60870-34-0Relevant academic research and scientific papers
Design and antiproliferative and antioxidant activities of furan-based thiosemicarbazides and 1,2,4-triazoles: their structure-activity relationship and SwissADME predictions
Sicak, Yusuf
, p. 1557 - 1568 (2021)
Due to the limited number of drugs in current clinical use, the diverse biological applications of furan have encouraged the preparation of a wide variety of thiosemicarbazide and triazole derivatives for the purpose of developing new drug agents. This study aimed to investigate the antiproliferative and antioxidant activities of thiosemicarbazides (1–12) and 1,2,4-triazoles (13–24). Out of the synthesized target compounds, 3, 4, 6, 7, 8, 9, 10, 11, 12, 15, 16, 18, 19, 20, 21, 22, 23, and 24 are novel while the synthesis of the remaining compounds is present in the literature. Compound 15 (IC50: 8.81 ± 0.28 μM) showed the highest antiproliferative activity against the cervical (HeLa) cancer cell line among the compounds. In the lipid peroxidation inhibitory activity, thiosemicarbazide derivatives 3, 10, and 9 showed highest activity with IC50 of 21.80 ± 0.69, 26.49 ± 0.61, and 29.07 ± 0.52 μM, respectively, while triazole derivatives 15, 18, 19, 20, 21, and 22 exhibited the highest activity. Moreover, physicochemical properties, pharmacokinetic properties, and drug-likeness of all synthesized products were calculated using SwissADME. In addition, the effect of the structure–activity relationships of the 1,2,4-triazole derivatives (13–24) on the results of antiproliferative and antioxidant activity assays was evaluated. [Figure not available: see fulltext.]
A KHSO4 mediated facile synthesis of 2-amino-1,3,4-oxadiazole derivatives
Gan, Zongjie,Han, Lei,Hu, Xiangnan,Long, Binyu,Tang, Qiang,Tian, Binghua,Wang, Chenyu,Wang, Zifan,Wu, Yue,Yu, Yu
supporting information, (2021/08/18)
A novel, efficient and mild KHSO4 mediated synthesis for 2-amino-1,3,4-oxadiazoles has been established via the cyclodesulfurization of benzoylhydrazine and isothiocyanate derivatives in one pot. The reactions proceeded smoothly at room tempera
Synthesis, antioxidant and antitumor activities of some of new cyclobutane containing triazoles derivatives
Koparir, Pelin
, p. 1028 - 1034 (2019/04/04)
Thiosemicarbazides (2a–e) were obtained by the interaction of furan-2-carboxylic acid hydrazide (1) with five different isothiocyanate (RNCS) derivatives. By addition of KOH to the reaction medium, ethyl, allyl, phenyl and benzyl, p-tolyl substituted 1,2,4-triazoles (3a–e) were obtained. 3a–e were dissolved in dry acetone containing K2CO3 in the presence of 2-chloro-1-(3-methyl-3-mesitylcyclobutyl) ethanone (4) to give 3,4,5-trisubstituted 1,2,4-triazole sulfanyl compounds containing a cyclobutane ring (5a–e). The structures of the final compounds were confirmed by elemental analyses, FT-IR, 1H-NMR and 13C-NMR. The antioxidant and antitumor properties of the synthesized compounds were also investigated. Three of the triazole derivatives with p-tolyl, benzyl and phenyl substituents (5c–e) displayed good antioxidant and antitumor activity in comparison to the standards.
Synthesis of a series of novel tetra-tert-butylcalix[4]arene linked to 1,2,4-triazole and 1,3,4-oxadiazole derivatives
Ghezelbash, Zahra Dono,Dilmaghani, Karim Akbari
, p. 790 - 797 (2016/12/18)
A series of tetra-tert-butylcalix[4]arene linked to 1,2,4-triazole-5-thiones and 1,3,4-oxadiazole-5-thiones derivatives at lower rim were synthesized by the reaction of 1,2,4-triazole-5-thione and 1,3,4-oxadiazole-5-thione with 5,11,17,23-tetra-tert-butyl-25,27-bis(3-bromopropoxy)-26,28-dihydroxycalix[4]arene (2). The synthesized compounds were characterized by FT-IR, 1H NMR, 13C NMR spectral data, elemental analysis and ESI-MS.
Synthesis of new 1,2,4-Triazole-5-thiones and their thioglycoside derivatives as potential antibacterial agents
Dilmaghani, Karim Akbari,Nasuhi Pur, Fazel,Jazani, Nima Hoseini,Alavi, Asma,Niknam, Zahra,Mirfakhraee, Farrin
, p. 81 - 87 (2014/01/06)
Abstract The glycosylation of 1,2,4-triazole-5-thiones has been performed with peracetylated β-pyranosyl bromide in the presence of potassium carbonate. The synthesized compounds were tested for their antimicrobial activity against bacterial (Gram-negative and Gram-positive) and yeasts strains in vitro. The synthetic compounds showed different inhibition zones against tested bacterial and yeasts strains. Among them, compounds which possessed 2-furyl and p-bromophenyl moieties showed the best results against Acinetobacter calcoaceticus ATCC 23055.
Alkylsulfanyl-1,2,4-triazoles, a New Class of allosteric valosine containing protein inhibitors. Synthesis and structure-activity relationships
Polucci, Paolo,Magnaghi, Paola,Angiolini, Mauro,Asa, Daniela,Avanzi, Nilla,Badari, Alessandra,Bertrand, Jay,Casale, Elena,Cauteruccio, Silvia,Cirla, Alessandra,Cozzi, Liviana,Galvani, Arturo,Jackson, Peter K.,Liu, Yichin,Magnuson, Steven,Malgesini, Beatrice,Nuvoloni, Stefano,Orrenius, Christian,Sirtori, Federico Riccardi,Riceputi, Laura,Rizzi, Simona,Trucchi, Beatrice,O'Brien, Tom,Isacchi, Antonella,Donati, Daniele,D'Alessio, Roberto
, p. 437 - 450 (2013/04/10)
Valosine containing protein (VCP), also known as p97, is a member of AAA ATPase family that is involved in several biological processes and plays a central role in the ubiquitin-mediated degradation of misfolded proteins. VCP is an ubiquitously expressed, highly abundant protein and has been found overexpressed in many tumor types, sometimes associated with poor prognosis. In this respect, VCP has recently received a great deal of attention as a potential new target for cancer therapy. In this paper, the discovery and structure-activity relationships of alkylsulfanyl-1,2,4-triazoles, a new class of potent, allosteric VCP inhibitors, are described. Medicinal chemistry manipulation of compound 1, identified via HTS, led to the discovery of potent and selective inhibitors with submicromolar activity in cells and clear mechanism of action at consistent doses. This represents a first step toward a new class of potential anticancer agents.
Synthesis of 1,2,4,5-tetrakis(1,2,4-triazolyl) benzene and 1,2,4,5-tetrakis(1,3,4-oxadiazolyl) benzene derivatives
Nikoo, Abbas,Dilmaghani, Karim Akbari
experimental part, p. 268 - 275 (2012/02/16)
A series of 1,2,4,5-tetrakis(1,2,4-triazolyl)benzenes and 1,2,4,5-tetrakis(1,3,4-oxadiazolyl)benzenes was synthesized by nucleophilic addition of sodium salts of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 1,3,4-oxadiazole-2(3H)-thiones to 1,2,4,5-tetrakis(bromomethyl)benzene. The structure of the newly synthesized compounds was confirmed by elemental analysis, IR and 1H and 13C NMR spectra. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: 1H and 13C NMR spectra of products (Figures S1-S24).
Small molecule inhibitors of HIV RT Ribonuclease H
Grandi, Martin Di,Olson, Matthew,Prashad, Amar S.,Bebernitz, Geraldine,Luckay, Amara,Mullen, Stanley,Hu, Yongbo,Krishnamurthy, Girija,Pitts, Keith,O'Connell, John
scheme or table, p. 398 - 402 (2010/04/05)
Two classes of compounds, thiocarbamates 1 and triazoles 2, have been identified as HIV RT RNase H inhibitors using a novel FRET-based HTS assay. The potent analogs in each series exhibited selectivity and were active in cell-based assays. In addition, sa
Synthesis of some new 4,5-substituted-4H-1,2,4-triazole-3-thiol derivatives
Cansiz,Koparir,Demirdag
, p. 204 - 212 (2007/10/03)
In this study appropriate hydrazide compounds, furan-2-carboxylic acid hydrazide (1) and phenylacetic acid hydrazide (2) were converted into 1,4-substituted thiosemicarbazides 4a-e and 5a-e and 4-amino-5-(furan-2-yl or benzyl)-4H-1,2,4-triazole-3-thiols 7
