N,N-bis(2-pyridylmethyl)-2-aminoethanethiol | 87145-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N-bis(2-pyridylmethyl)-2-aminoethanethiol
• 英文别名: Ethanethiol, 2-[bis(2-pyridinylmethyl)amino]-；2-[bis(pyridin-2-ylmethyl)amino]ethanethiol
• CAS: 87145-34-4
• 化学式: C₁₄H₁₇N₃S
• 分子量: 259.375
• InChiKey: PHIIPQGPGULPHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(99)technetium(I)(carbonyl)3(H2O)3] 、 N,N-bis(2-pyridylmethyl)-2-aminoethanethiol 以 水 、 二甲基亚砜 为溶剂， 生成 tricarbonyl(N,N-bis(2-pyridylmethyl)aminoethanethiolato)technetium-99
  参考文献：
  名称：

  Thiol- and Thioether-Based Bifunctional Chelates for the {M(CO)₃}⁺ Core (M = Tc, Re)

  摘要：

  By analogy to the recently described single amino acid chelate (SAAC) technology for complexation of the {M(CO)(3)}(+) core (M = Tc, Re), a series of tridentate ligands containing thiolate and thioether groups, as well as amino and pyridyl nitrogen donors, have been prepared: (NC5H4CH2)(2)NCH2CH2SEt (L1); (NC5H4CH2)(2)NCH2CH2SH (L2); NC5H4CH2N(CH2CH2SH)2 (L3); (NC5H4CH2)N(CH2CH2SH)(CH2CO2R) [R = H (L4); R = -C2H5 (L5). The {Re(CO)(3)}(+) core complexes of L1-L5 were prepared by the reaction of [Re(CO)(3)(H2O)(3)]Br or [NEt4](2)[Re(CO)(3)Br-3] with the appropriate ligand in methanol and characterized by infrared spectroscopy, H-1 and C-13 NMR spectroscopy, mass spectrometry, and in the case of [Re(CO)(3)(L2)] (Re-2) and [Re(CO)(3)(L1)Re(C0)(3)Br-2] (Re-1a) by X-ray crystallography. The structure of Re-2 consists of discrete neutral monomers with a fac-Re(CO)3 coordination unit and the remaining coordination sites occupied by the amine, pyridyl, and thiolate donors of L2, leaving a pendant pyridyl arm. In contrast, the structure of Re-la consists of discrete binuclear units, constructed from a {Re(CO)(3)-(L1)}(+) subunit linked to a {Re(CO)(3)Br-2}(-) group through the sulfur donor of the pendant thioether arm. The series of complexes establishes that thiolate donors are effective ligands for the {M(CO)(3)}(+) core and that a qualitative ordering of the coordination preferences of the core may be proposed: pyridyl nitrogen - thiolate > carboxylate > thioether sulfur > thiophene sulfur. The ligands L1 and L2 react cleanly with [Tc-99m(CO)(3)(H2O)(3)](+) in H2O/DMSO to give [99mTc(CO)(3)(L1)]+ (Tc-99m-1) and [Tc-99m(CO)(3)(L2)] (Tc-99m-2), respectively, in ca. 90% yield after HPLC purification. The Tc analogues Tc-99m-1 and 99mTc-2 were subjected to ligand challenges by incubating each in the presence of 1000-fold excesses of both cysteine and histidine. The radiochromatograms showed greater than 95% recovery of the complexes.

  DOI：

  10.1021/ic050735a
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以82%的产率得到N,N-bis(2-pyridylmethyl)-2-aminoethanethiol
  参考文献：
  名称：

  一种金属β-内酰胺酶抑制剂及其制备方法与 应用

  摘要：

  本发明公开了一种金属β‑内酰胺酶抑制剂及其制备方法与应用。本发明通过将吡啶胺化合物溶于溶剂1中，再加入酯类化合物和碳酸盐，在80～100℃下搅拌11～13小时，将反应产物冷却至室温、萃取、真空干燥以及纯化后得到产物1；将产物1溶于溶剂2中，加入酯基水解物，在室温下搅拌1.5～2.5小时，将反应产物萃取、真空干燥以及纯化后得到Zn2+螯合剂；将β‑内酰胺化合物溶于溶剂3中，加入Zn2+螯合剂和碱，室温下搅拌11～13小时，将反应产物萃取、真空干燥以及纯化，得到金属β‑内酰胺酶抑制剂，该金属β‑内酰胺酶抑制剂可作为抗生素的联合用剂用于抑制细菌增殖。本发明抑制剂制备更加简单、材料成本低，并且该抑制剂降低了分子的生物毒性，具有更高的抑菌效率。

  公开号：

  CN111718361B

文献信息

• A model for ZnII-containing-β-lactamase: synthesis, X-ray crystal structure of a zinc(II) complex bearing thiol groupand hydrolysis of phosphate diester
  作者：Hiromasa Kurosaki、Toshiaki Tawada、Satomi Kawasoe、Yoko Ohashi、Masafumi Goto

  DOI：10.1016/s0960-894x(00)00238-9

  日期：2000.6

  A novel N3S1 typed tripodal ligand bearing an SH group, N-(mercaptoethyl)-di(2-pyridylmethyl)amine, DPASH, was prepared and its zinc(II) complex, [ZnII(DPAS)Cl], was structurally characterized by X-ray crystallography. [ZnII(DPAS)Cl] promoted hydrolysis of sodium bis(p-nitrophenyl)hydrogenphosphate), BNP-.

  制备了具有SH基团的新型N3S1型三脚架配体N-（巯基乙基）-二（2-吡啶基甲基）胺DPASH，并用X对其结构的锌（II）配合物[ZnII（DPAS）Cl]进行了表征。射线晶体学。[ZnII（DPAS）Cl]促进了双（对硝基苯基）磷酸氢钠，BNP-的水解。
• Live-Cell Pyrophosphate Imaging by in Situ Hot-Spot Generation
  作者：Mingmin Li、Jin Li、Huixia Di、Huiqiao Liu、Dingbin Liu

  DOI：10.1021/acs.analchem.6b04786

  日期：2017.3.21

  significant anion, in living cells. Intracellular PPi is able to induce the nanoparticle dimerization, thus creating an intense electromagnetic hot spot and dramatically enhancing the signal of the Raman reporters residing in the hot spot. More impressively, the reporter we used in this study provides a strong and sharp single peak in the cellular Raman-silent region (1800–2800 cm–1), thus eliminating the possible

  对于表面增强拉曼散射（SERS）分析，控制电磁热点的产生至关重要。当前基于热点的SERS分析已在溶液或底物上进行了广泛的研究。但是，到目前为止，尚未证明通过控制生物系统中的热点组装来探测生物物种。在此，我们报道了一种无背景SERS探针，用于在活细胞中成像焦磷酸（PPi），一种生化上重要的阴离子。细胞内PPi能够诱导纳米颗粒二聚化，从而产生强烈的电磁热点，并显着增强驻留在该热点中的拉曼报道分子的信号。更令人印象深刻的是，我们在本研究中使用的报告者在细胞拉曼沉默区（1800–2800 cm –1）中提供了一个强而尖锐的单峰。），从而消除了可能的背景干扰。通过仅替换识别配体，该策略可以很容易地扩展到检测其他生物标记。
• A mercury(<scp>ii</scp>) ion sensor device based on an organic field effect transistor with an extended-gate modified by dipicolylamine
  作者：Tsuyoshi Minami、Yui Sasaki、Tsukuru Minamiki、Petr Koutnik、Pavel Anzenbacher、Shizuo Tokito

  DOI：10.1039/c5cc07893h

  日期：——

  The detection of mercury(ii) ions (Hg²⁺) in water was successfully achieved by a disposable and reusable extended-gate organic transistor modified with an artificial receptor.

  水中汞（Hg2+）离子的检测成功地通过一种一次性和可重复使用的扩展栅有机晶体管实现，该晶体管经过人工受体修饰。
• Homo- and Heteronuclear Group 12 Metallothionein Type B Cluster Analogs: Synthesis, Structure, ¹H NMR and ESI-MS
  作者：Haley M. Brennan、Sophia G. Bunde、Qiaoyue Kuang、Tana V. Palomino、Joshua S. Sacks、Steven M. Berry、Ray John Butcher、John C. Poutsma、Robert D. Pike、Deborah C. Bebout

  DOI：10.1021/acs.inorgchem.2c03088

  日期：2022.12.12

  metal-binding proteins involved in metal homeostasis and detoxification with highly versatile metal binding properties. Despite the long-standing association of MT with M3S3 and M4S5 metal clusters, synthetic complexes with these core architectures are exceptionally rare. Here, we demonstrate an approach to synthesizing and characterizing aggregates of group 12 metal ions with monocyclic M3S3 cores in

  金属硫蛋白 (MT) 是一类普遍存在的富含半胱氨酸的小金属结合蛋白，参与金属稳态和解毒，具有高度通用的金属结合特性。尽管 MT 与 M 3 S 3和 M 4 S 5金属簇有着长期的联系，但具有这些核心结构的合成配合物非常罕见。在这里，我们展示了一种在没有蛋白质保护的情况下在乙腈溶液中合成和表征具有单环 M 3 S 3核的第 12 族金属离子聚集体的方法。多齿单硫醇配体N , N -双(2-吡啶基甲基)-2-氨基乙硫醇 ( L1H) 提供了 [Cd 3 ( L1 ) 3 ](ClO 4 ) 3 ( 1 )，这是第一个具有金属硫蛋白样单环 Cd 3 S 3核心的结构特征非蛋白质聚集体。此外，对[Zn 3 ( L1 ) 3 ](ClO 4 ) 3 ·4CH 3 CN ( 2 ·4CH 3 CN) 进行了X射线晶体学表征。1和2的复杂阳离子尽管是非同构的，但具有相似的结构。可变温度和浓度1 H NMR
• Aggregation behavior of group 12 complexes of a tripodal mixed NS(thiolato) donor ligand
  作者：Michelle A. Sturner、Isla D. Thomas、Joshua E. Owusu-Koramoah、Todd M. Reynolds、Steven M. Berry、Raymond J. Butcher、Deborah C. Bebout

  DOI：10.1039/d3nj05532a

  日期：——

  histidine and cysteine in the active sites of proteins associated with Zn2+, Cd2+ and Hg2+, coordination studies of these metal ions with chelating ligands containing a combination of aromatic amine and alkylthiolate (NAxSy−) donors have been rare. The potentially tetradentate ligand 2-[bis(2-pyridinylmethyl)amino]ethanethiol (LH) and chloride salts were used to prepare new complexes of Cd2+ and Hg2+ for

  尽管在与 Zn 2+、Cd 2+和 Hg 2+相关的蛋白质的活性位点中同时存在组氨酸和半胱氨酸，但这些金属离子与含有芳香胺和烷基硫醇盐组合的螯合配体的配位研究（N A x S y − ) 捐赠者很少。潜在的四齿配体2-[双(2-吡啶基甲基)氨基]乙硫醇( LH )和氯化物盐被用来制备新的Cd 2+和Hg 2+配合物，以便与已知的Zn 2+配合物进行比较。溶液核磁共振研究揭示了 CD 3 CN中新复合物的聚集形式之间的浓度依赖性平衡。同核和异核耦合的趋势提供了有关溶液平衡的额外见解。乙腈溶液的 ESI-MS 支持与溶液 NMR 研究一致的首选聚集状态的差异。