N-((1-methyl-1H-imidazol-2-yl)methyl)-N-(phenylmethyl)amine dihydrochloride | 474448-87-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((1-methyl-1H-imidazol-2-yl)methyl)-N-(phenylmethyl)amine dihydrochloride
• 英文别名: N-(1-methyl-1H-imidazol-2-ylmethyl)pyrid-2-ylmethylamine；N-((1-methyl-1H-imidazol-2-yl)methyl)-N-(phenylmethyl)amine*2HCl；benzyl-(1-methyl-1H-imidazol-2-ylmethyl)-amine；benzyl(1-methyl-1H-imidazol-2-ylmethyl)amine；N-[(1-methylimidazol-2-yl)methyl]-1-phenylmethanamine
• CAS: 474448-87-8
• 化学式: C₁₂H₁₅N₃
• mdl: MFCD06740614
• 分子量: 201.271
• InChiKey: YKRXJFHSEYGWQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-(Toluene-4-sulfonylamino)-benzoyl chloride 、 N-((1-methyl-1H-imidazol-2-yl)methyl)-N-(phenylmethyl)amine dihydrochloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-Benzyl-N-(1-methyl-1H-imidazol-2-ylmethyl)-2-(toluene-4-sulfonylamino)-benzamide
  参考文献：
  名称：

  Pharmacophore-based search, synthesis, and biological evaluation of anthranilic amides as novel blockers of the Kv1.5 channel

  摘要：

  The search for novel, potent Kv1.5 blockers based on an anthranilic amide scaffold employing a pharmacophore-based virtual screening approach is described. The synthesis and structure-activity relationships (SAR) with respect to inhibition of the Kv1.5 channel are discussed. The most potent compounds display sub-micromolar inhibition of Kv1.5 and no significant effect on the HERG channel. In addition, good oral bioavailability is demonstrated for compound X in rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.057
• 作为产物：
  描述：

  1-甲基-1H-咪唑-2-甲醛 在 5%-palladium/activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、2.03 MPa 条件下， 反应 24.0h， 生成 N-((1-methyl-1H-imidazol-2-yl)methyl)-N-(phenylmethyl)amine dihydrochloride
  参考文献：
  名称：

  Cytotoxic effect of (1-methyl-1 H -imidazol-2-yl)-methanamine and its derivatives in Pt II complexes on human carcinoma cell lines: A comparative study with cisplatin

  摘要：

  The synthesis and pharmacological characterisation of (1-methyl-1H-imidazol-2-yl)-methanamine and its derivatives in Pt-II complexes are described. Six out of eleven new Pt-II complexes showed a significant cytotoxic effect on NCI-H460 lung cancer cell line with EC50 values between 1.1 and 0.115 mM, determined by MTT assay. Compound Pt-4a showed a particularly more potent cytotoxic effect than the previously described Pt-II complex with 2,2'-bipyridine, [Pt(bpy)Cl-2], with an EC50 value equal to 172.7 mu M versus 726.5 mu M respectively, and similar potency of cisplatin (EC50 = 78.3 mu M) in NCI-H460 cell line. The determination of the intracellular and DNA-bound concentrations of Pt-195, as marker of the presence of the complexes, showed that the cytotoxic compound Pt-4a readily diffused into the cells to a similar extent of cisplatin and directly interacted with the nuclear DNA. Pt-4a induced both p53 and p21(Waf) expression in NCI-H460 cells similar to cisplatin. A direct comparison of the cytotoxic effect between compound Pt-4a and cisplatin on 12 different cancer cell lines demonstrated that compound Pt-4a was in general less potent than cisplatin, but it had a comparable cytotoxic effect on non-small-cell lung cancer NCI-H460 cells, and the colorectal cancer cells HCT-15 and HCT-116. Altogether, these results suggested that the Pt-II complex with 1-methyl-1H-imidazol-2-yl)-methanamine (compound Pt-4a), displayed a significant cytotoxic activity in cancer cells. Similarly to cisplatin this compound interacts with nuclear DNA and induces both p53 and p21(waf), and thus it represents an interesting starting point for future optimisation of new Pt-II complexes forming DNA adducts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.063

文献信息

• [EN] CXCR7 RECEPTOR MODULATORS<br/>[FR] MODULATEURS DU RÉCEPTEUR DE CXCR7
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2014191929A1

  公开（公告）日：2014-12-04

  The present invention relates to derivatives of formula (I) Formula (I) wherein (R1)n, R 2a, R 2b, R 3a, R 3b, R 4, L1, L2, X, Y and Ar1 are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as CXCR7 receptor modulators.

  本发明涉及公式（I）的衍生物 公式（I）其中（R1）n，R 2a，R 2b，R 3a，R 3b，R 4，L1，L2，X，Y 和 Ar1 如描述中所述，其制备方法，其药学上可接受的盐，以及其作为药物的用途，含有一个或多个公式（I）化合物的药物组合物，特别是其作为CXCR7受体调节剂的用途。
• Poly(ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors Based on a Tetrahydro-1(2<i>H</i>)-isoquinolinone Scaffold: Synthesis, Biological Evaluation and X-ray Crystal Structure
  作者：Stefan Peukert、Uwe Schwahn、Stefan Güssregen、Herman Schreuder、Armin Hofmeister

  DOI：10.1055/s-2005-865324

  日期：——

  The synthesis, activity and physical properties of two series of novel potent tetrahydro-1(2H)-isoquinolinone based PARP-1 inhibitors are described. The new structural classes with a non-planar ring system interact specifically with the PARP-1 protein at the nicotinamide-binding site.

  本文描述了两系列新型强力四氢-1(2H)-异喹啉酮类PARP-1抑制剂的合成、活性和物理特性。这些具有非平面环系统的新结构类别，特异性结合于PARP-1蛋白的尼古丁酰胺结合位点。
• Anthranilamides and methods of their use
  申请人：——

  公开号：US20030187033A1

  公开（公告）日：2003-10-02

  The present invention is related to anthranilamides of formula I, 1 in which R(1) to R(7) have the meanings indicated herein, a process for their preparation, their use as medicaments, and pharmaceutical preparations containing them. The compounds act on the Kv1.5 potassium channel and inhibit a potassium current which is referred to as the ultra-rapidly activating delayed rectifier in the atrium of the human heart. The compounds are therefore suitable for use as novel antiarrhythmic agents for the treatment and prophylaxis of atrial arrhythmias (e.g., atrial fibrillation (AF) or atrial flutter).

  本发明涉及具有式I的蒽酰胺，其中R(1)至R(7)具有本文中指示的含义，其制备方法，它们作为药物的用途，以及含有它们的药物制剂。这些化合物作用于Kv1.5钾通道，抑制一种被称为人类心房中超快速激活延迟整流器的钾电流。因此，这些化合物适用于作为新型抗心律失常药物，用于治疗和预防心房心律失常（例如心房颤动（AF）或心房扑动）。
• Anthranilamides with heteroarylsulfonyl side chain, process of preparation, and use
  申请人：——

  公开号：US20030114499A1

  公开（公告）日：2003-06-19

  This invention encompasses anthranilamides with heteroarylsulfonyl side chain, process for their preparation, their use as medicament or diagnostic aid, and pharmaceutical preparations containing them. Compounds of formula I, 1 in which R1 to R7 have the meanings stated in the claims, act on the Kv1.5 potassium channel and inhibit a potassium current which is referred to as the ultra-rapidly activating delayed rectifier in the atrium of the human heart. They are therefore suitable as novel antiarrhythmic ingredients, such as for the treatment and prophylaxis of atrial arrhythmias, e.g. atrial fibrillation (AF) or atrial flutter.

  这项发明涵盖了具有杂环磺酰基侧链的蒽酰胺，其制备方法，它们作为药物或诊断辅助剂的用途，以及含有它们的制药制剂。具有式I的化合物，在其中R1至R7具有权利要求中所述的含义，作用于Kv1.5钾通道，并抑制被称为人类心房中超快速激活延迟整流器的钾电流。因此，它们适用作为新型抗心律失常成分，例如用于治疗和预防心房心律失常，如心房颤动（AF）或心房扑动。
• Bioinspired manganese(<scp>ii</scp>) complexes with a clickable ligand for immobilisation on a solid support
  作者：Jérémy Chaignon、Salah-Eddine Stiriba、Francisco Lloret、Consuelo Yuste、Guillaume Pilet、Laurent Bonneviot、Belén Albela、Isabel Castro

  DOI：10.1039/c3dt53636j

  日期：——

  superexchange bis(μ1,1-azido)dimanganese(II) complexes has been proposed using both structural parameters, the Mn–N–Mn bridging angle and the Mn–Nazido distance. In MeOH–EtOH solution the dimeric species are present together with few percents of mononuclear manganese(II) complexes as evidenced by electron paramagnetic resonance (EPR) spectroscopy. Grafting the complexes onto mesoporous silica of MCM-41

  可点击的配体，例如N，N'-双（（吡啶-2-基）甲基）丙-2-炔-1-胺（L 1）和N -（（1-甲基-1 H-咪唑-2-基）甲基）-N-（吡啶-2-基甲基）丙-2-yn-1-胺（L 2）已用于合成一系列锰（II）用于接枝到合适的固体支持物上的络合物。这些配体模拟了依赖于锰的双加氧酶（MndD）活性位点中存在的2-His-1-羧酸盐面部螯合，而炔烃的侧基功能允许使用“点击化学”方法将配体接枝到叠氮基官能化的支持物上。在固体状态下的MndD结晶的这种合成的类似物如双卤化物或拟卤化物桥连的双核锰（II）通式的配合物[锰2（μ-X）2 X 2大号2 ] [L = L 1，其中X = Cl（1），Br（2）和N 3（3）；L = L 2X = N 3（4）]。配合物1-4的特征在于由两个高自旋的Mn之间的弱磁性的交换相互作用II通过两个X离子-桥（Ĵ在-0.059至5.30厘米-1，ħ = - Ĵ