thiomorpholine-4-carbothiohydrazide | 41197-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: thiomorpholine-4-carbothiohydrazide
• CAS: 41197-43-7
• 化学式: C₅H₁₁N₃S₂
• mdl: MFCD00462763
• 分子量: 177.294
• InChiKey: GUAAZEQFLZVAMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178 °C(Solv: dimethyl sulfoxide (67-68-5))
• 沸点：
  315.0±52.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  98.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  thiomorpholine-4-carbothiohydrazide 以 乙醇 、 苯 为溶剂， 反应 2.5h， 生成 7,8,9-Trifluoro-6-oxo-2-thiomorpholin-4-yl-6H-1-thia-3,3a-diaza-phenalene-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Lipunova; Sidorova; Nosova, Russian Journal of Organic Chemistry, 1999, vol. 35, # 11, p. 1698 - 1705

  摘要：

  DOI：
• 作为产物：
  描述：

  在 一水合肼 作用下， 反应 2.0h， 以89%的产率得到thiomorpholine-4-carbothiohydrazide
  参考文献：
  名称：

  Anticancer activity of the thiosemicarbazones that are based on di-2-pyridine ketone and quinoline moiety

  摘要：

  Thiosemicarbazones (TSC) are a subclass of iron-chelating agents that are believed to have an anticancer activity. The high potential for the application of this compound class can be illustrated by a fact that three TSC have entered clinical trials. The ability to chelate metal ions results in several biochemical changes in the cellular metabolism and growth. An important factor that determines the antitumor activity of TSC is a level of iron regulatory proteins and the antioxidant potential that is specific for each type of cancer cell. However, despite the increasing interest in TSC, their mechanism of anticancer activity is still unclear. For a more effective and rational design, it is crucial to determine and describe the abovementioned issues. In this report, we describe a series of new TSC that are designed on the four main structural scaffolds. The anticancer activity of these compounds was evaluated against a panel of cancer cell lines including colon and breast cancers and gliomas. Special attention was paid to the metal dependent proteins. The impact of the tested TSC on the cell cycle and redox homeostasis was also determined. These results confirm a p53-independent mechanism of apoptosis. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.03.027

文献信息

• Exploration of anticancer potency of N(4) thiomorpholinyl isatin/5-haloisatin thiosemicarbazones on coordination to Cu2+ ion
  作者：Narendra Kumar Singh、Shivani Sharma、Abarna Krishnakumar、Ravinder Kumar Choudhary、Anupa A. Kumbhar、Raymond J. Butcher、Yuba Raj Pokharel、Paras Nath Yadav

  DOI：10.1016/j.inoche.2022.109767

  日期：2022.9

  compounds against cancer cells; MCF-7 (breast cancer), A431(skin cancer), and PNT2 (human normal prostate epithelium) showed significant antiproliferative activity for both ligands and complexes. Compound 4 showed higher cell growth inhibition (39%) than the corresponding complex 8 (27%) toward the MCF-7 cell line. Although compound 4 did not show a good effect in the A431 cell line, it was the least

  制备了一系列 N( 4 ) 硫代吗啉基靛红/5-卤代靛红氨基硫脲及其铜 (II) 配合物 ( 1-8 )，并通过元素分析、NMR、IR、ESI-HRMS、UV-Visible、EPR、TGA、 PXRD 和单晶 X 射线衍射研究。铜 (II) 配合物具有扭曲的方形平面几何形状。化合物( 1-3 )的单晶 X 射线研究揭示了它们以硫酮互变异构体形式存在。化合物对癌细胞的体外抗增殖研究；MCF-7（乳腺癌）、A431（皮肤癌）和 PNT2（人正常前列腺上皮）对配体和复合物均显示出显着的抗增殖活性。化合物4对 MCF-7 细胞系的细胞生长抑制 (39%) 高于相应的复合物8 (27%)。虽然化合物4在 A431 细胞系中没有显示出良好的效果，但它在 PNT2 细胞系中毒性最小。化合物3和5对 A431 具有显着的抗增殖活性，细胞生长抑制率分别为 53% 和 54%。配体与 Cu(II) 离子的螯合导致对
• Impact of thiosemicarbazones on the accumulation of PpIX and the expression of the associated genes
  作者：Robert Gawecki、Katarzyna Malarz、Marta Rejmund、Jaroslaw Polanski、Anna Mrozek-Wilczkiewicz

  DOI：10.1016/j.jphotobiol.2019.111585

  日期：2019.10

  Thiosemicarbazone derivatives are known for their broad biological activity including their antitumor potency. The aim of the current study was to examine the effect of a novel series of non-toxic iron chelators on the accumulation of protoporphyrin IX after external 5-aminolevulonic acid administration. From this series we selected one the most promising derivative which causes a pronounced increase in the concentration of protoporphyrin IX. The increase of the photosensitizer concentration is necessary for the trigger the efficient therapeutic effect of the photodynamic reaction. For selected compound 2 we performed an examination of a panel of the genes that are involved in the heme biosynthesis and degradation. Results indicated the crucial roles of ferrochelatase and heme oxygenase in the described processes. Surprisingly, there was a strict dependence on the type of the tested cell line. A decrease in the expression of the two aforementioned enzymes after incubation with compound 2 and 5-aminolevulonic acid is a commonly known fact and we detected this trend for the MCF-7 and HCT 116 cell lines. However, we noticed the upregulation of the tested targets for the Hs683 cells. These unconventional results prompted us to do a more in-depth analysis of the described processes. In conclusion, we found that compound 2 is a novel, highly effective booster of photodynamic therapy that has prospective applications.
• Fluorine-containing heterocycles: XVI. Reactions of tetrafluorobenzoyl isothiocyanate with hydrazines and their derivatives
  作者：E. V. Nosovoa、G. N. Lipunova、A. A. Laeva、L. P. Sidorova、V. N. Charushin

  DOI：10.1134/s1070428007010083

  日期：2007.1

  Fluorinated derivatives of 4H-1,3-benzothiazin-4-one, [1,2,4]triazolo[4,3-a]pyrimidine, [1,2,4]triazolo[3,4-b][1,3]benzazoles, and 1,5-dihydro-1,2,4-triazole-5-thione were synthesized by addition of hydrazines and their derivatives to tetrafluorobenzoyl isothiocyanate, followed by cyclization of intermediate thiosemicarbazides.
• Discovery of 2-pyridineformamide thiosemicarbazones as potent antiausterity agents
  作者：Bhushan Shakya、Paras Nath Yadav、Jun-ya Ueda、Suresh Awale

  DOI：10.1016/j.bmcl.2013.12.044

  日期：2014.1

  Series of 2-pyridineformamide thiosemicarbazones were synthesized. Their preferential cytotoxicity in nutrient deprived medium (NDM) was evaluated using PANC-1 human pancreatic cancer cells by employing an antiausterity strategy. 2-Pyridineformamide thiosemicarbazones induced apoptosis and exhibited preferential cytotoxic activity toward PANC-1 cells in NDM, with potencies in the submicromolar range. These compounds are potential candidates for the development of therapeutics against pancreatic cancer. (C) 2013 Elsevier Ltd. All rights reserved.
• 2-Pyridineformamide N(4)-ring incorporated thiosemicarbazones inhibit MCF-7 cells by inhibiting JNK pathway
  作者：Bhushan Shakya、Nerina Shahi、Faiz Ahmad、Paras Nath Yadav、Yub Raj Pokharel

  DOI：10.1016/j.bmcl.2019.04.031

  日期：2019.7

  In an effort to develop a more potent anticancer therapeutic agent, a series of 2-pyridineformamide thiosemi-carbazones (R = H, 4-CH3, 5-F, 6-CH3 and[GRAPHICS]) have been synthesized and evaluated for their anti-cancer activities against the cancer cells MCF-7 (breast cancer cell line), A-431 and A375 (epidermoid carcinoma cell line), and HeLa (cervical cancer cell line) using MTT assay. All these 2-pyridineformamide thiosemicarbazones exhibited anti-proliferative activities towards these cell lines. 5FAmPyrr possess most profound effects against MCF-7 cells with IC50 of 0.9 mu M. In flow cytometry using Propidium Iodide, 5FAmPyrr was found to induce cell death significantly in a dose dependent manner (100 nM-3 mu M) and inhibited colony formation of MCF-7 cells. This compound induced pro-apoptotic protein Box and inhibited anti apoptotic protein Bcl-2 as well as both c-Jun and Jun N-terminal kinase (abbreviated as JNK) in concentration dependent manner. Further pro-caspase 3 and PARP were inhibited by 5FAmPyrr at concentration of 3 mu M. The results suggest that 5FAmPyrr exhibit anticancer potency and induced cell death by inhibiting MAPK signaling and inducing intrinsic apoptotic pathway. All these indicate that 2-pyridineformamide thiosemicarbazones could be developed as future therapeutics agents to treat cancer.[GRAPHICS].