2,2,2-三氟-N-(咪唑并[1,2-A]吡啶-2-基)乙酰胺 | 504413-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 2,2,2-三氟-N-(咪唑并[1,2-A]吡啶-2-基)乙酰胺
• 英文名称: trifluoro-N-imidazo[1,2-a]pyridin-2-ylacetamide
• 英文别名: 2,2,2-trifluoro-N-(imidazo[1,2-a]pyridin-2-yl)acetamide；2,2,2-trifluoro-N-imidazo[1,2-a]pyridin-2-ylacetamide
• CAS: 504413-26-7
• 化学式: C₉H₆F₃N₃O
• 分子量: 229.161
• InChiKey: UUNDTHNXCSUIRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟-N-(咪唑并[1,2-A]吡啶-2-基)乙酰胺 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 咪唑并[1,2-a]吡啶-2-胺
  参考文献：
  名称：

  2-氨基咪唑并[1,2- a ]吡啶的选择性C-酰化反应：在咪唑并吡啶[1,3]二氮杂吡啶酮类化合物的合成中的应用

  摘要：

  一系列20个光学纯的3,4-二氢-5 H-吡啶并[1'，2'：1,2]咪唑并[4,5- d ] [1,3]二氮杂-5-酮形成一个新家族分四步合成了氮杂杂环融合的[1,3]二氮杂ze，总产率为17-66％。关键步骤包括在C-3处容易获得的2-氨基咪唑并[1,2- a ]吡啶的选择性C-酰化反应。

  DOI：

  10.1021/jo300364d
• 作为产物：
  描述：

  N-(2-pyridyl)-p-toluenesulfonamide 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2,2,2-三氟-N-(咪唑并[1,2-A]吡啶-2-基)乙酰胺
  参考文献：
  名称：

  2-氨基咪唑并[1,2- a ]吡啶的选择性C-酰化反应：在咪唑并吡啶[1,3]二氮杂吡啶酮类化合物的合成中的应用

  摘要：

  一系列20个光学纯的3,4-二氢-5 H-吡啶并[1'，2'：1,2]咪唑并[4,5- d ] [1,3]二氮杂-5-酮形成一个新家族分四步合成了氮杂杂环融合的[1,3]二氮杂ze，总产率为17-66％。关键步骤包括在C-3处容易获得的2-氨基咪唑并[1,2- a ]吡啶的选择性C-酰化反应。

  DOI：

  10.1021/jo300364d

文献信息

• [EN] TRPC5 INHIBITORS AND METHODS OF USING SAME<br/>[FR] INHIBITEURS DE TRPC5 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV NEBRASKA

  公开号：WO2019051197A1

  公开（公告）日：2019-03-14

  Provided herein are TRPC5 inhibitors and methods of using the same, e.g., to protect podocytes and/or treat kidney disease.

  本文提供了TRPC5抑制剂及其使用方法，例如用于保护足细胞和/或治疗肾脏疾病。
• TRPC5 inhibitors and methods of using same
  申请人：BOARD OF REGENTS OF THE UNIVERSITY OF NEBRASKA

  公开号：US11370769B2

  公开（公告）日：2022-06-28

  Provided herein are TRPC5 inhibitors and methods of using the same, e.g., to protect podocytes and/or treat kidney disease.

  本文提供了TRPC5抑制剂及其使用方法，例如保护荚膜细胞和/或治疗肾病的方法。
• Imidazopyridine-fused [1,3]diazepinones: modulations of positions 2 to 4 and their impacts on the anti-melanoma activity
  作者：Paul Le Baccon-Sollier、Yohan Malki、Morgane Maye、Lamiaa M. A. Ali、Laure Lichon、Pierre Cuq、Laure-Anaïs Vincent、Nicolas Masurier

  DOI：10.1080/14756366.2020.1748024

  日期：2020.1.1

  A series of 19 novel pyrido-imidazodiazepinones, with modulations of positions 2, 3 and 4 of the diazepine ring were synthesised and screened for their in vitro cytotoxic activities against two melanoma cell lines (A375 and MDA-MB-435) and for their potential toxicity against NIH-3T3 non-cancerous cells. Selected compounds were also evaluated on the NCI-60 cell line panel. The SAR study revealed that the molecular volume and the cLogP of compounds modified at position 2 were significantly correlated with the activity of these compounds on melanoma cell lines. Moreover, introduction of a heterocyclic group at position 2 or an azido-alkyl chain at position 4 led to compounds displaying a significantly different activity profile on the NCI-60 cell line panel, compared to phenyl-substituted compounds at position 2 of the diazepinone. This study provides us crucial information for the development of new derivatives active against melanoma.
• Pyrido-imidazodiazepinones as a new class of reversible inhibitors of human kallikrein 7
  作者：Dominique P. Arama、Feryel Soualmia、Vincent Lisowski、Jean-François Longevial、Elodie Bosc、Ludovic T. Maillard、Jean Martinez、Nicolas Masurier、Chahrazade El Amri

  DOI：10.1016/j.ejmech.2015.02.008

  日期：2015.3

  The human tissue kallikrein-7 (KLK7) is a chymotryptic serine protease member of tissue kallikrein family. KLK7 is involved in skin homeostasis and inflammation. Excess of KLK7 activity is also associated with tumor metastasis processes, especially in ovarian carcinomas, prostatic and pancreatic cancers. Development of Kallikrein 7 inhibitors is thus of great interest in oncology but also for treating skin diseases. Most of the developed synthetic inhibitors present several drawbacks such as poor selectivity and unsuitable physico-chemical properties for in vivo use. Recently, we described a practical sequence for the synthesis of imidazopyridine-fused [1,3]-diazepines. Here, we report the identification of pyrido-imidazodiazepinone core as a new potential scaffold to develop selective and competitive inhibitors of kallikrein-related peptidase 7. Structure-activity relationships (SAR), inhibition mechanisms and selectivity as well as cytotoxicity against selected cancer cell lines were investigated. (C) 2015 Elsevier Masson SAS. All rights reserved.
• An efficient synthesis of pyrido-imidazodiazepinediones
  作者：Dominique P. Arama、Vincent Lisowski、Eliana Scarlata、Pierre Fulcrand、Ludovic T. Maillard、Jean Martinez、Nicolas Masurier

  DOI：10.1016/j.tetlet.2012.12.087

  日期：2013.3

  We herein report the synthesis of a series of 12 optically pure 3,4-dihydro-1H-pyrido-[1',2':1,21-imidazo[4,5-d][1,31diazepine-2,5-diones, which form a new family of azaheterocycle-fused [1,3]diazepines. The key step of the synthesis consists in a selective C-acylation of 2-amino-imidazo[1,2-a]pyridine by various natural amino-acids, followed by an intracarbonylation reaction. (C) 2012 Elsevier Ltd. All rights reserved.