2-(2-苯并呋喃)-2-咪唑啉 | 72583-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 2-(2-苯并呋喃)-2-咪唑啉
• 英文名称: 3H-2-(2-benzofuranyl)-2-imidazoline
• 英文别名: 2-(2-benzofuranyl)-2-imidazoline；[3H]-2-BFI；2-(1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole
• CAS: 72583-92-7
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: YTJOHEUHUVBKSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-苯并呋喃)-2-咪唑啉 以 二甲基亚砜 为溶剂， 反应 48.0h， 以72%的产率得到LSL 60101
  参考文献：
  名称：

  New One-Step Synthesis of 2-Aryl-1H-Imidazoles: Dehydrogenation of 2-Aryl-Δ2-Imidazolines with Dimethylsulfoxide

  摘要：

  描述了一种新的一步法制备2-芳基-1H-咪唑的3，基于对2-芳基-Δ2-咪唑啉的DMSO脱氢作用。还开展了DMSO与10% Pd/C（在这一转化中使用的最佳催化剂）之间的比较研究。两种方法均在120°C下进行48小时。

  DOI：

  10.1055/s-2000-8237
• 作为产物：
  描述：

  苯并[b]呋喃-2-甲醛 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 为溶剂， 反应 0.28h， 生成 2-(2-苯并呋喃)-2-咪唑啉
  参考文献：
  名称：

  Ultrasound promoted synthesis of 2-imidazolines in water: A greener approach toward monoamine oxidase inhibitors

  摘要：

  A series of sixteen 2-substituted-2-imidazolines (where the substituent R = Ph, Me-4-Ph; MeO-4-Ph; (MeO) 2-3,4-Ph; (MeO)(3)-3,4,5-Ph; Ph-4-O-C(O)-Ph; Cl-4-Ph; Cl-2-Ph; Cl-2-2,4-Ph; NO2-4-Ph; NO2-3-Ph; Naphth-2-yl; Fur-2-yl; Benzofur-2-yl; Pyridin-2-yl; Quinolin-2-yl) has been synthesized from the reaction of the substituted-aldehydes and ethylenediamine by ultrasound irradiation with NBS in an aqueous medium in high yields (80-99%). The 2-imidazoline ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) was investigated and some of them showed potent and selective MAO inhibitory activity especially for the MAO-B isoform and could become promising candidates for future development. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.001

文献信息

• [EN] 6-1H-IMIDAZO-QUINAZOLINE AND QUINOLINES DERIVATIVES, NEW MAO INHIBITORS AND IMIDAZOLINE RECEPTOR LIGANDS<br/>[FR] DÉRIVÉS DE 6-1H-IMIDAZO-QUINAZOLINE ET QUINOLÉINES, NOUVEAUX INHIBITEURS DE MAO ET LIGANDS DES RÉCEPTEURS D'IMIDAZOLINES
  申请人：ROTTAPHARM SPA

  公开号：WO2009152868A1

  公开（公告）日：2009-12-23

  The present invention is directed to 6-(1H-imidazo-1-yl)-2-aryl and 2-heteroaryl quinazoline and quinolines derivatives, compounds of formula (I), their pharmaceutical acceptable salts and solvates and corresponding pharmaceutical compositions, that acts as Monoamine Oxidase (MAO) inhibitors and Imidazoline Receptor ligands: wherein: X is independently selected from -CH group or a nitrogen atom (-N), W is independently selected from an aryl group, an heteroaryl group, or a benzocondensed heteroaryl group such as 1,3-benzodioxole, benzofuran, 2,3-dihydrobenzofuran, benzothiophene, 2,3-dihydrobenzothiophene, indole, 2,3-dihydroindole, benzimidazole, benzoxazole, benzothiazole, 2H-3,4-dihydrobenzopyran, [l,4]-benzodioxine, 2,3-dihydro-[1,4]-benzodioxine (1,4-benzodioxan). R1 is independently selected from hydrogen (-H), C1-C4alkyl, hydroxymethyl (-CH2OH), aminomethyl (-CH2NH2), alkylaminomethyl [CH2NH(R2)], or di-alkylaminomethyl [CH2N(R2)2], trifiuoromethyl (-CF3). Compounds of formula (I) elicited a pharmacological profile suitable for the clinical treatment of depression and related disorders, Parkinson disease, drug abuse, and morphine tolerance and dependence.

  本发明涉及6-(1H-咪唑-1-基)-2-芳基和2-杂芳基喹唑啉和喹啉衍生物，这些衍生物的化学式为(I)，以及它们的药用盐和溶剂化物以及相应的药物组合物，作为单胺氧化酶（MAO）抑制剂和咪唑啉受体配体：其中：X独立地选自-CH基团或氮原子(-N)，W独立地选自芳基团、杂芳基团或如1,3-苯并二氧杂环戊烷、苯并呋喃、2,3-二氢苯并呋喃、苯并噻吩、2,3-二氢苯并噻吩、吲哚、2,3-二氢吲哚、苯并咪唑、苯并噁唑、苯并噻唑、2H-3,4-二氢苯并吡喃、[1,4]-苯并二氧杂环戊烷、2,3-二氢-[1,4]-苯并二氧杂环戊烷(1,4-苯并二氧杂环戊烷)。R1独立地选自氢(-H)、C1-C4烷基、羟甲基(-CH2OH)、氨基甲基(-CH2NH2)、烷基氨甲基[CH2NH(R2)]或二烷基氨甲基[CH2N(R2)2]、三氟甲基(-CF3)。化学式(I)的化合物展现出适合于临床治疗抑郁症和相关障碍、帕金森病、药物滥用以及吗啡耐受性和依赖性的药理特性。
• Synthesis and pharmacological evaluation of imidazoline sites I1 and I2 selective ligands
  作者：Maria Anastassiadou、Saı̈da Danoun、Louis Crane、Geneviève Baziard-Mouysset、Marc Payard、Daniel-Henri Caignard、Marie-Claire Rettori、Pierre Renard

  DOI：10.1016/s0968-0896(00)00280-7

  日期：2001.3

  heterocyclic-imidazoline compounds have been prepared and evaluated in vitro as imidazoline sites (I1 and I2) and alpha-adrenergic (alpha1 and alpha2) receptor ligands. Their pKi values indicate that linkage of the imidazoline moiety at the 2-position with an aromatic substituent dramatically decreases alpha-adrenergic affinity. I1 sites are more accessible by phenyl imidazolines substituted by a methyl or a methoxy

  已经制备了几种系列的2-芳基或杂环-咪唑啉化合物，并在体外评估为咪唑啉位点（I1和I2）和α-肾上腺素能（α1和α2）受体配体。它们的pKi值表明2-位咪唑啉部分与芳族取代基的连接显着降低了α-肾上腺素的亲和力。通过在邻位或间位上被甲基或甲氧基取代的苯基咪唑啉更易于接近I1位点。实际上，2-（2'-甲氧基苯基）-咪唑啉（17）是有史以来最好的I1配体之一（pKi = 8.53，I1 / I2> 3388）。另一方面，在对位中存在甲基时，I 2选择性增加。原始化合物2-（3'-氟-4'-甲苯基）-咪唑啉（31）是I2位点的新有效配体，具有高选择性（pKi = 8。
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• 6-1H-IMIDAZO-QUINAZOLINE AND QUINOLINES DERIVATIVES, NEW MAO INHIBITORS AND IMIDAZOLINE RECEPTOR LIGANDS
  申请人：Giordani Antonio

  公开号：US20110118289A1

  公开（公告）日：2011-05-19

  The present invention is directed to 6-(1H-imidazo-1-yl)-2-aryl and 2-heteroaryl quinazoline and quinolines derivatives, compounds of formula (I), their pharmaceutical acceptable salts and solvates and corresponding pharmaceutical compositions, that acts as Monoamine Oxidase (MAO) inhibitors and Imidazoline Receptor ligands: wherein: X is independently selected from —CH group or a nitrogen atom (—N), W is independently selected from an aryl group, an heteroaryl group, or a benzocondensed heteroaryl group such as 1,3-benzodioxole, benzofuran, 2,3-dihydrobenzofuran, benzothiophene, 2,3-dihydrobenzothiophene, indole, 2,3-dihydroindole, benzimidazole, benzoxazole, benzothiazole, 2H-3,4-dihydrobenzopyran, [1,4]-benzodioxine, 2,3-dihydro-[1,4]-benzodioxine (1,4-benzodioxan). R 1 is independently selected from hydrogen (—H), C 1 -C 4 alkyl, hydroxymethyl (—CH 2 OH), aminomethyl (—CH 2 NH 2 ), alkylaminomethyl [CH 2 NH(R 2 )], or di-alkylaminomethyl [CH 2 N(R 2 ) 2 ], trifluoromethyl (—CF 3 ). Compounds of formula (I) elicited a pharmacological profile suitable for the clinical treatment of depression and related disorders, Parkinson disease, drug abuse, and morphine tolerance and dependence.

  本发明涉及6-(1H-咪唑-1-基)-2-芳基和2-杂环芳基喹唑啉和喹啉衍生物，公式(I)的化合物，它们的药学可接受的盐和溶剂以及相应的药物组合物，作为单胺氧化酶（MAO）抑制剂和咪唑啉受体配体。其中：X独立地选自—CH基团或氮原子（—N），W独立地选自芳基，杂环芳基或苯并杂环芳基，例如1,3-苯并二氧杂环、苯并呋喃、2,3-二氢苯并呋喃、苯并噻吩、2,3-二氢苯并噻吩、吲哚、2,3-二氢吲哚、苯并咪唑、苯并噁唑、苯并噻唑、2H-3,4-二氢苯并吡喃、[1,4]-苯并二氧茂、2,3-二氢-[1,4]-苯并二氧茂（1,4-苯并二氧杜香）。R1独立地选自氢（—H）、C1-C4烷基、羟甲基（—CH2OH）、氨甲基（—CH2NH2）、烷基氨甲基[CH2NH(R2)]或双烷基氨甲基[CH2N(R2)2]、三氟甲基（—CF3）。公式（I）的化合物表现出适合于临床治疗抑郁症和相关疾病、帕金森病、药物滥用以及吗啡耐受和依赖的药理特性。
• Imidazoline derivatives
  申请人：RECKITT AND COLMAN PRODUCTS LIMITED

  公开号：EP0071368A1

  公开（公告）日：1983-02-09

  Imidazoline derivatives of the formula wherein R' is hydrogen or alkyl C1-6; R2 is hydrogen, methyl, chloro, bromo or fluoro; R3 is hydrogen, methyl, hydroxy, methoxy, fluoro, chloro or bromo; and their non-toxic salts. Processes for their preparation and pharmaceutical compositions thereof. The compounds exhibit presynaptic α2-adrenoreceptor antagonist activity.

  式中R'为氢或C1-6烷基；R2为氢、甲基、氯、溴或氟；R3为氢、甲基、羟基、甲氧基、氟、氯或溴的咪唑啉衍生物及其无毒盐。 其制备方法及其药物组合物。 这些化合物具有突触前α2-肾上腺素受体拮抗剂活性。