tert-butyl N-[1-[(3aR,6R,6aS)-2,2-dimethyl-4-(trityloxymethyl)-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]-7-bromoimidazo[4,5-c]pyridin-4-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate | 1392424-80-4

• 分子结构分类: 有机化合物
• 英文名称: tert-butyl N-[1-[(3aR,6R,6aS)-2,2-dimethyl-4-(trityloxymethyl)-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]-7-bromoimidazo[4,5-c]pyridin-4-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate
• CAS: 1392424-80-4
• 化学式: C₄₄H₄₇BrN₄O₇
• 分子量: 823.784
• InChiKey: KRXNBBQKQAWMIJ-WCUKECLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  56
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[1-[(3aR,6R,6aS)-2,2-dimethyl-4-(trityloxymethyl)-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]-7-bromoimidazo[4,5-c]pyridin-4-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate 在 盐酸 、 甲醇 作用下， 以67%的产率得到3-bromo-3-deaza-neplanocin
  参考文献：
  名称：

  3-Bromo-3-deazaneplanocin and 3-bromo-3-deazaaristeromycin: Synthesis and antiviral activity

  摘要：

  As an outgrowth of our program to explore 3-deazaadenine carbocyclic nucleosides, 3-bromo-3-deazaneplanocin (5) and 3-bromo-3-deazaaristeromycin (6) have been synthesized from a readily available cyclopentenol and cyclopentanone and either 4-amino- or 4-chloro-1H-imidazo[4,5-c]pyridine (6-amino- or 6-chloro-3-deazaadenine) in 5 steps and 7 steps, respectively. Antiviral analysis found 5 to display significant activity towards a number of (-)-ssRNA and a few dsDNA viruses. Compound 6 was less active than 5 against selected examples of those viruses affected by 5. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.075
• 作为产物：
  描述：

  tert-butyl 4-(bis(tert-butoxycarbonyl)amino)-1H-imidazo[4,5-c]pyridine-1-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 tert-butyl N-[1-[(3aR,6R,6aS)-2,2-dimethyl-4-(trityloxymethyl)-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]-7-bromoimidazo[4,5-c]pyridin-4-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate
  参考文献：
  名称：

  3-Bromo-3-deazaneplanocin and 3-bromo-3-deazaaristeromycin: Synthesis and antiviral activity

  摘要：

  As an outgrowth of our program to explore 3-deazaadenine carbocyclic nucleosides, 3-bromo-3-deazaneplanocin (5) and 3-bromo-3-deazaaristeromycin (6) have been synthesized from a readily available cyclopentenol and cyclopentanone and either 4-amino- or 4-chloro-1H-imidazo[4,5-c]pyridine (6-amino- or 6-chloro-3-deazaadenine) in 5 steps and 7 steps, respectively. Antiviral analysis found 5 to display significant activity towards a number of (-)-ssRNA and a few dsDNA viruses. Compound 6 was less active than 5 against selected examples of those viruses affected by 5. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.075

文献信息

• 2- and 3-Fluoro-3-deazaneplanocins, 2-fluoro-3-deazaaristeromycins, and 3-methyl-3-deazaneplanocin: Synthesis and antiviral properties
  作者：Chong Liu、Qi Chen、John D. Gorden、Stewart W. Schneller

  DOI：10.1016/j.bmc.2015.07.039

  日期：2015.9

  direction, this paper reports the strategic placement of a fluorine atom at the C-2 and C-3 positions and a methyl at the C-3 site of the 3-deazaadenine ring of the aforementioned compounds. The synthesis and S-adenosylhomocysteine hydrolase inhibitory and antiviral properties of these targets are described. Some, but not all, compounds in this series showed significant activity toward herpes, arena

  天然存在的基于腺嘌呤的碳环核苷阿里霉素和奈普罗星的3-deaza类似物具有尚未优化的生物学特性。在这个方向上，本文报道了上述化合物在3-deazaadenine环的C-2和C-3位置上的氟原子和C-3位置上的甲基的战略位置。描述了这些靶标的合成和S-腺苷同型半胱氨酸水解酶的抑制和抗病毒特性。该系列中的某些（但不是全部）化合物对疱疹，竞技场，布尼亚，黄病毒和正粘病毒显示出显着活性。