3862-85-9

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 4426-72-6 hydrazine carboxamide 
• 563-41-7 semicarbazide hydrochloride 

Downstream Products

• 7659-07-6 2-amino-5-(4-fluorophenyl)-1,3,4-oxadiazole 
• 1338084-18-6 C₁₈H₁₇FN₆O₄ 
• 1338083-63-8 C₁₃H₉FN₆O₃ 
• 1338083-85-4 C₁₅H₁₂FN₅O₃ 
• 1338084-42-6 C₁₃H₈FN₅O₃ 
• 1261138-34-4 3-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-2-phenylquinazolin-4(3H)-one 
• 1370641-56-7 2-[2-(4-fluorophenyl)-1,3,4-oxodiazol-5-yl]benzisoselenazol-3(2H)-one 
• 1421633-61-5 C₉H₇FN₄O₂ 
• 1421633-72-8 C₉H₈FN₅O₂ 
• 1277127-61-3 C₁₅H₁₀FN₃O₂ 

Relevant academic research and scientific papers

Ultrapotent Inhibitor of Clostridioides difficile Growth, Which Suppresses Recurrence in Vivo

Clostridioides difficile is the leading cause of healthcare-associated infection in the U.S. and considered an urgent threat by the Centers for Disease Control and Prevention (CDC). Only two antibiotics, vancomycin and fidaxomicin, are FDA-approved for the treatment of C. difficile infection (CDI), but these therapies still suffer from high treatment failure and recurrence. Therefore, new chemical entities to treat CDI are needed. Trifluoromethylthio-containing N-(1,3,4-oxadiazol-2-yl)benzamides displayed very potent activities [sub-μg/mL minimum inhibitory concentration (MIC) values] against Gram-positive bacteria. Here, we report remarkable antibacterial activity enhancement via halogen substitutions, which afforded new anti-C. difficile agents with ultrapotent activities [MICs as low as 0.003 μg/mL (0.007 μM)] that surpassed the activity of vancomycin against C. difficile clinical isolates. The most promising compound in the series, HSGN-218, is nontoxic to mammalian colon cells and is gut-restrictive. In addition, HSGN-218 protected mice from CDI recurrence. Not only does this work provide a potential clinical lead for the development of C. difficile therapeutics but also highlights dramatic drug potency enhancement via halogen substitution.

Semicarbazone derivatives as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation

A series of hydrazinecarboxamide derivatives were synthesized and examined against urease for their inhibitory activity. Among the series, the 1-(3-fluorobenzylidene)semicarbazide (4a) (IC50 = 0.52 ± 0.45 μM), 4u (IC50 = 1.23 ± 0.32 μM) and 4h (IC50 = 2.22 ± 0.32 μM) were found most potent. Furthermore, the molecular docking study was also performed to demonstrate the binding mode of the active hydrazinecarboxamide with the enzyme, urease. In order to estimate drug likeness of compounds, in silico ADME evaluation was carried out. All compounds exhibited favorable ADME profiles with good predicted oral bioavailability.

Ultrasound-assisted synthesis of 2-amino-1,3,4-oxadiazoles through NBS-mediated oxidative cyclization of semicarbazones

A ultrasound-assisted oxidative cyclization of semicarbazones using N-bromosuccinimide in the presence of sodium acetate was established providing efficient and rapid access to a variety of 2-amino-1,3,4-oxadiazoles. Moreover, the new synthetic protocol provides a simple procedure utilizing a safer oxidizing system that affords the target products in high regioselectivity, satisfactory yields, and elevated purities.

Thiosemicarbazones as Aedes aegypti larvicidal

Abstract A set of aryl- and phenoxymethyl-(thio)semicarbazones were synthetized, characterized and biologically evaluated against the larvae of Aedes aegypti (A. egypti), the vector responsible for diseases like Dengue and Yellow Fever. (Q)SAR studies were useful for predicting the activities of the compounds not included to create the QSAR model as well as to predict the features of a new compound with improved activity. Docking studies corroborated experimental evidence of AeSCP-2 as a potential target able to explain the larvicidal properties of its compounds. The trend observed between the in silico Docking scores and the in vitro pLC50 (equals -log LC50, at molar concentration) data indicated that the highest larvicidal compounds, or the compounds with the highest values for pLC50, are usually those with the higher docking scores (i.e., greater in silico affinity for the AeSCP-2 target). Determination of cytotoxicity for these compounds in mammal cells demonstrated that the top larvicide compounds are non-toxic.

Synthesis and antitubercular activity of 2-(1H-pyrrol-1-Yl)-5- substituted-1,3,4-oxadiazoles

A series of 2-(1H-pyrrol-1-yl)-5-substituted-1,3,4-oxadiazole derivatives were prepared and evaluated for their antitubercular activity. These derivatives were synthesized by the reaction of 5-substituted-1,3,4-oxadiazol-2-amines (4a-j) with 2,5- dimethoxytetrahydrofuran in dried acetic acid. Structures of the newly synthesized compounds were confirmed on the basis of physico-chemical and spectral data. All the synthesized compounds were screened for their antitubercular activity using microplate almar blue assay (MABA) method. Compounds have shown moderate to good antitubercular activity against M. tuberculosis H37Rv microorganism.

Electrochemical synthesis of 2-amino-5-substituted-1,3,4-oxadiazole derivatives and evaluation of antibacterial activity

Some new 2-amino-5-substituted-1,3,4-oxadiazoles have been synthesized at platinum electrode through the electrochemical oxidation of semicarbazone at room temperature and studied for their antibacterial activity. This is an environmentally benign method in the field of electroorganic synthesis under controlled potential electrolysis in an undivided cell. The electrolysis have been carried out in the acetonitrile solvent and lithium perchlorate is used as a supporting electrolyte. Two platinum plates are used as working as well as counter electrode and saturated calomel electrode as the reference electrode. These compounds have been characterized by microanalyses, IR, Mass, 1H NMR and 13C NMR spectral data. All the compounds have been evaluated for their antibacterial activity against Klebsilla penumoniae, Escherichia coli, Streptococcus aureus and Shigella dysenteriea at 25 and 50 ppm concentrations.

Novel limonene and citral based 2,5-disubstituted-1,3,4-oxadiazoles: A natural product coupled approach to semicarbazones for antiepileptic activity

Two novel series of N4-(5-(2/3/4-substituted-phenyl)-1,3,4- oxadiazol-2-yl)-N1-(2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene) semicarbazide and N4-(5-(2/3/4-substituted-phenyl)-1,3,4-oxadiazol-2- yl)-N1-(3,7-dimethylocta-3,6-dienylidene)-semicarbazide were synthesized to meet structural prerequisite indispensable for anticonvulsant activity. The anticonvulsant activities of the compounds were investigated using maximal electroshock seizure (MES), subcutaneous pentylenetrtrazole (scPTZ) and subcutaneous strychnine (scSTY) models. The rotorod test was conducted to evaluate neurotoxicity. Some of the selected active compounds were subjected to GABA assay to confirm their mode of action. The outcome of the present investigations proved that the four binding sites pharmacophore model is vital for anticonvulsant activity. The efforts were also made to establish structure-activity relationships among test compounds.

Synthesis and in vitro antitumor activity of 1,3,4-oxadiazole derivatives based on benzisoselenazolone

A series of novel 1,3,4-oxadiazole derivatives based on benzisoselenazolone has been prepared and tested for antiproliferative activity in vitro against the cells of human cancer cell lines: SSMC-7721 (human liver cancer cell), MCF-7 (human breast cancer cell) and A549 (human lung cancer cell). All the compounds obtained exhibited antiproliferative activity and showed selective cytotoxicity against different cancer cells. Compounds 7d and 7i showed significant antiproliferative activities against MCF-7 cells, with IC50 values of 1.07 and 1.76/μM respectively. Compound 7d were found to be the most potent compound against SSMC-7721 cells, with IC50 values 4.46/μM.

Microwave assisted synthesis and characterization of semicarbazones

An efficient and simple microwave assisted procedure has been developed for conversion of substituted aryl aldehyde to corresponding semicarbazone by reaction with semicarbazide hydrochloride in presence of sodium acetate. The synthesized semicarbazones have been characterized by physico-chemical and spectral data.

2,5-Disubstituted-1,3,4-oxadiazoles/thiadiazole as surface recognition moiety: Design and synthesis of novel hydroxamic acid based histone deacetylase inhibitors

The enzymatic inhibition of histone deacetylase activity has come out as a novel and effectual means for the treatment of cancer. Two novel series of 2-[5-(4-substitutedphenyl)-[1,3,4]-oxadiazol/thiadiazol-2-ylamino] -pyrimidine-5-carboxylic acid (tetrahydro-pyran-2-yloxy)-amides were designed and synthesized as novel hydroxamic acid based histone deacetylase inhibitors. The antiproliferative activities of the compounds were investigated in vitro using histone deacetylase inhibitory assay and MTT assay. The synthesized compounds were also tested for antitumor activity against Ehrlich ascites carcinoma cells in Swiss albino mice. The efforts were also made to establish structure-activity relationships among synthesized compounds. The results of the present studying indicates 2,5-disubstituted 1,3,4-oxadiazole/thiadiazole as promising surface recognition moiety for development of newer hydroxamic acid based histone deacetylase inhibitor.