N,N'-bis-(3-aminopropyl)-1,4-benzenedicarboxamide | 22734-32-3

• 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,N'-bis-(3-aminopropyl)-1,4-benzenedicarboxamide
• 英文别名: 1-N,4-N-bis(3-aminopropyl)benzene-1,4-dicarboxamide
• CAS: 22734-32-3
• 化学式: C₁₄H₂₂N₄O₂
• 分子量: 278.354
• InChiKey: NGCUYIRNGXEVCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R,4S)-3-acetamido-4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-[(S)-(4-nitrophenoxy)carbonyloxy-[(4R)-2-oxo-1,3-dioxolan-4-yl]methyl]-3,4-dihydro-2H-pyran-6-carboxylate 、 N,N'-bis-(3-aminopropyl)-1,4-benzenedicarboxamide 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 生成 methyl (2R,3R,4S)-3-acetamido-2-[(S)-3-[[4-[3-[[(S)-[(2R,3R,4S)-3-acetamido-4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-6-methoxycarbonyl-3,4-dihydro-2H-pyran-2-yl]-[(4R)-2-oxo-1,3-dioxolan-4-yl]methoxy]carbonylamino]propylcarbamoyl]benzoyl]amino]propylcarbamoyloxy-[(4R)-2-oxo-1,3-dioxolan-4-yl]methyl]-4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  Dimeric Zanamivir Conjugates with Various Linking Groups Are Potent, Long-Lasting Inhibitors of Influenza Neuraminidase Including H5N1 Avian Influenza

  摘要：

  The synthesis, antiviral and pharmacokinetic properties of zanamivir (ZMV) dimers 8 and 13 are described. The compounds are highly potent neuraminidase (NA) inhibitors which, along with dimer 3, are being investigated as potential second generation inhaled therapies both for the treatment of influenza and for prophylactic use. They show outstanding activity in a 1 week mouse influenza prophylaxis assay, and compared with ZMV, high concentrations of 8 and 13 are found in rat lung tissue after 1 week. Retention of compounds in rat lung tissue correlated both with molecular weight (excluding 3 and 15) and with a capacity factor K derived from immobilized artificial membrane (IAM) chromatography (including 3 and 15). Pharmacokinetic parameters for 3, 8 and 13 in rats show the compounds have short to moderate plasma half-lives, low clearances and low volumes of distribution. Dimer 3 shows NA inhibitory activity against N1 viruses including the recent highly pathogenic H5N1 A/Chicken/Vietnam/8/2004. In plaque reduction assays, 3, 8 and 13 show good to outstanding potency against a panel of nine flu A and B virus strains. Consistent with its shorter and more rigid linking group, dimer 8 has been successfully crystallized.

  DOI：

  10.1021/jm040891b
• 作为产物：
  描述：

  对苯二甲酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N,N'-bis-(3-aminopropyl)-1,4-benzenedicarboxamide
  参考文献：
  名称：

  Dimeric Zanamivir Conjugates with Various Linking Groups Are Potent, Long-Lasting Inhibitors of Influenza Neuraminidase Including H5N1 Avian Influenza

  摘要：

  The synthesis, antiviral and pharmacokinetic properties of zanamivir (ZMV) dimers 8 and 13 are described. The compounds are highly potent neuraminidase (NA) inhibitors which, along with dimer 3, are being investigated as potential second generation inhaled therapies both for the treatment of influenza and for prophylactic use. They show outstanding activity in a 1 week mouse influenza prophylaxis assay, and compared with ZMV, high concentrations of 8 and 13 are found in rat lung tissue after 1 week. Retention of compounds in rat lung tissue correlated both with molecular weight (excluding 3 and 15) and with a capacity factor K derived from immobilized artificial membrane (IAM) chromatography (including 3 and 15). Pharmacokinetic parameters for 3, 8 and 13 in rats show the compounds have short to moderate plasma half-lives, low clearances and low volumes of distribution. Dimer 3 shows NA inhibitory activity against N1 viruses including the recent highly pathogenic H5N1 A/Chicken/Vietnam/8/2004. In plaque reduction assays, 3, 8 and 13 show good to outstanding potency against a panel of nine flu A and B virus strains. Consistent with its shorter and more rigid linking group, dimer 8 has been successfully crystallized.

  DOI：

  10.1021/jm040891b

文献信息

• Dimeric compounds and their use as anti-viral agents
  申请人：Dowle D. Michael

  公开号：US20070293564A1

  公开（公告）日：2007-12-20

  A method for the prevention of an orthomyxovirus or paramyxovirus infection comprising the step of administration to a subject in need thereof of an effective amount of a compound of formula (I)

  一种预防正黏病毒或副黏病毒感染的方法，包括向需要的受试者注射有效量的化合物(I)。
• DIMERIC COMPOUNDS AND THEIR USE AS ANTI-VIRAL AGENTS
  申请人：BIOTA SCIENTIFIC MANAGEMENT PTY. LTD.

  公开号：EP1451182B1

  公开（公告）日：2008-06-11
• COPOLYAMIDES WITH ALTERNATING REPEAT UNITS
  申请人：DSM IP ASSETS B.V

  公开号：US20170298181A1

  公开（公告）日：2017-10-19

  The invention relates to a process for the preparation of a PA XY/XZ polyamide, more particular a copolyamide having alternating XY units and XZ units and a process for the manufacture thereof. Further, the present invention relates to compositions and articles comprising said copolyamide. Furthermore, the present invention relates to diamines and salts which are intermediary products of the process for the manufacture of said copolyamide.
• Dimeric Zanamivir Conjugates with Various Linking Groups Are Potent, Long-Lasting Inhibitors of Influenza Neuraminidase Including H5N1 Avian Influenza
  作者：Simon J. F. Macdonald、Rachel Cameron、Derek A. Demaine、Rob J. Fenton、Graham Foster、David Gower、J. Nicole Hamblin、Stephanie Hamilton、Graham J. Hart、Alan P. Hill、Graham G. A. Inglis、Betty Jin、Haydn T. Jones、Darryl B. McConnell、Jennifer McKimm-Breschkin、Gail Mills、Van Nguyen、Ian J. Owens、Nigel Parry、Stephen E. Shanahan、Donna Smith、Keith G. Watson、Wen-Yang Wu、Simon P. Tucker

  DOI：10.1021/jm040891b

  日期：2005.4.1

  The synthesis, antiviral and pharmacokinetic properties of zanamivir (ZMV) dimers 8 and 13 are described. The compounds are highly potent neuraminidase (NA) inhibitors which, along with dimer 3, are being investigated as potential second generation inhaled therapies both for the treatment of influenza and for prophylactic use. They show outstanding activity in a 1 week mouse influenza prophylaxis assay, and compared with ZMV, high concentrations of 8 and 13 are found in rat lung tissue after 1 week. Retention of compounds in rat lung tissue correlated both with molecular weight (excluding 3 and 15) and with a capacity factor K derived from immobilized artificial membrane (IAM) chromatography (including 3 and 15). Pharmacokinetic parameters for 3, 8 and 13 in rats show the compounds have short to moderate plasma half-lives, low clearances and low volumes of distribution. Dimer 3 shows NA inhibitory activity against N1 viruses including the recent highly pathogenic H5N1 A/Chicken/Vietnam/8/2004. In plaque reduction assays, 3, 8 and 13 show good to outstanding potency against a panel of nine flu A and B virus strains. Consistent with its shorter and more rigid linking group, dimer 8 has been successfully crystallized.