4-氯-1H-咪唑并[4,5-C]吡啶 | 881844-11-7

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 4-氯-1H-咪唑并[4,5-C]吡啶
• 英文名称: 4-chloro-1-(p-methoxybenzyl)-1H-imidazo[4,5-c]pyridine
• 英文别名: 4-chloro-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine；4-chloro-1-[(4-methoxyphenyl)methyl]imidazo[4,5-c]pyridine
• CAS: 881844-11-7
• 化学式: C₁₄H₁₂ClN₃O
• 分子量: 273.722
• InChiKey: PRKHXXIHHSVLFA-UHFFFAOYSA-N

物化性质

• 沸点：
  483.0±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯-1H-咪唑并[4,5-C]吡啶 在 氢气 、 镍 、 三氟乙酸 、 肼 作用下， 以 丙醇 、 水 为溶剂， 反应 3.0h， 生成 1H-咪唑并(4,5-c)吡啶-4-胺
  参考文献：
  名称：

  Synthesis of 3-deaza-3-nitro-2′-deoxyadenosine

  摘要：

  Photoactivable deoxyadenosine mimic, 3-deaza-3-nitro-2'-deoxyadetiosine (2), was prepared using two different synthetic routes. The first route involved base catalyzed glycosylation of 3-deaza-3-nitroadenine, which was prepared by regioselective nitration of 3-deazaadenine. In the second route, the convertible nucleoside 6-O-(2,4,6-trimethylphenyl)-3-deaza-2'-deoxyadenosine (28) was used to introduce 6-NH2 group in the last step. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.040
• 作为产物：
  描述：

  2,4-二氯-3-硝基吡啶 在 氢气 、 乙酸酐 、 镍 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 4-氯-1H-咪唑并[4,5-C]吡啶
  参考文献：
  名称：

  Synthesis of 3-deaza-3-nitro-2′-deoxyadenosine

  摘要：

  Photoactivable deoxyadenosine mimic, 3-deaza-3-nitro-2'-deoxyadetiosine (2), was prepared using two different synthetic routes. The first route involved base catalyzed glycosylation of 3-deaza-3-nitroadenine, which was prepared by regioselective nitration of 3-deazaadenine. In the second route, the convertible nucleoside 6-O-(2,4,6-trimethylphenyl)-3-deaza-2'-deoxyadenosine (28) was used to introduce 6-NH2 group in the last step. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.040

文献信息

• Design and synthesis of purine analogues as highly specific ligands for FcyB, a ubiquitous fungal nucleobase transporter
  作者：Nikolaos Lougiakis、Efthymios-Spyridon Gavriil、Markelos Kairis、Georgia Sioupouli、George Lambrinidis、Dimitra Benaki、Emilia Krypotou、Emmanuel Mikros、Panagiotis Marakos、Nicole Pouli、George Diallinas

  DOI：10.1016/j.bmc.2016.09.055

  日期：2016.11

  In the course of our study on fungal purine transporters, a number of new 3-deazapurine analogues have been rationally designed, based on the interaction of purine substrates with the Aspergillus nidulans FcyB carrier, and synthesized following an effective synthetic procedure. Certain derivatives have been found to specifically inhibit FcyB-mediated [3H]-adenine uptake. Molecular simulations have

  在我们对真菌嘌呤转运蛋白的研究过程中，基于嘌呤底物与构巢曲霉FcγB载体的相互作用，合理地设计了许多新的3-脱氮嘌呤类似物，并按照有效的合成程序进行了合成。已经发现某些衍生物特异性抑制FcγB介导的[ 3 H]-腺嘌呤摄取。已经进行了分子模拟，表明所有活性化合物都通过与Asn163形成氢键与FcyB相互作用，而在3- deazaadenine的9和N 6位插入疏水片段增强了抑制作用。
• Synthesis and antimycobacterial activities of non-purine analogs of 6-aryl-9-benzylpurines: Imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles
  作者：Abhijit Datta Khoje、Colin Charnock、Baojie Wan、Scott Franzblau、Lise-Lotte Gundersen

  DOI：10.1016/j.bmc.2011.04.023

  日期：2011.6

  6,9-Disubstituted purines and 7-deazapurines are known to be powerful inhibitors of Mycobacterium tuberculosis (Mtb) in vitro. Analogs modified in the six-membered ring (imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles) were synthesized and evaluated as Mtb inhibitors. The targets were prepared by functionalization on the bicyclic heterocycle or from simple pyridines. The results reported herein, indicate that the purine N-1, but not N-3, is important for binding to the unknown target. The 3-deazapurines appears to be slightly more active compared to the parent purines and slightly less active than their 7-deazapurine isomers. Removal of both the purine N-3 and N-7 did not result in further enhanced antimycobacterial activity but the toxicity towards mammalian cells was increased. Both 3-deaza and 3,7-dideazapurines exhibited a modest activity against of the Mtb isolate in the state of non-replicating persistence. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of 3-deaza-3-nitro-2′-deoxyadenosine
  作者：Caroline Crey-Desbiolles、Mitsuharu Kotera

  DOI：10.1016/j.bmc.2005.10.040

  日期：2006.3

  Photoactivable deoxyadenosine mimic, 3-deaza-3-nitro-2'-deoxyadetiosine (2), was prepared using two different synthetic routes. The first route involved base catalyzed glycosylation of 3-deaza-3-nitroadenine, which was prepared by regioselective nitration of 3-deazaadenine. In the second route, the convertible nucleoside 6-O-(2,4,6-trimethylphenyl)-3-deaza-2'-deoxyadenosine (28) was used to introduce 6-NH2 group in the last step. (c) 2005 Elsevier Ltd. All rights reserved.