10444-89-0Relevant academic research and scientific papers
2-Amino-5-trifluoromethyl-1,3,4-thiadiazole and a redetermination of 2-amino-1,3,4-thiadiazole, both at 120 K: Chains of edge-fused R 22(8) and R44(10) rings, and sheets of R22(8) and R66(20) rings
Boechat, Nubia,Ferreira, Sabrina B.,Glidewell, Christopher,Low, John N.,Skakle, Janet M.S.,Wardell, Solange M.S.V.
, p. o42-o44 (2006)
Molecules of 2-amino-5-trifluoromethyl-1,3,4-thiadiazole, C 3H2F3N3S, are linked by two independent N - H...N hydrogen bonds into sheets of alternating R 22(8) and R66(20) rings, while the molecules of the unsubstituted 2-amino-1,3,4-thiadiazole, C2H 3N3S, are linked, again by two independent N - H...N hydrogen bonds, but into chains of edge-fused R22(8) and R44(10) rings.
Synthesis, Structure and Biological Activities of Novel 2-(Trifluoromethyl)- 6-arylimidazo[2,1-b][1,3,4]-thiadiazole (bis-)Mannich Base Derivatives Containing Substitutedpiperazine Moiety
Zhang, Yan,Li, Zhengming,Song, Haibin,Wang, Baolei
, p. 635 - 638 (2018)
A convenient and practicable method for the synthesis of the novel 2-(trifluoromethyl)-6-arylimidazo[2,1-b][1,3,4]-thiadiazole (bis-)Mannich base derivatives containing various substitutedpiperazine motif has been developed based on the fused-heterocycle intermediate. The new structures were identified through melting points, 1H NMR, 13C NMR, 19F NMR, elemental analysis (or HRMS) and X-ray single-crystal diffraction. The pesticidal bioassays showed that some of compounds exhibited good fungicidal activities against Cercospora arachidicola, Physalospora piricola and Rhizoctonia cereali at 50?mg/L; some of them displayed favourable insecticidal activities against oriental armyworm (Mythimna separata Walker) at 200?mg/L, particularly, Vk and Vm with mortality rate of 75% and 80% respectively, could be considered as new insecticidal lead compounds for further structural optimization.
N-(5-(Trifluoromethyl)-1,3,4-Thiadiazol-2-Yl)Benzamide and Benzothioamide Derivatives Induce Apoptosis Via Caspase-Dependent Pathway
Aliabadi, Alireza,Afnanzade, Nazanin-Sadat,Hosseinzadeh, Leila,Mohammadi-Farani, Ahmad,Shafiee, Mohammad Hossein,Nazari, Hanifeh,Ahmadi, Farahnaz,Foroumadi, Alireza
, p. 521 - 526 (2019)
New 1,3,4-thiadiazole-based compounds were designed, synthesized, and their anticancer effects were assessed by MTT assay against PC3 (prostate cancer), HT-29 (colon cancer), and SKNMC (neuroblastoma) cell lines. The results were compared to that of doxorubicin. According to MTT assay, some of the synthesized compounds exhibit higher cytotoxic activity (IC 50 , μM range) than doxorubicin against PC3 and SKNMC cells but not HT29 cells. According to the analysis of structure – activity relationship, compounds with methoxy group as an electron donating moiety rendered higher activity than nitro group as an electron withdrawing group. Compound 4d with ortho position of methoxy moiety activated caspases 3 and 9 in both PC3 and HT-29 cell lines.
Metal-free synthesis of 2-aminothiadiazoles via TBHP-Mediated oxidative C-S bond formation
Hatvate, Navnath T.,Ghodse, Shrikant M.,Telvekar, Vikas N.
, p. 285 - 290 (2018)
An efficient one-pot synthesis of 2-amino-1,3,4-thiadiazoles from easily available aldehydes and thiosemicarbazide using TBHP as an oxidant has been described. Notably, these reactions were carried out at room temperature using ethanol as solvent. This is the first example for one-pot synthesis of 2-amino-1,3,4-thiadiazole derivatives from aldehydes. This new synthetic methodology provides a simple procedure utilizing a safer oxidizing system that affords the target products in mild reaction condition with satisfactory yields and wide substrate scope.
Fe3+-selective naked-eye 'off-on' fluorescent probe: Its crystal structure and imaging in living cells
Meng, Wen-Fei,Yang, Mei-Pan,Li, Bo,Cheng, Zhao,Yang, Bing-Qin
, p. 8577 - 8581 (2014)
Four novel rhodamine-active probes L1-L4 have been proposed and characterized as fluorescent chemosensors for Fe3+. An 'off-on' type fluorescent enhancement was observed, which was induced by the interactions between Fe3+ and the probe, proven to adopt a 1:1 binding stoichiometry. The recognition properties of the target compounds with metal ions have been investigated in methanol-water (1:1, v/v) solution by the fluorescence and ultraviolet spectrum. In addition, a plausible application of probes in the imaging of HepG2 (liver cells) under the condition of reoxygenation (95% air, 5% CO2) exposed to Fe3+ ions was also demonstrated.
N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound
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Paragraph 0051; 0057; 0114-0116, (2021/06/09)
The invention belongs to the technical field of medicines, relates to a compound with antitumor activity and a specific chemical structure, and in particular relates to an N-((6, 7-dimethoxyquinoline-4-yl) oxy) methyl)-N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound and a preparation method and an application thereof. The structural general formula of the compound is shown in the specification, wherein an R group is mono-substituted or double-substituted phenyl, fluorophenyl, chlorphenyl, bromophenyl, benzyl, benzyloxy, benzene nitro or trifluoromethyl substituted at 2-position, 3-position or 4-position. Pharmacological studies show that the compound provided by the invention has a relatively remarkable proliferation inhibition effect on HER-2 positive breast cancer cells SK-Br-3, the effect is obviously superior to that of HER-2 negative breast cancer cells MCF-7, the compound can be used for preparing antitumor drugs, and a new way is opened up for deep research and development of tumor drugs in the future. The preparation method provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.
Synthesis of novel trifluoro methylated imidazothiadiazole derivatives via one-pot isocyanide-based three-component reaction under catalyst and solvent-free conditions
Sarchahi, Maryam,Esmaeili, Abbas Ali
supporting information, p. 1071 - 1077 (2021/08/25)
A catalyst and solvent-free synthesis of imidazo[2,1-b][1,3,4]thiadiazole derivatives containing one trifluoromethyl (CF3) group is reported via a three-component reaction between 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine, aromatic aldehydes, and isocyanides. This green reaction is characterized by operational simplicity and good-to-excellent yields of products. The structure of all products was deduced by 1H NMR,13C NMR, FT-IR, mass spectrometry, and elemental analysis.
Ionic liquid-promoted one-pot synthesis of thiazole-imidazo[2,1-b][1,3,4]thiadiazole hybrids and their antitubercular activity
Ramprasad, Jurupula,Nayak, Nagabhushana,Dalimba, Udayakumar,Yogeeswari, Perumal,Sriram, Dharmarajan
, p. 338 - 344 (2016/03/01)
In this paper, we report the facile and efficient one-pot three-component synthesis of 1-((6-phenylimidazo[2,1-b][1,3,4]thiadiazol-5-yl)methylene)-2-(4-phenylthiazol-2-yl)hydrazine derivatives (5a-w) using an ionic liquid, namely 1-butyl-3-methylimidazolium bromide ([Bmim]Br). The compounds were screened for their in vitro antimycobacterial activity against Mycobacterium tuberculosis. Compound 5s showed the highest inhibitory activity with an MIC of 6.03 μM which is slightly lower than the MIC values of standard drugs ethambutol (15.3 μM) and ciprofloxacin (9.4 μM). Four other compounds of the series viz.5e, 5i, 5t and 5w also showed significant inhibitory activity with MIC values in the range of 11.7-13.9 μM. The structure-activity relationship revealed that the trifluoromethyl substitution at position-2 and p-chlorophenyl substitution at position-6 of the imidazo[2,1-b][1,3,4]thiadiazole ring enhanced the inhibitory activity. Also, the methyl, methoxy, fluoro or nitro substituents on the thiazole ring enhanced the activity of the compounds. None of the active compounds were toxic to a normal cell line (NIH 3T3), which signifies the lack of general cellular toxicity of the molecules. In silico molecular docking studies revealed the favourable interaction of the potent compounds with the target enzymes InhA and CYP121.
Aminothiazoles as Potent and Selective Sirt2 Inhibitors: A Structure-Activity Relationship Study
Schiedel, Matthias,Rumpf, Tobias,Karaman, Berin,Lehotzky, Attila,Oláh, Judit,Gerhardt, Stefan,Ovádi, Judit,Sippl, Wolfgang,Einsle, Oliver,Jung, Manfred
, p. 1599 - 1612 (2016/03/05)
Sirtuins are NAD+-dependent protein deacylases that cleave off acetyl but also other acyl groups from the ε-amino group of lysines in histones and other substrate proteins. Dysregulation of human Sirt2 (hSirt2) activity has been associated with the pathogenesis of cancer, inflammation, and neurodegeneration, which makes the modulation of hSirt2 activity a promising strategy for pharmaceutical intervention. The sirtuin rearranging ligands (SirReals) have recently been discovered by us as highly potent and isotype-selective hSirt2 inhibitors. Here, we present a well-defined structure-activity relationship study, which rationalizes the unique features of the SirReals and probes the limits of modifications on this scaffold regarding inhibitor potency. Moreover, we present a crystal structure of hSirt2 in complex with an optimized SirReal derivative that exhibits an improved in vitro activity. Lastly, we show cellular hyperacetylation of the hSirt2 targeted tubulin caused by our improved lead structure.
Synthesis, biological evaluation and molecular modeling study of thiadiazolo[3,2-a][1,3]diazepine analogues of HIE-124 as a new class of short acting hypnotics
El-Subbagh, Hussein I.,Hassan, Ghada S.,El-Taher, Kamal E.H.,El-Messery, Shahenda M.,El-Azab, Adel S.,Abdelaziz, Alaa A.-M.,Hefnawy, Mohamed M.
, p. 237 - 247 (2016/09/09)
A new series of 6,7-dihydro-[1,3,4]thiadiazolo[3,2-a][1,3]diazepine analogues were synthesized, and biological evaluated. Compound GS-62 (33) exhibited potent in?vivo short acting hypnotic activity with onset time, duration of sleep and therapeutic index of 6.4?±?0.2, 94.8?±?5.3?min, 6.62, respectively), in comparison to thiopental sodium (6). Compounds 33 did not show any sign of acute tolerance reported with the maintenance dose of 6. Meanwhile 33 potentiated the in?vivo hypnotic effect of 6 in an equimolar amounts (0.06?mmol) combination showing an onset and duration of 7.5?±?1.3, 62.5?±?5.9?min, respectively. This combination allowed the use of lower doses of both drugs to avoid the undesirable side effects. Docking studies revealed favorable interactions and binding to BDZ binding site of the GABAAreceptor especially with Arg87, Arg149, and Thr151 amino acid residues.
