benzyl (S)-4-(2-aminoimidazo[1,2-a]pyridin-3-yl)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoate | 1423171-50-9

• 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: benzyl (S)-4-(2-aminoimidazo[1,2-a]pyridin-3-yl)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoate
• CAS: 1423171-50-9
• 化学式: C₂₃H₂₆N₄O₅
• 分子量: 438.483
• InChiKey: DZKYQOHGHKWUEB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  125.02
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzyl (S)-4-(2-aminoimidazo[1,2-a]pyridin-3-yl)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoate 在 碘 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4S)-benzyl [2-(4-bromophenyl)-5-oxo-4,5-dihydro-3H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-4-yl]acetate
  参考文献：
  名称：

  Imidazopyridine-fused [1,3]diazepinones: modulations of positions 2 to 4 and their impacts on the anti-melanoma activity

  摘要：

  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.

  DOI：

  10.1080/14756366.2020.1748024
• 作为产物：
  描述：

  2,2,2-三氟-N-(咪唑并[1,2-A]吡啶-2-基)乙酰胺 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 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 benzyl (S)-4-(2-aminoimidazo[1,2-a]pyridin-3-yl)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoate
  参考文献：
  名称：

  An efficient synthesis of pyrido-imidazodiazepinediones

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2012.12.087