5315-87-7

Usage

Uses

Used in Pharmaceutical Industry:
4-NP-SCA is used as a precursor for the synthesis of benzimidazole derivatives, which are important in the development of various pharmaceutical compounds due to their diverse biological activities.
Additionally, 4-NP-SCA is used as a starting material for the development of histone deacetylase inhibitors. These inhibitors play a crucial role in epigenetic regulation and have potential therapeutic applications in the treatment of various diseases, including cancer.

InChI:InChI=1/C8H8N4O3/c9-8(13)11-10-5-6-1-3-7(4-2-6)12(14)15/h1-5H,(H3,9,11,13)/b10-5+

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 2143-99-9 1,2-bis(4-nitrobenzylidene)hydrazine 
• 4426-72-6 hydrazine carboxamide 
• 563-41-7 semicarbazide hydrochloride 
• 79-19-6 thiosemicarbazide 
• 1129-37-9 4-nitrobenzaldehyde oxime 

Downstream Products

• 2829-27-8 4-nitro-benzaldehyde phenylhydrazone 
• 62329-45-7 {[5-(4-nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-thiocarbamoylsulfanyl}-acetic acid 
• 180045-62-9 C₁₂H₁₇N₅O₄ 
• 2143-99-9 1,2-bis(4-nitrobenzylidene)hydrazine 
• 555-16-8 4-nitrobenzaldehdye 
• 22354-75-2 C₈H₆N₄O₃ 
• 1338084-15-3 C₁₈H₁₇N₇O₆ 
• 1338083-60-5 C₁₃H₉N₇O₅ 
• 1338083-82-1 C₁₅H₁₂N₆O₅ 
• 1338084-39-1 C₁₃H₈N₆O₅ 
• 1261138-33-3 C₂₂H₁₃N₅O₄ 
• 1456733-50-8 methyl (2-(2-(4-nitrobenzylidene)hydrazono)-4-oxo-thiazolidin-5-ylidene)acetate 
• 729-13-5 2-(4-nitrophenyl)benzimidazole 
• 51891-79-3 5-(4-nitrophenyl)-1,3,4-oxadiazol-2-amine 

Relevant academic research and scientific papers

Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide

A series of N-(substituted benzothiazole-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a-i) and substituted-[3-((5-phenyl-1,3,4-oxadiazole-2-yl)imino)indolene-2-one] (5a-f) were designed, synthesized fulfilling the structural requirement of pharmacophore and evaluated for anticonvulsant activities using maximal electroshock test (MES), subcutaneous pentylenetetrazole (scPTZ) seizures and neurotoxicity by motor impairment model in mice. The most active compoundN-(5-chlorobenzo[d]thiazol-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a) has shown significant anticonvulsant activity against both MES and scPTZ screens and emerged as most effective anticonvulsant compound with median dose of 35.7 mg/kg (MES ED50), 88.15 mg/kg (scPTZ ED50) and toxic dose (TD50) was found to be > 500mg/kg. In silico studies including molecular docking study was carried to establish the molecular interaction of potent compound (4a) in both Na+ channel and GABAA receptors. The prediction of pharmacokinetic parameters and distance mapping of compounds were also performed to establish the drug likeness property.

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.

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.

Synthesis of 2-amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via sequential condensation and I2-mediated oxidative C-O/C-S bond formation

2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I2-mediated oxidative C-O/C-S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.

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).

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.

Oxadiazolo pyrrolidine carboxamides as enoyl-ACP reductase inhibitors: Design, synthesis and antitubercular activity screening

Pyrrolidine carboxamides have been recognized as potent direct enoyl-acyl carrier protein reductase inhibitors. In our study, the search for new pyrrolidine carboxamides incorporated with various heterocyclic moieties, possessing antitubercular activities is been done. A series of oxadiazolyl pyrrolidine carboxamides (2a-e) were synthesized by reacting pyrrolidine carboxylic acid and oxadiazole amines using HBTU as amide forming agent. The purity of the synthesized compounds was confirmed by physical characterization like melting point and thin layer chromatography. The functional group identification was done based on spectral characterization utilizing, FT-IR, 1H NMR, 13C NMR, mass spectral data and elemental analysis. Invitro antitubercular screening was performed by alamar blue assay method on mycobacterium tuberculosis H37Rv.

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.

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.