96776-00-0

Upstream product

• 3226-37-7 4-chlorophenyl thiocyanate 
• 613-94-5 benzoic acid hydrazide 
• 93-89-0 benzoic acid ethyl ester 
• 93-58-3 benzoic acid methyl ester 
• 93-99-2 benzoic acid phenyl ester 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 3004-42-0 5-phenyl-1,3,4-oxadiazole-2(3H)-thione 
• 106-47-8 4-chloro-aniline 

Relevant academic research and scientific papers

A KHSO4 mediated facile synthesis of 2-amino-1,3,4-oxadiazole derivatives

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 and anti-endoplasmic reticulum stress activity of N-substituted-2-arylcarbonylhydrazinecarbothioamides

Misfolded or unfolded proteins are accumulated in lumen of endoplasmic reticulum (ER) in ER stress condition. It has been implicated in many pathological conditions such as Alzheimer’s disease, diabetic retinopathy, atherosclerosis, β-cell apoptosis and lung inflammation. We found a series of N-substituted-2-arylcarbonylhydrazinecarbothioamides to potently decrease ER stress signal, showing up to almost 300-fold better activity than 1-hydroxynaphthoic acid and tauro-ursodesoxycholic acid, positive controls, respectively. Structure?activity relationship (SAR) study showed that 2-arylcarbonyl moiety is critical for the activity of the hydrazinecarbothioamide analogues and side chains tethering on thioamide moiety were relatively insensitive to the activity. Some analogues were found to consistently exert the potency under more physiologically relevant condition where ER stress was induced by palmitic acid. ER stress markers such as CHOP and phosphorylated eIF2α and PERK were accordingly decreased in western blotting upon treatment of compound 4h. Potential ER stress inhibitory activity and novel structures could provide a novel platform for new chemical chaperone and therapy for protein misfolding diseases.

Design and Synthesis of 1,3,4-Thiadiazole Derivatives as Novel Anticancer and Antitubercular Agents

A series of novel 5-phenyl-substituted 1,3,4-thiadiazole-2-amines were designed, synthesized, and screened for their antitumor and antitubercular activities. The target compounds were synthesized starting from isocyanates and acid hydrazides by convention

1-(2-Hydroxybenzoyl)-thiosemicarbazides are promising antimicrobial agents targeting D-alanine-D-alanine ligase in bacterio

The bacterial cell wall and the enzymes involved in peptidoglycan synthesis are privileged targets for the development of novel antibacterial agents. In this work, a series of 1-(2-hydroxybenzoyl)-thiosemicarbazides inhibitors of D-Ala-D-Ala ligase (Ddl) were designed and synthesized in order to target resistant strains of bacteria. Among these, the 4-(3,4-dichlorophenyl)-1-(2-hydroxybenzoyl)-3-thiosemicarbazide 29 was identified as a potent Ddl inhibitor with activity in the micromolar range. This compound, possessing strong antimicrobial activity including against multidrug resistant strains, was proven to act through a bactericidal mechanism and demonstrated very low cytotoxicity on THP-1 human monocytic cell line. Inhibition of Ddl activity by 29 was confirmed in bacterio using UPLC-MS/MS by demonstrating an increase in D-Ala intracellular pools accompanied by a commensurate decrease in D-Ala-D-Ala. Further structure-activity relationships (SARs) studies provided evidence that the hydroxyl substituent in the 2-position (R1) of the benzoylthiosemicarbazide scaffold is essential for the enzymatic inhibition. This work thus highlights the 1-(2-hydroxybenzoyl)-thiosemicarbazide motif as a very promising tool for the development of novel antibacterial compounds acting through an interesting mechanism of action and low cytotoxicity.

Efficient and mild synthesis of substituted 2-amino-1,3,4-oxadiazoles mediated by (tosylimino)phenyl-γ3-iodane

A simple and convenient one-pot protocol for the synthesis of substituted 2-amino-1,3,4-oxadiazoles mediated by (tosylimino)phenyl-γ3- iodane has been described. Acylthiosemicarbazides prepared from the corresponding acylhydrazides undergo effi

Antimicrobial and Physicochemical Characterizations of Thiosemicarbazide and S-Triazole Derivatives

Two series of thiosemicarbazide derivatives and three series of s-triazole derivatives have been synthesized. All of these compounds were tested for their in vitro antibacterial activity against Gram-positive and Gram-negative bacterial strains. Among tested thiosemicarbazide derivatives, the best bioactivity was detected for two 1-formylthiosemicarbazides with 3-/4-tolyl substitution (1 l, 1 m) (MICs range between 31.25 and 250 μg/mL). All tested s-triazole derivatives exhibited lower antibacterial activity than their acyclic precursors.

A new and efficient synthesis of 1,3,4-oxadiazole derivatives using TBTU

An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from isothiocyanates and hydrazides through cyclodesulfurization in the presence of (O-(benzotriazol-1-yl)-N,N,N′, N′-tetramethyluronium tetrafluoroborate) TBTU as an uronium cou

Fragmentation and skeletal rearrangements of 2-arylylamino-5-aryl-1,3,4- oxadiazoles and their noncovalent complexes with cobalt cation and cyclodextrin studied by mass spectrometry

Mass spectrometric fragmentation pathways of title compounds were studied by electron ionization (EI) and electrospray ionization (ESI) as methods of ion generation. To explain the observed complex skeletal rearrangements, tandem mass spectrometry, accurate mass measurement and isotope labeling (compounds containing one 13C atom in oxadiazole ring) were used. Loss of CO, N2 and H atoms under EI conditions led to the formation of 9,10-dihydroacridine-type ions, loss of NH3 under ESI conditions yielded the 4-phenylphthalazinone-type ions and the loss of HNCO under ESI conditions produced N-arylamino-benzonitrilium ions; however, this process can be affected by the electron-donor/electron-withdrawing properties of groups substituted at the phenyl rings. The ESI was used to study the complexes of the compounds with cobalt as well as with cyclodextrin. It was found that the compounds studied tend to form inclusion complexes with cyclodextrin of stoichiometry 1:1 and complexes of different stoichiometries with cobalt, although those of stoichiometry 6:1 and 4:1 are favored and the attachment of counter ion may stabilize the complexes 3:1 and 2:1. Copyright

1,3,4-Thiadiazole derivatives. Synthesis, structure elucidation, and structure-antituberculosis activity relationship investigation

A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl) -1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.

Solvent-free synthesis of acyl thiosemicarbazides with microwave activation

A new and rapid synthesis of acyl thiosemicarbazides has been reported for the first time using domestic microwave oven. Comparing with the conventional methods, this process has advantages such as shorter reaction time, higher yields and environmental acceptability.