3-(1H-benzimidazol-2-yl)-1H-indazole | 1097816-83-5

• 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: 3-(1H-benzimidazol-2-yl)-1H-indazole
• 英文别名: ZINC14961821；2-(1H-indazol-3-yl)-1H-benzimidazole
• CAS: 1097816-83-5
• 化学式: C₁₄H₁₀N₄
• mdl: MFCD11547580
• 分子量: 234.26
• InChiKey: JTKFRFMSUBOCIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯磺酸 、 3-(1H-benzimidazol-2-yl)-1H-indazole 以 甲醇 为溶剂， 以70.2 %的产率得到
  参考文献：
  名称：

  基于苯并咪唑和吲唑骨架的调制发光材料：合成、晶体结构和赫什菲尔德表面分析

  摘要：

  为了开发新型发光材料，三种含有苯并咪唑和吲唑部分的新化合物，即[H]··HO ()、[H]··2HO () 和 [H]· () ( = 3-(1-苯并咪唑- 2-基）-1-吲唑，=苯磺酸，=对甲苯磺酸，=5-磺酸水杨酸），与一组芳香族磺酸反应得到。化合物 – 已通过单晶 X 射线衍射、粉末 X 射线衍射、IR、H NMR、C NMR、热重分析 (TGA) 和差示扫描量热法 (DSC) 进行了表征。这些化合物中存在氢键（N/OH⋯O/N），可以明显观察到堆积相互作用。 – 的发光行为表明，分别在 404、448 和 410 nm 处观察到发射最大值，这与分子间相互作用一致，并且与咪唑环和吡唑环之间的二面角成反比。与自身相比，化合物的发射峰明显地向色（）或向色（）分别偏移了26、18和20 nm。化合物 和 的发光寿命分别为 1.12、1.67、1.21 和 1.56 ns。化合物 和 的绝对量子产率分别为

  DOI：

  10.1016/j.molstruc.2024.138439
• 作为产物：
  描述：

  吲唑-3-羧酸 在 lithium aluminium tetrahydride 、 p-iodoxybenzoic acid 、 sulfur 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(1H-benzimidazol-2-yl)-1H-indazole
  参考文献：
  名称：

  Identification of a buried pocket for potent and selective inhibition of Chk1: Prediction and verification

  摘要：

  Inhibition of the Chk1 kinase by small molecules binding to its active site is a strategy of great therapeutic interest for oncology. We report how computational modelling predicted the binding mode of ligands of special interest to the Chk1 ATP site, for representatives of an indazole series and debromohymenialdisine. These binding modes were subsequently confirmed by X-ray crystallography. The binding mode of a potent indazole derivative involves non-conventional C-H center dot center dot center dot O and N-H center dot center dot center dot pi-aromatic interactions with the protein. These interactions are formed in a buried pocket at the periphery of the ATP-binding site, the importance of which has previously been overlooked for ligand design against Chk1. It is demonstrated that filling this pocket can confer ligands with dramatically enhanced affinity for Chk1. Structural arguments in conjunction with assay data explain why targeting this pocket is also advantageous for selective binding to Chk1. Structural overlays of known inhibitors complexed with Chk1 show that only the indazole series utilizes the pocket of interest. Therefore, the analysis presented here should prove helpful in guiding future structure-based ligand design efforts against Chk1. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.022

文献信息

• [EN] BINDING FUNCTION3 (BF3) SITE COMPOUNDS AS THERAPEUTICS AND METHODS FOR THEIR USE<br/>[FR] COMPOSÉS DE SITE DE (BF3) AYANT UNE FONCTION 3 DE LIAISON UTILISÉS EN TANT QU'AGENTS THÉRAPEUTIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2015154169A1

  公开（公告）日：2015-10-15

  This invention provides compound having a structure of Formulas: Uses of such compounds for treatment of various indications, including prostate cancer as well as methods of treatment involving such compounds are also provide.

  这项发明提供了具有以下结构的化合物：这些化合物的用途包括治疗各种症状，包括前列腺癌，还提供了涉及这些化合物的治疗方法。
• INDAZOLES AS WNT/B-CATENIN SIGNALING PATHWAY INHIBITORS AND THERAPEUTIC USES THEREOF
  申请人：Hood John

  公开号：US20110034441A1

  公开（公告）日：2011-02-10

  Described herein are methods of treating a disorder or disease in which aberrant Wnt signaling is implicated, with a variety of compounds, including Wnt inhibitor compounds. More particularly, it concerns the use of an indazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, Alzheimer's disease and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases due to mutations in Wnt signaling components.

  本文描述了一种治疗与异常Wnt信号传导有关的疾病或紊乱的方法，使用各种化合物，包括Wnt抑制剂化合物。更具体地，涉及使用吲唑化合物或其类似物治疗由Wnt途径信号激活所特征的疾病（如癌症、异常细胞增殖、血管生成、阿尔茨海默病和骨关节炎），调节由Wnt途径信号介导的细胞事件，以及由于Wnt信号传导组分突变引起的遗传疾病。
• [EN] BISARYLUREA DERIVATIVES USEFUL FOR INHIBITING CHK1<br/>[FR] DÉRIVÉS DE BISARYLURÉE UTILES POUR INHIBER CHK1
  申请人：ICOS CORP

  公开号：WO2006012308A1

  公开（公告）日：2006-02-02

  Aryl- and heteroaryl-substituted urea compounds useful in the treatment of diseases and conditions related to DNA damage or lesions in DNA replication are disclosed. Methods of making the compounds, and their use as therapeutic agents, for example, in treating cancer and other diseases characterized by defects in DNA replication, chromosome segregation, or cell division also are disclosed. Formula (I).

  披苯基和杂环基取代的脲化合物可用于治疗与DNA损伤或DNA复制中的损伤相关的疾病和病况。公开了制备这些化合物的方法，以及它们作为治疗剂的用途，例如在治疗癌症和其他以DNA复制缺陷、染色体分离或细胞分裂为特征的疾病中的应用。公式（I）。
• Indazole benzimidazole compounds
  申请人：Chiron Corporation

  公开号：US20030207883A1

  公开（公告）日：2003-11-06

  Organic compounds having the structure I are provided where the variables have the values described herein. 1 Pharmaceutical formulations and medicaments include the organic compound or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier and may be prepared by mixing the organic compound or a pharmaceutically acceptable salt of the organic compound with a carrier and water. A method of treating a patient includes administering a pharmaceutical formulation or medicament according to the invention to a patient in need thereof.

  提供具有结构I的有机化合物，其中变量具有所述的值。1药物制剂和药物包括该有机化合物或其药学上可接受的盐和药学上可接受的载体，并可通过将该有机化合物或其药学上可接受的盐与载体和水混合制备。治疗患者的方法包括向需要该药物的患者施用本发明的药物制剂或药物。
• [EN] SUBSTITUTED 3-(1H-BENZO{D}IMIDAZOL-2-YL)-1H-INDAZOLE-ANALOGS AS INHIBITORS OF THE PDK1 KINASE<br/>[FR] ANALOGUES DE 3-(1H-BENZO[D]IMIDAZOL-2-YL)-1H-INDAZOLE SUBSTITUÉS EN TANT QU'INHIBITEURS DE LA PDK1 KINASE
  申请人：UNIV UTAH RES FOUND

  公开号：WO2012135799A1

  公开（公告）日：2012-10-04

  In one aspect, the invention relates to substituted 3-(lH-benzo[d]imidazol-2-yl)-lH- indazole analogs, derivatives thereof, and related compounds, which are useful as inhibitors of the PDK1 kinase; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds and compositions for treating disorders associated with dysfunction of the PDK1 kinase. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本发明涉及被取代的3-(1H-苯并[d]咪唑-2-基)-1H-吲唑类似物、其衍生物和相关化合物，它们可用作PDK1激酶的抑制剂；制备这些化合物的合成方法；包含这些化合物的药物组合物；以及使用这些化合物和组合物治疗与PDK1激酶功能障碍相关的疾病的方法。本摘要旨在作为特定领域搜索的扫描工具，不限制本发明。