1-pyrenecarboxaldehyde thiosemicarbazone | 867130-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-pyrenecarboxaldehyde thiosemicarbazone
• 英文别名: 1-pyrenaldehyde-3-thiosemicarbazone；1-pyrenethiosemicarbazone
• CAS: 867130-19-6
• 化学式: C₁₈H₁₃N₃S
• 分子量: 303.387
• InChiKey: LWAYWNMXLKHYLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.41
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  二氯二羰基双(三苯基膦)钌 、 1-pyrenecarboxaldehyde thiosemicarbazone 以 甲苯 为溶剂， 反应 12.0h， 以88%的产率得到
  参考文献：
  名称：

  Studies on ruthenium complexes of pyrene-appended Schiff base ligands

  摘要：

  DOI：

  10.1016/j.poly.2014.06.005
• 作为产物：
  描述：

  1-芘甲醛 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以80%的产率得到1-pyrenecarboxaldehyde thiosemicarbazone
  参考文献：
  名称：

  Synthesis and biological evaluation of copper(ii) pyrenethiosemicarbazone

  摘要：

  一种荧光铜（II）吡啶硫脲半胱氨酮配合物在光激发下表现出增强的DNA裂解和细胞毒性。

  DOI：

  10.1039/c5ra00020c

文献信息

• “Extra stabilisation” of a pyrene based molecular couple by γ-cyclodextrin in the excited electronic state
  作者：Prasun Ghosh、Soumik Mandal、Tarasankar Das、Arnab Maity、Parna Gupta、Pradipta Purkayastha

  DOI：10.1039/c2cp41921a

  日期：——

  semicarbazide functionalized pyrene labeled Schiff base compounds have been synthesized. The pyrene moieties in the compounds result in formation of π–π coupled complexes in aqueous medium in the excited electronic state. Added γ-cyclodextrin allows incorporation of the pyrene head inside its less polar core and promotes hydrogen bonding of the thio and oxo groups of the compounds with its rim hydroxyl groups

  二 硫代氨基脲 和氨基脲功能化 芘已经合成了标记的席夫碱化合物。化合物中的pyr部分会在水介质中以激发电子态形成π-π偶联的配合物。添加的γ-环糊精可将the头并入其极性较小的核中，并促进化合物的硫和氧代氢与边缘羟基的氢键键合，以“稳定”单体。FT-IR和吸收光谱法证实了这一点。稳定的单体导致稳定的受激准分子的形成，如通过改变实验条件通过稳态和时间分辨荧光光谱法所监测的。通过与两种对照化合物的荧光光谱变化进行比较，证明了拟议的Schiff碱单体稳定模型。可以稳定地利用the基准分子进行生物利用。
• Cyclometallated ruthenium(II) carbonyl complexes with 1-pyrenaldehyde 4-R-3-thiosemicarbazones: Regioselective ruthenation of the 1-pyrenyl group
  作者：RUPESH NARAYANA PRABHU、SAMUDRANIL PAL

  DOI：10.1007/s12039-015-0812-3

  日期：2015.4

  susceptibility and spectroscopic (ESI-MS, IR, UV-Vis, emission and 1H-NMR) measurements. Electronic spectra of the complexes display multiple strong absorptions in the range 440–224 nm due to intraligand transitions. All the complexes exhibit emission bands that are characteristic of ligand centred emissive states. X-ray diffraction studies with representative complexes reveal a pincer-like 5,5-membered fused chelate

  一种简便的方法，用于合成一系列环金属化的钌（II）羰基配合物与1-苯甲醛4- R -3-硫代半氨基甲酮（H \（_ 2} \ textit L} ^ \ mathrm n}} \ ），其中两个H代表可分解的硫代酰胺和and质子；R = H，Me和Ph）。通过元素（CHN）分析，磁化率和光谱学（ESI）对具有通式反式-[Ru（L n）（CO）（EPh 3）2 ]（其中E = P或As）的配合物进行表征-MS，IR，UV-Vis，发射和1H-NMR）测量。由于配体内的跃迁，络合物的电子光谱在440-224 nm范围内显示出多个强吸收。所有配合物均表现出以配体中心发射态为特征的发射带。用代表性配合物进行的X射线衍射研究显示，通过1-吡啶基邻位C–H的区域选择性活化，形成了钳形的5,5元稠合的螯合环，形成了硫代半氨基甲酸酯配体（L n）2的 CNS配位模式。钌（II）中心周围的八面体C 2
• Biological activities of pyrenyl-derived thiosemicarbazone half-sandwich complexes
  作者：Nandhagopal Raja、Neelakandan Devika、Gajendra Gupta、Vadithe Lakshma Nayak、Ahmed Kamal、Narayana Nagesh、Bruno Therrien

  DOI：10.1016/j.jorganchem.2015.06.036

  日期：2015.10

  Pyrenyl-derived thiosemicarbazone half-sandwich complexes of the types [(eta(6)-p-MeC6H4Pri)Ru(L-n)Cl](+) and [(eta(5)-C5Me5)M(L-n)Cl](+) (M = Rh, Ir; L-1 = pyrenecarboxaldehyde-3-thiosemicarbazone, L-2 = pyrenecarboxaldehyde-4-methyl-3-thiosemicarbazone, L-3 = pyrenecarboxaldehyde-4-phenyl-3-thiosemicarbazone) were synthesized and isolated as their chloride salts by reacting in THF the dinuclear complexes [(eta(6)-P-MeC6H4Pri)(2)Ru-2(mu-Cl)(2)Cl-2] and [(eta(5)-C5Me5)(2)M-2(mu-Cl)(2)Cl-2] with the corresponding ligand. All complexes were isolated in good yields and were fully characterized by spectroscopic methods, including single-crystal X-ray structure analyses of the ruthenium complex [(eta(6)-p-MeC6H4Pri) Ru(L1)Cl]Cl and the rhodium derivative [(eta(5)-C5Me5)Rh(L-2)Cl]Cl. The complexes were found to have IC50 values in the micromolar range against cancer cells (A-549, DU-145, HeLa, MCF-7), with a lower cytotoxicity in the noncancerous human HEK-293 embryonic kidney cells. The best two candidates, the rhodium derivatives [(eta(5)-C5Me5)Rh(L-1)Cl]Cl and [(eta(5)-C5Me5)Rh(L-3)Cl]Cl, show anticancer activities comparable to doxorubicin. These two complexes were further evaluated, showing an inhibition of the cell cycle at the G2/M and subG1 stages. (C) 2015 Elsevier B.V. All rights reserved.
• 2-(Hetero(aryl)methylene)hydrazine-1-carbothioamides as Potent Urease Inhibitors
  作者：Aamer Saeed、Aqeel Imran、Pervaiz A. Channar、Mohammad Shahid、Wajahat Mahmood、Jamshed Iqbal

  DOI：10.1111/cbdd.12379

  日期：2015.2

  A small series of 2‐(hetero(aryl)methylene) hydrazine‐1‐carbothioamides including two aryl derivatives was synthesized and tested for their inhibitory activity against urease. Compound (E)‐2‐(Furan‐2‐ylmethylene) hydrazine‐1‐carbothioamide (3f), having a furan ring, was the most potent inhibitor of urease with an IC50 value of 0.58 μm. Molecular modeling was carried out through docking the designed compounds into the urease binding site to predict whether these derivatives have analogous binding mode to the urease inhibitors. The study revealed that all of the tested compounds bind with both metal atoms at the active site of the enzyme. The aromatic ring of the compounds forms ionic interactions with the residues, Ala(440), Asp(494), Ala(636), and Met(637).
• 1-Pyrenecarboxaldehyde thiosemicarbazone: A novel fluorescent molecular sensor towards mercury (II) ion
  作者：Xue Mei Wang、Hua Yan、Xin Lu Feng、Yong Chen

  DOI：10.1016/j.cclet.2010.04.029

  日期：2010.9

  A novel and simple fluorescent molecular sensor, 1-pyrenecarboxaldehyde thiosemicarbazone (Hpytsc), was synthesized. Its higher sensitivity and selectivity to mercury (II) ion were studied through absorption and emission channels. The UV-vis spectra show that the increasing mercury (II) ion concentrations result in the decreasing absorption intensity. The fluorescence monomer emission of Hpytsc is enhanced upon binding mercury (II) ion, which should be due to the 1:1 complex formation between Hpytsc and metal ion. (C) 2010 Xue Mei Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.