(3-Aminomethyl-benzyl)-pyridin-2-yl-amine | 775278-53-0

• 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: (3-Aminomethyl-benzyl)-pyridin-2-yl-amine
• 英文别名: N-[[3-(aminomethyl)phenyl]methyl]pyridin-2-amine
• CAS: 775278-53-0
• 化学式: C₁₃H₁₅N₃
• mdl: MFCD12079079
• 分子量: 213.282
• InChiKey: YXRKGJQKCRGKHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-二氢-1H-咪唑-2-磺酸 、 (3-Aminomethyl-benzyl)-pyridin-2-yl-amine 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 1-[(4,5-dihydro-1H-imidazol-2-yl)aminomethyl]-3-(2-pyridylaminomethyl)benzene
  参考文献：
  名称：

  Metal-Free Catalysts for the Hydrolysis of RNA Derived from Guanidines, 2-Aminopyridines, and 2-Aminobenzimidazoles

  摘要：

  2-Aminopyridine and 2-aminobenzimidazole were chosen as structural analogues to substitute guanidinium groups in receptor molecules designed as phosphoryl transfer catalysts. Shifting the pK(a) of the guanidinium analogues toward 7 was expected to raise catalytic activities in aqueous buffer. Although the pK(a)'s of both heterocycles are similar (6.2 and 7.0), only 2-aminobenzimidazole led to active RNA cleavers. All cleavage assays were run with fluorescently labeled substrates and a DNA sequencer. RNase contaminations would degrade RNA enantioselectively. In contrast, achiral catalysts such as 9b and 10b necessarily induce identical cleavage patterns in RNA and its mirror image. This principle allowed us to safely rule out contamination effects in this study. The most active catalysts, tris(2-aminobenzimidazoles) 9b and 1 Ob, were shown by fluorescence correlation spectroscopy (FCS) to aggregate with oligonucleotides. However, at very low concentrations the compounds are still active in the nonaggregated state. Conjugates of 10b with antisense oligonucleotides or RNA binding peptides, therefore, will be promising candidates as site specific artificial ribonucleases.

  DOI：

  10.1021/ja0443934
• 作为产物：
  描述：

  间苯二甲胺 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 (3-Aminomethyl-benzyl)-pyridin-2-yl-amine
  参考文献：
  名称：

  Metal-Free Catalysts for the Hydrolysis of RNA Derived from Guanidines, 2-Aminopyridines, and 2-Aminobenzimidazoles

  摘要：

  2-Aminopyridine and 2-aminobenzimidazole were chosen as structural analogues to substitute guanidinium groups in receptor molecules designed as phosphoryl transfer catalysts. Shifting the pK(a) of the guanidinium analogues toward 7 was expected to raise catalytic activities in aqueous buffer. Although the pK(a)'s of both heterocycles are similar (6.2 and 7.0), only 2-aminobenzimidazole led to active RNA cleavers. All cleavage assays were run with fluorescently labeled substrates and a DNA sequencer. RNase contaminations would degrade RNA enantioselectively. In contrast, achiral catalysts such as 9b and 10b necessarily induce identical cleavage patterns in RNA and its mirror image. This principle allowed us to safely rule out contamination effects in this study. The most active catalysts, tris(2-aminobenzimidazoles) 9b and 1 Ob, were shown by fluorescence correlation spectroscopy (FCS) to aggregate with oligonucleotides. However, at very low concentrations the compounds are still active in the nonaggregated state. Conjugates of 10b with antisense oligonucleotides or RNA binding peptides, therefore, will be promising candidates as site specific artificial ribonucleases.

  DOI：

  10.1021/ja0443934

文献信息

• COMPOSES BICYCLIQUES ANTAGONISTES DES RECEPTEURS DE LA VITRONECTINE, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS QUI LES CONTIENNENT
  申请人：Les Laboratoires Servier

  公开号：EP1268429B1

  公开（公告）日：2004-08-18
• [EN] VITRONECTIN RECEPTOR ANTAGONIST BICYCLIC COMPOUNDS, PREPARATION METHOD AND COMPOSITIONS CONTAINING SAME<br/>[FR] COMPOSES BICYCLIQUES ANTAGONISTES DES RECEPTEURS DE LA VITRONECTINE, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS QUI LES CONTIENNENT
  申请人：ADIR

  公开号：WO2001079172A1

  公开（公告）日：2001-10-25

  Composée de formule (I) dans laquelle: G représente un phényle ou un hétérocycle éventuellement substitué, G1 et G2 étant N ou C; T1 représente -CH2-CH2-, -CH=CH-, =CH-CH2-, et T2 est une liaison, ou bien T1 représente -CH2-, =CH- et T2 est -CH2-, =CH-, (a) ou (b); R5 représente -(CH2)m-COOR6; R6 et R6', représentent hydrogène, alkyle, aryle éventuellement substitué, ou arylalkyle éventuellement substitué; A représente -CO-, -CH2-, =CH-, -CH= et W représente -CH-, =C- ou -C=, ou bien A représente -CO-, -CH2- et W représente N; X représente- CO-X1-, -CO-NR6-X1-, -NR6-CO-X1-, -O-X1-, -SO2-NR6-X1-, ou -S(O)n-X1-; Y représente -Y1-, -Y2-Y1- ou- Y1-Y2-Y1-, Y1 étant un alkylène, alkénylène ou alkynylène, et Y2 étant un arylène, hétéroarylène, cycloalkylène, ou hétérocycloalkylène; Z représente -Z1-, -Z10-NR6-, et -Z10-NR6-CO-, Z1 étant un hétéroaryle, hétérocycloalkyle, hétéroarylalkyle, hétérocycloalkylalkyle, arylhétéroaryle fusionné, arylhétérocycloalkyle fusionné, hétéroarylhétérocycloalkyle fusionné, hétérocycloalkylhétéroaryle fusioné, ou hétéroarylhétéroaryle fusionné, tous éventuellement substitués, ou un groupement (c), Z2-NR6, ou Z2-NR6-CO, Z2 étant un groupement Z1, alkyle ou hétéroalkyle, et Z10 représente Z1 ou un alkyle, Médicaments.
• Metal-Free Catalysts for the Hydrolysis of RNA Derived from Guanidines, 2-Aminopyridines, and 2-Aminobenzimidazoles
  作者：Ute Scheffer、Andreas Strick、Verena Ludwig、Sascha Peter、Elisabeth Kalden、Michael W. Göbel

  DOI：10.1021/ja0443934

  日期：2005.2.1

  2-Aminopyridine and 2-aminobenzimidazole were chosen as structural analogues to substitute guanidinium groups in receptor molecules designed as phosphoryl transfer catalysts. Shifting the pK(a) of the guanidinium analogues toward 7 was expected to raise catalytic activities in aqueous buffer. Although the pK(a)'s of both heterocycles are similar (6.2 and 7.0), only 2-aminobenzimidazole led to active RNA cleavers. All cleavage assays were run with fluorescently labeled substrates and a DNA sequencer. RNase contaminations would degrade RNA enantioselectively. In contrast, achiral catalysts such as 9b and 10b necessarily induce identical cleavage patterns in RNA and its mirror image. This principle allowed us to safely rule out contamination effects in this study. The most active catalysts, tris(2-aminobenzimidazoles) 9b and 1 Ob, were shown by fluorescence correlation spectroscopy (FCS) to aggregate with oligonucleotides. However, at very low concentrations the compounds are still active in the nonaggregated state. Conjugates of 10b with antisense oligonucleotides or RNA binding peptides, therefore, will be promising candidates as site specific artificial ribonucleases.