1-苯基-3-(喹啉-8-基)硫脲 | 24005-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 1-苯基-3-(喹啉-8-基)硫脲
• 英文名称: 1-phenyl-3-(quinolin-8-yl)thiourea
• 英文别名: 1-phenyl-3-quinolin-8-ylthiourea
• CAS: 24005-49-0
• 化学式: C₁₆H₁₃N₃S
• 分子量: 279.365
• InChiKey: GOLSAEOIHBTSNN-UHFFFAOYSA-N

物化性质

• 熔点：
  167-169 °C(Solv: methanol (67-56-1))
• 沸点：
  451.6±37.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1-苯基-3-(喹啉-8-基)硫脲 以 甲醇 为溶剂， 反应 24.0h， 以70%的产率得到[RuCl(η⁶-p-Cym)(1-phenyl-3-(quinoline-8-yl) thiourea)]
  参考文献：
  名称：

  Protein binding affinity of biologically active thiourea based half-sandwich Ru(II) cymene complexes

  摘要：

  Half-sandwich (eta(6)-p-cymene) complexes bearing either neutral functionalized N,S-bidentate thiourea ligands or a mono-negative N,N-aminoquinoline ligand were screened for their antibacterial and antifungal activities as well as cell viability against non-malignant HEK293 (human embryonic kidney cells). The haemolysis parameters (HC10 and HC50) were determined to get some information about the compatibility of the toxic compounds with the blood components. The protein binding affinity of hen white egg lysozyme (HEWL), a model protein, towards the synthesized (eta(6)-p-cymene) complexes was investigated by ESI-MS. Metalation of HEWL was achieved through both covalent and non-covalent modes of interaction. To recognize if the metalation site of HEWL is the His15 side chain, the reactions between the complexes and imidazole were theoretically and experimentally studied by quantum chemical calculations, UV-Vis and NMR. Exchange of the nitrogen coordination site of the thiourea ligand from the pyridine to the benzothiazole moiety induced higher potency against Staphylococcus aureus, Candida albicans and Cryptococcus neoformans var. grubii. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2019.114175
• 作为产物：
  描述：

  8-硝基喹啉 在 铁粉 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 50.0h， 生成 1-苯基-3-(喹啉-8-基)硫脲
  参考文献：
  名称：

  WO2008/74068

  摘要：

  公开号：

文献信息

• Synthesis and evaluation of unsymmetrical heterocyclic thioureas as potent β-glucuronidase inhibitors
  作者：Muhammad Taha、Nor Hadiani Ismail、Waqas Jamil、Khalid Mohammed Khan、Uzma Salar、Syed Muhammad Kashif、Fazal Rahim、Yawar Latif

  DOI：10.1007/s00044-015-1369-x

  日期：2015.8

  Thiourea analogs 1–20 were synthesized and evaluated for their in vitro β-glucuronidase inhibitory potential. The compounds 9 (0.86 ± 0.01 μM), 6 (1.24 ± 0.01 μM), 16 (1.64 ± 0.02 μM) and 15 (2.12 ± 0.02 μM) showed potent activity. Other analogs 1–5, 7, 8, 10, 11, 13, 17, 20 showed better activity than standard drug d-saccharic acid 1,4-lactone (47.34 ± 0.21 μM) ranging 4.36–34.4 μM. All synthetic

  合成了硫脲类似物1 – 20，并评估了其体外β-葡萄糖醛酸苷酶抑制潜力。化合物9（0.86±0.01μM），6（1.24±0.01μM），16（1.64±0.02μM）和15（2.12±0.02μM）显示出有效的活性。其他类似物1 - 5，7，8，10，11，13，17，20显示出比标准药物更好的活性d-蔗糖酸1,4-内酯（47.34±0.21μM）范围为4.36–34.4μM。所有合成化合物均通过不同的光谱方法表征。这项研究确定了一种新型的有效抑制剂β-葡萄糖醛酸酶。
• PORADOWSKA H.; NOWAK K.; CZUBA W., POL. J. CHEM., 1979, 53, NO 9, 1895-1900
  作者：PORADOWSKA H.、 NOWAK K.、 CZUBA W.

  DOI：——

  日期：——
• [EN] SUBSTITUTED QUINOLINE DERIVATIVES AS ANTIAMYLOIDOGENEIC AGENTS<br/>[FR] DÉRIVÉS DE QUINOLINE SUBSTITUÉS UTILISÉS COMME AGENTS NON-AMYLOÏDOGÉNIQUES
  申请人：PRANA BIOTECHNOLOGY LTD

  公开号：WO2008074068A1

  公开（公告）日：2008-06-26

  [EN] The present invention relates to heterocyclic compounds, processes for their preparation and their use as pharmaceutical or veterinary agents, in particular for the treatment, amelioration and/or prophylaxis of conditions caused by or associated with unbalanced metal levels and/or oxidative stress, such as neurological conditions and cellular proliferative disorders, for example Alzheimer's disease, Parkinson's disease, Huntington's disease or brain cancer or tumours.
  [FR] La présente invention concerne des composés hétérocycliques, leur méthodes de préparation et leur utilisation comme agents pharmaceutiques ou vétérinaires, en particulier pour le traitement, l'amélioration et/ou la prophylaxie d'états causés par ou associés à des taux de métal non équilibrés et/ou au stress oxydant, tels que des états neurologiques et des troubles liés à la prolifération de cellules, notamment la maladie d'Alzheimer, la maladie de Parkinson, la chorée de Huntington ou le cancer du cerveau ou des tumeurs cérébrales.
• WO2008/74068
  申请人：——

  公开号：——

  公开（公告）日：——
• Protein binding affinity of biologically active thiourea based half-sandwich Ru(II) cymene complexes
  作者：Ahmed M. Mansour、Krzysztof Radacki

  DOI：10.1016/j.poly.2019.114175

  日期：2020.1

  Half-sandwich (eta(6)-p-cymene) complexes bearing either neutral functionalized N,S-bidentate thiourea ligands or a mono-negative N,N-aminoquinoline ligand were screened for their antibacterial and antifungal activities as well as cell viability against non-malignant HEK293 (human embryonic kidney cells). The haemolysis parameters (HC10 and HC50) were determined to get some information about the compatibility of the toxic compounds with the blood components. The protein binding affinity of hen white egg lysozyme (HEWL), a model protein, towards the synthesized (eta(6)-p-cymene) complexes was investigated by ESI-MS. Metalation of HEWL was achieved through both covalent and non-covalent modes of interaction. To recognize if the metalation site of HEWL is the His15 side chain, the reactions between the complexes and imidazole were theoretically and experimentally studied by quantum chemical calculations, UV-Vis and NMR. Exchange of the nitrogen coordination site of the thiourea ligand from the pyridine to the benzothiazole moiety induced higher potency against Staphylococcus aureus, Candida albicans and Cryptococcus neoformans var. grubii. (C) 2019 Elsevier Ltd. All rights reserved.