N,N-bis(pyridin-2-ylmethyl)naphthalene-1-sulfonamide | 1136626-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-bis(pyridin-2-ylmethyl)naphthalene-1-sulfonamide
• CAS: 1136626-82-8
• 化学式: C₂₂H₁₉N₃O₂S
• 分子量: 389.478
• InChiKey: IYEMGCOAFMSFCN-UHFFFAOYSA-N

物化性质

• 沸点：
  607.8±65.0 °C(predicted)
• 密度：
  1.311±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  71.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bis(pyridin-2-ylmethyl)naphthalene-1-sulfonamide 、 zinc(II) chloride 以 甲醇 为溶剂， 反应 6.0h， 以67%的产率得到Zn(N(SO₂)(1-naphthalene)di(2-picolyl)amine)Cl₂
  参考文献：
  名称：

  第一个结构表征的磺酰胺衍生的具有八元螯合环的 Zn(II)-二吡啶甲胺配合物。合成和结构研究

  摘要：

  摘要 二(2-甲基吡啶)胺作为合成生物传感器中最常用的螯合基团来检测锌(II)离子而备受关注。这项研究揭示了磺酰胺衍生的二（2-甲基吡啶）胺 (dpa) 部分与罕见的八元螯合环的第一个结构特征锌配合物。新型合成锌(II)配合物；Zn(N(SO2R1dpa)Cl2 (C1)、Zn(N(SO2R2dpa)Cl2 (C2)、Zn(N(SO2R3dpa)Cl2 (C3)，其中 R1 = 1-萘，R2 = 2-萘，R3 = 5-使用单晶 X 射线衍射分析、1H NMR、FTIR、紫外-可见光和荧光光谱对（二甲氨基）萘进行了表征。结构分析表明，配合物在锌中心周围具有扭曲的四面体几何形状，并且锌金属中心以双齿方式与 dpa 基团的两个吡啶基氮结合，形成一个大的八元螯合环。在游离配体光谱中归因于亚甲基 (CH2) 的信号在锌配合物的 1H NMR 光谱中仍然是单线态，但已转移到更多的低场。复合物的光谱研究表明，该复合物在

  DOI：

  10.1016/j.molstruc.2020.128310
• 作为产物：
  描述：

  1-萘磺酰氯 、 二甲基吡啶胺 以 1,4-二氧六环 为溶剂， 反应 26.0h， 以77%的产率得到N,N-bis(pyridin-2-ylmethyl)naphthalene-1-sulfonamide
  参考文献：
  名称：

  Fluorescent di-(2-picolyl)amine based drug-like ligands and their Re(CO)3 complexes towards biological applications

  摘要：

  Herein we report two new fac-Re(I) tricarbonyl complexes, fac-[Re(CO)(3)(N(SO2)(1-nap)dpa)]PF6 (C1) and fac-[Re(CO)(3)(N(SO2)(2-nap)dpa)]PF6 (C2), of two naphthalene derivatized tridentate ligands (N(SO2)(1-nap)dpa (L1) and N(SO2)(2-nap)dpa (L2)) and one reported Re(I) complex, fac-[Re(CO)(3)(N (SO(2)Me(2)Nnap)dpa)]PF6 (C3), of a dansyl appended di-2-picolylamine ligand (N(SO(2)Me(2)Nnap)dpa (L3)). The properties of the compounds were elucidated using spectrophotometric measurements (UV-Vis, FTIR and H-1 NMR). A single crystal X-ray study was carried out for the three ligands. The H-1 NMR spectra of the three complexes obtained in DMSO d(6) displayed two doublets (exo-CH and endo-CH) for the magnetically inequivalent methylene protons, compared to their uncoordinated ligands where the methylene protons show a singlet peak. The formation of the metal complexes was further supported by FTIR spectra in which the S-N stretching band for the metal complexes appears at lower wavenumbers compared to that of the corresponding free ligands. In comparison with the uncoordinated ligands, the Re(I) complexes, C1 and C3, displayed a bathochromic shift while C2 showed a hypsochromic shift in the absorption spectra in methanol. The fluorescent maxima and the fluorescence quantum yield (Phi F) of L1 and L2 were 338 nm (Phi F = 0.056) and 343 nm (Phi F = 0.039), respectively. Interestingly, all the compounds except C2 showed excellent fluorescent emissions. Biologically, the compounds were investigated for their cytotoxicity in vitro on human lymphocytes following the Trypan blue dye exclusion method. It was observed that both Re(I) complexes as well as the ligands show low toxicity towards human lymphocytes at working concentrations below 10 mg/ml (L1, L2: 0.026 M, L3: 0.023 M, C1, C2, C3: 0.012 M). In silico studies revealed that the ligands are potential candidates for anti-inflammatory agents and this was further supported by molecular docking studies, in which they showed a higher affinity for Prostaglandin synthase 2. These drug-like molecules, having an affinity to bovine serum albumin, are thus potential drug leads for anti-inflammatory agents. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2020.114592

文献信息

• Synthesis, characterization and biological evaluation of dipicolylamine sulfonamide derivatized platinum complexes as potential anticancer agents
  作者：Nadini Thushara、Taniya Darshani、Sameera R. Samarakoon、Inoka C. Perera、Frank R. Fronczek、W. M. C. Sameera、Theshini Perera

  DOI：10.1039/d1ra00842k

  日期：——

  Three new Pt complexes, [PtCl2(N(SO2(2-nap))dpa)], [PtCl2(N(SO2(1-nap))dpa)] and [PtCl2(N(SO2pip)dpa)], containing a rare 8-membered ring were synthesized in good yield and high purity by utilizing the ligands N(SO2(2-nap))dpa, N(SO2(1-nap))dpa and N(SO2pip)dpa, which contain a dipicolylamine moiety. Structural studies of all three complexes confirmed that the ligands are bound in a bidentate mode

  三种新的 Pt 配合物，[PtCl 2 (N(SO 2 (2-nap))dpa)]、[PtCl 2 (N(SO 2 (1-nap))dpa)] 和 [PtCl 2 (N(SO 2 pip ) )dpa)]，利用配体 N(SO 2 (2-nap))dpa、N(SO 2 (1-nap))dpa 和 N( SO 2 pip)dpa，它包含一个二乙醇胺部分。所有三种配合物的结构研究证实，配体通过Pt-N （吡啶基）以双齿模式结合键形成一个罕见的 8 元环。配体显示的强荧光在与 Pt 配位时猝灭。根据时间相关密度泛函理论 (TDDFT) 计算，N(SO 2 (2-nap))dpa 和 [PtCl 2 (N(SO 2 (1-nap))dpa)] 的关键激发涉及 2-nap -以配体为中心的 π → π* 激发。虽然所有六种化合物都显示出对人乳腺癌细胞 (MCF-7) 的抗增殖活性，但 N(SO 2 pip)dpa