1-methyl-9H-pyrido[3,4-b]indol-7-yl isopropylcarbamate | 1536469-78-9

• 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: 1-methyl-9H-pyrido[3,4-b]indol-7-yl isopropylcarbamate
• 英文别名: (1-methyl-9H-pyrido[3,4-b]indol-7-yl) N-propan-2-ylcarbamate
• CAS: 1536469-78-9
• 化学式: C₁₆H₁₇N₃O₂
• 分子量: 283.33
• InChiKey: SFXJSIVIIZZIAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.01
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  肉叶云香碱 在 氢溴酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 1-methyl-9H-pyrido[3,4-b]indol-7-yl isopropylcarbamate
  参考文献：
  名称：

  用于人类 β 细胞增殖的 7-取代 Harmine 类似物的构效关系和生物学评价

  摘要：

  最近，我们已经证明，harmine 通过 DYRK1A-NFAT 途径介导体外和体内 β 细胞增殖。我们基于我们之前在糖尿病和 β 细胞特异性靶向策略中对harmine 的相关构效关系研究，探索了harmine 的7 位对DYRK1A 激酶抑制和β 细胞增殖的构效关系。合成了 33 种 7 位取代基的苦胺类似物并评估了其生物活性。确定了两种新型抑制剂，它们显示出 DYRK1A 抑制和人类 β 细胞增殖能力。DYRK1A 抑制剂化合物 1-2b 在高三倍的浓度下诱导的 β 细胞增殖是harmine 的一半。

  DOI：

  10.3390/molecules25081983

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。
• WO2019183245A5
  申请人：——

  公开号：WO2019183245A5

  公开（公告）日：2022-03-25
• 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.