2-(diphenylmethylene)-N-phenylhydrazinecarbothioamide | 14673-58-6

• 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: 2-(diphenylmethylene)-N-phenylhydrazinecarbothioamide
• 英文别名: benzophenone 4-phenylthiosemicarbazone；benzophenone-N-phenylthiosemicarbazone；1-(benzhydrylideneamino)-3-phenylthiourea
• CAS: 14673-58-6
• 化学式: C₂₀H₁₇N₃S
• 分子量: 331.441
• InChiKey: OBVOWAVZQIYWEO-UHFFFAOYSA-N

物化性质

• 熔点：
  160-162 °C(Solv: ethanol (64-17-5))
• 沸点：
  478.7±28.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(diphenylmethylene)-N-phenylhydrazinecarbothioamide 、 zinc(II) chloride 以 甲醇 为溶剂， 反应 5.0h， 以63%的产率得到Dichlorozinc;1-phenyl-3-[[phenyl(pyridin-2-yl)methylidene]amino]thiourea
  参考文献：
  名称：

  一种以2-苯甲酰吡啶缩氨基硫脲为配体的锌配合物及其合成方法和应用

  摘要：

  本发明涉及一种2‑苯甲酰吡啶缩氨基硫脲为配体的锌配合物及其合成方法和应用，分别以2‑苯甲酰吡啶和氨基硫脲、4‑甲基‑3‑氨基硫脲、4，4‑二甲基‑3‑氨基硫脲、4‑苯基‑3‑氨基硫脲或4‑（2‑甲基）苯基‑3‑氨基硫脲为原料合成席夫碱配体；再将配体与氯化锌反应制得锌配合物。在体外试验中，合成的锌配合物对人肝癌细胞（HepG2）具有良好的抑制活性，治疗效果优于临床药物顺铂，适用于制备高效的抗肿瘤药物。此外，合成的锌配合物对金黄色葡萄球菌有良好的抑菌效果，适用于制备抑菌药物。

  公开号：

  CN112028911A
• 作为产物：
  描述：

  二苯甲酮 在 一水合肼 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 2-(diphenylmethylene)-N-phenylhydrazinecarbothioamide
  参考文献：
  名称：

  二苯甲酮半咔唑酮/硫代半咔唑酮的合成及其脲酶抑制活性

  摘要：

  二十五个二苯甲酮缩氨基脲和缩氨基硫脲3 - 27合成通过与在回流下不同的芳基异氰酸酯和isothiocyantes处理腙从二苯甲酮开始。评价所有合成衍生物的脲酶抑制潜力。与标准硫脲相比（IC 50  = 21.2±1.3 µM），观察到的对脲酶的良好至中度抑制趋势，IC 50值为8.7-119.5 µM 。化合物15的抑制作用优于IC 50值为8.7±0.6 µM的标准品。化合物3，4，8，11 -14，16，和17与IC 50至43.6μM的26.1的范围内的值，表现出优良至适中的活动，同时化合物9（IC 50  = 119.5±1.6μM）显示非常弱的活性。进行了对活性最高的化合物15和17的酶动力学研究，以推导它们的抑制方式和解离常数K i。

  DOI：

  10.1007/s00044-016-1673-0

文献信息

• Synthesis, Characterization, and Anticancer Activity of a Series of Ketone-N⁴-Substituted Thiosemicarbazones and Their Ruthenium(II) Arene Complexes
  作者：Wei Su、Quanquan Qian、Peiyuan Li、Xiaolin Lei、Qi Xiao、Shan Huang、Chusheng Huang、Jianguo Cui

  DOI：10.1021/ic401362s

  日期：2013.11.4

  A series of ketone-N-4-substituted thiosemicarbazone (TSC) compounds (L1-L9) and their corresponding [(eta(6)-p-cymene)Ru-II(TSC)Cl](+/0) complexes (1-9) were synthesized and characterized by NMR, IR, elemental analysis, and HR-ESI-mass spectrometry. The molecular structures of L4, L9, 1-6, and 9 were determined by single-crystal X-ray diffraction analysis. The compounds were further evaluated for their in vitro antiproliferative activities against the SGC-7901 human gastric cancer, BEL-7404 human liver cancer, and HEK-293T noncancerous cell lines. Furthermore, the interactions of the compounds with DNA were followed by electrophoretic mobility spectrometry studies.
• Reactions of flavonoid thiosemicarbazones under acetylating conditions
  作者：László Somogyi

  DOI：10.1016/s0040-4020(01)96219-2

  日期：1991.11

  Upon acetylation, (2-phenyl)dihydrobenzopyrone- and 2'-hydroxychalcone thiosemicarbazones (1c, 2c, 3c, and 7c) form 2,2-disubstituted 5-acetamido-3-acetyl-2,3-dihydro-1,3,4-thiadiazoles (1i, 2i, 4i, and 8i) instead of the diacetylthiosemicarbazones (2e, 8e) claimed in the literature. Similarly, the reactions of the aromatic ketone thiosemicarbazones 9c, 10c and 11d result in the formation of thiadiazolines (9i, 10i, and 11k, respectively), flavone thiosemicarbazone (6c), however, is degraded to flavone diacetylhydrazone (6g) under the same conditions. The synthesis of the flavanone spiro-1,3,4-oxadiazoline 2h is also described.
• Thiosemicarbazonates of palladium(II): The presence of methyl/phenyl substituents (R2) at C2 carbon atom induces C–H activation of R1 rings of thiosemicarbazones {R1R2C2N3–N2H–C1(S)–N1HR3}
  作者：Tarlok S. Lobana、Poonam Kumari、Ray J. Butcher、Takashiro Akitsu、Yoshikazu Aritake、Josefina Perles、Francisco J. Fernandez、M. Cristina Vega

  DOI：10.1016/j.jorganchem.2011.11.028

  日期：2012.3

  A series of palladium(II) complexes involving C-H and N-H bond activations of the R-1 rings of thiosemicarbazones R-1(R-2)C-2-N-3-N-2(H)-C-1(=S)-(NHR3)-H-1; R-1, R-2: thiopheneyl, Me, H2L1 (R-3 = Me), H2L2 (R-3 = Ph); R-1, R-2: Ph, Me, H2L3 (R-3 = Me), H2L4 (R-3 = Ph); R-1, R-2: Ph, Ph, H2L5 (R-3 = Me), H2L6 (R-3 = Ph) and R-1, R-2: pyrrole, Me, H2L7 (R-3 = Me), H2L8 (R-3 = Ph)} are described. Methyl group (R-2) at C-2 carbon in H2L1 and H2L2 induced C-H bond activation of the thiopheneyl ring and formed cyclometallated complexes, [Pd(kappa(3)-C-4,N-3,S-L)(PPh3)] (L - L-1, 1; L-2, 2). Similarly, phenyl rings (R-1) in H2L3, H2L4, H2L5, H2L6 at C-2 carbon have shown C-H activations forming cyclometallated complexes, [Pd(kappa(3)-C-4,N-3, S-L)(PPh3)] (L = L-3, 3; L-4, 4; L-5, 5; L-6, 6). However, pyrrole ring did not exhibit similar C-H activation behavior, rather involved N-H activation and formed complexes, [Pd(kappa(3)-N-4,N-3, S-L)(PPh3)] L = L-7, 7; L-8, 8}. All these complexes have been characterized with the help of analytical data, spectroscopic techniques (IR, H-1 and P-31 NMR), and single crystal X-ray crystallography (1, 2, 4, 5, 7 and 8). The thiosemicarbazone ligands behave as dinegative C-4, N-3, S-chelating in 1-6 and N-4, N-3, S-chelating in complexes 7 and 8. Interestingly, complexes 2, 4 and 8, with phenyl substituent at N-1 atom, have two independent molecules in their respective crystal lattices. (C) 2011 Elsevier B.V. All rights reserved.
• Kabashima, Shigeru; Okawara, Tadashi; Yamasaki, Tetsuo, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 8, p. 1957 - 1960
  作者：Kabashima, Shigeru、Okawara, Tadashi、Yamasaki, Tetsuo、Furukawa, Mitsuru

  DOI：——

  日期：——
• 一种以2-苯甲酰吡啶缩氨基硫脲为配体的锌配合物及其合成方法和应用
  申请人：广西师范大学

  公开号：CN112028911A

  公开（公告）日：2020-12-04

  本发明涉及一种2‑苯甲酰吡啶缩氨基硫脲为配体的锌配合物及其合成方法和应用，分别以2‑苯甲酰吡啶和氨基硫脲、4‑甲基‑3‑氨基硫脲、4，4‑二甲基‑3‑氨基硫脲、4‑苯基‑3‑氨基硫脲或4‑（2‑甲基）苯基‑3‑氨基硫脲为原料合成席夫碱配体；再将配体与氯化锌反应制得锌配合物。在体外试验中，合成的锌配合物对人肝癌细胞（HepG2）具有良好的抑制活性，治疗效果优于临床药物顺铂，适用于制备高效的抗肿瘤药物。此外，合成的锌配合物对金黄色葡萄球菌有良好的抑菌效果，适用于制备抑菌药物。