Tert-butyl 2-[2-(3-chlorophenyl)tetrazol-5-yl]pyrrolidine-1-carboxylate | 1238287-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Tert-butyl 2-[2-(3-chlorophenyl)tetrazol-5-yl]pyrrolidine-1-carboxylate
• CAS: 1238287-79-0
• 化学式: C₁₆H₂₀ClN₅O₂
• 分子量: 349.82
• InChiKey: VGIMHPGWRYIFSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-[2-(3-chlorophenyl)tetrazol-5-yl]pyrrolidine-1-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 2-(3-Chlorophenyl)-5-(2-pyrrolidinyl)-2H-tetrazole
  参考文献：
  名称：

  Hit-to-lead optimization of disubstituted oxadiazoles and tetrazoles as mGluR5 NAMs

  摘要：

  Here we report the discovery and early SAR of a series of mGluR5 negative allosteric modulators ( NAMs). Starting from a moderately active HTS hit we synthesized 3,5-disubstituted-oxadiazoles and tetrazoles as mGluR5 NAMs. Based on the analysis of ligand efficiency and lipophilic efficiency metrics we identified a promising lead candidate as a starting point for further optimization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.075
• 作为产物：
  描述：

  C₁₇H₂₅N₃O₄S 、 3-氯苯胺 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 、 乙醇 为溶剂， 反应 1.5h， 生成 Tert-butyl 2-[2-(3-chlorophenyl)tetrazol-5-yl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Hit-to-lead optimization of disubstituted oxadiazoles and tetrazoles as mGluR5 NAMs

  摘要：

  Here we report the discovery and early SAR of a series of mGluR5 negative allosteric modulators ( NAMs). Starting from a moderately active HTS hit we synthesized 3,5-disubstituted-oxadiazoles and tetrazoles as mGluR5 NAMs. Based on the analysis of ligand efficiency and lipophilic efficiency metrics we identified a promising lead candidate as a starting point for further optimization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.075

文献信息

• MGluR5 modulators I
  申请人：Wallberg Andreas

  公开号：US20070259862A1

  公开（公告）日：2007-11-08

  The present invention is directed to novel compounds, to a process for their preparation, their use in therapy and pharmaceutical compositions comprising the novel compounds.

  本发明涉及新化合物，以及用于它们的制备方法，它们在治疗中的应用以及包含这些新化合物的药物组合物。
• mGluR5 modulators III
  申请人：Isaac Methvin

  公开号：US20070259926A1

  公开（公告）日：2007-11-08

  The present invention is directed to novel compounds, to a process for their preparation, their use in therapy and pharmaceutical compositions comprising the novel compounds.

  本发明涉及新化合物，涉及它们的制备方法，它们在治疗中的应用以及包含这些新化合物的药物组合物。
• US7678796B2
  申请人：——

  公开号：US7678796B2

  公开（公告）日：2010-03-16
• [EN] TETRAZOLE DERIVATIVES AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS<br/>[FR] DERIVES DE TETRAZOLE UTILISES COMME MODULATEURS DE RECEPTEURS METABOTROPIQUES DU GLUTAMATE
  申请人：RICHTER GEDEON VEGYESZET

  公开号：WO2007039782A1

  公开（公告）日：2007-04-12

  [EN] The present invention relates to new compounds of formula (I) wherein Y₁ and Y₂ selected from the group consisting of hydrogen, halogen atom, C_1-4 alkyl, C_1-4 alkoxy or cyano group, X is oxygen or two hydrogen atoms; Z is -(CH₂)n- group or S; n is 1 or 2; R is selected from the group consisting of optionally substituted C_1-7 alkyl, C_1-4 haloalkyl, C_1-4 hydroxyalkyl, C_1-3OC_1-3 alkyl, C_1-4 cyanoalkyl, C_0-2(NR¹R²)alkyl, C_1-4-alkylCOOC_1-4-alkyl, C_1-4-alkylOCOC_1-4-alkyl, C_1-4-alkylNHCOC_1-4-alkyl, C_2-7 alkenyl, C_2-7 alkynyl, CH₂O-(CH₂)_1-3-OCH₃; an optionally substituted C_3-7 cycloalkyl; phenyl; C_3-7 saturated or unsaturated heterocyclyl or heteroaryl group containing 1-4 heteroatom; R¹ and R² are independently selected from hydrogen, C_1-7 alkyl or C_1-6 alkanoyl group - and/or enantiomers and/or racemates and/or diastereomers and/or geometric isomers and/or pharmaceutically acceptable salts thereof formed with acids and bases, to the process for producing said compounds, to pharmaceutical compositions containing said compounds and to their use in the prevention and/or treatment of mGluR5 receptor-mediated disorders.
  [FR] L'invention concerne de nouveaux composés de formule (I) dans laquelle Y₁ et Y₂ sont sélectionnés dans le groupe constitué par hydrogène, un atome halogène, C_1-4 alkyle, C_1-4 alkoxy ou cyano, X représente l'oxygène ou deux atomes hydrogène; Z désigne le groupe -(CH₂)n- ou S; n est égal à 1 ou à 2; R est sélectionné dans le groupe constitué par C_1-7 alkyle, C_1-4 haloalkyle, C_1-4 hydroxyalkyle, C_1-3OC_1-3 alkyle, C_1-4 cyanoalkyle, C_0-2(NR¹R²)alkyle, C_1-4-alkylCOOC_1-4-alkyle, C_1-4-alkylOCOC_1-4-alkyle, C_1-4-alkylNHCOC_1-4-alkyle, C_2-7 alcényle, C_2-7 alkynyle, CH₂O-(CH₂)_1-3-OCH₃éventuellement substitués ; par un cycloalkyle en C_3-7 éventuellement substitué; phényle; hétérocyclyle saturé ou insaturé en C_3-7 ou par un groupe hétéroaryle contenant 1 à 4 hétéroatomes; R¹ et R² sont sélectionnés indépendamment dans le groupe constitué par hydrogène ou C_1-7 alkyle ou C_1-6 alkanoyle; et/ou par des énantiomères et/ou des racémates et/ou des diastéréoisomères et/ou des isomères géométriques et/ou des sels pharmaceutiquement acceptables formés d'acides et de bases; l'invention porte également sur des procédés de production desdits composés, des compositions pharmaceutiques renfermant lesdits composés et leur utilisation dans la prévention et/ou le traitement de troubles induits par le récepteur de mGluR5.
• Hit-to-lead optimization of disubstituted oxadiazoles and tetrazoles as mGluR5 NAMs
  作者：Gábor Wágner、Csaba Wéber、Olga Nyéki、Katalin Nógrádi、Attila Bielik、László Molnár、Amrita Bobok、Attila Horváth、Béla Kiss、Sándor Kolok、József Nagy、Dalma Kurkó、Krisztina Gál、István Greiner、Zsolt Szombathelyi、György M. Keserű、György Domány

  DOI：10.1016/j.bmcl.2010.04.075

  日期：2010.6

  Here we report the discovery and early SAR of a series of mGluR5 negative allosteric modulators ( NAMs). Starting from a moderately active HTS hit we synthesized 3,5-disubstituted-oxadiazoles and tetrazoles as mGluR5 NAMs. Based on the analysis of ligand efficiency and lipophilic efficiency metrics we identified a promising lead candidate as a starting point for further optimization. (C) 2010 Elsevier Ltd. All rights reserved.