5315-85-5

Upstream product

• 563-41-7 semicarbazide hydrochloride 
• 89-98-5 2-chloro-benzaldehyde 
• 4426-72-6 hydrazine carboxamide 
• 79-19-6 thiosemicarbazide 

Downstream Products

• 2138-98-9 2-amino-5-(o-chlorophenyl)-1,3,4-oxadiazole 
• 62036-22-0 C₈H₆ClN₃O 
• 1491167-89-5 methyl (2-(2-(2-chlorobenzylidene)hydrazono)-4-oxothiazolidin-5-ylidene)acetate 
• 1338084-44-8 C₁₃H₈ClN₅O₃ 
• 1338083-87-6 C₁₅H₁₂ClN₅O₃ 
• 1338083-65-0 C₁₃H₉ClN₆O₃ 
• 1338084-20-0 C₁₈H₁₇ClN₆O₄ 
• 62329-63-9 3-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-5-(4-dimethylamino-benzylidene)-2-thioxo-thiazolidin-4-one 
• 62329-53-7 5-(4-chloro-benzylidene)-3-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-thioxo-thiazolidin-4-one 
• 62329-58-2 3-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-5-(3-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one 
• 62329-47-9 3-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-thioxo-thiazolidin-4-one 
• 312324-91-7 1-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-3-(4-fluoro-phenyl)-urea 
• 312324-89-3 [5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-carbamic acid ethyl ester 
• 89-98-5 2-chloro-benzaldehyde 

Relevant academic research and scientific papers

Synthesis, antibacterial activities and molecular docking study of thiouracil derivatives containing oxadiazole moiety

A series of novel thiouracil derivatives 9 containing an oxadiazole moiety have been synthesized by structural modification of a lead SecA inhibitor, 2. These compounds have been evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus and Bacillus subtilis. Among them, compounds 9g and 9n exhibited promising antibacterial activities against the tested strains. Compound 9g was also tested for its inhibitory activities against SecA ATPase, and the IC50 value of compound 9g was 19.9 μg/mL, lower than that of compound 2 (20.8 μg/mL). Molecular docking work indicates that compound 9g likely occupies the pocket formed by SecA IRA2 and NBD domain.

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.

Synthesis and antimicrobial evaluation of novel 3-(arylideneamino)-3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-diones and their 2-thioxo analogues

The preparation of some novel 3-(arylideneamino)-3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-diones 8(i–xiv) and 3-(arylideneamino)-3a,8a-dihydroxy-2-thioxo-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(2H)-ones 9(i–xiv) have been reported through one-pot catalyst-free reaction of aldehydes, semicarbazide hydrochloride/thiosemicarbazide with ninhydrin. All the synthesized compounds have been screened for antimicrobial activity and some of them were observed to possess broad spectrum antibacterial potential as well as significant antagonistic potential against fungal pathogens.

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.

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.

Synthesis and antiviral activity of new substituted methyl [2-(arylmethylene-hydrazino)-4-oxo-thiazolidin-5-ylidene]acetates

A series of new methyl [2-(arylmethylene-hydrazono)-4-oxo-thiazolidin-5- ylidene]acetates (5a-o) were synthesized via cyclocondensation of thiosemicarbazones (3a-o) with dimethyl but-2-ynedioate (4) in good yields under solvent-free conditions. The environmentally friendly solvent-free protocol overcomes the limitations associated with the customary protracted solution phase synthesis and afforded the title compounds in a few minutes. Compounds 5b-i and 5h-o were evaluated for their antiviral activity against the replication activity of HIV-1 and HIV-2 in MT-4 using the MTT assay. The same compounds were also evaluated in vitro for their selective antiviral activity against hepatitis C virus (HCV) in the Huh 5-2 replicon system (type 1b, Con1 strain).

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.

Synthesis, antimicrobial and insecticidal activity of some 4H-1, 2, 4 triazole derivatives

1-(Substituted benzylidene) semicarbazide has been used as a precursor to synthesize some important biologically active 3- substituted phenyl, 4H-1, 2, 4 triazole derivatives. Reaction of ethanolic solution of schiff s base of substituted aromatic aldehyde 1 with ethanolic solution of FeCl 3.6H2O (1 mole FeCl3.6H2O in 10 mL ethanol) yields the 4N-1, 2, 4 triazole-3-derivative 2. Several derivatives have been synthesized and screened for their antibacterial efficacy against Bacillus subtilis, Escherichia coli, Staphyllococcus aureus and Klebsiella pneumoniae, Antifungal activity against Aspergillus flavus, Fusarium oxysporum, Aspergillus niger and Trichoderma viridae and insecticidal activity against Periplaneta americana.

Effect of semicarbazones on endogenous protein hydrolysis in liver homogenate

Semicarbazones of substituted benzaldehydes were synthesized and their effect on endogenous protein hydrolysis in liver homogenate was studied. It was found that p-nitrobenzaldehyde semicarbazone exerted maximum effect.