EL-1176 | 56361-01-4

• 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: EL-1176
• 英文别名: 2-Propenamide, N-[2-(3,4-dimethoxyphenyl)ethyl]-；N-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-enamide
• CAS: 56361-01-4
• 化学式: C₁₃H₁₇NO₃
• mdl: MFCD12091142
• 分子量: 235.283
• InChiKey: FDOGAUMRQAXNTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  EL-1176 在 硼烷 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 96.0h， 生成 N-[2-(3,4-dimethoxyphenyl)-ethyl]-N'-(3-dimethylamino-propyl)-propane-1,3-diamine trihydrochloride
  参考文献：
  名称：

  Discovery of non-carbohydrate inhibitors of aminoglycoside-modifying enzymes

  摘要：

  Chemical modification and inactivation of aminoglycosides by many different enzymes expressed in pathogenic bacteria are the main mechanisms of bacterial resistance to these antibiotics. In this work, we designed inhibitors that contain the 1,3-diamine pharmacophore shared by all aminoglycoside antibiotics that contain the 2-deoxystreptamine ring. A discovery library of molecules was prepared by attaching different side chains to both sides of the 1,3-diamine motif. Several of these diamines showed inhibitory activity toward two or three different representative aminoglycoside-modifying enzymes (AGMEs). These studies yielded the first non-carbohydrate inhibitor N-cyclohexyl-N'-(3-dimethylamino-propyl)-propane-1,3-diamine (Compound G,H) that is competitive with respect to the aminoglycoside binding to the enzyme aminoglycoside-2 ''-nucleotidyltransferase-la (ANT(2 '')). Another diamine molecule N-[2-(3,4-dimethoxyphenyl)-ethyl]-N'-(3-dimethylamino-propyl)-propane-1,3-diamine (Compound H,I) was shown to be a competitive inhibitor of two separate enzymes (aminoglycoside-3'-phosphotransferase-IIIa (APH(3')) and ANT(2 '')) with respect to metal-ATP. Thermodynamic and structural-binding properties of the complexes of APH(3') with substrates and inhibitor were shown to be similar to each other, as determined by isothermal titration calorimetry and NMR spectroscopy. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.059
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 、 丙烯酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 EL-1176
  参考文献：
  名称：

  Discovery of non-carbohydrate inhibitors of aminoglycoside-modifying enzymes

  摘要：

  Chemical modification and inactivation of aminoglycosides by many different enzymes expressed in pathogenic bacteria are the main mechanisms of bacterial resistance to these antibiotics. In this work, we designed inhibitors that contain the 1,3-diamine pharmacophore shared by all aminoglycoside antibiotics that contain the 2-deoxystreptamine ring. A discovery library of molecules was prepared by attaching different side chains to both sides of the 1,3-diamine motif. Several of these diamines showed inhibitory activity toward two or three different representative aminoglycoside-modifying enzymes (AGMEs). These studies yielded the first non-carbohydrate inhibitor N-cyclohexyl-N'-(3-dimethylamino-propyl)-propane-1,3-diamine (Compound G,H) that is competitive with respect to the aminoglycoside binding to the enzyme aminoglycoside-2 ''-nucleotidyltransferase-la (ANT(2 '')). Another diamine molecule N-[2-(3,4-dimethoxyphenyl)-ethyl]-N'-(3-dimethylamino-propyl)-propane-1,3-diamine (Compound H,I) was shown to be a competitive inhibitor of two separate enzymes (aminoglycoside-3'-phosphotransferase-IIIa (APH(3')) and ANT(2 '')) with respect to metal-ATP. Thermodynamic and structural-binding properties of the complexes of APH(3') with substrates and inhibitor were shown to be similar to each other, as determined by isothermal titration calorimetry and NMR spectroscopy. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.059

文献信息

• MARKARYAN EH. A.; AJRAPETYAN G.K., AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH. <AUKZ-AN>, 1975, 28, HO 4, 317-32+
  作者：MARKARYAN EH. A.、 AJRAPETYAN G.K.

  DOI：——

  日期：——
• MARKARYAN EH. A.; AJRAPETYAN G. K., AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1978, 31, HO 10, 757-762
  作者：MARKARYAN EH. A.、 AJRAPETYAN G. K.

  DOI：——

  日期：——
• US3994891A
  申请人：——

  公开号：US3994891A

  公开（公告）日：1976-11-30
• Discovery of non-carbohydrate inhibitors of aminoglycoside-modifying enzymes
  作者：Karen T. Welch、Kristopher G. Virga、Neil A. Whittemore、Can Özen、Edward Wright、Cynthia L. Brown、Richard E. Lee、Engin H. Serpersu

  DOI：10.1016/j.bmc.2005.06.059

  日期：2005.11

  Chemical modification and inactivation of aminoglycosides by many different enzymes expressed in pathogenic bacteria are the main mechanisms of bacterial resistance to these antibiotics. In this work, we designed inhibitors that contain the 1,3-diamine pharmacophore shared by all aminoglycoside antibiotics that contain the 2-deoxystreptamine ring. A discovery library of molecules was prepared by attaching different side chains to both sides of the 1,3-diamine motif. Several of these diamines showed inhibitory activity toward two or three different representative aminoglycoside-modifying enzymes (AGMEs). These studies yielded the first non-carbohydrate inhibitor N-cyclohexyl-N'-(3-dimethylamino-propyl)-propane-1,3-diamine (Compound G,H) that is competitive with respect to the aminoglycoside binding to the enzyme aminoglycoside-2 ''-nucleotidyltransferase-la (ANT(2 '')). Another diamine molecule N-[2-(3,4-dimethoxyphenyl)-ethyl]-N'-(3-dimethylamino-propyl)-propane-1,3-diamine (Compound H,I) was shown to be a competitive inhibitor of two separate enzymes (aminoglycoside-3'-phosphotransferase-IIIa (APH(3')) and ANT(2 '')) with respect to metal-ATP. Thermodynamic and structural-binding properties of the complexes of APH(3') with substrates and inhibitor were shown to be similar to each other, as determined by isothermal titration calorimetry and NMR spectroscopy. (c) 2005 Elsevier Ltd. All rights reserved.