6823-89-8Relevant academic research and scientific papers
Design and efficient synthesis of novel 4,5-dimethylthiazole-hydrazone derivatives and their anticancer activity
Evren, Asaf Evrim,Yurtta?, Leyla,Ekselli, Bü?ra,Aksoy, Onur,Akalin-?ift?i, Gül?en
, p. 372 - 386 (2021/06/17)
Background: Recently, researchers have been warning about the increased mortality of the various cancer types. Also, the lung adenocarcinoma and the glioma types are burning issues for world's health due to late or wrong diagnosis and/or insufficient treatment methods. For this purpose, our research group designed and synthesized novel 4,5-dimethyl thiazole-hydrazone derivatives which were tested against cancer and normal cell lines to understand the structure-activity relationship (SAR). Methods: The lead compounds were obtained by reacting 2-(substituted aryl-2-ylmethylene) hydrazin-1-carbothioamide with 3-chloro-2-butanone derivatives. The structural elucidation of the compounds was performed by1H-NMR,13C-NMR, and LC/MS-IT-TOF spectral and elemental analyses. The synthesized compounds were tested in vitro for the anticancer activity against A549 human lung adenocarcinoma and C6 rat glioma cells and investigated for which pathway to induce cell death. Also, the docking study of the active compounds was achieved to understand the SAR. Results: The targeted compounds (2a-2l) were synthesized successfully above 70% yields, and the analysis findings proved their purity. In general, the results of activity studies displayed significant effects against at least one cell line, except compounds 2e (indol-3-yl) and 2h (4-dimethylaminophenyl). Furthermore, compounds 2b and 2f displayed potential anticancer activity. With the help of molecular docking study, a potential selectivity of compound 2f was observed for type II protein kinase. On the other hand, compound 2b interacted with the active site nearly the same as Dasatinib. Therefore, these two compounds could be used as a base on developing selective anticancer drugs. Conclusion: Pyridin-2-yl (2b) derivative was found to be a favorable molecule with high anticancer potency against C6 and A549 cell lines. Additionally, 1-naphthyl (2f) derivative was a worthy compound for potential selectivity. In future studies, it will be our priority to focus on developing derivatives of these two compounds (2b and 2f) and elucidate their mechanisms.
Novel Structural Hybrids of Pyrrole and Thiazole Moieties: Synthesis and Evaluation of Antibacterial and Antifungal Activities
Abbas, Samir Y.,Ali, Tarik E.,Assiri, Mohammed A.,El-Sharief, Marwa A. M. Sh,Gouda, Moustafa A.,Helal, Mohamed H.,Salem, Mohamed A.
, p. 990 - 996 (2021/12/29)
One of the best ways to design new biocidal agents is synthesizing hybrid molecules by combining two or more bioactive moieties in a single molecular scaffold. So, new series of pyrroles bearing a thiazole moiety were synthesized using 1-methyl-1H-pyrrole-2-carbaldehyde thiosemicarbazones 1a–c. Cyclization of thiosemicarbazone derivatives 1a–c with ethyl chloroacetate, ethyl 2-chloropropanoate, chloroacetone and phenacyl bromide afforded the corresponding thiazolidin-4-ones 2a–c, 5-methylthiazolidin-4-ones 3a–c, 4-methyl-2,3-dihydrothiazoles 4a–c, and 4-phenyl-2,3-dihydrothi-azoles 5a–c, respectively. The antimicrobial activity of the new thiazole derivatives was evaluated.
New hydrazinothiazole derivatives of usnic acid as potent TDP1 inhibitors
Filimonov, Aleksander S.,Chepanova, Arina A.,Luzina, Olga A.,Zakharenko, Alexandra L.,Zakharova, Olga D.,Ilina, Ekaterina S.,Dyrkheeva, Nadezhda S.,Kuprushkin, Maxim S.,Kolotaev, Anton V.,Khachatryan, Derenik S.,Patel, Jinal,Leung, Ivanhoe K.H.,Chand, Raina,Ayine-Tora, Daniel M.,Reynisson, Johannes,Volcho, Konstantin P.,Salakhutdinov, Nariman F.,Lavrik, Olga I.
, (2019/10/28)
Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is a promising therapeutic target in cancer therapy. Combination chemotherapy using Tdp1 inhibitors as a component can potentially improve therapeutic response to many chemotherapeutic regimes. A new set of usnic acid derivatives with hydrazonothiazole pharmacophore moieties were synthesized and evaluated as Tdp1 inhibitors. Most of these compounds were found to be potent inhibitors with IC50 values in the low nanomolar range. The activity of the compounds was verified by binding experiments and supported by molecular modeling. The ability of the most effective inhibitors, used at non-toxic concentrations, to sensitize tumors to the anticancer drug topotecan was also demonstrated. The order of administration of the inhibitor and topotecan on their synergistic effect was studied, suggesting that prior or simultaneous introduction of the inhibitor with topotecan is the most effective.
Synthesis and antimicrobial activity of some new hydrazone-bridged thiazole-pyrrole derivatives
Yurttas, Leyla,Oezkay, Yusuf,Kaplancikli, Zafer Asim,Tunali, Yagmur,Karaca, Huelya
, p. 830 - 835 (2013/07/26)
In this work, we synthesized fourteen different compounds which contain hydrazone bridged thiazole and pyrrole rings. For this purpose, pyrrole-2-carboxaldehydes were reacted directly with thiosemicarbazide in ethanol and then obtained thiosemicarbazones
Gold complexes with thiosemicarbazones: Reactions of bi- And tridentate thiosemicarbazones with dichloro2-(dimethylaminomethylphenyl-CilgoldCm), [Au(damp-C1A)Cl2]
Abram, Ulrich,Ortner, Kirstin,Gusf, Ronald,Sommer, Klaus
, p. 735 - 744 (2007/10/03)
Dichloro[2-(A,A-dimethylaminomethyl)phenyl-C1,A]gold(iii), [Au(damp-C,A)Cl2] (1), reacts with salicylaldchyde thiosemicarbazone (H2saltsc), vanilline thiosemicarbaezone (Hvantsc), N-methylpyrrole aldehyde thiosemicarbazone (Hmepyrtsc), pyridoxal methylthiosemicarbazone (H2pydoxmetsc), 2-diphenylphosphinobenzaldehyde thiosemicarbazone (HPtsc) or variously substituted acetylpyridine thiosemicarbazones (HapRtsc; R = H, Me, Ph) with cleavage of the Au-N bond and protonation of the dimethylamino group. Compounds of general formulae [Au(Hdamp-C1)CI(L)f (L = Hsaltsc-, vantsc-, mepyrtsc1), [Au(Hdamp-C1)Cl(L)]2+ (L = H2pydoxmetsc) or [Au(Hdamp-C1)(L)]2+ (L = Ptsc-, apRtsc-, R = H, Me, Ph) have been isolated and characterized. The presence of the (T-bonded 2-(dimethylaminomethyl)phenyl ligand is mandatory to prevent reduction of the gold(in) centre. The crystal structures of [Au(Hdanip-C1)CI(HsaItsc)](PF6) (3a), [Au(Hdamp-C')Cl(mepyrtsc)]Cl (3c), [Au(Hdamp-C1)-CI(H2pydo.xtnetsc)]Cl2-MeOH (4), [Au(Hdamp-C1)(apPhtsc)]Cl2-2 MeOH (5c) and [Au(Hdamp-C')(Ptsc)]Cl2-1.5MeOH (6) have been elucidated, showing the gold atoms in distorted square-planar co-ordination environments. The potentially O,N,S-tridentate ligands H2saltsc and H2pydoxmetsc co-ordinate in a bidentate fashion and do not incorporate the OH groups in the chelating framework, whereas HapRtsc or HPtsc co-ordinate in a tridentate manner. Generally, one or more hydrogen atoms of the heterocyclic ligands and/or the NMe2H+ group form hydrogen bridges in the solid state structures. The preliminary results of antiproliferation tests on tumor cells demonstrate the considerable cytotoxicity of these new gold complexes. The Royal Society of Chemistry 2000.
