- Synthesis, characterization, and antioxidant activity of some new N 4-arylsubstituted-5-methoxyisatin-β-thiosemicarbazone derivatives
-
Abstract: Firstly, thiosemicarbazides were prepared by the reaction of hydrazine monohydrate with isothiocyanates in cold dry ethanol at 0?°C for 1?h. After that, new isatin-β-thiosemicarbazones were synthesized by treatment of 5-methoxyisatin with thiose
- Mu?lu, Halit
-
p. 2083 - 2098
(2020/01/13)
-
- Synthesis and antitumor activity of novel pyridazinone derivatives containing 1,3,4-thiadiazole moiety
-
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
-
p. 592 - 599
(2020/03/16)
-
- Synthesis, molecular modeling and antiviral activity of novel 5-fluoro-1H-indole-2,3-dione 3-thiosemicarbazones
-
In this work, novel 5-fluoro-1-methyl/ethyl-1H-indole-2,3-dione 3-[4-(substituted phenyl)-thiosemicarbazones] 6a-n and 7a-n were synthesized. The antiviral effects of the compounds were tested against HSV-1 (KOS), HSV-2 (G) HSV-1 TK- KOS ACVr and VV in HEL cell cultures using acyclovir and ganciclovir as standards, and Coxsackie B4 virus in Vero cell cultures using ribavirin and mycophenolic acid as standards. R2 ethyl substituted 7 derivatives were found effective against viruses tested. R1 4-CF3 substituted 7d, R1 4-OCH3 substituted 7 g and R1 3-Cl substituted 7 l showed activity against HSV-1 (KOS), HSV-2 (G) HSV-1 TK- KOS ACVr and VV. Whereas only R1 4-Br substituted 7n has selective activity against coxsackie B4 virus. Molecular modeling studies of 7d and 7l were performed to determine binding side on HSV-1 glycoprotein B and D, HSV-2 glycoprotein B structures.
- ?zbil, Mehmet,Duran, Gizem Nur,Karal?, Nilgün,Sevin?li, Zekiye ?eyma
-
-
- Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives
-
Schiff-base–bearing new bis(thiosemicarbazone) derivatives were prepared from terephthalaldehyde and various thiosemicarbazides. FT–IR, 1 H NMR, 13 C NMR, and UV–Vis spectroscopic methods and elemental analysis were used to elucidate
- Yakan, Hasan
-
p. 1085 - 1099
(2020/09/16)
-
- Functionalized Oxoindolin Hydrazine Carbothioamide Derivatives as Highly Potent Inhibitors of Nucleoside Triphosphate Diphosphohydrolases
-
Ectonucleoside triphosphate diphosphohydrolases (NTPDases) are ectoenzymes that play an important role in the hydrolysis of nucleoside triphosphate and diphosphate to nucleoside monophosphate. NTPDase1, -2, -3 and -8 are the membrane bound members of this enzyme family that are responsible for regulating the levels of nucleotides in extracellular environment. However, the pathophysiological functions of these enzymes are not fully understood due to lack of potent and selective NTPDase inhibitors. Herein, a series of oxoindolin hydrazine carbothioamide derivatives is synthesized and screened for NTPDase inhibitory activity. Four compounds were identified as selective inhibitors of h-NTPDase1 having IC50 values in lower micromolar range, these include compounds 8b (IC50 = 0.29 ± 0.02 μM), 8e (IC50 = 0.15 ± 0.009 μM), 8f (IC50 = 0.24 ± 0.01 μM) and 8l (IC50 = 0.30 ± 0.03 μM). Similarly, compound 8k (IC50 = 0.16 ± 0.01 μM) was found to be a selective h-NTPDase2 inhibitor. In case of h-NTPDase3, most potent inhibitors were compounds 8c (IC50 = 0.19 ± 0.02 μM) and 8m (IC50 = 0.38 ± 0.03 μM). Since NTPDase3 has been reported to be associated with the regulation of insulin secretion, we evaluated our synthesized NTPDase3 inhibitors for their ability to stimulate insulin secretion in isolated mice islets. Promising results were obtained showing that compound 8m potently stimulated insulin secretion without affecting the NTPDase3 gene expression. Molecular docking studies of the most potent compounds were also carried out to rationalize binding site interactions. Hence, these compounds are useful tools to study the role of NTPDase3 in insulin secretion.
- Afzal, Saira,Hameed, Abdul,Iqbal, Jamshed,Pelletier, Julie,Sévigny, Jean,al-Rashida, Mariya
-
-
- Thiosemicarbazide, a fragment with promising indolamine-2,3-dioxygenase (IDO) inhibition properties
-
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
-
-
- Structural studies on acetophenone- and benzophenone-derived thiosemicarbazones and their zinc(II) complexes
-
In the present work N(3)-meta-chlorophenyl-(HAc3mCl, 1) and N(3)-meta-fluorphenyl-(HAc3mF, 2) acetophenone thiosemicarbazone, and N(3)-meta-chlorophenyl-(HBz3mCl, 3) and N(3)-meta-fluorphenyl-(HBz3mF, 4) benzophenone thiosemicarbazone were obtained, as we
- Ferraz, Karina S.O.,Silva, Nayane F.,Da Silva, Jeferson G.,Speziali, Nivaldo L.,Mendes, Isolda C.,Beraldo, Heloisa
-
experimental part
p. 102 - 107
(2012/03/12)
-
- Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors
-
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
-
scheme or table
p. 1948 - 1952
(2011/05/04)
-
- Synthesis and anticonvulsant evaluation of some novel (thio)semicarbazone derivatives of arylalkylimidazole
-
A number of novel 2-(1H-imidazole-1-yl)-1-aryl-substituted ethane-1-one N-substituted phenyl(thio)semicarbazones (1-14) were synthesized to test for their anticonvulsant activity against the two seizure models, maximal electroshock (MES) and subcutaneous
- Calis, Uensal,Septioglu, Ebubekir,Aytemir, Mutlu Dilsiz
-
experimental part
p. 327 - 334
(2012/02/02)
-
- Co(II), Ni(II) and Cu(II) complexes with coumarin-8-yl Schiff-bases: Spectroscopic, in vitro antimicrobial, DNA cleavage and fluorescence studies
-
A new series of Co(II), Ni(II) and Cu(II) complexes of the type ML·2H2O of Schiff-bases derived from m-substituted thiosemicarbazides and 8-acetyl-7-hydroxy-4-methylcoumarin have been synthesized and characterized by spectroscopic studies. Schiff-bases exhibit thiol-thione tautomerism wherein sulphur plays an important role in the coordination. The coordination possibility of the Schiff-bases towards metal ions have been proposed in the light of elemental analyses, spectral (IR, UV-vis, FAB-mass, ESR and fluorescence), magnetic and thermal studies. The low molar conductance values in DMF indicate that, the metal complexes are non-electrolytes. The cyclic voltammetric studies suggested that, the Cu(II) and Ni(II) complexes are of single electron transfer quasi-reversible nature. The Schiff-bases and its metal complexes have been evaluated for their in vitro antibacterial (Escherichia coli, Staphilococcus aureus, Bascillus subtilis and Salmonella typhi) and antifungal activities (Candida albicans, Cladosporium and Aspergillus niger) by MIC method. The Schiff-base I and its metal complexes exhibited DNA cleavage activity on isolated DNA of A. niger.
- Patil, Sangamesh A.,Unki, Shrishila N.,Kulkarni, Ajaykumar D.,Naik, Vinod H.,Badami, Prema S.
-
experimental part
p. 1128 - 1136
(2011/10/03)
-
- Microwave-assisted synthesis and antibacterial activity of novel chenodeoxycholic acid thiosemicarbazone derivatives
-
A rapid and efficient method for the synthesis of novel chenodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave irradiation is reported. Ten novel compounds have been synthesised in good yields. Their structures were elucidated by 1H NMR, IR, ESI-MS spectra and elemental analysis. Preliminary results showed that some of these compounds possess inhibitory effects against S. typhimurium and E. coli.
- Qiu, Liying,Shi, Zhichuan,Mei, Qinggang,Zhao, Zhigang
-
experimental part
p. 456 - 459
(2011/11/06)
-
- A series of α-heterocyclic carboxaldehyde thiosemicarbazones inhibit topoisomerase IIα catalytic activity
-
A series of novel thiosemicarbazone derivatives bearing condensed heterocyclic carboxaldehyde moieties were designed and synthesized. Among them, TSC24 exhibited broad antiproliferative activity in a panel of human tumor cells and suppressed tumor growth in mice. The mechanism research revealed that TSC24 was not only an iron chelator but also a topoisomerase IIα catalytic inhibitor. Its inhibition on topoisomerase IIα was due to direct interaction with the ATPase domain of topoisomerase IIα which led to the block of ATP hydrolysis. Molecular docking predicted that TSC24 might bind at the ATP binding site, which was confirmed by the competitive inhibition assay. These results about the mechanisms involved in the anticancer activities of thiosemicarbazones will aid in the rational design of novel topoisomerase II-targeted drugs and will provide insights into the discovery and development of novel cancer therapeutics based on the dual activity to chelate iron and to inhibit the catalytic activity of topoisomerase IIα.
- Huang, He,Chen, Qin,Ku, Xin,Meng, Linghua,Lin, Liping,Wang, Xiang,Zhu, Caihua,Wang, Yi,Chen, Zhi,Li, Ming,Jiang, Hualiang,Chen, Kaixian,Ding, Jian,Liu, Hong
-
experimental part
p. 3048 - 3064
(2010/09/05)
-
- Microwave-assisted synthesis of new steroidal thiosemicarbazones derived from methyl 3-oxocholanate under solvent-free conditions
-
A series of novel steroidal thiosemicarbazones derived from methyl 3-oxocholanate were synthesised in good yields via microwave irradiation under solvent-free conditions. The structures of the compounds were confirmed by spectroscopic data. Compared to the conventional method, microwave irradiation was a fast and simple method. These compounds were tested for antibacterial activity against S. aureus, S. pyogenes, and E. coli bacteria.
- Zhao, Zhigang,Liu, Xingli,Liu, Lingling,Li, Guohua
-
experimental part
p. 455 - 458
(2010/12/24)
-
- Synthesis of novel alkoxycarbonyl thiosemicarbazide molecular tweezers derived from deoxycholic acid under microwave irradiation
-
A series of novel 12α-alkoxycarbonyl thiosemicarbazide molecular tweezers based on 3α-(1-naphthoyl) deoxycholic acid methyl ester were synthesised under microwave irradiation. Their structures were characterised by 1H NMR, IR, MS spectra and elemental analysis. Their chiral recognition properties for the methyl esters of amino acids were investigated. The preliminary results showed that these molecular tweezers have good enantioselective recognition for D/L-amino acid methyl esters.
- Chen, Yu,Zhao, Zhi Gang,Liu, Xing Li,Shi, Zhi Chuan
-
scheme or table
p. 416 - 420
(2010/12/19)
-