(3,4-dimethylthien-2-yl)-1-trityl-imidazol-4-yl-methanol | 1027579-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3,4-dimethylthien-2-yl)-1-trityl-imidazol-4-yl-methanol
• 英文别名: (3,4-dimethylthiophen-2-yl)-(1-tritylimidazol-4-yl)methanol
• CAS: 1027579-86-7
• 化学式: C₂₉H₂₆N₂OS
• 分子量: 450.604
• InChiKey: GQTVMAOCKRCRBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3,4-dimethylthien-2-yl)-1-trityl-imidazol-4-yl-methanol 在 硼烷四氢呋喃络合物 、 三氟乙酸 、 盐酸 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 5.0h， 生成 4-(3,4-Dimethyl-thiophen-2-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：

  3,4-二甲基-2-噻吩甲酸 在 sodium tetrahydroborate 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 异丙醇 为溶剂， 反应 4.0h， 生成 (3,4-dimethylthien-2-yl)-1-trityl-imidazol-4-yl-methanol
  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

文献信息

• 4-[(thien-2-yl)methyl]-imidazole analgesics
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05621113A1

  公开（公告）日：1997-04-15

  The 4-[(thien-2-yl)methyl]-imidazoles of the formulae: ##STR1## wherein R is hydrogen or methyl, X is hydrogen, C.sub.1-4 alkyl, bromine or chlorine, and Y is hydrogen, C.sub.1-4 alkyl, bromine or chlorine; with the proviso that X and Y are not both simultaneously hydrogen. have exceptional analgesic activity.

  式为：##STR1## 其中 R 为氢或甲基，X 为氢、C.sub.1-4 烷基、溴或氯，Y 为氢、C.sub.1-4 烷基、溴或氯；但要求 X 和 Y 不能同时为氢。这些4-[(thien-2-yl)methyl]-imidazoles具有卓越的镇痛活性。
• 4-[(THIEN-2-YL)METHYL]IMIDAZOLE DERIVATIVES HAVING ALPHA2-ADRENOCEPTOR AGONISTIC ACTIVITY
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP0889891B1

  公开（公告）日：2001-06-06
• US5621113A
  申请人：——

  公开号：US5621113A

  公开（公告）日：1997-04-15
• [EN] 4-[(THIEN-2-YL)METHYL]IMIDAZOLE DERIVATIVES HAVING ALPHA2-ADRENOCEPTOR AGONISTIC ACTIVITY<br/>[FR] DERIVES DU 4-[(THIEN-2-YL)METHYL]-IMIDAZOLE AYANT UNE ACTIVITE AGONISTE VIS-A-VIS DE L'ADRENORECEPTEUR ALPHA2
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：WO1997035857A1

  公开（公告）日：1997-10-02

  (EN) The 4-[(THIEN-2-YL)methyl]-imidazoles of formula (I) wherein R is hydrogen or methyl; X is hydrogen, C1-4alkyl, bromine or chlorine; and Y is hydrogen, C1-4alkyl bromine or chlorine; with the proviso that X and Y are not both simultaneaously hydrogen, have exceptional analgesic activity.(FR) Les 4-[(thién-2-yl)méthyl]-imidazoles de formule (I) où R désigne hydrogène ou méthyle, où X désigne hydrogène, C1-4alkyle, brome ou chlore et où Y désigne hydrogène, C1-4alkyle, brome ou chlore, à condition que X et Y ne désignent pas tous deux hydrogène, 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.