N,N'-(3,3'-(piperazine-1,4-diyl)bis(propane-3,1-diyl))bis(4-methylbenzenesulfonamide) | 161123-21-3

• 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'-(3,3'-(piperazine-1,4-diyl)bis(propane-3,1-diyl))bis(4-methylbenzenesulfonamide)
• 英文别名: N,N'-bis<3-(p-tolylsulfonyl)aminopropyl>piperazine；N,N'-Bis(3-tosylaminopropyl)piperazine；4-methyl-N-[3-[4-[3-[(4-methylphenyl)sulfonylamino]propyl]piperazin-1-yl]propyl]benzenesulfonamide
• CAS: 161123-21-3
• 化学式: C₂₄H₃₆N₄O₄S₂
• 分子量: 508.706
• InChiKey: MLQFZSTUNPGXQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-(3,3'-(piperazine-1,4-diyl)bis(propane-3,1-diyl))bis(4-methylbenzenesulfonamide) 在 sodium ethanolate 、 lithium 作用下， 以 甲醇 、 乙醚 、 氨 为溶剂， 反应 2.5h， 生成 3,7,10,14,21,25,28,32-octaazapentacyclo<32.2.2^7,10.2^16,19.2^25,28>tetratetraconta-1(37),16(41),17,19(40),34(38),35-hexaene
  参考文献：
  名称：

  A reinforced polyaza[n.n]paracyclophane containing piperazine rings

  摘要：

  The new [n.n]paraazacyclophane 3,7,10,14,21,25,28,32-octaazapentacyclo[32.2.2(7,10).2(25,28)]tetratetraconta-1 (37),16(41),17,19(40),34(38),35-hexaene (L) has been prepared. Its protonation has been studied by means of potentiometry and direct microcalorimetry in 0.15 mol dm (3) NaClO4 at 298.1 K. A NMR analysis shows that protons bind alternately at both sides of L, the benzylic nitrogens being the first sites to be protonated. From dynamic variable-temperature NMR analysis an activation enthalpy of 61(2) kJ mol (1) has been derived for the chair-chair interconversion of the piperazine ring. The entropy is almost negligible. Compound L forms with Cu2+ in aqueous solution complexes [Cu(H(3)L)](3+) and [Cu(2)L](4+) with stability constants log beta(CuH3L) = 33.20(6) and log beta(Cu2L) 16.6(1) in 0.15 mol dm (3) NaClO4 at 298.1 K, respectively. The low stability of the binuclear complex is attributed to the energy loss due to interconversion between the chair and boat conformers of the piperazine moieties. The interaction of Pd2+ with L has been monitored by NMR analysis. The spectral features show formation of strong binuclear complexes with the involvement of all eight nitrogens of the macrocycle.

  DOI：

  10.1039/dt9960000239
• 作为产物：
  描述：

  对甲苯磺酰氯 在 碳酸氢钠 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.33h， 生成 N,N'-(3,3'-(piperazine-1,4-diyl)bis(propane-3,1-diyl))bis(4-methylbenzenesulfonamide)
  参考文献：
  名称：

  In silico identification, design and synthesis of novel piperazine-based antiviral agents targeting the hepatitis C virus helicase

  摘要：

  A structure-based virtual screening of commercial compounds was carried out on the HCV NS3 helicase structure, with the aim to identify novel inhibitors of HCV replication. Among a selection of 13 commercial structures, one compound was found to inhibit the subgenomic HCV replicon in the low micromolar range. Different series of new piperazine-based analogues were designed and synthesised, and among them, several novel structures exhibited antiviral activity in the HCV replicon assay. Some of the new compounds were also found to inhibit HCV NS3 helicase function in vitro, and one directly bound NS3 with a dissociation constant of 570 +/- 270 nM. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.10.043

文献信息

• Microwave-assisted synthesis and characterization of novel metal-free and metallophthalocyanines containing four 14-membered tetraaza macrocycles
  作者：Zekeriya Bıyıklıoğlu、Halit Kantekin、Musa Özil

  DOI：10.1016/j.jorganchem.2007.02.013

  日期：2007.5

  The novel tetrasubstituted metal-free phthalocyanine (6) and metallophthalocyanines (7, 8) bearing four 14-membered tetraaza macrocycles moieties on peripheral positions have been synthesized by cyclotetramerization reaction of phthalonitrile derivative (5) in a multi-step reaction sequence. The new compounds were characterized by a combination of IR, 1H NMR, 13C NMR, UV–vis, elemental analysis and

  该新型四取代的无金属酞菁（6）和金属酞菁（7，8）支承在周边位置4个14元大环氮杂部分已经由邻苯二甲腈衍生物（的cyclotetramerization反应合成5在一个多步反应序列）。新化合物的特点是结合了IR，1 H NMR，13 C NMR，UV-vis，元素分析和MS光谱数据。
• Design and synthesis of ionophores with multiple receptor sites: solution nuclear magnetic resonance studies of their interaction with chloride, sodium and potassium ions
  作者：Kenneth I. Kinnear、David P. Mousley、Ezzidin Arafa、Joyce C. Lockhart

  DOI：10.1039/dt9940003637

  日期：——

  Ionophores of the bis(crown ether) type, with polyamine linkers, examples of which are known to bind Simultaneously to a cation and its counter anion, have been prepared. One-pot reductive amination, used to couple a benzo-crown aldehyde with aliphatic (both linear and cyclic) and aromatic polyamines. proved to be the most efficient route. A strong inhibition of one synthetic route (amine benzylation) was observed. The competitive interaction between chloride and other anions for binding with the protonated ionophores was examined using Cl-35 NMR spectroscopy. Sandwich complexing of potassium contrasting with single-face complexation of sodium was demonstrated by C-13 NMR Spectroscopy
• In silico identification, design and synthesis of novel piperazine-based antiviral agents targeting the hepatitis C virus helicase
  作者：Marcella Bassetto、Pieter Leyssen、Johan Neyts、Mark M. Yerukhimovich、David N. Frick、Matthew Courtney-Smith、Andrea Brancale

  DOI：10.1016/j.ejmech.2016.10.043

  日期：2017.1

  A structure-based virtual screening of commercial compounds was carried out on the HCV NS3 helicase structure, with the aim to identify novel inhibitors of HCV replication. Among a selection of 13 commercial structures, one compound was found to inhibit the subgenomic HCV replicon in the low micromolar range. Different series of new piperazine-based analogues were designed and synthesised, and among them, several novel structures exhibited antiviral activity in the HCV replicon assay. Some of the new compounds were also found to inhibit HCV NS3 helicase function in vitro, and one directly bound NS3 with a dissociation constant of 570 +/- 270 nM. (C) 2016 Elsevier Masson SAS. All rights reserved.
• A reinforced polyaza[n.n]paracyclophane containing piperazine rings
  作者：Juan A. Aguilar、Enrique García-España、José A. Guerrero、José M. Llinares、José A. Ramírez、Conxa Soriano、Santiago V. Luis、Antonio Bianchi、Luca Ferrini、Vieri Fusi

  DOI：10.1039/dt9960000239

  日期：——

  The new [n.n]paraazacyclophane 3,7,10,14,21,25,28,32-octaazapentacyclo[32.2.2(7,10).2(25,28)]tetratetraconta-1 (37),16(41),17,19(40),34(38),35-hexaene (L) has been prepared. Its protonation has been studied by means of potentiometry and direct microcalorimetry in 0.15 mol dm (3) NaClO4 at 298.1 K. A NMR analysis shows that protons bind alternately at both sides of L, the benzylic nitrogens being the first sites to be protonated. From dynamic variable-temperature NMR analysis an activation enthalpy of 61(2) kJ mol (1) has been derived for the chair-chair interconversion of the piperazine ring. The entropy is almost negligible. Compound L forms with Cu2+ in aqueous solution complexes [Cu(H(3)L)](3+) and [Cu(2)L](4+) with stability constants log beta(CuH3L) = 33.20(6) and log beta(Cu2L) 16.6(1) in 0.15 mol dm (3) NaClO4 at 298.1 K, respectively. The low stability of the binuclear complex is attributed to the energy loss due to interconversion between the chair and boat conformers of the piperazine moieties. The interaction of Pd2+ with L has been monitored by NMR analysis. The spectral features show formation of strong binuclear complexes with the involvement of all eight nitrogens of the macrocycle.