2-ethylthiophene-3-carboxaldehyde | 156386-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethylthiophene-3-carboxaldehyde
• 英文别名: 2-Ethyl-3-formylthiophene；2-ethylthiophene-3-carbaldehyde
• CAS: 156386-50-4
• 化学式: C₇H₈OS
• 分子量: 140.206
• InChiKey: BZJVXWRAUTYFQJ-UHFFFAOYSA-N

物化性质

• 保留指数：
  1147

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethylthiophene-3-carboxaldehyde 在 palladium dihydroxide 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0~50.0 ℃ 、344.75 kPa 条件下， 生成 4-(2-Ethyl-thiophen-3-ylmethyl)-1H-imidazole
  参考文献：
  名称：

  α₂ Adrenoceptor Agonists as Potential Analgesic Agents. 3. Imidazolylmethylthiophenes

  摘要：

  A series of imidazolylmethylthiophenes has been prepared and evaluated as ligands for the at adrenoceptor. These compounds were tested in two animal models that are predictive of analgesic activity in humans. The 3-thienyl compounds were generally the most potent, particularly those with substitution in the 4-position. A subset of the most active compounds was further evaluated for adverse cardiovascular effects in the anesthetized rat model. In addition to excellent binding at the alpha (2D) adrenoceptor, the 4-bromo analogues 20e and 21e were very active in the rat abdominal irritant test (RAIT) with ED50 doses of 0.38 and 0.31 mg/kg, respectively. We constructed a pharmacophore model based on the biological activity of the present series, dexmedetomidine (1), and conformationally restrained analogues 3 and 4.

  DOI：

  10.1021/jm0003891
• 作为产物：
  描述：

  3-bromo-2-ethylthiophene 在 正丁基锂 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 以1.66 g (25%)的产率得到2-ethylthiophene-3-carboxaldehyde
  参考文献：
  名称：

  4-\x9b(thien-3-yl)methyl!-imidazole analgesics

  摘要：

  本文描述的是公式为4-（噻吩-3-基）甲基-咪唑的化合物：其中R为氢或甲基，X为C.sub.1-4烷基，溴或氯；或者其中Y为氢，C.sub.1-4烷基，溴或氯，Z为C.sub.1-4烷基，溴或氯的化合物，具有出色的镇痛活性。

  公开号：

  US05750720A1

文献信息

• 4- (THIEN-3-YL)METHYL] IMIDAZOLE DERIVATIVES HAVING ALPHA2-ADRENOCEPTOR AGONISTIC ACTIVITY
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP0954521A1

  公开（公告）日：1999-11-10
• US5750720A
  申请人：——

  公开号：US5750720A

  公开（公告）日：1998-05-12
• [EN] 4-[(THIEN-3-YL)METHYL] IMIDAZOLE DERIVATIVES HAVING alpha 2-ADRENOCEPTOR AGONISTIC ACTIVITY<br/>[FR] DERIVES DU 4-[(THIEN-3-YL)METHYL]-IMIDAZOLE AYANT UNE ACTIVITE AGONISTE VIS-A-VIS DE L'ADRENORECEPTEUR alpha 2
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：WO1997035858A1

  公开（公告）日：1997-10-02

  (EN) The 4-[(thien-3-yl)methyl]-imidazoles of formulae (I), wherein R is hydrogen or methyl, and X is C1-4alkyl, bromine or chlorine; or (II), wherein Y is hydrogen; C1-4alkyl, bromine or chlorine, and Z is C1-4alkyl, bromine or chlorine, have exceptional analgesic activity.(FR) Les 4-[(thien-3-yl)méthyl]-imidazoles de formule (I) où R désigne un hydrogène ou un méthyle et où X désigne un C1-4alkyle, un brome ou un chlore, ou de formule (II) où Y désigne un hydrogène, un C1-4alkyle, un brome ou un chlore et où Z désigne un C1-4alkyle, un brome ou un chlore, ont des propriétés analgésiques exceptionnelles.
• α₂ Adrenoceptor Agonists as Potential Analgesic Agents. 3. Imidazolylmethylthiophenes
  作者：Robert E. Boyd、C. Royce Rasmussen、Jeffery B. Press、Robert B. Raffa、Ellen E. Codd、Charlene D. Connelly、Quan S. Li、Rebecca P. Martinez、Martin A. Lewis、Harold R. Almond、Allen B. Reitz

  DOI：10.1021/jm0003891

  日期：2001.3.1

  A series of imidazolylmethylthiophenes has been prepared and evaluated as ligands for the at adrenoceptor. These compounds were tested in two animal models that are predictive of analgesic activity in humans. The 3-thienyl compounds were generally the most potent, particularly those with substitution in the 4-position. A subset of the most active compounds was further evaluated for adverse cardiovascular effects in the anesthetized rat model. In addition to excellent binding at the alpha (2D) adrenoceptor, the 4-bromo analogues 20e and 21e were very active in the rat abdominal irritant test (RAIT) with ED50 doses of 0.38 and 0.31 mg/kg, respectively. We constructed a pharmacophore model based on the biological activity of the present series, dexmedetomidine (1), and conformationally restrained analogues 3 and 4.
• 4-\x9b(thien-3-yl)methyl!-imidazole analgesics
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05750720A1

  公开（公告）日：1998-05-12

  Described herein are 4-\x9b(thien-3-yl)methyl!-imidazoles of the formula: ##STR1## wherein R is hydrogen or methyl, and X is C.sub.1-4 alkyl, bromine or chlorine; or ##STR2## wherein Y is hydrogen, C.sub.1-4 alkyl, bromine or chlorine, and Z is C.sub.1-4 4alkyl, bromine or chlorine which have exceptional analgesic activity.

  本文描述的是公式为4-（噻吩-3-基）甲基-咪唑的化合物：其中R为氢或甲基，X为C.sub.1-4烷基，溴或氯；或者其中Y为氢，C.sub.1-4烷基，溴或氯，Z为C.sub.1-4烷基，溴或氯的化合物，具有出色的镇痛活性。