- Thiosemicarbazone Scaffold as a Multidentate Ligand for Transition-Metal Ions: Synthesis, Characterization, In Vitro Antimicrobial, Anthelmintic, DNA Cleavage, and Cytotoxic Studies
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New series of Schiff bases derived from o-substituted thiosemicarbazides and 8-formyl-7-hydroxy-4-methylcoumarin have been synthesized and their coordination tendency toward Co(II), Ni(II), and Cu(II) metal ions is studied. Analytical, spectral (IR, UV-Vis, ESR, and FAB-mass), magnetic, and thermal studies suggests octahedral geometry of the type ML2for all the Co(II), Ni(II), and Cu(II) complexes. The complexes are soluble in DMF/DMSO and are non-electrolytes. The Schiff bases and their metal complexes have been screened for antibacterial (Escherichia coli, Staphylococcus aureus, Salmonella typhi, and Pseudomonas aeruginosa) and antifungal activities (Aspergillus flavus, Aspergillus niger, and Cladosporium) by minimum inhibitory concentration method. DNA cleavage is studied by agarose gel electrophoresis method. Metal (II) complexes show good anthelmintic activity when compared to Schiff bases.
- Maddireddy, Manjunatha,Kulkarni, Ajaykumar D.,Bagihalli, Gangadhar B.,Malladi, Shridhar
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- Synthesis and Antiproliferative Activity of New Thiosemicarboxamide Derivatives
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To discover new anticancer agents, two series of thiosemicarboxamide derivatives were synthesized and evaluated for their antiproliferative activity against human cancer cells in vitro. Most target compounds (especially 3f, 3g, and 3h) exhibit potent antiproliferative activity against HeLa cells. Importantly, compound 3h, bearing a 4-methylphenyl substituent at N position of thiourea moiety, has significant and broad-spectrum inhibitory activities against cancer cells (HepG2, HeLa, MDA-MB231, A875, and H460 cells) with low IC50 values (5.0 μM) and shows low toxicity to normal LO2 and MRC-5 cells. Further studies show that compound 3h exerts high inhibitory activity in cancer cells by inducing the G2/M-phase arrest of cancer cells. Collectively, this study presents compound 3h as a new entity for the development of cell cycle arrest inducers for the treatment of cancer.
- Chen, Jun,Fang, Meijuan,Guo, Yafei,Hu, Hongyu,Hu, Sangsang,Sun, Ke,Wu, Jun,Xue, Yuhua
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- Novel thiosemicarbazone derivatives: In vitro and in silico evaluation as potential mao-b inhibitors
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MAO-B inhibitors are frequently used in the treatment of neurodegenerative diseases such as Parkinson’s and Alzheimer’s. Due to the limited number of compounds available in this field, there is a need to develop new compounds. In the recent works, it was shown that various thiosemicarbazone derivatives show hMAO inhibitory activity in the range of micromolar concen-tration. It is thought that benzofuran and benzothiophene structures may mimic structures such as indane and indanone, which are frequently found in the structures of such inhibitors. Based on this view, new benzofuran/benzothiophene and thiosemicarbazone hybrid compounds were synthesized, characterized and screened for their hMAO-A and hMAO-B inhibitory activity by an in vitro fluorometric method. The compounds including methoxyethyl substituent (2b and 2h) were found to be the most effective agents in the series against MAO-B enzyme with the IC50 value of 0.042 ± 0.002 μM and 0.056 ± 0.002 μM, respectively. The mechanism of hMAO-B inhibition of compounds 2b and 2h was investigated by Lineweaver–Burk graphics. Compounds 2b and 2h were reversible and non-competitive inhibitors with similar inhibition features as the substrates. The Ki values of compounds 2b and 2h were calculated as 0.035 μM and 0.046 μM, respectively, with the help of secondary plots. The docking study of compound 2b and 2h revealed that there is a strong interaction between the active sites of hMAO-B and analyzed compound.
- ?zkay, Yusuf,Kaplanc?kl?, Zafer As?m,Kurban, Berkant,Levent, Serkan,Osmaniye, Derya,Sa?l?k, Begüm Nurpelin
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- Synthesis and antitumor activity of novel pyridazinone derivatives containing 1,3,4-thiadiazole moiety
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A series of novel pyridazinone derivatives containing the 1,3,4-thiadiazole moiety were synthesized and characterized by 1H NMR, 13C NMR, spectroscopies HRMS and IR. Among them, the structure of compound 5c (2-(Tert-butyl)?4-chloro-5-((5-((2-ethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was unambiguously confirmed via single crystal X-ray diffraction analysis. The inhibitory activity of all the target compounds against MGC-803 and Bcap-37 was determined by MTT assay, with doxorubicin (the inhibition rates were 95.5 ± 0.4% and 95.7 ± 1.0% respectively) as a control. The preliminary results showed that the inhibitory activity of compound 5n (2-(Tert-butyl)?4-chloro-5-((5-((3-fluorophenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was superior to the others. The inhibition rates of MGC-803 and Bcap-37 cells were 86.3 ± 2.2% and 92.3 ± 0.6% at a concentration of 10 μmol/L, respectively. The preliminary structure-activity relationship showed that when the 2-position of the benzene ring was substituted by a methyl group, such as compound 5j (2-(Tert-butyl)?4-chloro-5-((5-((2,3-dimethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), it exhibited good anticancer activity on MGC-803 cells. Besides, introducing fluorine, chlorine, or trifluoromethyl group onto the benzene ring, such as compound 5 m (2-(Tert-butyl)?4-chloro-5-((5-((4-(trifluoromethoxy)phenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), displayed good anticancer activity on MGC-803 and Bcap-37 cells.
- Qin, Junhu,Zhu, Mei,Zhu, Hongmei,Zhang, Liqiong,Fu, Yihong,Liu, Jiamin,Wang, Zhenchao,OuYang, Guiping
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p. 592 - 599
(2020/03/16)
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- Synthesis and spectroscopic studies of Ru(II) complexes of steroidal thiosemicarbazones by multi step reaction: As anti-bacterial agents
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Ru(II) steroidal metal complexes were synthesized by the reaction of dichlorodicarbonyl ruthenium(II) [Ru(CO)2Cl2]n with Steroidal thiosemicarbazones. Coordination via the thionic sulfur and the azomethine nitrogen atom of
- Khan, Salman A.,Asiri, Abdullah M.
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- Thiosemicarbazide, a fragment with promising indolamine-2,3-dioxygenase (IDO) inhibition properties
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With the aim to explore the interest of the thiosemicarbazide scaffold for the inhibition of the indoleamine 2,3-dioxygenase (IDO), a promising therapeutic target for anticancer immunotherapy, a series of 32 phenylthiosemicarbazide derivatives was prepared and their IDO inhibition evaluated. Our study demonstrated that among these derivatives, compound 14 characterized with a 4-cyanophenyl group on the thiosemicarbazide was the more potent IDO inhibitor in this series being endowed with an IC50 of 1.2 μM. The SAR depicted showed that substitution in the 3- and 4-position relative to the phenylthiosemicarbazide are very promising whereas substitution in the 2-position always leads to less potent or inactive derivatives. In fact the study highlighted a novel interesting scaffold for IDO inhibition for further development.
- Serra, Silvia,Moineaux, Laurence,Vancraeynest, Christelle,Masereel, Bernard,Wouters, Johan,Pochet, Lionel,Frédérick, Rapha?l
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- Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors
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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.
- 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
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p. 1948 - 1952
(2011/05/04)
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- Synthesis and anticonvulsant and neurotoxicity evaluation of N 4-phthalimido phenyl (thio) semicarbazides
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The phenyl (thio) semicarbazide derivatives of phthalimido pharmacophore were synthesized and evaluated for their anticonvulsant and neurotoxic properties. Initial anticonvulsant screening was performed using intraperitoneal (i.p.), maximal electroshock-induced seizure (MES), subcutaneous pentylenetetrazole (scPTZ) and subcutaneous strychnine (sc STY)-induced seizure threshold tests in mice. Compound 2c afforded protection in all the three screens. Compounds except 1d, 2a and 2d showed no neurotoxicity up to 300mg/kg. Compounds 1a, 1b, 2c, 2d, 2g and 2i were found to show oral MES activity. The compounds exhibited CNS depression and behavioral despair side effects, lesser than the conventional antiepileptic drugs.
- Yogeeswari,Sriram,Saraswat,Ragavendran, J. Vaigunda,Kumar, M. Mohan,Murugesan,Thirumurugan,Stables
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p. 341 - 346
(2007/10/03)
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