2-(dimethylaminomethylene)aminoimidazole | 164583-72-6

• 英文名称: 2-(dimethylaminomethylene)aminoimidazole
• 英文别名: 2-[(Dimethylamino)methylene] aminoimidazole；N'-(1H-imidazol-2-yl)-N,N-dimethylmethanimidamide
• CAS: 164583-72-6
• 化学式: C₆H₁₀N₄
• 分子量: 138.172
• InChiKey: VEMHGBRKKQAHQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  硬脂基溴 、 2-(dimethylaminomethylene)aminoimidazole 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以71%的产率得到(E)-N,N-dimethyl-N'-(1-octadecyl-1H-imidazol-2-yl)formimidamide
  参考文献：
  名称：

  Construction of anti-1,2-diols bearing chiral tertiary alcohol moiety using free hydroxyacetone as aldol donor by imidazole-based prolineamide catalyst

  摘要：

  A direct aldol reaction of free hydroxyacetone and activated ketone has been firstly achieved with a newly developed imidazole-based prolineamide catalyst. The adducts anti-1,2-diols bearing a chiral tertiary alcohol moiety were obtained in high yield (up to 92%) and stereoselectivity (up to 15:1 dr and 90% ee). (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.07.015
• 作为产物：
  描述：

  2-氨基咪唑硫酸盐 、 N,N-二甲基甲酰胺二甲基缩醛 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 0.67h， 以81%的产率得到2-(dimethylaminomethylene)aminoimidazole
  参考文献：
  名称：

  Construction of anti-1,2-diols bearing chiral tertiary alcohol moiety using free hydroxyacetone as aldol donor by imidazole-based prolineamide catalyst

  摘要：

  A direct aldol reaction of free hydroxyacetone and activated ketone has been firstly achieved with a newly developed imidazole-based prolineamide catalyst. The adducts anti-1,2-diols bearing a chiral tertiary alcohol moiety were obtained in high yield (up to 92%) and stereoselectivity (up to 15:1 dr and 90% ee). (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.07.015

文献信息

• Dienophilicity of imidazole in inverse electron demand Diels–Alder reactions: cycloadditions with 1,2,4,5-tetrazines and the structure of zarzissine
  作者：Zhao-Kui Wan、Grace H.C. Woo、John K. Snyder

  DOI：10.1016/s0040-4020(01)00476-8

  日期：2001.6

  The inverse electron demand cycloadditions of 2-substituted imidazoles with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate produced imidazo[4,5-d]pyridazines in good yields. This chemistry was applied to the synthesis of 2-amino-1H-imidazo[4,5-d]pyridazine (1), the structure reported for zarzissine, a cytotoxic marine alkaloid. Differences in the 1H- and 13C NMR spectra of 1 with those reported for zarzissine

  2-取代的咪唑与1,2,4,5-四嗪-3,6-二羧酸二甲酯的反电子需环加成反应可得到高产率的咪唑并[4,5- d ]哒嗪。该化学方法被用于2-氨基-1 H-咪唑并[4,5- d ]哒嗪（1）的合成，该结构报道了具有细胞毒性的海洋生物碱zarzissine的结构。在差异1 H-和13的C NMR光谱1与文献报道为zarzissine必要的结构修改，然后zarzissine被认为是相应的2-氨基-1 ħ -咪唑并[4,5- b ]吡嗪（2），随后由母体杂环合成。
• Glutaminase inhibitory compounds, compositions, and methods of use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05552427A1

  公开（公告）日：1996-09-03

  There is disclosed a pharmaceutical composition for inhibiting glutaminase which comprises a imidazole derivative or a salt thereof. This compound selectively inhibits the proliferation of tumor cells, and the composition is useful as an anti-cancer agent. There is also disclosed a imidazole derivative having glutaminase inhibitory activity.

  本发明公开了一种用于抑制谷氨酰胺酶的药物组合物，其包括咪唑衍生物或其盐。该化合物能够选择性地抑制肿瘤细胞的增殖，该组合物可用作抗癌剂。本发明还公开了一种具有谷氨酰胺酶抑制活性的咪唑衍生物。
• LINKERS FOR ANCHORING TARGETING LIGANDS
  申请人：McGhee William D.

  公开号：US20080305037A1

  公开（公告）日：2008-12-11

  An improved linker which lacks chiral centers between a hydrophobic anchor for coupling to lipid-based particles and a targeting agent has suitable hydrophobic/hydrophilic properties for use in vivo.

  一种改进的连接剂，其在疏水锚与靶向剂之间缺乏手性中心，适用于体内使用，具有适当的疏水/亲水性质，用于与基于脂质的颗粒耦合。
• Linkers for anchoring targeting ligands
  申请人：Kereos, Inc.

  公开号：US07998462B2

  公开（公告）日：2011-08-16

  An improved linker which lacks chiral centers between a hydrophobic anchor for coupling to lipid-based particles and a targeting agent has suitable hydrophobic/hydrophilic properties for use in vivo.

  一种改进的连接剂，其在疏水锚点和靶向剂之间缺乏手性中心，适用于体内使用，具有适当的疏水/亲水性能，可用于与基于脂质的粒子进行耦合。
• Hit-to-lead optimization of a 2-aminobenzimidazole series as new candidates for chagas disease
  作者：Celso de Oliveira Rezende Júnior、Pablo David Grigol Martinez、Rafael Augusto Alves Ferreira、Paul John Koovits、Bruna Miranda Soares、Leonardo L.G. Ferreira、Simone Michelan-Duarte、Rafael Consolin Chelucci、Adriano D. Andricopulo、An Matheeussen、Natascha Van Pelt、Guy Caljon、Louis Maes、Simon Campbell、Jadel M. Kratz、Charles E. Mowbray、Luiz Carlos Dias

  DOI：10.1016/j.ejmech.2022.114925

  日期：2023.1

  including long duration, variable efficacy and serious side effects, there is an urgent need to explore new antitrypanosomal drugs. The present study describes the hit-to-lead optimization of a 2-aminobenzimidazole hit 1 identified through in vitro phenotypic screening of a chemical library against intracellular Trypanosoma cruzi amastigotes, which focused on optimizing potency, selectivity, microsomal

  南美锥虫病是由克氏锥虫引起的一种被忽视的热带病。由于目前的治疗存在一些局限性，包括持续时间长、疗效可变和严重的副作用，因此迫切需要探索新的抗锥虫药物。本研究描述了通过针对细胞内克氏锥虫的化学文库的体外表型筛选鉴定的 2-氨基苯并咪唑命中1的命中到先导优化amastigotes，专注于优化效力、选择性、微粒体稳定性和亲脂性。使用一组 277 个衍生物研究了多参数结构-活性关系。尽管最初命中的物理化学和生物学特性得到改善，但低动力学溶解度和体外对哺乳动物细胞的细胞毒性的结合阻止了最佳化合物的进展，以使用南美锥虫病小鼠模型进行功效研究。