N1–5-bromosalicylidene-S-propylthiosemicarbazone | 86950-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N1–5-bromosalicylidene-S-propylthiosemicarbazone
• 英文别名: S-propyl-N¹-2-hydroxy-5-bromobenzylidene thiosemicarbazone；N¹-5-bromosalicylidene-S-propylthiosemicarbazone
• CAS: 86950-12-1
• 化学式: C₁₁H₁₄BrN₃OS
• 分子量: 316.222
• InChiKey: SAJFWKNVDIQLHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  70.97
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  nickel(II) chloride hexahydrate 、 N1–5-bromosalicylidene-S-propylthiosemicarbazone 、 2-氨基-3,5-二溴苯甲醛 以 乙醇 、 氯仿 为溶剂， 反应 2.0h， 以38%的产率得到N¹-2-hydroxy-5-bromobenzylidene-N⁴-2-amino-3,5-dibromobenzylidene-S-propylthiosemicarbazidato nickel(II)
  参考文献：
  名称：

  Effective copper(II) and nickel(II) complexes with N3O and ON3 thiosemicarbazidato ligands. Synthesis, structural analysis and in vitro cytotoxity on melanoma B16F10 cells

  摘要：

  Novel copper(II) and nickel(II) complexes were newly synthesized by template condensation using 2-amino-3,5-dibromo- or 2-hydroxy-5-bromo-benzaldehyde S-propyl thiosemicarbazones as starting materials. The complexes with asymmetric donor atom set were identified through use of analytical and spectroscopic methods (IR, H NMR, ESI-MS and X-ray crystallography). Cytotoxicity potents of the N3O and ON3-type complexes were determined on melanoma B16F10 and fibroblast BJ ATCC CRL-2522 cell lines. The cell lines were exposed to the complexes in the concentration range of 6-500 mu M for 24 h. The results indicated selective effect of the nickel and copper complexes in favor of healthy cells. Namely, relative low concentrations of the test molecules resulted in cytotoxic effects on malignant cells while higher concentrations were required for normal cell death. The nickel complexes were more effective than the copper complexes and a nickel complex (1a) showed selectively cytotoxcity by IC50 value of 1978 mu g/ml on B16F10 cells compared to the 5464 mu g/ml value of CRL-2522 cells.

  DOI：

  10.1016/j.ica.2019.119347
• 作为产物：
  描述：

  溴丙烷 、 氨基硫脲 、 5-溴水杨醛 以 乙醇 、 氯仿 为溶剂， 反应 7.0h， 以90%的产率得到N1–5-bromosalicylidene-S-propylthiosemicarbazone
  参考文献：
  名称：

  Effective copper(II) and nickel(II) complexes with N3O and ON3 thiosemicarbazidato ligands. Synthesis, structural analysis and in vitro cytotoxity on melanoma B16F10 cells

  摘要：

  Novel copper(II) and nickel(II) complexes were newly synthesized by template condensation using 2-amino-3,5-dibromo- or 2-hydroxy-5-bromo-benzaldehyde S-propyl thiosemicarbazones as starting materials. The complexes with asymmetric donor atom set were identified through use of analytical and spectroscopic methods (IR, H NMR, ESI-MS and X-ray crystallography). Cytotoxicity potents of the N3O and ON3-type complexes were determined on melanoma B16F10 and fibroblast BJ ATCC CRL-2522 cell lines. The cell lines were exposed to the complexes in the concentration range of 6-500 mu M for 24 h. The results indicated selective effect of the nickel and copper complexes in favor of healthy cells. Namely, relative low concentrations of the test molecules resulted in cytotoxic effects on malignant cells while higher concentrations were required for normal cell death. The nickel complexes were more effective than the copper complexes and a nickel complex (1a) showed selectively cytotoxcity by IC50 value of 1978 mu g/ml on B16F10 cells compared to the 5464 mu g/ml value of CRL-2522 cells.

  DOI：

  10.1016/j.ica.2019.119347

文献信息

• Dioxouranium(VI) complexes with N₂O₂ chelating thiosemicarbazones [UO₂L(R-OH)]
  作者：Musa Şahın、Tülay Bal-demırcı、Namik Özdemır、Bahrı Ülküseven

  DOI：10.1080/00958972.2013.843679

  日期：2013.10.20

  zones in the presence of dioxouranium(VI) were investigated. Six dioxouranium(VI) (1a–3b) complexes were synthesized. Propyl or allyl alcohol used as second ligand completed the seventh coordination site of . The synthesized thiosemicarbazones and template complexes were characterized by elemental analysis, UV-visible, FTIR, and 1H NMR. The structure of the dioxouranium(VI) complex, [UO2L(allylalcohol)]

  使用 5-溴水杨醛作为起始材料合成了三个在硫上取代的烷基化缩氨基硫脲 (1-3)。研究了 S-烷基缩氨基硫脲在二氧铀 (VI) 存在下的模板反应。合成了六种二氧铀 (VI) (1a-3b) 配合物。用作第二配体的丙醇或烯丙醇完成了 的第七配位位点。合成的缩氨基硫脲和模板复合物通过元素分析、紫外-可见光、FTIR 和 1H NMR 进行了表征。通过单晶衍射研究了二氧铀 (VI) 配合物 [UO2L(烯丙醇)] 的结构。铀在五边形双锥体排列中是七坐标，两个氧代基团占据顶端位置。
• Synthesis and Characterization of New Nickel(II) Chelates With S-Alkyl-Salicylaldehyde Thiosemicarbazones
  作者：Musa Şahin、Bahri Ülküseven

  DOI：10.1080/10426507.2012.710673

  日期：2013.5.1

  Abstract The template reactions of salicylidene-, 5-bromosalicylidene-, and 3,5-dichlorosalicylidene-S-R-thiosemicarbazone (R: propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, dodecyl) with 5-bromo- and 3,5-dichlorosalicylaldehyde in the presence of nickel(II) yielded N1,N4-diarylidene-S-alkyl-thiosemicarbazone chelates. The N2O2 type complexes were isolated as stable solid compounds and characterized

  摘要 水杨基-、5-溴水杨基-和3,5-二氯水杨基-SR-缩氨基硫脲（R：丙基、丁基、戊基、己基、庚基、辛基、壬基、十二烷基）与5-溴-和3的模板反应，在镍 (II) 存在下，5-二氯水杨醛生成 N1,N4-二亚芳基-S-烷基-氨基硫脲螯合物。N2O2 型配合物被分离为稳定的固体化合物，并通过元素分析、电子、红外、1H 核磁共振和质谱进行表征。室温 (rt) 下的磁化率测量表明复合物的抗磁性。清楚地显示了镍 (II) 模板配合物的熔点 (mp) 值与烷基部分的链长之间的关系。补充材料可用于本文。转至出版商的 Phosphorus 在线版，硫、硅和相关元素查看免费补充文件。图形概要