N,N'-(hexane-1,6-diyl)bis(hydrazinecarbothioamide) | 56473-15-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-(hexane-1,6-diyl)bis(hydrazinecarbothioamide)
• 英文别名: 4,4′-hexanediyl-bis(thiosemicarbazide)；1,6-di(thiosemicarbazido-4)hexane；hexane-1,6-dithiosemicarbazide；4,4'-hexanediyl-bis thiosemicarbazide；4,4'-Hexandiyl-bis-thiosemicarbazid；1,6-Bis--hexan；3-Amino-1-{6-[(aminocarbamothioyl)amino]hexyl}thiourea；1-amino-3-[6-(aminocarbamothioylamino)hexyl]thiourea
• CAS: 56473-15-5
• 化学式: C₈H₂₀N₆S₂
• 分子量: 264.419
• InChiKey: KAKKWWUVNBMWPI-UHFFFAOYSA-N

物化性质

• 熔点：
  145 °C
• 沸点：
  433.0±55.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  164
• 氢给体数：
  6
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-(hexane-1,6-diyl)bis(hydrazinecarbothioamide) 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Dinuclear zinc bis(thiosemicarbazone) complexes: Synthesis, in vitro anticancer activity, cellular uptake and DNA interaction study

  摘要：

  Four dinucleating bis(thiosemicarbazone) ligands and their zinc complexes have been synthesized and characterized by multinuclear NMR (H-1 and C-13), IR, UV-Vis, ESI-MS and fluorescence spectroscopic techniques. Their purity was assessed by elemental analysis. Cytotoxicity was tested against five human cancer cell lines using the sulphorhodamine B (SRB) assay, where one of the complexes, 1,3-bis{biacetyl-2'-(4 ''-N-pyrrolidinylthiosemicarbazone)-3'-(4 ''-N-pyrrolidinylthiosemicarbazone) zinc(II)} propane (6), was found to be quite cytotoxic against MCF-7 (breast cancer) and HepG2 (hepatoma cancer) cell lines, with a potency similar to that of the well known anticancer drug adriamycin. It is evident from the cellular uptake studies that the uptake is same for the active complex 6 and the inactive complex 8 (1,6-bis{biacetyl- 2'-(4 ''-N-pyrrolidinylthiosemicarbazone)-3'-(4 ''-N-pyrrolidinylthiosemicarbazone) zinc(II)} hexane) in MCF-7 and HepG2 cell lines. In vitro DNA binding and cleavage studies revealed that all complexes bind with DNA through electrostatic interaction, and cause no significant cleavage of DNA. (C) 2'13 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.09.014
• 作为产物：
  描述：

  1,6-己二异氰酸脂 在 肼 作用下， 以 氯仿 为溶剂， 生成 N,N'-(hexane-1,6-diyl)bis(hydrazinecarbothioamide)
  参考文献：
  名称：

  Synthesis of new antimicrobials. V. Synthesis of alkylenebis-(thiosemicarbazides) and their related compounds.

  摘要：

  为了检测其抗微生物活性，合成了几种烷基亚甲基双（硫脲素）和烷基亚甲基双（二硫脲）衍生物。1, 1'-二苄叉-4, 4'-烷基亚甲基双（硫脲素）是通过4, 4'-烷基亚甲基双（硫脲素）和芳醛的反应制备的，而1, 1'-二芳酰-4, 4'-六亚甲基双（硫脲素）则是通过4, 4'-六亚甲基双（硫脲素）与芳酰氯的反应制备的。1, 1'-二烷基或二芳基-6, 6'-烷基亚甲基双（二硫脲）是通过4, 4'-烷基亚甲基双（硫脲素）与烷基或芳基异硫氰酸酯的反应合成的。N, N'-六亚甲基-双[2-氨基-5-(2-甲氧基苯基)噻二唑]是通过1, 1'-双(2-甲氧基苄叉)-4, 4'-六亚甲基双（硫脲素）的环合反应制备的。

  DOI：

  10.1248/cpb.23.668

文献信息

• Multi-point interaction-based recognition of fluoride ions by <i>tert</i>-butyldihomooxacalix[4]arenes bearing phenolic hydroxyls and thiourea
  作者：Ling-Ling Zhao、Xiao-Song Yang、Hui Chong、Yang Wang、Chao-Guo Yan

  DOI：10.1039/c8nj06333h

  日期：——

  phenolic hydroxyls and thiourea moieties were prepared to investigate their anion binding behavior. These compounds showed F− binding according to 1H NMR titration experiments. Among them, dihomooxacalix[4]arenes bearing phenyl and benzyl thiourea (2a and 2b) showed multiple interactions with added F−, including N–H⋯F, O–H⋯F hydrogen bonds and “through-space” C–H⋯F− interactions between F− and the attached

  制备了一系列带有酚羟基和硫脲部分的对-叔丁基二高氧杂acalix [4]芳烃，以研究它们的阴离子结合行为。这些化合物显示˚F -根据结合1个1 H NMR滴定实验。其中，dihomooxacalix [4]芳烃轴承苯基和苄基硫脲（图2a和图2b）显示多个交互与添加的F - ，包括N-H⋯F，O-H⋯˚F氢键和“通过空间” C-H⋯ ˚F - F的作用-和硫脲的芳香部分。还观察到了二高氧acalix [4]芳烃腔的构象变化，并通过理论计算证明了这一点。所述dihomooxacalix [4]芳烃轴承甲基硫脲（图2c）也显示出N-H⋯F，O-H⋯˚F氢键的形成，但dihomooxacalix的较少的构象变化[4]根据芳烃空腔1个1 H NMR滴定结果。双- dihomooxacalix [4]芳烃（3）在加入的F显示出清晰的N-H⋯˚F氢键形成-为特征的1个H NMR光谱。
• Synthesis and biological evaluation of 2-benzoylpyridine thiosemicarbazones in a dimeric system: Structure–activity relationship studies on their anti-proliferative and iron chelation efficacy
  作者：Adeline Y. Lukmantara、Danuta S. Kalinowski、Naresh Kumar、Des R. Richardson

  DOI：10.1016/j.jinorgbio.2014.07.020

  日期：2014.12

  Thiosemicarbazone chelators represent an exciting class of biologically active compounds that show great potential as anti-tumor agents. Our previous studies demonstrated the potent anti-tumor activity of the 2'-benzoylpyridine thiosemicarbazone series. While extensive studies have been performed on monomeric thiosemicarbazone compounds, dimeric thiosemicarbazone chelators have received comparatively less attention. Thus, it was of interest to investigate the anti-proliferative activity and iron chelation efficacy of dimeric thiosemicarbazones. Two classes of dimeric thiosemicarbazones were designed and synthesized. The first class consisted of two benzoylpyridine-based thiosemicarbazone units connected via a hexane or dodecane alkyl bridge, while the second class of dimer consisted of two thiosemicarbazones attached to a 2,6-dibenzoylpyridine core. These dimeric ligands demonstrated greater anti-proliferative activity than the clinically used iron chelator, desferrioxamine. This study highlights the importance of optimal lipophilicity as a factor influencing the cytotoxicity and iron chelation efficacy of these chelators. (C) 2014 Elsevier Inc. All rights reserved.
• Synthesis and Characterization of New Thiazolidin-4-one Derivatives
  作者：Bao Xiang Hu、Zhen Lu Shen、Jun Lu、Xin Quan Hu、Wei Min Mo、Nan Sun、Dong Xu

  DOI：10.1080/10426500802203053

  日期：2009.2.3

  The synthesis of some new functionalized thiazolidin-4-one derivatives has been described. The N-substituted-thiosemicarbazides 3a-3i were obtained though the reaction of alkylamines 2a-2i, carbon disulfide, and hydrazine hydrate. The condensation reaction between 3a-3i and 4-amino-2-methanesulfanylpyrimidine-5-carboxaldehyde 1 afforded the thiosemicarbazones 4a-4i. The corresponding thiazolidin-4-ones 5a-5i were prepared by cyclization of 4a-4i with ethyl bromoacetate. The structures of the final products were confirmed by IR, 1H NMR, 13C NMR, and HRMS.
• Tanaka et al., Chemical and pharmaceutical bulletin, 1959, vol. 7, p. 252
  作者：Tanaka et al.

  DOI：——

  日期：——
• Orlinskii, Russian Journal of Applied Chemistry, 1996, vol. 69, # 8, p. 1254 - 1255
  作者：Orlinskii

  DOI：——

  日期：——