5-nitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one | 22902-67-6

• 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: 5-nitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
• 英文别名: 5-nitro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one；1,3-Dihydro-5-nitro-2H-imidazo[4,5-B]pyridin-2-one；5-nitro-1,3-dihydroimidazo[4,5-b]pyridin-2-one
• CAS: 22902-67-6
• 化学式: C₆H₄N₄O₃
• mdl: MFCD00184169
• 分子量: 180.123
• InChiKey: TXAMXRHQYUGXOV-UHFFFAOYSA-N

物化性质

• 熔点：
  350-353 °C(Solv: water (7732-18-5))
• 密度：
  2.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one 在 一水合肼 作用下， 反应 14.0h， 以80%的产率得到5-氨基-1,3-二氢-2H-苯并咪唑-2-酮
  参考文献：
  名称：

  Synthesis of 1-(1,3-dialkyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acids

  摘要：

  Nitration of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one gave its 5-nitro derivative which was subjected to alkylation with dimethyl sulfate, diethyl sulfate, and benzyl(dimethyl)phenylammonium chloride. The resulting 1,3-dimethyl-, 1,3-diethyl-, and 1,3-dibenzyl-5-nitro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones were reduced to the corresponding 1,3-dialkyl-5-amino-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, and the latter reacted with itaconic acid to produce 1-(1,3-dialkyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acids. 1-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acid was obtained by analogous reaction with 5-amino-2,3-dihydro-1H-imidazo[4,5-b]-pyridin-2-one.

  DOI：

  10.1134/s1070428007110206
• 作为产物：
  描述：

  1,3-二氢咪唑并[4,5-b]吡啶-2-酮 在 硫酸 、 硝酸 作用下， 反应 3.0h， 以82%的产率得到5-nitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮衍生物的硝化

  摘要：

  Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one and its N-methyl derivatives at 0-5 degrees C and 60 degrees C gives 5-nitro- and 5,6-dinitro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones, respectively. The latter can also be obtained by nitration of 5-mononitro derivatives under similar conditions. The nitration of 6-chloro- and 6-bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones and their N-methyl-substituted analogs leads to the formation of the corresponding 6-chloro(bromo)-5 -nitro compounds. The same products are formed in the nitration of 5,6-dichloro- and 5,6-dibromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones. In this case, the process involves replacement of the halogen atom in position 5 of the pyridine fragment by nitro group. The nitration of 6-bromo-5-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one is accompanied by oxidation of the 5-methyl group to carboxy.

  DOI：

  10.1134/s1070428007030153

文献信息

• 组蛋白乙酰转移酶小分子抑制剂及其制备方法和用途
  申请人：复旦大学

  公开号：CN117820236A

  公开（公告）日：2024-04-05

  本发明属药物化学技术领域，涉及组蛋白乙酰转移酶(HAT)抑制剂及其制备方法和用途。具体涉及通式(I)的芳基羧酸类化合物、具药学上可接受的盐、立体异构体、前药分子或它们的混合物，其制备方法和作为组蛋白乙酰化抑制剂的用途。具可用于多种乙酰化过表达相关的疾病的治疗，主要包括肿瘤、炎症反应和神经退行性疾病等。#imgabs0#
• Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one derivatives
  作者：N. N. Smolyar、Kh. Ya. Lopatinskaya、A. B. Vasilechko、D. A. Lomov、Yu. M. Yutilov

  DOI：10.1134/s1070428007030153

  日期：2007.3

  Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one and its N-methyl derivatives at 0-5 degrees C and 60 degrees C gives 5-nitro- and 5,6-dinitro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones, respectively. The latter can also be obtained by nitration of 5-mononitro derivatives under similar conditions. The nitration of 6-chloro- and 6-bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones and their N-methyl-substituted analogs leads to the formation of the corresponding 6-chloro(bromo)-5 -nitro compounds. The same products are formed in the nitration of 5,6-dichloro- and 5,6-dibromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones. In this case, the process involves replacement of the halogen atom in position 5 of the pyridine fragment by nitro group. The nitration of 6-bromo-5-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one is accompanied by oxidation of the 5-methyl group to carboxy.
• Synthesis of 1-(1,3-dialkyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acids
  作者：N. N. Smolyar、N. N. Troyan、A. B. Vasilechko、D. A. Lomov、Yu. M. Yutilov

  DOI：10.1134/s1070428007110206

  日期：2007.11

  Nitration of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one gave its 5-nitro derivative which was subjected to alkylation with dimethyl sulfate, diethyl sulfate, and benzyl(dimethyl)phenylammonium chloride. The resulting 1,3-dimethyl-, 1,3-diethyl-, and 1,3-dibenzyl-5-nitro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones were reduced to the corresponding 1,3-dialkyl-5-amino-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, and the latter reacted with itaconic acid to produce 1-(1,3-dialkyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acids. 1-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acid was obtained by analogous reaction with 5-amino-2,3-dihydro-1H-imidazo[4,5-b]-pyridin-2-one.