolfes; Ivers, E. Merck's Jahresberichte, 1928, vol. 42, p. 8
  作者：Wolfes、Ivers

  DOI：——

  日期：——
• 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.