ethyl (1S,3S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate | 55857-67-5

• 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: ethyl (1S,3S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 55857-67-5
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: DKRAXVHYKRTHRE-ZANVPECISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (1S,3S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 哌啶 、 吡啶 、 lithium aluminium tetrahydride 、 sulfur 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 (E)-3-(1-methyl-9H-pyrido[3,4-b]indol-3-yl)-acrylic acid
  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：

  L-色氨酸 在 氯化亚砜 、 硫酸 作用下， 以 水 为溶剂， 反应 5.0h， 生成 ethyl (1S,3S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  基于植物来源的病毒抑制剂的1,2,3,4-四氢-β-咔啉-3-羧酸衍生物的设计，合成，抗TMV，杀真菌和杀虫活性评估

  摘要：

  借鉴植物农药的创作思路，设计合成了一系列四氢-β-咔啉-3-羧酸衍生物，并对其抗TMV，杀真菌和杀虫活性进行了评价。这些衍生物中的大多数在体外和体内均表现出对TMV的良好抗病毒活性。特别是，化合物8和15的体内活性高于利巴韦林。化合物8显示出超过70种％的杀菌活性对尾孢堀花生，茄链格孢，蠕玉米小斑病，和稻纹枯病菌在50毫克/公斤，化合物16和20表现出对Mythimna sepepa和Ostrinia nubilalis的60％以上的杀虫活性。

  DOI：

  10.1016/j.bmcl.2014.09.063

文献信息

• 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。
• 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.
• Le Men; Fan, Bulletin de la Societe Chimique de France, 1959, p. 1866,1868
  作者：Le Men、Fan

  DOI：——

  日期：——
• 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。