1-benzyl-5-(2,3-dichlorophenyl)-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-5-(2,3-dichlorophenyl)-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-5-(2,3-dichlorophenyl)triazole
• 化学式: C₁₅H₁₁Cl₂N₃
• 分子量: 304.178
• InChiKey: IIJRJMVBKYENMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二氯碘苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 1-benzyl-5-(2,3-dichlorophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Novel and potent 3-(2,3-dichlorophenyl)-4-(benzyl)-4H-1,2,4-triazole P2X7 antagonists

  摘要：

  Structure-activity relationship (SAR) studies were conducted around early tetrazole-based leads 3 and 4. Replacements for the tetrazole core were investigated and the pendant benzyl substitution was reoptimized with a triazole isostere. Triazole-based P2X(7) antagonists were identified with similar potency to the lead compound 4 but with improved physiochemical properties. Compound 12 was active in a rat model of neuropathic pain. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.075

文献信息

• P2X7 receptor antagonists and methods of use
  申请人：Carroll A. William

  公开号：US20070105842A1

  公开（公告）日：2007-05-10

  The invention is directed to compounds that are P2X 7 antagonist and have the formula (I) or (II) or a pharmaceutically acceptable salt, prodrug, salt of a prodrug or a combination thereof, wherein R 1 , R 2 , and R 3 are defined in the specification. The invention is also directed to a method of selectively inhibiting P2X 7 activity comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of formula (III), (IV) or (V) wherein R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are defined in the specification.

  这项发明涉及具有化学式(I)或(II)的P2X7拮抗剂化合物，或其药学上可接受的盐、前药、前药的盐或二者的组合，其中R1、R2和R3在规范中有定义。该发明还涉及一种选择性抑制P2X7活性的方法，包括向需要此类治疗的患者施用化合物的治疗有效量，其化学式为(III)、(IV)或(V)，其中R6、R7、R8、R9、R10和R11在规范中有定义。
• P2X7 RECEPTOR ANTAGONISTS AND METHODS OF USE
  申请人：ABBOTT LABORATORIES

  公开号：EP1951689A1

  公开（公告）日：2008-08-06
• US7709469B2
  申请人：——

  公开号：US7709469B2

  公开（公告）日：2010-05-04
• [EN] P2X7 RECEPTOR ANTAGONISTS AND METHODS OF USE<br/>[FR] ANTAGONISTES DES RECEPTEURS P2X7 ET METHODES D'UTILISATION
  申请人：ABBOTT LAB

  公开号：WO2007056046A1

  公开（公告）日：2007-05-18

  [EN] The invention is directed to compounds that are P2X₇ antagonist and have the formula (I) or (II) or a pharmaceutically acceptable salt, prodrug, salt of a prodrug or a combination thereof, wherein R₁, R₂, and R₃ are defined in the specification. The invention is also directed to a method of selectively inhibiting P2X₇ activity comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of formula (III), (IV) or (V) wherein R₆, R₇, R₈, R₉, R₁₀, and R₁₁ are defined in the specification.
  [FR] L'invention concerne des composés qui sont des antagonistes des P2X₇ et représentés par la formule (I) ou (II), ou un sel, un promédicament, un sel d'un promédicament ou une combinaison de ces derniers pharmaceutiquement acceptables. Dans lesdites formules, R₁, R₂ et R₃ sont tels que définis dans la description. L'invention concerne également une méthode d'inhibition sélective de l'activité des P2X₇ consistant à administrer à un patient en attente d'un tel traitement une quantité thérapeutiquement efficace d'un composé représenté par les formules (III), (IV) ou (V), dans lesquelles R₆, R₇, R₈, R₉, R₁₀ et R₁₁ sont tels que définis dans la description.
• Novel and potent 3-(2,3-dichlorophenyl)-4-(benzyl)-4H-1,2,4-triazole P2X7 antagonists
  作者：William A. Carroll、Douglas M. Kalvin、Arturo Perez Medrano、Alan S. Florjancic、Ying Wang、Diana L. Donnelly-Roberts、Marian T. Namovic、George Grayson、Prisca Honoré、Michael F. Jarvis

  DOI：10.1016/j.bmcl.2007.04.075

  日期：2007.7

  Structure-activity relationship (SAR) studies were conducted around early tetrazole-based leads 3 and 4. Replacements for the tetrazole core were investigated and the pendant benzyl substitution was reoptimized with a triazole isostere. Triazole-based P2X(7) antagonists were identified with similar potency to the lead compound 4 but with improved physiochemical properties. Compound 12 was active in a rat model of neuropathic pain. (C) 2007 Elsevier Ltd. All rights reserved.