2-Propanone, 2-(5-bromo-2-pyridinyl)hydrazone | 321438-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-Propanone, 2-(5-bromo-2-pyridinyl)hydrazone
• 英文别名: 5-bromo-N-(propan-2-ylideneamino)pyridin-2-amine
• CAS: 321438-89-5
• 化学式: C₈H₁₀BrN₃
• 分子量: 228.091
• InChiKey: BXGPSUSWHZBIBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Propanone, 2-(5-bromo-2-pyridinyl)hydrazone 在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以60%的产率得到6-bromo-3,3-difluoro-2-(propan-2-ylidene)-2,3-dihydro[1,2,4,3]triazaborolo[4,5-a]pyridin-2-ium-3-uide
  参考文献：
  名称：

  Design and Synthesis of a New Class of Membrane-Permeable Triazaborolopyridinium Fluorescent Probes

  摘要：

  A new class of fluorescent triazaborolopyridinium compounds was synthesized from hydrazones of 2-hydrazinylpyridine (HPY) and evaluated as potential dyes for live-cell imaging applications. The HPY dyes are small, their absorption/emission properties are tunable through variation of pyridyl or hydrazone substituents, and they offer favorable photophysical characteristics featuring large Stokes shifts and general insensitivity to solvent or pH. The stability, neutral charge, cell membrane permeability, and favorable relative influences on the water solubility of HPY conjugates are complementary to existing fluorescent dyes and offer advantages for the development of receptor-targeted small-molecule probes. This potential was assessed through the development of a new class of cysteine-derived HPY-conjugate imaging agents for the kinesin spindle protein (KSP) that is expressed in the cytoplasm during mitosis and is a promising chemotherapeutic target. Conjugates possessing the neutral HPY or charged Alexa Fluor dyes that function as potent, selective allosteric inhibitors of the KSP motor were compared using biochemical and cell-based phenotypic assays and live-cell imaging. These results demonstrate the effectiveness of the HPY dye moiety as a component of probes for an intracellular protein target and highlight the importance of dye structure in determining the pathway of cell entry and the overall performance of small-molecule conjugates as imaging agents.

  DOI：

  10.1021/ja2005175
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 在 氢溴酸 、 溴 、 一水合肼 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 13.17h， 生成 2-Propanone, 2-(5-bromo-2-pyridinyl)hydrazone
  参考文献：
  名称：

  费歇尔环化法制备2,3-二取代的5-溴-1H-吡咯并[2,3-b]吡啶骨架

  摘要：

  摘要 通过在多磷酸中的Fisher吲哚环化反应，已经开发出一些简单的难以合成的含有2,3-二取代的5-溴-1 H-吡咯并[2,3- b ]吡啶骨架的杂环。该合成路线的一个特别有价值的特征是可以从可用的起始原料构建在2和3位具有烷基或芳基取代基的5-溴-7-氮杂吲哚支架。 通过在多磷酸中的Fisher吲哚环化反应，已经开发出一些简单的难以合成的含有2,3-二取代的5-溴-1 H-吡咯并[2,3- b ]吡啶骨架的杂环。该合成路线的一个特别有价值的特征是可以从可用的起始原料构建在2和3位具有烷基或芳基取代基的5-溴-7-氮杂吲哚支架。

  DOI：

  10.1055/s-0034-1381040

文献信息

• Preparation of 2,3-Disubstituted 5-Bromo-1H-pyrrolo[2,3-b]pyridine Framework by Fischer Cyclization
  作者：Roman Alekseyev、Sabina Amirova、Vladimir Terenin

  DOI：10.1055/s-0034-1381040

  日期：——

  starting materials. A simple synthesis of some hard-to-reach heterocycles containing 2,3-disubstituted 5-bromo-1H-pyrrolo[2,3-b]pyridine framework by Fisсher indole cyclization in polyphosphoric acid has been developed. A particularly valuable feature of this synthetic route is the possibility to build a 5-bromo-7-azaindole scaffold with alkyl or aryl substituents at positions 2 and 3 from available starting

  摘要 通过在多磷酸中的Fisher吲哚环化反应，已经开发出一些简单的难以合成的含有2,3-二取代的5-溴-1 H-吡咯并[2,3- b ]吡啶骨架的杂环。该合成路线的一个特别有价值的特征是可以从可用的起始原料构建在2和3位具有烷基或芳基取代基的5-溴-7-氮杂吲哚支架。 通过在多磷酸中的Fisher吲哚环化反应，已经开发出一些简单的难以合成的含有2,3-二取代的5-溴-1 H-吡咯并[2,3- b ]吡啶骨架的杂环。该合成路线的一个特别有价值的特征是可以从可用的起始原料构建在2和3位具有烷基或芳基取代基的5-溴-7-氮杂吲哚支架。
• Design and Synthesis of a New Class of Membrane-Permeable Triazaborolopyridinium Fluorescent Probes
  作者：Sudath Hapuarachchige、Gilbert Montaño、Chinnasamy Ramesh、Delany Rodriguez、Lauren H. Henson、Casey C. Williams、Samuel Kadavakkollu、Dennis L. Johnson、Charles B. Shuster、Jeffrey B. Arterburn

  DOI：10.1021/ja2005175

  日期：2011.5.4

  A new class of fluorescent triazaborolopyridinium compounds was synthesized from hydrazones of 2-hydrazinylpyridine (HPY) and evaluated as potential dyes for live-cell imaging applications. The HPY dyes are small, their absorption/emission properties are tunable through variation of pyridyl or hydrazone substituents, and they offer favorable photophysical characteristics featuring large Stokes shifts and general insensitivity to solvent or pH. The stability, neutral charge, cell membrane permeability, and favorable relative influences on the water solubility of HPY conjugates are complementary to existing fluorescent dyes and offer advantages for the development of receptor-targeted small-molecule probes. This potential was assessed through the development of a new class of cysteine-derived HPY-conjugate imaging agents for the kinesin spindle protein (KSP) that is expressed in the cytoplasm during mitosis and is a promising chemotherapeutic target. Conjugates possessing the neutral HPY or charged Alexa Fluor dyes that function as potent, selective allosteric inhibitors of the KSP motor were compared using biochemical and cell-based phenotypic assays and live-cell imaging. These results demonstrate the effectiveness of the HPY dye moiety as a component of probes for an intracellular protein target and highlight the importance of dye structure in determining the pathway of cell entry and the overall performance of small-molecule conjugates as imaging agents.