8-hydroxymethyl-2-phenylimidazo[1,2-a]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-hydroxymethyl-2-phenylimidazo[1,2-a]pyridine
• 英文别名: 2-phenyl-8-hydroxymethyl-imidazo[1,2-a]pyridine；(2-phenylimidazo[1,2-a]pyridin-8-yl)methanol
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: GDYSTSFOXNAZAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-hydroxymethyl-2-phenylimidazo[1,2-a]pyridine 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 18.0h， 以29%的产率得到2-phenylimidazo[1,2-a]pyridine-8-carbaldehyde
  参考文献：
  名称：

  Synthesis and antiviral activity of an imidazo[1,2-a]pyrrolo[2,3-c]pyridine series against the bovine viral diarrhea virus

  摘要：

  A series of imidazo[1,2-a]pyrrolo[2,3-c]pyridines has been prepared and evaluated for their anti-BVDV activities in MDBK cells. From the synthesized analogues bearing modifications of the substituents at positions 2, 3, 7 and 8, compounds 10a, b, 16, 24, 25 and 26 exhibited significant anti-BVDV activities. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.023
• 作为产物：
  描述：

  ethyl 2-phenylimidazo[1,2-a]pyridine-8-carboxylate 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以92%的产率得到8-hydroxymethyl-2-phenylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis and antiviral activity of an imidazo[1,2-a]pyrrolo[2,3-c]pyridine series against the bovine viral diarrhea virus

  摘要：

  A series of imidazo[1,2-a]pyrrolo[2,3-c]pyridines has been prepared and evaluated for their anti-BVDV activities in MDBK cells. From the synthesized analogues bearing modifications of the substituents at positions 2, 3, 7 and 8, compounds 10a, b, 16, 24, 25 and 26 exhibited significant anti-BVDV activities. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.023

文献信息

• Direct Introduction of Dithiocarbamates onto Imidazoheterocycles under Mild Conditions
  作者：Jing Jiao、Liang Wei、Xiao‐Ming Ji、Mao‐Lin Hu、Ri‐Yuan Tang

  DOI：10.1002/adsc.201500780

  日期：2016.1.21

  This paper discloses an iodine‐mediated CH thiolation strategy for introduction of dithiocarbamates onto imidazoheterocycles under mild conditions. Imidazole derivatives, including imidazopyridines, imidazothiazoles, and benzoimidazoles, were well tolerated to afford diverse imidazoheterocycles‐dithiocarbamates compounds. These compounds are expected to be significant for drug discovery.

  本文揭示了碘介导的CH硫醇化策略，可在温和条件下将二硫代氨基甲酸酯引入咪唑杂环上。咪唑衍生物（包括咪唑并吡啶，咪唑并噻唑和苯并咪唑）具有良好的耐受性，可提供各种咪唑杂环-二硫代氨基甲酸酯化合物。预期这些化合物对于药物发现具有重要意义。
• IMIDAZO [1, 2-A] PYRROLO [3, 2-C] PYRIDINE COMPOUNDS USEFUL AS PESTIVIRUS INHIBITORS
  申请人：Neyts Johan

  公开号：US20100093781A1

  公开（公告）日：2010-04-15

  The present invention relates to a series of novel imidazo[1,2-α]pyrrolo[3,2-c]pyridines (or also named 6H-1,3a,6-Tri-aza-αy-indacenes) and derivatives thereof, according to formula: (I); The present invention also relates to processes for the preparation of imidazo[1,2-α]pyrrolo[3,2-c]pyridines, their use as. a, medicine, their use to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, particularly infections with viruses belonging to the family of the Flaviviridae and more preferably infections with Bovine Viral Diarrhea virus (BVDV).

  本发明涉及一系列新型咪唑[1,2-α]吡咯并[3,2-c]吡啶（或称为6H-1,3a,6-三氮杂-α-吲哚烯）及其衍生物，其化学式如下：（I）；本发明还涉及制备咪唑[1,2-α]吡咯并[3,2-c]吡啶的方法，它们作为药物的用途，用于治疗或预防病毒感染以及用于制造用于治疗或预防病毒感染的药物，特别是用于感染属于黄病毒科家族的病毒，更好地用于治疗或预防感染牛病毒性腹泻病毒（BVDV）的感染。
• Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur
  作者：Yong-Chao Gao、Zhuo-Bin Huang、Li Xu、Zhao-Dong Li、Zhi-Sheng Lai、Ri-Yuan Tang

  DOI：10.1039/c8ob03191f

  日期：——

  found to be effective alkyl radical sources for direct alkyl sulfuration with imidazopyridines using elemental sulfur under metal-free conditions. Iodine, an inexpensive and mild reagent, could promote alkyl sulfuration. A variety of quaternary cyanoalkyl radicals were successfully coupled with elemental sulfur. A subsequent C–H sulfuration of imidazopyridines afforded a diverse array of imidazopyridine

  发现二烷基偶氮化合物是在无金属条件下使用元素硫直接与咪唑并吡啶进行烷基硫化的有效烷基自由基来源。碘是一种廉价而温和的试剂，可以促进烷基硫化。各种季氰基烷基自由基已成功与元素硫偶联。随后的咪唑并吡啶进行C–H硫化，得到了各种带有氰基烷硫基的咪唑并吡啶衍生物。可以将氰基改性，并进一步与2-氨基噻唑缩合，得到有趣的杂环酰胺。对照实验表明，碘可以极大地抑制氰基烷基自由基的自偶联，从而使硫化过程顺利进行。
• 4-bicyclically substituted dihydropyridines and their use in medicaments
  申请人：Bayer Aktiengesellschaft

  公开号：US05545646A1

  公开（公告）日：1996-08-13

  The invention relates to new 4-bicyclically substituted dihydropyridines of the general formula (I) ##STR1## in which R.sub.1 to R.sub.5 have the meaning given in the description, processes for their preparation and their use in medicaments, in particular in agents for the treatment of cardiovascular diseases.

  该发明涉及一般式（I）的新的4-环戊二氢吡啶取代物，其中R.sub.1至R.sub.5的含义如描述中所述，以及它们的制备方法和它们在药物中的应用，特别是用于治疗心血管疾病的药剂。
• Sulfite-Promoted C–H Fluoroalkyl Sulfuration of Imidazoheterocycles with Bromofluoroacetate and Elemental Sulfur
  作者：Zi-Ning Cui、Ri-Yuan Tang、Yong-Chao Gao、Zi-Hao Huang、Zhao-Sheng Zhang、Jin-Xin Xie

  DOI：10.1055/s-0040-1707120

  日期：2020.9

  A transition-metal-free sulfite-promoted three-component C–H sulfuration between imidazoheterocycles, elemental sulfur, and bromofluoroacetate is developed. Sulfites, including Na2S2O4, NaHSO3, and Na2S2O3, are able to promote the formation of two C–S bonds in one step using elemental sulfur as a green sulfurating agent, allowing the rapid introduction of the synthetically useful S-fluoroacetate group

  开发了一种在咪唑杂环，元素硫和溴氟乙酸盐之间的无过渡金属的亚硫酸盐促进的三组分C–H硫化反应。亚硫酸盐，包括Na 2 S 2 O 4，NaHSO 3和Na 2 S 2 O 3，能够使用元素硫作为绿色硫化剂，一步一步促进两个C–S键的形成，从而可以快速引入将合成上有用的S-氟乙酸酯基转变成咪唑杂环。这些带有S-氟乙酸酯基团的新的咪唑杂环衍生物可以容易地改性以产生药学上有吸引力的化合物。