6-氯-1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮 | 304861-88-9

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 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: 6-氯-1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮
• 中文别名: 2-羟基-5-氯吡啶并咪唑；2-羟基-6-氯咪唑并[4,5-B]吡啶
• 英文名称: 6-chloro-1H-imidazo[4,5-b]pyridin-2(3H)-one
• 英文别名: 6-chloro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one；6-Chlor-1,3-dihydro-imidazo[4,5-b]pyridin-2-on；6-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one
• CAS: 304861-88-9
• 化学式: C₆H₄ClN₃O
• mdl: MFCD00222293
• 分子量: 169.57
• InChiKey: IYVCQOHFGFWGEG-UHFFFAOYSA-N

物化性质

• 熔点：
  338-340℃
• 沸点：
  171.0±28.0 °C(Predicted)
• 密度：
  1.82

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 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：
  54
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-氯-1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮 在 Lindlar's catalyst 作用下， 生成 1,3-二氢咪唑并[4,5-b]吡啶-2-酮
  参考文献：
  名称：

  Triazolo and Imidiazopyridines

  摘要：

  DOI：

  10.1021/ja01173a527
• 作为产物：
  描述：

  2-氨基-5-氯-3-硝基吡啶 在 sodium dithionite 、 水 作用下， 生成 6-氯-1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮
  参考文献：
  名称：

  Triazolo and Imidiazopyridines

  摘要：

  DOI：

  10.1021/ja01173a527

文献信息

• Halogenation of Imidazo[4,5-b]pyridin-2-one Derivatives
  作者：Yu. M. Yutilov、Kh. Ya. Lopatinskaya、N. N. Smolyar、S. V. Gres’ko

  DOI：10.1007/s11178-005-0206-y

  日期：2005.4

  Chlorination and bromination of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one and its N-methyl-substituted derivatives in acetic acid at 90–95°C leads to formation of the corresponding 5,6-dichloro(dibromo)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones. Iodination of the same substrates with ICl under analogous conditions yields 6-iodo derivatives. Chlorination of 6-iodo-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one is accompanied by replacement of the iodine atom by chlorine with formation of 5,6-dichloro-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one. Bromination of 6-bromo- and 6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones gives 5,6-dibromo- and 5-bromo-6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, respectively.

  在醋酸中，以90–95°C对2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮及其N-甲基取代衍生物进行氯化和溴化，会形成相应的5,6-二氯（或二溴）-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮。在类似条件下，使用ICl对相同底物进行碘化会生成6-碘衍生物。对6-碘-1,3-二甲基-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮进行氯化时，碘原子被氯取代，生成5,6-二氯-1,3-二甲基-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮。对6-溴和6-氯-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮进行溴化分别得到5,6-二溴-和5-溴-6-氯-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮。
• Optimization of 5-substituted thiazolyl ureas and 6-substituted imidazopyridines as potential HIV-1 latency reversing agents
  作者：William Nguyen、Jonathan Jacobson、Kate E. Jarman、Timothy R. Blackmore、Helene Jousset Sabroux、Sharon R. Lewin、Damian F. Purcell、Brad E. Sleebs

  DOI：10.1016/j.ejmech.2020.112254

  日期：2020.6

  A persistent latent reservoir of virus in CD4(+) T cells is a major barrier to cure HIV. Activating viral transcription in latently infected cells using small molecules is one strategy being explored to eliminate latency. We previously described the use of a FlpIn.FM HEK293 cellular assay to identify and then optimize the 2-acylaminothiazole class to exhibit modest activation of HIV gene expression. Here, we implement two strategies to further improve the activation of viral gene expression and physicochemical properties of this class. Firstly, we explored rigidification of the central oxy-carbon linker with a variety of saturated heterocycles, and secondly, investigated bioisosteric replacement of the 2-acylaminothiazole moiety. The optimization process afforded lead compounds (74 and 91) from the 2-piperazinyl thiazolyl urea and the imidazopyridine class. The lead compounds from each class demonstrate potent activation of HIV gene expression in the FlpIn.FM HEK293 cellular assay (both with LTR EC(50)s of 80 nM) and in the Jurkat Latency 10.6 cell model (LTR EC50 220 and 320 nM respectively), but consequently activate gene expression non-specifically in the FlpIn.FM HEK293 cellular assay (CMV EC50 70 and 270 nM respectively) manifesting in cellular cytotoxicity. The lead compounds have potential for further development as novel latency reversing agents. (C) 2020 Elsevier Masson SAS. All rights reserved.
• 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.