4,5-dihydro-2-(3-methyl-2-thienyl)-1H-imidazole | 127199-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: 4,5-dihydro-2-(3-methyl-2-thienyl)-1H-imidazole
• 英文别名: 2-(3-methylthiophen-2-yl)-4,5-dihydro-1H-imidazole
• CAS: 127199-59-1
• 化学式: C₈H₁₀N₂S
• 分子量: 166.247
• InChiKey: MCGKHSFUMBTMDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-2-(3-methyl-2-thienyl)-1H-imidazole 在 正丁基锂 、 四甲基乙二胺 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 20.5h， 生成 5-<4-<2-(3,4,5-trimethoxyphenyl)ethyl>phenyl>-2,3-dihydroimidazo<1,2-a>thieno<2,3-c>pyridine
  参考文献：
  名称：

  Structural modification of 5-aryl-2,3-dihydroimidazo[2,1-a]isoquinoline platelet activating factor receptor antagonists

  摘要：

  In an effort to determine the effect of modification of the imidazo[2,1-a]isoquinoline portion of the PAF-receptor antagonist SDZ 64-412 (1), several new analogs were prepared and evaluated in vitro and in vivo. One of these, 5-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]phenyl]-2,3-dihydroimidazo[1,2-a]thieno[2,3-c]pyridine (6) was 4-5 times more potent than 1 in inhibiting PAF-induced bronchoconstriction and hemoconcentration when administered po to the guinea pig.

  DOI：

  10.1021/jm00073a008
• 作为产物：
  描述：

  3-甲基噻吩-2-甲酸甲酯 、 乙二胺 在 三甲基铝 作用下， 生成 4,5-dihydro-2-(3-methyl-2-thienyl)-1H-imidazole
  参考文献：
  名称：

  Structural modification of 5-aryl-2,3-dihydroimidazo[2,1-a]isoquinoline platelet activating factor receptor antagonists

  摘要：

  In an effort to determine the effect of modification of the imidazo[2,1-a]isoquinoline portion of the PAF-receptor antagonist SDZ 64-412 (1), several new analogs were prepared and evaluated in vitro and in vivo. One of these, 5-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]phenyl]-2,3-dihydroimidazo[1,2-a]thieno[2,3-c]pyridine (6) was 4-5 times more potent than 1 in inhibiting PAF-induced bronchoconstriction and hemoconcentration when administered po to the guinea pig.

  DOI：

  10.1021/jm00073a008

文献信息

• 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。
• 5-Aryl-substituted-2,3-dihydro-imidazo [1,2-a]furo[3,2-c]- or thieno[2,3-c]pyridines
  申请人：SANDOZ AG

  公开号：EP0341213A2

  公开（公告）日：1989-11-08

  5-Aryl-substituted-2,3-dihydro-imidazo[1,2-a]furo[3,2-c]-or thieno[2,3-c]pyridines. The intention discloses compounds of formula I wherein the substituents have various significances. They can be prepared by dehydration. They are indicated for use as inhibitors of platelet activating factor (PAF) and as anti-tumor agents.

  5-Aryl-substituted-2,3-dihydro-imidazo[1,2-a]furo[3,2-c]-or thieno[2,3-c]pyridines. 该意向书公开了式 I 的化合物 其中的取代基具有各种意义。 它们可以通过脱水制备。它们可用作血小板活化因子（PAF）抑制剂和抗肿瘤剂。
• Structural modification of 5-aryl-2,3-dihydroimidazo[2,1-a]isoquinoline platelet activating factor receptor antagonists
  作者：William J. Houlihan、Seung H. Cheon、Vincent A. Parrino、Dean A. Handley、Douglas A. Larson

  DOI：10.1021/jm00073a008

  日期：1993.10

  In an effort to determine the effect of modification of the imidazo[2,1-a]isoquinoline portion of the PAF-receptor antagonist SDZ 64-412 (1), several new analogs were prepared and evaluated in vitro and in vivo. One of these, 5-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]phenyl]-2,3-dihydroimidazo[1,2-a]thieno[2,3-c]pyridine (6) was 4-5 times more potent than 1 in inhibiting PAF-induced bronchoconstriction and hemoconcentration when administered po to the guinea pig.