tert-butyl 2-aminobenzimidazole-1-carboxylate

• 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: tert-butyl 2-aminobenzimidazole-1-carboxylate
• 英文别名: Tert-butyl 2-amino-1H-benzo[D]imidazole-1-carboxylate
• 化学式: C₁₂H₁₅N₃O₂
• 分子量: 233.27
• InChiKey: XLOVZUNVXPPLKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-aminobenzimidazole-1-carboxylate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 19.0h， 生成 1-(1H-benzimidazol-2-yl)-3-hexyl-urea
  参考文献：
  名称：

  Pharmacophore Identification and Scaffold Exploration to Discover Novel, Potent, and Chemically Stable Inhibitors of Acid Ceramidase in Melanoma Cells

  摘要：

  Acid ceramidase (AC) hydrolyzes ceramides, which are central lipid messengers for metabolism and signaling of sphingolipids. A growing body of evidence links deregulation of sphingolipids to several diseases, including cancer. Indeed, AC expression is abnormally high in melanoma cells. AC inhibition may thus be key to treating malignant melanoma. Here, we have used a systematic scaffold exploration to design a general pharmacophore for AC inhibition. This pharmacophore comprises a 6 + 5 fused ring heterocycle linked to an aliphatic substituent via a urea moiety. We have thus identified the novel benzimidazole derivatives 10, 21, 27, and 30, which are highly potent AC inhibitors. Their chemical and metabolic stabilities are comparable or superior to those of previously reported AC inhibitors. Moreover, they are potent against endogenous AC in intact melanoma cells. These novel inhibitors merit further characterization and can serve as a promising starting point for the discovery of new antimelanoma therapeutics.

  DOI：

  10.1021/acs.jmedchem.7b00472
• 作为产物：
  描述：

  2-氨基苯并咪唑 、 二碳酸二叔丁酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以85%的产率得到tert-butyl 2-aminobenzimidazole-1-carboxylate
  参考文献：
  名称：

  设计，合成，抗菌评估和分子对接的新型吲哚，苯并咪唑和苯并噻唑支架的手性尿素/硫脲衍生物

  摘要：

  设计，合成尿素/硫脲衍生物和杂芳族支架（如吲哚，苯并咪唑和苯并噻唑），并在体外试验中评估其潜在的抗菌活性，以针对蜡状芽孢杆菌，金黄色葡萄球菌，大肠杆菌和铜绿假单胞菌建立抗性。我们的结果表明化合物仅在革兰氏阳性细菌中具有活性。对最有效的化合物进行了分子对接研究，以了解其与肽聚糖合成中涉及的蛋白质的相互作用。ADME计算表明，这些化合物更可能通过口服途径服用。总之，这些发现可能有助于设计和开发生物系统中更有效的治疗方法的候选药物。

  DOI：

  10.1016/j.molstruc.2021.130566

文献信息

• [EN] PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS<br/>[FR] PROCÉDÉ POUR LE CLIVAGE CATALYTIQUE DIRIGÉ DE COMPOSÉS CONTENANT UN AMIDE
  申请人：UNIV ANTWERPEN

  公开号：WO2017046133A1

  公开（公告）日：2017-03-23

  The present invention relates to a catalytic method for the conversion of amide-containing compouds by means of a build-in directing group and upon the action of a heteronucleophilic compound (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or a thiol (RSH)) in the presence of a metal catalyst to respectively esters, thioesters, carbonates, thiocarbonates and to what is defined as amide-containing compounds (such as carboxamides, urea, carbamates, thiocarbamates). The present invention also relates to these amide-containing compounds having a build-in directing group (DG), as well as the use of such directing groups in the catalytic directed cleavage of N-DG amides with the use of heteronucleophiles (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or thiol (RSH)).

  本发明涉及一种催化方法，通过内置导向基团和在异核亲核化合物的作用下（例如胺（RNH2或RNHR'）或醇（ROH）或硫醇（RSH））在金属催化剂存在下将酰胺含有化合物分别转化为酯、硫酯、碳酸酯、硫代碳酸酯以及所定义的酰胺含有化合物（如羧酰胺、脲、氨基甲酸酯、硫代氨基甲酸酯）。本发明还涉及具有内置导向基团（DG）的这些酰胺含有化合物，以及在催化定向裂解N-DG酰胺时使用此类导向基团与异核亲核化合物（例如胺（RNH2或RNHR'）或醇（ROH）或硫醇（RSH））的用途。
• Unveiling RNA‐Binding Properties of Verapamil and Preparation of New Derivatives as Inhibitors of HIV‐1 Tat‐TAR Interaction
  作者：Céline Martin、Serena De Piccoli、Marc Gaysinski、Cécile Becquart、Stéphane Azoulay、Audrey Di Giorgio、Maria Duca

  DOI：10.1002/cplu.201900650

  日期：2020.1

  therapeutic applications since coding and non‐coding RNAs bear a pivotal role both in viral and bacterial infections as well as in human pathologies such as cancer. Here, we focused on the targeting of HIV‐1 TAR RNA as a promising target for the development of new anti‐HIV therapies but also as an ideal model to validate the discovery of original RNA ligands. First, we performed an initial screening of a

  由于编码和非编码RNA在病毒和细菌感染以及人类病理疾病（例如癌症）中都起着关键作用，因此现在已经确立了使用小分子靶向RNA的许多治疗应用前景非常广阔的策略。在这里，我们专注于将HIV-1 TAR RNA作为开发新的抗HIV疗法的有希望的目标，同时也是验证原始RNA配体发现的理想模型。首先，我们对抗TAR的化合物库进行了初步筛选，从而发现了市售的钙通道阻滞剂维拉帕米，作为开发新RNA配体的有前途的化学结构。一系列维拉帕米类似物的合成导致了有希望的结构活性关系，并导致了化合物2h的发现，维拉帕米与吲哚片段之间的结合物，作为一种有效且选择性的TAR结合物，能够抑制Tat / TAR相互作用，IC50为18.8 µM。这项工作为发现原始和选择性的RNA配体提供了库筛选的潜力，并说明了如何仍需要研究针对蛋白质靶标的现有药物进行RNA结合，这是小分子靶向RNA领域中的一种有前途的策略。
• Design, synthesis, antimicrobial evaluation, and molecular docking of novel chiral urea/thiourea derivatives bearing indole, benzimidazole, and benzothiazole scaffolds
  作者：Ferruh Lafzi、Deryanur Kilic、Melike Yildiz、Nurullah Saracoglu

  DOI：10.1016/j.molstruc.2021.130566

  日期：2021.10

  Urea/thiourea derivatives with heteroaromatic scaffolds such as indole, benzimidazole, and benzothiazole were designed, synthesized, and evaluated for their potential antimicrobial activity in vitro assays to establish against B. cereus, S. aureus, E. coli, and P. aeruginosa. Our results indicate that compounds are only active in gram-positive bacteria. Molecular docking studies were carried out for

  设计，合成尿素/硫脲衍生物和杂芳族支架（如吲哚，苯并咪唑和苯并噻唑），并在体外试验中评估其潜在的抗菌活性，以针对蜡状芽孢杆菌，金黄色葡萄球菌，大肠杆菌和铜绿假单胞菌建立抗性。我们的结果表明化合物仅在革兰氏阳性细菌中具有活性。对最有效的化合物进行了分子对接研究，以了解其与肽聚糖合成中涉及的蛋白质的相互作用。ADME计算表明，这些化合物更可能通过口服途径服用。总之，这些发现可能有助于设计和开发生物系统中更有效的治疗方法的候选药物。
• RUBBER COMPOSITION, AND PNEUMATIC TIRE USING SAME
  申请人：YUKIMURA Noriaki

  公开号：US20150361248A1

  公开（公告）日：2015-12-17

  The invention provides a rubber composition prepared by mixing, per 100 parts by mass of a rubber component comprising at least 50% by mass of a diene-based rubber, from 20 to 150 parts by mass of a filler, and from 0.05 to 30 parts by mass of a compound A which has a specific guanidine structure and has a functional group reactive with the diene-based rubber. The rubber composition improves both a high elastic modulus and a low tan δ. The invention also provides a pneumatic tire using the rubber composition.

  本发明提供了一种橡胶组合物，其中包括：100份质量份的橡胶组分，至少包括50份质量份的二烯基橡胶；20至150份质量份的填料；以及0.05至30份质量份的化合物A，其具有特定的胍基结构并具有与二烯基橡胶反应的功能性基团。该橡胶组合物提高了高弹性模量和低tanδ。本发明还提供了使用该橡胶组合物的充气轮胎。
• Rubber composition, and pneumatic tire using same
  申请人：BRIDGESTONE CORPORATION

  公开号：US10053553B2

  公开（公告）日：2018-08-21

  The invention provides a rubber composition prepared by mixing, per 100 parts by mass of a rubber component comprising at least 50% by mass of a diene-based rubber, from 20 to 150 parts by mass of a filler, and from 0.05 to 30 parts by mass of a compound A which has a specific guanidine structure and has a functional group reactive with the diene-based rubber. The rubber composition improves both a high elastic modulus and a low tan δ. The invention also provides a pneumatic tire using the rubber composition.

  本发明提供了一种橡胶组合物，其制备方法是将每 100 份质量的橡胶组分（包括至少 50%质量的二烯基橡胶）、20 至 150 份质量的填料以及 0.05 至 30 份质量的化合物 A（具有特定的胍基结构并具有与二烯基橡胶反应的官能团）混合在一起。本发明还提供了一种使用该橡胶组合物的充气轮胎。