2,3,5,6,7,8-六氢-1H-吡咯里嗪-1-胺 | 170442-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 中文名称: 2,3,5,6,7,8-六氢-1H-吡咯里嗪-1-胺
• 英文名称: hexahydro-1H-pyrrolizin-1-amine
• 英文别名: 2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-amine
• CAS: 170442-12-3
• 化学式: C₇H₁₄N₂
• 分子量: 126.202
• InChiKey: NEZWZGLYKBFCQX-UHFFFAOYSA-N

物化性质

• 沸点：
  160.7±8.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2,3,5,6,7,8-六氢-1H-吡咯里嗪-1-胺 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以29 mg的产率得到(±)-exo-1-acetamidopyrrolizidine
  参考文献：
  名称：

  Ether bridge formation in loline alkaloid biosynthesis

  摘要：

  Lolines are potent insecticidal agents produced by endophytic fungi of cool-season grasses. These alkaloids are composed of a pyrrolizidine ring system and an uncommon ether bridge linking carbons 2 and 7. Previous results indicated that 1-aminopyrrolizidine was a pathway intermediate. We used RNA interference to knock down expression of lob, resulting in the accumulation of an alkaloid identified as exo-l-acetamidopyrrolizidine based on high-resolution MS and NMR. Genomes of endophytes differing in alkaloid profiles were sequenced, revealing that those with mutated lolO accumulated exo-1-acetamidopyrrolizidine but no lolines. Heterologous expression of wild-type lolO complemented a lolO mutant, resulting in the production of N-acetylnorloline. These results indicated that the non-heme iron oxygenase, LolO, is required for ether bridge formation, probably through oxidation of exo-1-acetamidopyrrolizidine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.11.015
• 作为产物：
  描述：

  (±)-1-oximinopyrrolizidine 在 Raney nickel 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 2,3,5,6,7,8-六氢-1H-吡咯里嗪-1-胺
  参考文献：
  名称：

  Ether bridge formation in loline alkaloid biosynthesis

  摘要：

  Lolines are potent insecticidal agents produced by endophytic fungi of cool-season grasses. These alkaloids are composed of a pyrrolizidine ring system and an uncommon ether bridge linking carbons 2 and 7. Previous results indicated that 1-aminopyrrolizidine was a pathway intermediate. We used RNA interference to knock down expression of lob, resulting in the accumulation of an alkaloid identified as exo-l-acetamidopyrrolizidine based on high-resolution MS and NMR. Genomes of endophytes differing in alkaloid profiles were sequenced, revealing that those with mutated lolO accumulated exo-1-acetamidopyrrolizidine but no lolines. Heterologous expression of wild-type lolO complemented a lolO mutant, resulting in the production of N-acetylnorloline. These results indicated that the non-heme iron oxygenase, LolO, is required for ether bridge formation, probably through oxidation of exo-1-acetamidopyrrolizidine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.11.015

文献信息

• [EN] PROGRANULIN MODULATORS AND METHODS OF USING THE SAME<br/>[FR] MODULATEURS DE LA PROGRANULINE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ARKUDA THERAPEUTICS

  公开号：WO2020252222A1

  公开（公告）日：2020-12-17

  Provided herein are compounds that modulate progranulin and methods of using the compounds in progranulin-associated disorders, such as Frontotemporal dementia (FTD).

  本文件提供了调节颗粒蛋白的化合物及其在颗粒蛋白相关疾病中的使用方法，例如额颞痴呆（FTD）。
• [EN] SUBSTITUTED PYRIMIDINE DERIVATIVES AS NICOTINIC ACETYLCHOLINESTERASE RECEPTOR ALPHA 6 MODULATOR<br/>[FR] DÉRIVÉS DE PYRIMIDINE SUBSTITUÉS SERVANT DE MODULATEUR ALPHA 6 DU RÉCEPTEUR DE L'ACÉTYLCHOLINESTÉRASE NICOTINIQUE
  申请人：CEREVANCE INC

  公开号：WO2022053823A1

  公开（公告）日：2022-03-17

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts, solvates and prodrugs thereof wherein m, R1, R2, R3, L and X are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy particularly for use in treating disorders associated with nicotinic acetylcholine receptor α6 (nAChRα6) activity.

  本发明提供了式（I）的化合物及其药学上可接受的盐、溶剂化合物和前药，其中m、R1、R2、R3、L和X如规范中所定义，以及它们的制备方法、包含它们的药物组合物以及它们在治疗中的使用，特别是用于治疗与尼古丁乙酰胆碱受体α6（nAChRα6）活性相关的疾病。
• Pesticidal plant extract containing loline derivatives
  申请人：GRASSLANZ TECHNOLOGY LTD

  公开号：US10149476B2

  公开（公告）日：2018-12-11

  This invention relates to a pesticidal compositions containing at least one pyrrolizidine alkaloid compound derived from a plant and endophyte combination, and applying the pesticidal compositions to another plan without pesticidal protection, where upon application of the composition, the plant confers pest protection. The pyrrolizidine alkaloid compound is of Formula (I) wherein: R═H or CH3 and R′═H, CH3, CHO, COCH3.

  本发明涉及一种杀虫组合物，其中含有至少一种来自植物和内生菌组合的吡咯里西啶生物碱化合物，将该杀虫组合物施用到另一种没有杀虫保护的植物上，施用该组合物后，该植物可获得害虫保护。吡咯烷类生物碱化合物为式(I) 其中：R═H或CH3和R′═H、CH3、CHO、COCH3。
• Fungal endophytes
  申请人：GRASSLANZ TECHNOLOGY LIMITED

  公开号：US10251365B2

  公开（公告）日：2019-04-09

  The present invention relates to at least one epichloae fungal endophyte strain combined with at least one species of Secale spp., which confers at least some level of pest protection on the Secale spp. plant. In particular, the invention relates to an isolated strain of epichloae fungal endophyte selected from the group consisting of AR3039 (NRRL# 50716), AR3046 (NRRL# 50576), AR3049 (NRRL#50577), AR3050 (NRRL# 50578), AR3064 (NRRL# 50718), AR3067 (NRRL# 50719), AR3068 (NRRL# 50720), AR3073 (NRRL# 50721), AR3074 (NRRL# 50722), AR3076 (NRRL# 50723), and AR3078 (NRRL# 50724), and combinations thereof; a Secale spp. plant infected with a fungal endophyte wherein Secale spp. is not a natural host of the endophyte; a method of making a stable host plant/epichloae fungal endophyte combination; a method of conferring at least some level of pest protection on a host Secale spp. plant; and a Secale spp. seed infected with an epichloae fungal endophyte.

  本发明涉及至少一种表生真菌内生菌株与至少一种山苍子属植物的结合，该菌株对山苍子属植物具有至少某种程度的害虫保护作用。特别是，本发明涉及一种分离的表皮真菌内生菌株，该菌株选自 AR3039 (NRRL# 50716)、AR3046 (NRRL# 50576)、AR3049 (NRRL# 50577)、AR3050 (NRRL# 50578)、AR3064 (NRRL# 50718)、AR3067 (NRRL# 50719)、AR3068 (NRRL# 50720)、AR3073 (NRRL# 50721)、AR3074 (NRRL# 50722)、AR3076 (NRRL# 50723)和 AR3078 (NRRL# 50724)及其组合；一种感染了真菌内生菌的 Secale spp.一种感染了真菌内生菌的山苍子属植物，其中山苍子属植物不是该内生菌的天然宿主；一种制造稳定的宿主植物/表生真菌内生菌组合的方法；一种使宿主山苍子属植物至少具有某种程度的害虫保护作用的方法；以及一种感染了表生真菌内生菌的山苍子属种子。
• Loline alkaloid gene clusters of the fungal endophyte neotyphodium uncinatum
  申请人：——

  公开号：US20040139496A1

  公开（公告）日：2004-07-15

  Loline alkaloids (LA), which are 1-aminopyrrolizidines with an oxygen bridge, are produced by Epichloë (anamorph=Neotyphodium) species, endophytes of grasses. LA are insecticidal, thus helping protect host plants from insect herbivory. Suppression subtractive hybridization PCR was used to isolate transcripts up-regulated during loline alkaloid production in cultures of Neotyphodium uncinatum . Subtracted cDNAs were cloned, and a &lgr;-phage cDNA library from an LA-expressing N. uncinatum culture was screened with subtracted cDNA. In BLAST searches, several cDNAs identified had sequence similarities to aspartate kinases, and another with O-acetylhomoserine-(thiol)lyase. Differential expression of these two genes in LA-producing cultures of N. uncinatum was confirmed, and in a survey of 23 isolates from 21 Neotyphodium and Epichloë species these two genes strictly correlated with LA production. Two nucleic acid molecules encoding two loline alkaloid gene clusters have been identified.

  洛林生物碱（Loline alkaloids，LA）是一种带有氧桥的 1-aminopyrrolizidines，由禾本科植物的内生菌 Epichloë （anamorph=Neotyphodium）物种产生。LA 具有杀虫作用，因此有助于保护寄主植物免受昆虫的草食性侵害。利用抑制减弱杂交聚合酶链式反应（PCR）分离了在禾本科内生菌 Neotyphodium uncinatum 的培养物中产生洛林生物碱过程中上调的转录本。 Neotyphodium uncinatum .克隆了减去的 cDNA，并从表达 LA 的 Neotyphodium uncinatum 中获得了一个 &lgr;-phage cDNA 文库。 N. uncinatum 培养物的噬菌体 cDNA 文库进行筛选。在 BLAST 搜索中，发现几个 cDNA 与天冬氨酸激酶序列相似，另一个与 O-乙酰高丝氨酸（硫醇）裂解酶序列相似。在 N. uncinatum 的 LA 生产培养物中，这两个基因的表达存在差异。 N. uncinatum 这两个基因与 LA 的产生密切相关。已经确定了两个核酸分子编码两个洛林生物碱基因簇。