2,6-bis(((1H-benzo[d]imidazol-2-yl)thio)methyl)pyridine | 123771-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2,6-bis(((1H-benzo[d]imidazol-2-yl)thio)methyl)pyridine
• 英文别名: 2,6-bis((benzimidazol-2'-ylthio)methyl)pyridine；2,6-Bis(benzimidazol-2'-ylthiomethyl)pyridine；2,6-bis((1H-benzo[d]imidazol-2-ylthio)methyl)pyridine；2-[[6-(1H-benzimidazol-2-ylsulfanylmethyl)pyridin-2-yl]methylsulfanyl]-1H-benzimidazole
• CAS: 123771-22-2
• 化学式: C₂₁H₁₇N₅S₂
• 分子量: 403.531
• InChiKey: TYMDRIURLRAWCF-UHFFFAOYSA-N

物化性质

• 沸点：
  698.9±65.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  双(乙腈)氯化钯(II) 、 2,6-bis(((1H-benzo[d]imidazol-2-yl)thio)methyl)pyridine 在 1H-苯并咪唑-2-硫醇 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以75%的产率得到
  参考文献：
  名称：

  Synthesis, spectroscopic characterization and density functional studies of a bis-benzimidazole derivative and of its complexes with palladium(II) halides

  摘要：

  摘要 2,6-bis(苯并咪唑-2'-基硫甲基)吡啶（L）配体及其钯(II)络合物[Pd(L)X]X（X = Cl, Br, 和 I）已被合成并通过光谱数据进行表征。该配体（L）通过常规加热以及微波辐射法制备。微波辐射法显示出额外特点，包括易于处理，反应速度更快且产率更高。摩尔电导率数据表明，络合物在DMSO中形成1:1电解质。通过量子化学计算阐明了(L)及其络合物的几何结构、基态能量和振动光谱。在单核络合物中，钯原子与三个氮原子和一个末端卤素原子以略微扭曲的平面方形排列配位。当前的元素分析、FT-IR（中红外和远红外）、1H和13C NMR光谱与Pd离子周围的平面方形几何形状一致。通过热重和差热分析评估了络合物的热行为。

  DOI：

  10.1016/j.crci.2013.10.016
• 作为产物：
  描述：

  2,6-吡啶二羧酸二丁酯 在 sodium tetrahydroborate 、 sodium 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 12.5h， 生成 2,6-bis(((1H-benzo[d]imidazol-2-yl)thio)methyl)pyridine
  参考文献：
  名称：

  Synthesis, spectroscopic characterization and density functional studies of a bis-benzimidazole derivative and of its complexes with palladium(II) halides

  摘要：

  摘要 2,6-bis(苯并咪唑-2'-基硫甲基)吡啶（L）配体及其钯(II)络合物[Pd(L)X]X（X = Cl, Br, 和 I）已被合成并通过光谱数据进行表征。该配体（L）通过常规加热以及微波辐射法制备。微波辐射法显示出额外特点，包括易于处理，反应速度更快且产率更高。摩尔电导率数据表明，络合物在DMSO中形成1:1电解质。通过量子化学计算阐明了(L)及其络合物的几何结构、基态能量和振动光谱。在单核络合物中，钯原子与三个氮原子和一个末端卤素原子以略微扭曲的平面方形排列配位。当前的元素分析、FT-IR（中红外和远红外）、1H和13C NMR光谱与Pd离子周围的平面方形几何形状一致。通过热重和差热分析评估了络合物的热行为。

  DOI：

  10.1016/j.crci.2013.10.016

文献信息

• [EN] 2,6-BIS(((1H-BENZO[D]IMIDAZOL-2-YL)THIO)METHYL)PYRIDINE AND N2,N6-DIBENZYLPYRIDINE-2,6-DICARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS AS PHOSPHOINOSITIDE 3-KINASE (PI3K) INHIBITORS FOR TREATING CANCER<br/>[FR] DÉRIVÉS DE 2,6-BIS(((1H-BENZO[D]IMIDAZOL-2-YL)THIO)MÉTHYL)PYRIDINE ET DE N2,N6-DIBENZYLPYRIDINE-2,6-DICARBOXAMIDE ET COMPOSÉS ASSOCIÉS EN TANT QU'INHIBITEURS DE PHOSPHOINOSITIDE 3-KINASE (PI3K) DANS LE TRAITEMENT DU CANCER
  申请人：BIOMEDICAL RES FOUNDATION OF THE ACADEMY OF ATHENS BRFAA

  公开号：WO2020039097A1

  公开（公告）日：2020-02-27

  2,6-bis(((lH-benzo[d]imidazol-2-yl)thio)methyl)pyridine and N2, N6-dibenzylpyridine-2, 6-dicarboxamide derivatives and related compounds as phosphoinositide 3-kinase (PI3K) inhibitors for treating cancer. The present invention relates to pharmaceutically active 2,6- bis(((lH-benzo[d]imidazol-2-yl)thio)methyl)pyridine, N2,N6- dibenzylpyridine-2, 6-dicarboxamide and N2,N6-bis(3-hydroxyphenyl) pyridine-2, 6-dicarboxamide, as well as to derivatives thereof, and to structurally related compounds. These compounds are phosphoinositide 3-kinase inhibitors (PI3K) and useful in treating or preventing cancerous diseases. The invention further relates methods of manufacturing such compounds as well as to pharmaceutical compositions and formulations comprising such compounds, optionally together with other pharmaceutically active compounds. The invention further relates to a method for determining the activity of PI3Kalpha or PI3Kalpha mutants, which method includes: a) providing a solid phase which is functionalized by immobilization of GST-GRPl-molecules onto the solid phase, b) performing a PI3Kalpha or PI3Kalpha mutant catalyzed enzyme reaction to convert PIP2 to PIP3, c) adding competitor PIP3 carrying a detectable label or reporter molecule, and d) determining enzyme activity based on the amount of PIP3 obtained in step b) which competes with competitor PIP3 for binding to the functionalized solid phase.

  2,6-双(((1H-苯并[d]咪唑-2-基)硫)甲基)吡啶和N2，N6-二苄基吡啶-2,6-二甲酰胺衍生物及相关化合物作为治疗癌症的磷脂酰肌醇3-激酶（PI3K）抑制剂。本发明涉及具有药用活性的2,6-双(((1H-苯并[d]咪唑-2-基)硫)甲基)吡啶，N2，N6-二苄基吡啶-2,6-二甲酰胺和N2，N6-双(3-羟基苯基)吡啶-2,6-二甲酰胺，以及其衍生物和结构相关化合物。这些化合物是磷脂酰肌醇3-激酶抑制剂（PI3K），可用于治疗或预防癌症性疾病。本发明还涉及制造这类化合物的方法，以及包含这类化合物的药物组合物和配方，可选地与其他药用活性化合物一起使用。本发明还涉及一种确定PI3Kalpha或PI3Kalpha突变体活性的方法，该方法包括：a)提供通过将GST-GRPl分子固定在固相上而功能化的固相，b)执行PI3Kalpha或PI3Kalpha突变体催化的酶反应将PIP2转化为PIP3，c)添加携带可检测标签或报告分子的竞争物PIP3，d)根据步骤b)中获得的与竞争物PIP3竞争与功能化固相结合的PIP3的数量确定酶活性。
• Trigonal Planar Copper(I) Complex:  Synthesis, Structure, and Spectra of a Redox Pair of Novel Copper(II/I) Complexes of Tridentate Bis(benzimidazol-2‘-yl) Ligand Framework as Models for Electron-Transfer Copper Proteins
  作者：Ramalingam Balamurugan、Mallayan Palaniandavar、R. Srinivasa Gopalan

  DOI：10.1021/ic0003372

  日期：2001.5.1

  of the green complex [Cu(bbtmp)(NO(3))]NO(3) possesses an almost perfectly square planar coordination geometry in which the corners are occupied by the pyridine and two benzimidazole nitrogen atoms of the bbtmp ligand and an oxygen atom of the nitrate ion. The light-yellow complex [Cu(bbtmp)]NO(3) contains copper(I) with trigonal planar coordination geometry constituted by the pyridine and two benzimidazole

  螯合配体2,6-双（苯并咪唑-2'-基硫基甲基）吡啶（bbtmp）和N，N-双（苯并咪唑-2'-基硫基乙基）甲胺（bbtma）的铜（II）和铜（I）配合物已通过电子和EPR光谱进行了分离和表征。Cu（II / I）配合物氧化还原对的分子结构，即[Cu（bbtmp）（NO（3））] NO（3），1和[Cu（bbtmp）] NO（3）， [Cu（bbtmp）Cl] 2和[Cu（bbtmp）Cl] 3的测定已通过单晶X射线晶体学确定。绿色络合物[Cu（bbtmp）（NO（3））] NO（3）的阳离子具有几乎完美的正方形平面配位几何结构，其中的角被吡啶和bbtmp配体的两个苯并咪唑氮原子和硝酸根离子的氧原子。浅黄色络合物[Cu（bbtmp）] NO（3）包含具有三角形平面配位几何结构的铜（I），该结构由吡啶和bbtmp配体的两个苯并咪唑氮原子组成。在黄色氯化物络合物[Cu（bbtmp）Cl]中，不
• Wahlgren, Curtis G.; Addison, Anthony W., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 541 - 543
  作者：Wahlgren, Curtis G.、Addison, Anthony W.

  DOI：——

  日期：——
• COMPOUNDS AND THERAPEUTIC USES
  申请人：Unity Biotechnology, Inc.

  公开号：US20170281649A1

  公开（公告）日：2017-10-05

  Disclosed herein are compounds that are effective for treatment of various disease states associated with senescence. The disclosed compounds can be used to eliminate senescent cells for disease treatment. The dosing of the compounds includes both single administration and regimens of cycling dosages.
• METHOD OF PREPARATION AND USE OF PHOSPHOINOSITIDE 3-KINASE INHIBITORS IN TREATING CANCER
  申请人：COURNIA Zoe

  公开号：US20210246120A1

  公开（公告）日：2021-08-12

  2,6-bis(((1H-benzo[d]imidazol-2-yl)thio)methyl)pyridine and N2, N6-dibenzylpyridine-2, 6-dicarboxamide derivatives and related compounds as phosphoinositide 3-kinase (PI3K) inhibitors for treating cancer. The present invention relates to pharmaceutically active 2,6-bis((1H-benzo[d]imidazol-2-yl)thio)methyl)pyridine, N2,N6-dibenzylpyridine-2, 6-dicarboxamide and N2,N6-bis(3-hydroxyphenyl) pyridine-2, 6-dicarboxamide, as well as to derivatives thereof, and to structurally related compounds. These compounds are phosphoinositide 3-kinase inhibitors (PI3K) and useful in treating or preventing cancerous diseases. The invention further relates methods of manufacturing such compounds as well as to pharmaceutical compositions and formulations comprising such compounds, optionally together with other pharmaceutically active compounds. The invention further relates to a method for determining the activity of PI3Kalpha or PI3Kalpha mutants, which method includes: a) providing a solid phase which is functionalized by immobilization of GST-GRP1-molecules onto the solid phase, b) performing a PI3Kalpha or PI3Kalpha mutant catalyzed enzyme reaction to convert PIP2 to PIP3, c) adding competitor PIP3 carrying a detectable label or reporter molecule, and d) determining enzyme activity based on the amount of PIP3 obtained in step b) which competes with competitor PIP3 for binding to the functionalized solid phase.