5-(dimethylamino)-N,N-bis(pyridin-2-ylmethyl) naphthalene-1-sulfonamide | 1334062-64-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(dimethylamino)-N,N-bis(pyridin-2-ylmethyl) naphthalene-1-sulfonamide
• 英文别名: 5-(dimethylamino)-N,N-bis(pyridin-2-ylmethyl)naphthalene-1-sulfonamide
• CAS: 1334062-64-4
• 化学式: C₂₄H₂₄N₄O₂S
• 分子量: 432.546
• InChiKey: HQRCVBLUPMYSCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(dimethylamino)-N,N-bis(pyridin-2-ylmethyl) naphthalene-1-sulfonamide 、 zinc(II) chloride 以 甲醇 为溶剂， 反应 6.0h， 以88%的产率得到Zn(N(SO₂(5-(dimethylamino)naphthalene))di(2-picolyl)amine)Cl₂*CHCl₃
  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：

  在 水 作用下， 以 四氢呋喃 为溶剂， 生成 5-(dimethylamino)-N,N-bis(pyridin-2-ylmethyl) naphthalene-1-sulfonamide
  参考文献：
  名称：

  通过荧光OFF-ON传感器检测有机溶剂和生食品中的水分

  摘要：

  据报道，基于新型新型荧光OFF-ON传感器1.Cu的铜配合物可通过荧光发射检测多种有机溶剂（例如CH 3 OH，THF，CH 3 CN和丙酮）中的痕量水。强度。探针对THF中的水具有高度响应性（DL = 0.003 wt％）。铜从探针1.Cu在水存在下的解离是荧光变化的原因，并通过电喷雾电离质谱（ESI-MS），质子核磁共振证实（1H-NMR）和荧光寿命研究。探针的实际应用已成功用于检测商品中的水分，例如盐，糖，小麦和洗衣粉中的水分。

  DOI：

  10.1021/acs.analchem.6b03949

文献信息

• Formation of a Metal-to-Nitrogen Bond of Normal Length by a Neutral Sufonamide Group within a Tridentate Ligand. A New Approach to Radiopharmaceutical Bioconjugation
  作者：Theshini Perera、Pramuditha Abhayawardhana、Patricia A. Marzilli、Frank R. Fronczek、Luigi G. Marzilli

  DOI：10.1021/ic302180t

  日期：2013.3.4

  tertiary sulfonamide group, N(SO2R)R′2, can rehybridize to form a M–N bond of normal length even when the group is in a linear tridentate ligand, such as in the new tridentate N(SO2R)dpa ligands derived from di-(2-picolyl)amine (N(H)dpa). N(SO2R)dpa ligands were used to prepare fac-[Re(CO)3(N(SO2R)dpa)](PF6 or BF4) complexes. Structural characterization of the new complexes established that the tertiary

  我们证明叔磺酰胺基团N (SO 2 R)R' 2可以再杂交形成正常长度的 M-N 键，即使该基团处于线性三齿配体中，例如在新的三齿N (SO 2 R)dpa 配体衍生自二-(2-甲基吡啶)胺 ( N (H)dpa)。N (SO 2 R)dpa 配体用于制备fac -[Re(CO) 3 ( N (SO 2 R)dpa)](PF 6或 BF 4) 复合体。新复合物的结构表征确定叔磺酰胺氮原子与 Re 结合，伴随 sp 2 -sp 3再杂交，促进面部协调。新的fac -[Re(CO) 3 ( N (SO 2 R)dpa)]X 结构为任何金属提供了唯一的例子，其中磺酰胺作为非环状线性三齿配体的一部分和正常的金属 - 氮（叔磺酰胺）键长。以前罕见的这种正常 M-N 键的例子只在更受限制的情况下被发现，例如三足四齿配体。我们对新三齿N (SO 2R)dpa 配体将开发与fac -[M I (CO) 3
• Co-Registered Molecular Logic Gate with a CO-Releasing Molecule Triggered by Light and Peroxide
  作者：Upendar Reddy G、Jörg Axthelm、Patrick Hoffmann、Nandaraj Taye、Steve Gläser、Helmar Görls、Samantha L. Hopkins、Winfried Plass、Ute Neugebauer、Sylvestre Bonnet、Alexander Schiller

  DOI：10.1021/jacs.7b00867

  日期：2017.4.12

  light and matter. We introduce a biocompatible CO-releasing molecule (CORM, A) as Mn(I) tricarbonyl complex with the ligand 5-(dimethylamino)-N, N-bis(pyridin-2-ylmethyl) naphthalene-1-sulfonamide (L). CO release is chaperoned by turn-on fluorescence and can be triggered by light (405 nm) as well as with hydrogen peroxide in aqueous phosphate buffer. Complex A behaves as a logic "OR" gate via co-registering

  共同注册的分子逻辑门结合了两种不同的输入和输出，例如光和物质。我们引入了一种生物相容性 CO 释放分子 (CORM, A) 作为 Mn(I) 三羰基复合物与配体 5-(二甲氨基)-N, N-双(吡啶-2-基甲基) naphthalene-1-sulfonamide (L)。CO 的释放受开启荧光的影响，可以由光 (405 nm) 以及磷酸盐缓冲液中的过氧化氢触发。通过将辐射（光）和过氧化物（物质）的输入共同记录到伴随输出的荧光（光）和 CO（物质）中，复合体 A 表现为逻辑“或”门。细胞活力测定证实了 A 对不同人类细胞系的低毒性。CORM 已被用于追踪 A 进入癌细胞的情况。
• Incorporation of a Theranostic “Two-Tone” Luminescent Silver Complex into Biocompatible Agar Hydrogel Composite for the Eradication of ESKAPE Pathogens in a Skin and Soft Tissue Infection Model
  作者：Miguel N. Pinto、Jorge Martinez-Gonzalez、Indranil Chakraborty、Pradip K. Mascharak

  DOI：10.1021/acs.inorgchem.8b00901

  日期：2018.6.4

  of silver cation (Ag+) makes its incorporation into delivery materials quite challenging. Herein we report a novel soft agar hydrogel composite for the delivery of Ag+ into infected wound sites. This material incorporates a Ag(I) complex [Ag2(DSX)2(NO3)2] (1; DSX = 5-(dimethylamino)-N,N-bis(pyridin-2-ylmethyl) naphthalene-1-sulfonamide) that exhibits a change in fluorescence upon Ag+ release and qualitatively

  皮肤和下面的软组织的微生物入侵和定植是最常见的感染类型，在医院环境中变得越来越普遍。由于出现耐药性的革兰氏阳性和多重耐药的革兰氏阴性细菌菌株，目前系统的抗生素化学疗法受到极大限制。局部施用抗菌素为治疗皮肤和软组织感染（SSTI）提供了有效途径。因此，开发用于递送这些试剂的新的有效材料至关重要。银是一种广谱抗生素，自古以来就用于治疗和预防感染。但是，银阳离子（Ag +）使得将其合并到交付材料中具有很大的挑战性。在这里，我们报告了一种新型的软琼脂水凝胶复合材料，用于将Ag +输送到感染的伤口部位。该材料包含Ag（I）络合物[Ag 2（DSX）2（NO 3）2 ]（1； DSX = 5-（二甲基氨基）-N，N-双（吡啶-2-基甲基）萘-1-磺酰胺）在释放Ag +时荧光发生变化，并定性地指示了银释放的终点。在SSTI模型中测试了该材料对几种细菌菌株的抗菌功效。复杂1事实证明，琼脂复合材料可有效根除
• Fluorescent di-(2-picolyl)amine based drug-like ligands and their Re(CO)3 complexes towards biological applications
  作者：Taniya Darshani、Nadini Thushara、Piyumali Weerasuriya、Frank R. Fronczek、Inoka C. Perera、Theshini Perera

  DOI：10.1016/j.poly.2020.114592

  日期：2020.7

  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.