18212-20-9

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 4-METHYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is used as a chemical intermediate for the preparation of compounds with potent fungicidal activity for the treatment and prevention of fungal infections.
Used in Agricultural Industry:
ETHYL 4-METHYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is used as a chemical intermediate for the development of fungicides to protect crops from fungal diseases, thereby improving crop yield and quality.
Used in Chemical Synthesis:
ETHYL 4-METHYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is used as a building block in the synthesis of various heterocyclic compounds with potential applications in medicinal chemistry, materials science, and other fields.
Used in the Preparation of 1,2,3-Thiadiazole Bearing Hydrazone Derivatives:
ETHYL 4-METHYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is used as a starting material for the synthesis of 1,2,3-thiadiazole bearing hydrazone derivatives, which exhibit potent fungicidal activity.
Used in the Preparation of 2-(4′-Methyl-1′,2′,3′-thiadiazol)-5-Substituted-1,3,4-Oxadiazole Derivatives:
ETHYL 4-METHYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is used as a precursor in the synthesis of 2-(4′-methyl-1′,2′,3′-thiadiazol)-5-substituted-1,3,4-oxadiazole derivatives, which are known for their fungicidal properties.
Used in the Preparation of 1,2,3-Thiadiazole Bearing 1,2,4-Triazole Derivatives:
ETHYL 4-METHYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is used as a reactant in the preparation of 1,2,3-thiadiazole bearing 1,2,4-triazole derivatives, which are compounds with significant fungicidal activity.

InChI:InChI=1/C6H8N2O2S/c1-3-10-6(9)5-4(2)7-8-11-5/h3H2,1-2H3

Upstream product

• 5982-65-0 N-carboxiamino-hidrazona del acetilacetato de etilo 
• 50981-14-1 ethyl 2-(4-ethoxy-4-oxobutan-2-ylidene)hydrazinecarboxylate 
• 141-97-9 ethyl acetoacetate 
• 356102-30-2 3-methoxycarbonylhydrazonoacetic acid ethyl ester 
• 4114-31-2 ethylhydrazine carboxylate 
• 98337-14-5 3-ethoxycarbonylhydrazonoacetic acid ethyl ester 
• 64-17-5 ethanol 
• 18212-21-0 4-methyl-[1,2,3]thiadiazole-5-carboxylic acid 

Downstream Products

• 18212-21-0 4-methyl-[1,2,3]thiadiazole-5-carboxylic acid 
• 463-58-1 carbon oxide sulfide 
• 59944-62-6 4-hydroxymethyl-[1,2,3]thiadiazole-5-carboxylic acid ethyl ester 
• 163008-86-4 5-hydroxymethyl-4-methyl-1,2,3-thiadiazole 
• 77196-89-5 4-methyl-1,2,3-thiadiazole-5-carbohydroxamic acid 
• 69635-76-3 4-methyl-1,2,3-thiadiazole-5-carboxylic acid-(cyclohexylmethyl)-amide 

Relevant academic research and scientific papers

Design and synthesis of novel cylopentapyrazoles bearing 1,2,3-thiadiazole moiety as potent antifungal agents

In drug-resistant phytopathogenic fungi, there has been extensive research on microbiological and antifungal drug development. In this study, a novel series of cylopentapyrazole bearing a 1,2,3-thiadiazole ring 2a-e were designed and synthesized according to the principle of combination of bioactive structures. Thus, we have employed a [3 + 2] cycloaddition with 4-methyl-[1,2,3] thiadiazole-5-carboxylic acid hydrazones 1a-e and cyclopentadiene ring. Novel synthesized compounds were identified with IR, 1H and 13C NMR, mass spectrometry and elemental analysis then, antifungal activities were assayed. Based on our study, a combination of the compounds 1a and 2b possess remarkable antifungal activity against Botrytis cinerea AHU 9424 with 100% inhibition. EC50 values were calculated by studying different doses in combinations with high inhibition rates. The combination of 1a + 2b has an EC50 value at 6.37 and 13.85 μg/ml concentrations against B. cinerea and F. culmorum, respectively. The combination of compound 1a + 2b, having a cylopentapyrazole ring on the 1,2,3-thiadiazole backbone, shows promising fungicidal activity and deserves further development. Additionally, the homology model of the CYP51 enzyme that belongs to Fusarium moniliforme was generated using CYP51B (PDB ID: 6CR2), and molecular docking was performed using this homology model for each compound. The results of this study clearly indicate that these novel compounds can be identified as promising lead compounds and potential fungicidal agents in future.

Synthesis, Crystal Structure, and Biological Activity of Some Novel Sulfoxide Compounds Containing 1,2,3-Thiadiazole Moiety

Some new sulfoxide compounds containing 1,2,3-thiadiazole moiety were synthesized from diethyl carbonate and hydrazine hydrate by multi-step reactions. Their structures were confirmed by NMR, MS, and elemental analysis. One of the title compounds, 5-(4-cyclopropyl-5-((3-fluorobenzyl)sulfinyl)-4H-1,2,4-triazol-3-yl)-4-methyl-1,2,3-thiadiazole (C15H14FN5OS2), was structurally determined by a single crystal X-ray diffraction study. The biological activity of the title compound was determined, and the results showed that it displays moderate biological activities.

Traceless solid-phase synthesis of 1,2,3-thiadiazole derivatives from resin-bound acylhydrazine

A novel synthesis of 1,2,3-thiadiazole derivatives using a traceless solid-phase approach is described, in which many kinds of 1,2,3-thiadiazole derivatives were efficiently obtained in good yields and high purities via traceless cyclization cleavage of resin-bound acylhydrazones with thionyl chloride. Copyright Taylor & Francis Group, LLC.

Phase transfer catalyzed synthesis and biological activity of thiourea derivatives containing 1,2,3-thiadiazole moiety

A series of N-(substituted-phenyl)-N′-(4-methyl-1,2,3-thiadiazole-5-yl)-thiourea (7a-7e) were synthesized and characterized. The chemical structures of all the compounds were confirmed by 1H NMR, MS and elemental analysis. All the compounds were investigated for fungicidal activity and plant growth regulatory activity. The bioassay results indicated that some of these compound exhibit moderate fungicidal activities.

Synthesis and biological activities of (E)-β-farnesene analogues containing 1,2,3-thiadiazole

In order to discover novel compounds with high-activity to control aphid, a series of novel (E)-β-farnesene analogues containing 1,2,3-thiadiazole were designed and synthesized, and their structures were confirmed by IR,1H NMR,13C NMR, and HRMS (ESI). The stability of representative compounds was studied by HPLC and1H NMR techniques. Repellent activity results indicated that compounds 8h and 8j displayed 60.3% and 62.0% repellent rates, respectively. The aphicidal bioassay results showed that most analogues exhibited considerable aphicidal activity against Myzus persicae. Especially, analogues 8l, 8s and 8t exhibited high activity with LC50values of 33.4?μg/mL, 50.2?μg/mL and 61.8?μg/mL, respectively, which were higher than the lead compound (E)-β-farnesene, but lower than commercial insecticide pymetrozine with a LC50of 7.1?μg/mL.

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

Design, synthesis, and evaluation of substituted 2-acylamide-1,3-benzo[d]zole analogues as agents against MDR- and XDR-MTB

N-(5-Chlorobenzo[d]oxazol-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamideox-amide has been identified as a potent inhibitor of Mtb H37Rv, with a minimum inhibitory concentration (MIC) of 0.42 μM. In this study, a series of substituted 2-acylamide-1,3-zole analogues were designed and synthesized, and their anti-Mtb activities were analyzed. In total, 17 compounds were found to be potent anti-Mtb agents, especially against the MDR- and XDR-MTB strains, with MIC values 10 μM. These analogues can inhibit both drug-sensitive and drug-resistant Mtb. Four representative compounds were selected for further profiling, and the results indicate that compound 18 is acceptably safe and has favorable pharmacokinetic (PK) properties. In addition, this compound displays potent activity against Gram-positive bacteria, with MIC values in the range of 1.48–11.86 μM. The data obtained herein suggest that promising anti-Mtb candidates may be developed via structural modification, and that further research is needed to explore other compounds.

Synthesis and biological evaluation of 4-methyl-1,2,3-thiadiazole-5-carboxaldehyde benzoyl hydrazone derivatives

To find new lead compounds with high biological activity, a series of novel 4-methyl-1,2,3-thiadiazole-5-carboxaldehyde benzoyl hydrazone derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR, IR spectrum and elemental analysis. Preliminary bioassay indicated that the title compounds exhibited moderate to strong fungicidal activity against six fungi in vitro at 50?μg/mL. Moreover, some of the title compounds exhibited good curative activity against TMV in vivo at 500?μg/mL. The structure-activity relationship analysis of compounds against Valsa mali showed that compounds containing halogen at the para position on phenyl exhibited the best activity. Especially compound 8k showed broad spectrum fungicidal activities against Valsa mali, Botrytis cinerea, Pythium aphanidermatum, Rhizoctonia solani, Fusarium moniliforme and Alternaria solani with the EC50 values of 8.20, 24.42, 15.80, 40.53, 41.48, and 34.16?μg/mL, respectively.

Substituted benzo - 1, 3 - [...] compound, its preparation and use

The invention relates to a substituted benzo-1, 3-miscellaneous azole compound shown in the general formula I, and further relates to a preparation method of the compound and application to the preparation of antituberculosis drugs. The compound provided by the invention has effect not only on mycobacterium tuberculosis sensitive strains, but also on resistant strains which have drug resistance to isoniazid, rifampicin, and other traditional frontline antituberculosis drugs, and is a novel antimycobacterium tuberculosis compound.

1. 2, 3 - thiadiazole - 5 - a amidine compound synthesis method

The invention discloses a novel method for synthesizing a 1,2,3-thiadiazole-5-formamidine compound. The target compound shown in general formula TDCA is prepared from a compound as shown in general formula M by virtue of a methylation reaction. The target component as shown in the general formula M is prepared from a compound as shown in general formula A and a compound as shown in general formula N by virtue of a condensation reaction, wherein during the methylation reaction, preferably, a catalyst is an organic metallic catalyst consisting of cuprous iodide and a ligand, namely 2,2,6,6-tetramethyl-3,5-heptadione; during the reaction, preferably, dimethylbenzene is taken as a solvent, and the optimum reaction temperature is 100-140 DEG C. The method disclosed by the invention is high in yield and more environment-friendly (as shown in Specification).