α-<4-(4-Chlor-phenyl)-thiosemicarbazono>-toluol | 92291-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-<4-(4-Chlor-phenyl)-thiosemicarbazono>-toluol
• 英文别名: ω-<4-(4-Chlor-phenyl)-thiosemicarbazono>-toluol；benzaldehyde 4-(4-chloro-phenyl)-thiosemicarbazone；1-(benzylideneamino)-3-(4-chlorophenyl)thiourea
• CAS: 92291-11-7
• 化学式: C₁₄H₁₂ClN₃S
• 分子量: 289.788
• InChiKey: KKGZJWIMNXYCQI-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  416.3±47.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.42
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  α-<4-(4-Chlor-phenyl)-thiosemicarbazono>-toluol 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 水 为溶剂， 生成 N-(4-chlorophenyl)-5-phenyl-1,3,4-thiadiazole-2-amine
  参考文献：
  名称：

  Srinivasan,V.R.; Ramachander,G., Indian Journal of Chemistry, 1963, vol. 1, p. 234 - 236

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯胺 在 氨 、 sodium monochloroacetic acid 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 α-<4-(4-Chlor-phenyl)-thiosemicarbazono>-toluol
  参考文献：
  名称：

  Tiwari, Shailendra; Nizamuddin, Journal of the Indian Chemical Society, 2013, vol. 90, # 5, p. 679 - 683

  摘要：

  DOI：

文献信息

• Phenotypic and <i>in silico</i> studies for a series of synthetic thiosemicarbazones as New Delhi metallo-beta-lactamase carbapenemase inhibitors
  作者：Jonatham Souza Moreira、Danilo Santana Galvão、Carolina Ferreira Cavalcanti Xavier、Silvio Cunha、Samuel Silva da Rocha Pita、Joice Neves Reis、Humberto Fonseca de Freitas

  DOI：10.1080/07391102.2021.2001379

  日期：2022.12.26

  Inhibitory Concentration (FIC) ≤ 250 µM in the presence of meropenem (4 µg/mL). The most promising compound (FIC= 31.25 µM) also presented synergistic effect (FICI = 0.34). Docking and molecular dynamics studies on NDM-thiosemicarbazone complex suggested that 2,3-dihydro-1H-indol-2-one subunit interacts with catalytic zinc and interacted through hydrogen bonds with Asp124 acting like a carboxylic acid bioisostere

  摘要 过去二十年的特点是细菌对 β-内酰胺类药物产生耐药性，而碳青霉烯类衍生物是对抗多重耐药细菌的最终治疗方法。β-内酰胺酶表达与耐药性有关，这需要开发细菌耐药性阻断剂。丝氨酸-β-内酰胺酶和 β-内酰胺的药物抑制剂组合已成功用于治疗，尽管它们对新德里金属-β-内酰胺酶 (NDM) 没有活性。到目前为止，很少有化合物对产生 NDM 的细菌具有活性，也没有可用的特异性抑制剂。NDM抑制剂开发的合理策略从体外开始旨在寻找可以与 β-内酰胺抗生素协同作用的化合物的分析。因此，合成了八种缩氨基硫脲衍生物，并研究了它们逆转阴沟肠杆菌NDM 耐药表型的能力。 表型筛选表明，在美罗培南 (4 µg/mL) 存在的情况下，四种靛红-β-氨基硫脲显示分数抑制浓度 (FIC) ≤ 250 µM。最有前途的化合物 (FIC = 31.25 µM) 也呈现协同效应 (FICI = 0.34)。NDM-缩氨基硫脲络合物的对接和分子动力学研究表明，2
• Kumar; Singh; Pandeya, Bollettino Chimico Farmaceutico, 2001, vol. 140, # 4, p. 238 - 242
  作者：Kumar、Singh、Pandeya

  DOI：——

  日期：——
• Singh; Yadav; Chaudhary, Journal of the Indian Chemical Society, 1983, vol. 60, # 8, p. 768 - 771
  作者：Singh、Yadav、Chaudhary

  DOI：——

  日期：——
• Chande, Madhukar S.; Joshi, Rajesh D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 3, p. 251 - 255
  作者：Chande, Madhukar S.、Joshi, Rajesh D.

  DOI：——

  日期：——
• Synthesis, spectroscopic and redox properties of some ruthenium(II) thiosemicarbazone complexes: Structural description of four of these complexes
  作者：Dipankar Mishra、Subhendu Naskar、Michael G.B. Drew、Shyamal Kumar Chattopadhyay

  DOI：10.1016/j.ica.2005.11.001

  日期：2006.1

  Sixteen neutral mixed ligand thiosemicarbazone complexes of ruthenium having general formula [Ru(PPh3)(2)L-2], where LH = 1-(arylidine)4-aryl thiosemicarbazones, have been synthesized and characterized. All complexes are diamagnetic and hence ruthenium is in the +2 oxidation state (low-spin d(6), S = 0). The complexes show several intense peaks in the visible region due to allowed metal to ligand charge transfer transitions. The structures of four of the complexes have been determined by single-crystal X-ray diffraction and they show that thiosemicarbazone ligands coordinate to the ruthenium center through the hydrazinic nitrogen and sulfur forming four-membered chelate rings with ruthenium in N2S2P2 coordination environment. In dichloromethane solution, the complexes show two quasi-reversible oxidative responses corresponding to loss of electron from HOMO and HOMO - 1. The E-0 values of the above two oxidations shows good linear relationship with Hammett substituents constant (sigma) as well as with the HOMO energy of the molecules calculated by the EHMO method. A DFT calculation on one representative complex suggests that there is appreciable contribution of the sulfur p-orbitals to the HOMO and HOMO - 1. Thus, assignment of the oxidation state of the metal in such complexes must be made with caution. (c) 2005 Elsevier B.V. All rights reserved.