N-[3-(1H-imidazol-4-ylmethyl)phenyl]ethanesulfonamide | 258526-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[3-(1H-imidazol-4-ylmethyl)phenyl]ethanesulfonamide
• 英文别名: ABT-866；A 286666；4-[3-(1-ethylsulfonylamino)phenyl]methyl-1H-imidazole；Ethanesulfonamide, N-(3-(1H-imidazol-4-ylmethyl)phenyl)-；N-[3-(1H-imidazol-5-ylmethyl)phenyl]ethanesulfonamide
• CAS: 258526-74-8
• 化学式: C₁₂H₁₅N₃O₂S
• 分子量: 265.336
• InChiKey: ROUIPNDCVDWYEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(3-aminobenzyl)imidazole-1-sulfonic acid dimethylamide 在 吡啶 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-[3-(1H-imidazol-4-ylmethyl)phenyl]ethanesulfonamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Studies on N-[5-(1H-Imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an Imidazole-Containing α_1A-Adrenoceptor Agonist

  摘要：

  Structure-activity studies were performed on the alpha(1A)-adrenoceptor (AR) selective agonist N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide (4). Compounds were evaluated for binding activity at the alpha(1A), alpha(1b), alpha(1d), alpha(2a), and alpha(2B) subtypes. Functional activity in tissues containing the alpha(1A) (rabbit urethra), alpha(1B) (rat spleen), alpha(1D) (rat aorta), and alpha(2A) (rat prostatic vas deferens) was also evaluated. A dog in vivo model simultaneously measuring intraurethral pressure (IUP) and mean arterial pressure (ALAP) was used to assess the uroselectivity of the compounds. Many of the compounds that were highly selective in vitro for the alpha(1A)-AR subtype were also more uroselective in vivo for increasing IUP over MAP than the nonselective alpha(1)-agonists phenylpropanolamine (PPA) (1) and ST-1059 (2, the active metabolite of midodrine), supporting the hypothesis that greater alpha(1A) selectivity would reduce cardiovascular side effects. However, the data also support a prominent role of the alpha(1A)-AR subtype in the control of MAP.

  DOI：

  10.1021/jm030551a

文献信息

• 4-Imidazole derivatives of benzyl and restricted benzyl sulfonamides, sulfamides, ureas, carbamates, and amides and their use
  申请人：——

  公开号：US20030073850A1

  公开（公告）日：2003-04-17

  Compounds of formula I 1 are useful in treating diseases prevented by or ameliorated with &agr; 1A agonists. Also disclosed are &agr; 1A agonist compositions and a method of activating &agr; 1 adrenoceptors in a mammal.

  公式I的化合物在治疗由&agr; 1A激动剂预防或改善的疾病中很有用。还公开了&agr; 1A激动剂组合物和在哺乳动物中激活&agr; 1肾上腺素受体的方法。
• [EN] IMIDAZOLES AND RELATED COMPOUNDS AS alpha 1A AGONISTS<br/>[FR] IMIDAZOLES ET COMPOSES APPARENTES EN TANT QU'AGONISTES D' alpha 1A
  申请人：ABBOTT LAB

  公开号：WO2000007997A1

  公开（公告）日：2000-02-17

  Compounds having formula (I) are useful in treating diseases prevented by or ameliorated with α1A agonists. Also disclosed are α1A agonist compositions and a method of activating α1 adrenoceptors in a mammal.

  具有公式（I）的化合物在治疗由α1A激动剂预防或缓解的疾病方面具有用处。还披露了α1A激动剂组合物和在哺乳动物中激活α1肾上腺素受体的方法。
• β−３−アドレノセプターアゴニスト及びα−アゴニストから成る医薬組成物
  申请人：ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング

  公开号：JP2007509897A

  公开（公告）日：2007-04-19

  本発明は、αアゴニストとβ-3-アドレノセプターアゴニストを含有する、膀胱の機能不全を治療するための新規な組合せに関する。

  本发明涉及一种治疗膀胱功能障碍的新型组合物，其中包含一种α受体激动剂和一种β-3-肾上腺素受体激动剂。
• Pharmaceutical composition consisting of a beta-3-adrenoceptor agonist and alpha-agonist
  申请人：Michel Martin

  公开号：US20050154041A1

  公开（公告）日：2005-07-14

  This invention describes a new combination for the treatment of functional bladder disorders which comprises alpha agonists and a beta-3-adrenoceptor agonist.

  本发明描述了一种治疗功能性膀胱失调的新组合，其中包括α-激动剂和β-3-肾上腺素受体激动剂。
• <i>N</i>-[3-(1<i>H</i>-Imidazol-4-ylmethyl)phenyl]ethanesulfonamide (ABT-866, 1), a Novel α₁-Adrenoceptor Ligand with an Enhanced in Vitro and in Vivo Profile Relative to Phenylpropanolamine and Midodrine
  作者：Robert J. Altenbach、Albert Khilevich、Michael D. Meyer、Steven A. Buckner、Ivan Milicic、Anthony V. Daza、Michael E. Brune、Alyssa B. O'Neill、Donna M. Gauvin、John C. Cain、Masaki Nakane、Mark W. Holladay、Michael Williams、Jorge D. Brioni、James P. Sullivan

  DOI：10.1021/jm025550h

  日期：2002.9.1

  N-[3-(1H-Imidazol-4-ylmethyl)phenyl]ethanesulfonamide (ABT-866, 1) is a novel alpha(1) agent having the unique profile of alpha(1A) (rabbit urethra, EC50 = 0.60 muM) agonism with alpha(1B) (rat spleen, pA(2) = 5.4) and alpha(1D) (rat aorta, pA(2) = 6.2) antagonism. An in vivo dog model showed I to be more selective for the urethra over the vasculature than A-61603 (2), ST-1059 (3, the active metabolite of midodrine), and phenylpropanolamine (4).