2-乙基-2,3-二氢-2-苯并呋喃羧酰胺 | 170803-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 2-乙基-2,3-二氢-2-苯并呋喃羧酰胺
• 英文名称: 2,3-Dihydro-2-ethylbenzo[b]furan-2-carboxamide
• 英文别名: 2-Benzofurancarboxamide,2-ethyl-2,3-dihydro-；2-ethyl-3H-1-benzofuran-2-carboxamide
• CAS: 170803-36-8
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: UFJXRIWQJZLCGT-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙基-2,3-二氢-2-苯并呋喃羧酰胺 在 sodium methylate 、 phosphorus pentoxide 作用下， 以 甲苯 为溶剂， 反应 4.25h， 生成 依法克生
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003
• 作为产物：
  描述：

  苯并二氢呋喃-2-羧酸 在 正丁基锂 、 氯化亚砜 、 氨 、 二异丙胺 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 5.0h， 生成 2-乙基-2,3-二氢-2-苯并呋喃羧酰胺
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003

文献信息

• New imidazoline/α2-adrenoceptors affecting compounds—4(5)-(2-aminoethyl)imidazoline (dihydrohistamine) derivatives. Synthesis and receptor affinity studies
  作者：Adam P. Treder、Ryszard Andruszkiewicz、Włodzimierz Zgoda、Aleksandra Walkowiak、Celeste Ford、Alan L. Hudson

  DOI：10.1016/j.bmc.2010.11.039

  日期：2011.1

  imidazoline/α2-adrenoceptor ligands, 4(5)-(2-aminoethyl)imidazoline derivatives. In this study the exploration of previously unknown 4(5)-(2-aminoethyl)imidazolines including the analogues of reported imidazoline and α2-aderenoceptors ligands: clonidine, rilmenidine, idazoxan, efaroxan, antazoline, tracizoline is described. The synthesis of a variety of novel 4(5)-(2-aminoethyl)imidazolines and their I1, I2

  胍丁胺结构和咪唑啉结构部分引线的汇编咪唑啉/α的新组2肾上腺素能受体配体，4（5） - （2-氨基乙基）咪唑啉衍生物。在这项研究的探索以前未知的4（5） - （2-氨基乙基）包括报告的咪唑啉和α类似物咪唑啉2个-aderenoceptors配体：可乐定，利美尼定，咪唑克生，依法克生，安他唑啉，tracizoline进行说明。的多种新颖4（5）的合成- （2-氨基乙基）咪唑啉和它们的I 1，我2，α 2 -肾上腺素受体报道亲和力。
• Preparation of analogues of efaroxan and KU14R as potential imidazoline receptor subtype 3 ligands
  作者：Richard D. Farn、Christopher A. Ramsden、Noel G. Morgan

  DOI：10.1002/jhet.5570450338

  日期：2008.5

  The preparation and characterization of new analogues of the imidazoline insulin secretagogue efaroxan 1 are described. These include 1,2,4-triazole, 1,3,4-oxadiazole, pyrimidine, 1,4,5,6-tetrahydropyrimidine and 1,2-dihydro-1,2,4,5-tetrazine analogues. Bromination of 2,3-dihydro-2-ethylbenzo[b]furan-2-carbonitrile 19 gives the 3,3-dibromo analogue 28, which is readily hydrolysed to the corresponding

  描述了咪唑啉胰岛素促分泌剂依法洛辛1的新类似物的制备和表征。这些包括1,2,4-三唑，1,3,4-恶二唑，嘧啶，1,4,5,6-四氢嘧啶和1,2-二氢-1,2,4,5-四嗪类似物。2，3-二氢-2-乙基苯并[ b ]呋喃-2-腈19的溴化得到3，3-二溴类似物28，其易于水解为相应的酮29。还原该酮得到醇31，为非对映异构体的混合物，其使用三氟化二乙基氨基硫将其转化为氟化物32。
• Preparation of the I₃ Imidazoline Receptor Antagonist KU14R and Related 2,3-Dihydrobenzo[<b><i>b</i></b>]furan Derivatives
  作者：Christopher Ramsden、J. Clews、Noel Morgan

  DOI：10.1055/s-2001-16079

  日期：——

  The preparation and characterisation of a series of novel analogues of the imidazoline insulin secretagogue efaroxan, including the I3-receptor antagonist KU14R, are described. Replacement of the imidazoline ring of efaroxan by selected functional groups leads either to loss of activity or to very weak I3-agonist activity in insulin secretion studies. The imidazole analogue KU14R was found to be an I3-antagonist in this assay and useful as a biological tool.

  本文介绍了一系列新型咪唑啉胰岛素分泌剂依法罗生类似物（包括 I3 受体拮抗剂 KU14R）的制备和表征。在胰岛素分泌研究中，用选定的官能团取代依法罗生的咪唑啉环会导致其失去活性或产生极弱的 I3 受体拮抗剂活性。研究发现，咪唑类似物 KU14R 在该试验中是一种 I3-拮抗剂，可作为一种有用的生物学工具。
• [EN] METHOD FOR PREPARING AN OPTICALLY PURE BENZOFURAN CARBOXYLIC ACID AND USE THEREOF FOR PREPARING EFAROXAN<br/>[FR] PROCEDE DE PREPARATION D'UN DERIVE D'ACIDE BENZOFURANE CARBOXYLIQUE OPTIQUEMENT PUR, ET SON UTILISATION POUR PREPARER L'EFAROXAN
  申请人：PIERRE FABRE MEDICAMENT

  公开号：WO1996035682A1

  公开（公告）日：1996-11-14

  (EN) A novel method for preparing an optically pure 2-ethyl-2,3-dihydro-benzofurancarboxylic acid derivative of general formula (II) is described, wherein R is a hydrogen atom, a halogen, a lower alkyl, lower alkoxy or hydroxy radical. The method comprises separating the racemic mixture by selective crystallisation with the suitable optically pure enantiomer of 2-phenylglycinol, in a suitable solvent, whereafter the optically pure, crystallised acid of formula (II) is isolated and recovered. The invention also provides the optically pure 2-ethyl-2,3-dihydro-benzofurancarboxylic acid derivative thus obtained and the use thereof for the preparation of an optically pure derivative of efaroxan.(FR) La présente invention concerne un nouveau procédé de préparation d'un dérivé d'acide 2-éthyl-2,3-dihydro-benzofurane-carboxylique optiquement pur, de formule générale (II) dans laquelle R représente un atome d'hydrogène, un halogène, un radical alkyle inférieur, alkoxy inférieur ou hydroxy, procédé pour lequel on effectue une résolution du mélange racémique par cristallisation sélective avec l'énantiomère optiquement pur approprié du 2-phénylglycinol, dans un solvant approprié, puis on isole et on récupère l'acide de formule (II) optiquement pur cristallisé. La présente invention concerne également le dérivé d'acide 2-éthyl-2,3-dihydro-benzofurane-carboxylique optiquement pur ainsi obtenu et son utilisation pour la préparation d'un dérivé optiquement pur de l'efaroxan.

  一种制备光学纯的通式（II）中R为氢原子、卤素、低烷基、低烷氧基或羟基基团的2-乙基-2,3-二氢苯并呋喃羧酸衍生物的新方法被描述。该方法通过在适当的溶剂中使用适当的光学纯对映体的2-苯基甘氨酸进行选择性结晶来分离外消旋混合物，然后分离和回收公式（II）的光学纯结晶酸。本发明还提供了这样获得的光学纯的2-乙基-2,3-二氢苯并呋喃羧酸衍生物及其用于制备光学纯的efaroxan衍生物的用途。
• PROCEDE DE PREPARATION D'UN DERIVE D'ACIDE BENZOFURANE CARBOXYLIQUE OPTIQUEMENT PUR, ET SON UTILISATION POUR PREPARER L'EFAROXAN
  申请人：PIERRE FABRE MEDICAMENT

  公开号：EP0824531A1

  公开（公告）日：1998-02-25