(2S)-2-Boc-amino-1-(2-aminoimidazo[1,2-a]pyridin-3-yl)propan-1-one | 1369586-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: (2S)-2-Boc-amino-1-(2-aminoimidazo[1,2-a]pyridin-3-yl)propan-1-one
• 英文别名: tert-butyl N-[(2S)-1-(2-aminoimidazo[1,2-a]pyridin-3-yl)-1-oxopropan-2-yl]carbamate
• CAS: 1369586-10-6
• 化学式: C₁₅H₂₀N₄O₃
• 分子量: 304.349
• InChiKey: BJBYYHBQQFXOOB-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  98.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-Boc-amino-1-(2-aminoimidazo[1,2-a]pyridin-3-yl)propan-1-one 在 盐酸 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以92%的产率得到(2S)-2-amino-1-(2-aminoimidazo[1,2-a]pyridin-3-yl)-propan-1-one
  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 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 (2S)-2-Boc-amino-1-(2-aminoimidazo[1,2-a]pyridin-3-yl)propan-1-one
  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

• 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.
• 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.
• Imidazopyridine-fused [1,3]-diazepinones: Synthesis and antiproliferative activity
  作者：Audrey Gallud、Ophélie Vaillant、Ludovic T. Maillard、Dominique P. Arama、Joëlle Dubois、Marie Maynadier、Vincent Lisowski、Marcel Garcia、Jean Martinez、Nicolas Masurier

  DOI：10.1016/j.ejmech.2014.01.044

  日期：2014.3

  A series of 15 pyrido-imidazo-1,3-diazepin-5-ones and pyrido-1,3-diazepine-2,5-diones were synthesized and their anticancer activities were evaluated. Among tested compounds on a cell lines panel, compound 6a presents the best growth inhibition activity on 21 cell lines with a cytotoxic effect on MDA-MB-435 melanoma cells. This compound led to deep cell morphological changes and revealed to be an inhibitor of the Hepatocyte progenitor kinase-like kinase (HGK), which is known to be implicated in the migration, adhesion and invasion of various tumor cells. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Imidazopyridine-fused [1,3]-diazepinones part 2: Structure-activity relationships and antiproliferative activity against melanoma cells
  作者：Virginie Bellet、Laure Lichon、Dominique P. Arama、Audrey Gallud、Vincent Lisowski、Ludovic T. Maillard、Marcel Garcia、Jean Martinez、Nicolas Masurier

  DOI：10.1016/j.ejmech.2016.11.023

  日期：2017.1

  We recently described a pyrido-imidazodiazepinone derivative which could be a promising hit compound for the development of new drugs acting against melanoma cells. In this study, a series of 28 novel pyrido-imidazodiazepinones were synthesized and screened for their in vitro cytotoxic activities against the melanoma MDA-MB-435 cell line. Among the derivatives, seven of them showed 50% growth inhibitory activity at 1 mu M concentration, and high selectivity against the melanoma cell line MDA-MB-435. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Selective C-Acylation of 2-Aminoimidazo[1,2-<i>a</i>]pyridine: Application to the Synthesis of Imidazopyridine-Fused [1,3]Diazepinones
  作者：Nicolas Masurier、Roberta Aruta、Vincent Gaumet、Séverine Denoyelle、Emmanuel Moreau、Vincent Lisowski、Jean Martinez、Ludovic T. Maillard

  DOI：10.1021/jo300364d

  日期：2012.4.6

  2]imidazo[4,5-d][1,3]diazepin-5-ones which form a new family of azaheterocycle-fused [1,3]diazepines were synthesized in four steps with 17–66% overall yields. The key step consists of a selective C-acylation reaction of easily accessible 2-aminoimidazo[1,2-a]pyridine at C-3.

  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。