1-allyl-2-imidazolecarbaldehyde | 474623-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-allyl-2-imidazolecarbaldehyde
• 英文别名: 1-allyl-1H-imidazole-2-carboxaldehyde；1-Allyl-1H-imidazole-2-carbaldehyde；2-(N-allylimidazole)-carboxaldehyde；1-prop-2-enylimidazole-2-carbaldehyde
• CAS: 474623-05-7
• 化学式: C₇H₈N₂O
• 分子量: 136.153
• InChiKey: RSFGPQUOSRUFGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-allyl-2-imidazolecarbaldehyde 在 palladium dihydroxide 盐酸 、 氢气 、 magnesium sulfate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 48.0h， 生成 (6R*,8S*)-8-amino-6-hydroxy-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthetic approach to imidazo[1,2-a]pyridine derivatives by the intramolecular nitrone cycloaddition methodology

  摘要：

  N-Benzyl and (R)-N-(alpha-phenylethyl) nitrones derived from 1-allyl-2-imidazolecarbaldehyde underwent intramolecular cyclo-addition to give predominantly bridged-ring products. namely 5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1-d][1,2,5]oxadiazepine derivatives. Catalytic hydrogenation of the latter furnished both racemic and enantiopure 6,8-functionalised 5,6,7,8-tetrahydro-imidazo[1,2a]pyridines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00404-0
• 作为产物：
  描述：

  1-allyl-2-hydroxymethylimidazole 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以37%的产率得到1-allyl-2-imidazolecarbaldehyde
  参考文献：
  名称：

  Synthetic approach to imidazo[1,2-a]pyridine derivatives by the intramolecular nitrone cycloaddition methodology

  摘要：

  N-Benzyl and (R)-N-(alpha-phenylethyl) nitrones derived from 1-allyl-2-imidazolecarbaldehyde underwent intramolecular cyclo-addition to give predominantly bridged-ring products. namely 5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1-d][1,2,5]oxadiazepine derivatives. Catalytic hydrogenation of the latter furnished both racemic and enantiopure 6,8-functionalised 5,6,7,8-tetrahydro-imidazo[1,2a]pyridines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00404-0

文献信息

• Chemokine receptor binding heterocyclic compounds with enhanced efficacy
  申请人：——

  公开号：US20030220341A1

  公开（公告）日：2003-11-27

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  这项发明涉及由一个核心氮原子环绕着三个侧链基团的杂环化合物，其中三个侧链基团中的两个最好是苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N，并且可选地含有额外的环。这些化合物与趋化因子受体结合，包括CXCR4和CCR5，并且表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护作用。
• [EN] CATALYTIC SCAVENGERS OF ORGANOPHOSPHATES TO POTENTIATE BUTYRYLCHOLINESTERASE (BCHE) AS A CATALYTIC BIOSCAVENGER AND METHODS FOR MAKING AND USING THEM<br/>[FR] PIÉGEURS CATALYTIQUES D'ORGANOPHOSPHATES POUR POTENTIALISER LA BUTYRYLCHOLINESTÉRASE (HBCHE)
  申请人：UNIV CALIFORNIA

  公开号：WO2015057822A1

  公开（公告）日：2015-04-23

  Provided are N-alkyl imidazole 2-aldoximes, including cationic imidazolium and uncharged tertiary imidazole aldoximes, and compositions and methods for making and using them, including methods for reactivating human butyrylcholinesterase (hBChE) or acetylcholinesterase (hAChE ) inhibited by organophosphate (OP). By administration of a composition of the invention, the inactive or conjugated hBChE-OP or hAChE-OP is reactivated and the catalytic cycle of turnover and inactivation of the OP is completed; and in alternative embodiments, secondary mechanisms of reversible protection of hBChE and hAChE from irreversible inactivation by OPs and reactivation of tissue AChE also contribute to overall efficacy.

  提供了N-烷基咪唑-2-醛肟，包括阳离子咪唑盐和不带电的三级咪唑醛肟，以及制备和使用它们的组合物和方法，包括重新激活被有机磷酸酯（OP）抑制的人丁酰胆碱酯酶（hBChE）或乙酰胆碱酯酶（hAChE）的方法。通过给予本发明的组合物，不活性或结合的hBChE-OP或hAChE-OP被重新激活，完成了OP的催化周转和失活循环；在替代实施方案中，可逆保护hBChE和hAChE免受OP不可逆失活的次要机制以及再激活组织AChE也有助于整体功效。
• N-Heterocyclic carbene-catalysed intramolecular hydroacylation to form basic nitrogen-containing heterocycles
  作者：James A. Walker、Levi M. Stanley

  DOI：10.1039/c6ob01956k

  日期：——

  N-Heterocyclic carbene-catalysed intramolecular hydroacylation of N-allylimidazole-2-carboxaldehydes and N-allylbenzimidazole-2-carboxaldehydes is reported. These exo-selective hydroacylations of unactivated alkenes enable the synthesis of a variety of basic, polycyclic nitrogen heterocycles in good-to-excellent yields.

  报道了N-杂环卡宾催化的N-烯基咪唑-2-甲醛和N-烯基苯并咪唑-2-甲醛的分子内羟酰化反应。这些对外部选择性的羟酰化反应使得未活化的烯烃能够以良好至优秀的产率合成各种基础的、多环的氮杂环化合物。
• [EN] CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS WITH ENHANCED EFFICACY<br/>[FR] COMPOSES HETEROCYCLIQUES A EFFICACITE ACCRUE SE FIXANT SUR LES RECEPTEURS DE LA CHIMIOKINE
  申请人：ANORMED INC

  公开号：WO2003055876A1

  公开（公告）日：2003-07-10

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  本发明涉及由一个核心氮原子和三个侧链基团组成的杂环化合物，其中三个侧链基团中的两个首选为苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N并可选择性地含有其他环。这些化合物结合趋化因子受体，包括CXCR4和CCR5，并对人免疫缺陷病毒（HIV）感染靶细胞表现出保护作用。
• CXCR4 CHEMOKINE RECEPTOR BINDING COMPOUNDS
  申请人：BRIDGER Gary J.

  公开号：US20080255197A1

  公开（公告）日：2008-10-16

  The present invention relates to compounds that bind to chemokine receptors, and having the formula wherein each A, X, Y, R 1 , R 2 and R 3 are substituents. The present invention also relates to methods of using such compounds, such as in treating HIV infection and inflammatory conditions such as rheumatoid arthritis. Furthermore, the present invention relates to methods to elevate progenitor and stem cell counts, as well as methods to elevate white blood cell counts, using such compounds.

  本发明涉及与趋化因子受体结合的化合物，其具有以下式子： 其中每个A、X、Y、R1、R2和R3均为取代基。本发明还涉及使用这种化合物的方法，例如用于治疗HIV感染和炎症性疾病，如类风湿性关节炎。此外，本发明还涉及使用这种化合物提高祖细胞和干细胞数量的方法，以及提高白细胞计数的方法。