4-<2-(dimethylamino)ethyl>-3-thiosemicarbazide | 6990-67-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-<2-(dimethylamino)ethyl>-3-thiosemicarbazide
• 英文别名: 4-(N,N-dimethyl-2-aminoethyl)-3-thiosemicarbazide；N-(2-(dimethylamino)ethyl)hydrazinecarbothioamide；N-Amino-N'-(2-diethylamino-ethyl)-thioharnstoff；Hydrazinecarbothioamide, N-[2-(dimethylamino)ethyl]-；1-amino-3-[2-(dimethylamino)ethyl]thiourea
• CAS: 6990-67-6
• 化学式: C₅H₁₄N₄S
• 分子量: 162.259
• InChiKey: JTZCTJSJSXBGLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  85.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-<2-(dimethylamino)ethyl>-3-thiosemicarbazide 在 盐酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.0h， 生成 1-[2-(dimethylamino)ethyl]-3-[3-[[5-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]pyridin-2-yl]hydrazinylidene]butan-2-ylideneamino]thiourea
  参考文献：
  名称：

  [EN] METAL COMPLEXES AS IMAGING AGENTS
  [FR] COMPLEXES MÉTALLIQUES UTILISÉS COMME AGENTS D'IMAGERIE

  摘要：

  本发明涉及铜、镓和锝配合物硫代半胱氨酮-吡啶肼（在吡啶环上取代苯并噻唑或双苯乙烯基团）复合物及其方法。这些化合物在PET成像和淀粉样疾病的诊断中具有实用性。

  公开号：

  WO2013082661A1
• 作为产物：
  描述：

  (2-异硫代氰酰基-乙基)-二甲胺 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 4-<2-(dimethylamino)ethyl>-3-thiosemicarbazide
  参考文献：
  名称：

  硫代氨基甲酸的衍生物。第一部分。4-取代的硫代氨基脲的制备

  摘要：

  描述了伯胺和仲胺与二硫代氨基甲酸酯的一般反应。这些酯是硫代氨基脲的方便中间体。由异硫氰酸酯获得了4-（β-二甲基氨基乙基）化合物，其一些性质已被记录。

  DOI：

  10.1039/j39660000950

文献信息

• Nanoformulations of anticancer thiosemicarbazones to reduce methemoglobin formation and improve anticancer activity
  作者：Britta Fischer、Kushtrim Kryeziu、Sebastian Kallus、Petra Heffeter、Walter Berger、Christian R. Kowol、Bernhard K. Keppler

  DOI：10.1039/c6ra07659a

  日期：——

  half-life. Therefore, we encapsulated Triapine into polymeric nanoparticles and remote-loaded liposomes to improve the drug pharmacokinetics as well as targeted delivery. However, burst release of Triapine from both nanoformulations was observed, making the synthesis of two novel Triapine derivatives necessary in order to improve the remote-loading properties. Indeed, the encapsulation efficiency increased

  Triapine是一种有前途的抗癌药thiosemicarbazone，已在多项临床试验中进行了研究，该药对白血病有效，但对实体癌无效。这可能是由于血浆半衰期短导致肿瘤中药物水平不足所致。因此，我们将Triapine封装到聚合物纳米颗粒和远程装载的脂质体中，以改善药物的药代动力学以及靶向递送。但是，从两个纳米制剂中观察到了Triapine的突然释放，因此必须合成两种新颖的Triapine衍生物才能改善远程装载性能。实际上，包封效率提高了，并且对于一种衍生物，所需的连续药物释放也与针对癌细胞的细胞毒性活性大大降低相一致。体内这种最有前途的制剂的研究表明，与游离药物相比，动物的存活率显着提高。最后，我们研究了药物诱导的高铁血红蛋白的形成，这是一种经常被观察到的硫代氨基脲的副作用，脂质体制剂可以完全防止这种副作用。
• Antitumor agents. II. Bis(guanylhydrazones) of anthracene-9,10-dicarboxaldehydes
  作者：K. C. Murdock、R. G. Child、Yang I Lin、J. D. Warren、P. F. Fabio、Ving J. Lee、P. T. Izzo、S. A. Lang、Robert B. Angier

  DOI：10.1021/jm00347a006

  日期：1982.5

  9,10-Anthracenedicarboxaldehyde bis[(4,5-dihydro-1H-imidazol-2-yl)hydrazone] (bisantrene, VI-1) showed anticancer activity in mice vs. both leukemias and solid tumors. Increases in life span vs. the following neoplasms were: P-388 leukemia, 137%; B-16 melanoma, 122%; Lieberman plasma cell tumor, greater than 85%; colon tumor 26, 150%; Ridgway osteogenic sarcoma, 85%. There were significant numbers of long-term survivors. Both DNA and RNA synthesis were strongly inhibited. The drug was resistant to biodegradation and was bound strongly to tissues; in monkeys the half-life for disappearance from serum was 6 days. Related hydrazones were synthesized, and structure-activity relationships are discussed. Two routes to ring-substituted anthracene-9,10-dicarboxaldehyde intermediates were developed.
• Synthesis of new alkylaminoalkyl thiosemicarbazones of 3-acetylindole and their effect on DNA synthesis and cell proliferation
  作者：T Siatra-Papastaikoudi、A Tsotinis、CP Raptopoulou、C Sambani、H Thomou

  DOI：10.1016/0223-5234(96)88215-8

  日期：1995.1

  The preparation of a number of thiosemicarbazones of 3-acetylindole is described. These compounds were evaluated in vitro for their effect on proliferation and cell-division delays in cultured human peripheral blood lymphocytes, and their effect on DNA synthesis in T-cell leukemia Molt-4 cells.
• Diagnostic Imaging Agents for Alzheimer’s Disease: Copper Radiopharmaceuticals that Target Aβ Plaques
  作者：James L. Hickey、SinChun Lim、David J. Hayne、Brett M. Paterson、Jonathan M. White、Victor L. Villemagne、Peter Roselt、David Binns、Carleen Cullinane、Charmaine M. Jeffery、Roger I. Price、Kevin J. Barnham、Paul S. Donnelly

  DOI：10.1021/ja4057807

  日期：2013.10.30

  One of the pathological hallmarks of Alzheimer's disease is the presence of amyloid-beta plaques in the brain and the major constituent of these plaques is aggregated amyloid-beta peptide. New thiosemicarbazone-pyridylhydrazine based ligands that incorporate functional groups designed to bind amyloid-beta plaques have been synthesized. The new ligands form stable four coordinate complexes with a positron-emitting radioactive isotope of copper, Cu-64. Two of the new Cu-II complexes include a functionalized styrylpyridine group and these complexes bind to amyloid-beta plaques in samples of post-mortem human brain tissue. Strategies to increase brain uptake by functional group manipulation have led to a Cu-64 complex that effectively crosses the blood-brain barrier in wild-type mice. The new complexes described in this manuscript provide insight into strategies to deliver metal complexes to amyloid-beta plaques.
• [EN] METAL COMPLEXES AS IMAGING AGENTS<br/>[FR] COMPLEXES MÉTALLIQUES UTILISÉS COMME AGENTS D'IMAGERIE
  申请人：UNIV MELBOURNE

  公开号：WO2013082661A1

  公开（公告）日：2013-06-13

  The present invention relates to copper, gallium and technetium coordinated thiosemicarbazone- pyridylhydrazine (substitued at the pyridine ring with a substituted benzothiazole or stilbene moiety) complexes and methods thereof. Such compounds possess utility in PET imaging and diagnosis of amyloid diseases.

  本发明涉及铜、镓和锝配合物硫代半胱氨酮-吡啶肼（在吡啶环上取代苯并噻唑或双苯乙烯基团）复合物及其方法。这些化合物在PET成像和淀粉样疾病的诊断中具有实用性。