6499-15-6Relevant articles and documents
2-Pyridineformamide N(4)-ring incorporated thiosemicarbazones inhibit MCF-7 cells by inhibiting JNK pathway
Shakya, Bhushan,Shahi, Nerina,Ahmad, Faiz,Yadav, Paras Nath,Pokharel, Yub Raj
supporting information, p. 1677 - 1681 (2019/05/01)
In an effort to develop a more potent anticancer therapeutic agent, a series of 2-pyridineformamide thiosemicarbazones (R = H, 4-CH3, 5-F, 6-CH3 and (Figure presented.)(Figure presented.))have been synthesized and evaluated for their
Impact of thiosemicarbazones on the accumulation of PpIX and the expression of the associated genes
Gawecki, Robert,Malarz, Katarzyna,Rejmund, Marta,Polanski, Jaroslaw,Mrozek-Wilczkiewicz, Anna
, (2019/08/26)
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.
Thiosemicarbazone-based selective proliferation inactivators inhibit gastric cancer cell growth, invasion, and migration
Hu, Biao,Wang, Bo,Zhao, Bing,Guo, Qian,Li, Zhong-Hua,Zhang, Xin-Hui,Liu, Guang-Yao,Liu, Ying,Tang, Ying,Luo, Fan,Du, Ya,Chen, Ya-Xin,Ma, Li-Ying,Liu, Hong-Min
supporting information, p. 2173 - 2180 (2017/12/26)
A series of novel thiosemicarbazone derivatives were synthesized and evaluated for their antiproliferative activity against several selected tumor cell lines of different origins using the MTT assay. The preliminary results indicated that the MGC-803 cell line was remarkably sensitive to all the synthesized compounds. Among this series, compound 5n showed the best inhibitory activity with an IC50 value of 0.93 μM (about 10-fold more potent than 3-AP) against MGC-803. Further mechanism studies revealed that compound 5n could obviously inhibit the proliferation of MGC-803 cells by inducing apoptosis and arresting the cell cycle at the S phase. Compound 5n also showed marked inhibition of cell migration and invasion, without significant cytotoxicity against gastric epithelial immortalized GES-1 cells.
Pharmacologic evaluation of antidepressant activity and synthesis of 2-morpholino-5-phenyl-6H-1,3,4-thiadiazine hydrobromide
Sarapultsev, Alexey P.,Chupakhin, Oleg N.,Sarapultsev, Petr A.,Sidorova, Larisa P.,Tseitler, Tatiana A.
, (2016/06/14)
Substituted thiadiazines exert a reliable therapeutic effect in treating stress, and a schematic description of their ability to influence all aspects of a stress response has been depicted. This study was conducted to pharmacologically evaluate compound L-17, a substituted thiadiazine, (2-morpholino-5-phenyl-6H-1,3,4-thiadiazine, hydrobromide) for possible anti-psychotic/antidepressant activity. Compound L-17 was synthesized by cyclocondensation of α-bromoacetophenone with the original morpholine-4-carbothionic acid hydrazide. Pharmacologic evaluations were conducted using methods described by E.F. Lavretskaya (1985), and in accordance with published guidelines for studying drugs for neuroleptic activity. Compound L-17 was evaluated for various possible mechanisms of action, including its effects on cholinergic system agonists/antagonists, dopaminergic neurotransmission, the adrenergic system, and 5-HT3 serotonin receptors. One or more of these mechanisms may be responsible for the beneficial effects shown by thiadiazine compounds in experiments conducted to evaluate their activity in models of acute stress and acute myocardial infarction.
Synthesis and reactivity of 2-pyrrolidino-, 2-N-methylpiperazino-, 2-piperidino-, and 2-morpholino-1,3,4-thiadiazines
Knak, Stefanie,Pfeiffer, Wolf-Diethard,Dollinger, Horst,Langer, Peter
, p. 450 - 462 (2015/03/30)
A variety of 2-pyrrolidino-, 2-N-methylpiperazino-, 2-piperidino-, and 2-morpholino-1,3,4-thiadiazines were prepared by cyclocondensation of phenacyl halides with thiosemicarbazides. Heating of the products resulted in desulfurization and formation of pyrazoles. The rate of this process strongly depends on the substitution pattern of the 1,3,4-thiadiazines.
Exploring the anti-cancer activity of novel thiosemicarbazones generated through the combination of retro-fragments: Dissection of critical structure-activity relationships
Serda, Maciej,Kalinowski, Danuta S.,Rasko, Nathalie,Potu??ková, Eli?ka,Mrozek-Wilczkiewicz, Anna,Musiol, Robert,Ma?ecki, Jan G.,Sajewicz, Mieczys?aw,Ratuszna, Alicja,Muchowicz, Angelika,Go?a?b, Jakub,?imu?nek, Tomá?,Richardson, Des R.,Polanski, Jaroslaw
, (2015/01/08)
Thiosemicarbazones (TSCs) are an interesting class of ligands that show a diverse range of biological activity, including anti-fungal, anti-viral and anti-cancer effects. Our previous studies have demonstrated the potent in vivo anti-tumor activity of nov
Discovery of 2-pyridineformamide thiosemicarbazones as potent antiausterity agents
Shakya, Bhushan,Yadav, Paras Nath,Ueda, Jun-Ya,Awale, Suresh
supporting information, p. 458 - 461 (2014/01/23)
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 thios
The synthesis and tuberculostatic activity of benzenesulfonohydrazide derivatives
Wisterowicz, Krystyna,Gobis, Katarzyna,Foks, Henryk,Augustynowicz-Kopec, Ewa
scheme or table, p. 99 - 104 (2012/04/04)
The series of novel N'-aminocarbonothioyl-benzenesulfonohydrazides were synthesized in a reaction of benzenesulphonyl chlorides with various aminocarbothiohydrazides. The structures were confirmed by IR and NMR spectra as well as elemental analysis. All o
Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors
Kang, Iou-Jiun,Wang, Li-Wen,Hsu, Tsu-An,Yueh, Andrew,Lee, Chung-Chi,Lee, Yen-Chun,Lee, Ching-Yin,Chao, Yu-Sheng,Shih, Shin-Ru,Chern, Jyh-Haur
scheme or table, p. 1948 - 1952 (2011/05/04)
A series of isatin-β-thiosemicarbazones have been designed and evaluated for antiviral activity against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in a plaque reduction assay. Their cytotoxicity was examined using human rhabdomyosarcoma cells (RD cells). Several derivatives of isatin-β-thiosemicarbazone exhibited significant and selective antiviral activity with low cytotoxicity. It was found that the thiourea group at thiosemicarbazone and the NH functionality at isatin were essential for their antiherpetic activity. The synthesis and structure-activity relationship studies are presented.
Synthesis of 2-aminoaryl-5-substituted-1,3,4-thiadiazoles in a thermal 1,3-dipolar cycloaddition reaction
Gobis, Katarzyna,Foks, Henryk,Zwolska, Zofia,Augustynowicz-Kopec, Ewa
, p. 2653 - 2666 (2007/10/03)
The preparation of a series of new 2-aminoaryl-1,3,4-thiadiazoles substituted with methylsulfanyl, methansulfinyl, or amine in the 5-position is described in this article. The compounds were obtained from N-hydroxyimidoyl chlorides and methyl dithiocarbazinate or 4-substituted thiosemicarbazides in a thermal 1,3-dipolar cycloaddition reaction. The new derivatives were tested for their activity against Mycobacterium tuberculosis. Copyright Taylor & Francis Inc.
