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Upstream product

• 1694-29-7 3-chloropentane-2,4-dione 
• 106-40-1 4-bromo-aniline 
• 2028-85-5 (4-bromophenyl)diazonium chloride 

Downstream Products

• 88860-91-7 1-[4-Acetyl-1-(4-bromo-phenyl)-1H-pyrazol-3-yl]-ethanone 
• 149353-69-5 3-acetyl-1-(4-bromophenyl)-4-hydroxy-5-methyl-1,4,5,6-tetrahydro-1,2,5,4λ⁵-triazaphosphorine-4,6-dione 
• 1063737-35-8 C₂₂H₁₅BrN₂O₂S 
• 1063737-24-5 5-acetyl-3-(4-bromophenyl)-spiro-thioxanthene-9',2-[1,3,4]thiadiazole 
• 1198306-50-1 3-(2-(5-[(4-bromophenyl)diazenyl]-4-methylthiazol-2-yl)hydrazono)indolin-2-one 
• 1242412-48-1 1-(4-methylpiperazin-1-yl)-1,2-propandione 1-[2-(4-bromophenyl)hydrazone] 
• 1242412-49-2 1-(4-ethylpiperazin-1-yl)-1,2-propandione 1-[2-(4-bromophenyl)hydrazone] 
• 1242412-50-5 1-(4-phenylpiperazin-1-yl)-1,2-propandione 1-[2-(4-bromophenyl)hydrazone] 
• 1242412-51-6 1-[4-(4-fluorophenyl)piperazin-1-yl]-1,2-propandione 1-[2-(4-bromophenyl)hydrazone] 
• 1262436-35-0 2-{2-[1-(1H-indol-3-yl)ethylidene]hydrazinyl}-5-[(4-bromophenyl)diazenyl]-4-methylthiazole 
• 216169-47-0 1-ethoxycarbonyl-1-methyl-2-[1-(4-bromophenyl)hydrazonopropan-2-one]hydrazine 
• 216169-53-8 6-acetyl-4-(4-bromophenyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydro-1,2,4,5-tetrazine 

Relevant academic research and scientific papers

Synthesis, X-ray crystallographic analysis, DFT studies and biological evaluation of triazolopyrimidines and 2-anilinopyrimidines

Inspired by the reported antiviral activity of pyrimidines and triazolopyrimidines, two series of 2-anilinopyrimidines (5a-e) and 1-aryl-[1,2,4]triazolo[4,3-a]pyrimidines (14a-k) were designed and synthesized as potential antiviral agents. X-ray crystallographic study of compounds (14d) and (14k) confirmed the structure of the desired isomer and revealed the coplanarity of the fused [1,2,4]triazolo[4,3-a]pyrimidine rings with the aryl side group. DFT studies revealed insights into the mechanism of the micro-reversible cyclisation step using DFT [B3LYP-D3(BJ)/6–31++G(d,p)]. The pharmacokinetic properties and calculation of drug likeness scores (DLS) of (5a-e) and (14a-k) suggested good traditional drug-like properties and led to the synthesis of derivatives (14a-k) which were evaluated for their anti-viral activity with the most potent derivatives subjected to cytotoxicity screening. Compounds (14a), (14c), (14e), (14f) and (14k) showed moderate to strong antiviral activity with EC50 values 38 - 186 μM. Compound (14e) (DLS = 0.29) showed the best anti-CHIKV activity (EC50 = 38 μM) and lowest cytotoxicity (CC50 > 300 μg/ml) against breast cancer cell lines, MCF-7 and MD-AMB-231 and normal cell line EA.hy926. Simplification of [1,2,4]triazolo[4,3-a]pyrimidine ring, led to series (5a-e) (DLS = 0.03 - 0.77). Derivatives (5a-d) showed fair anti-CHIKV activity (EC50 > 200 μM), while (5e) emerged as the most active antiviral agent, however the most cytotoxic.

Synthesis and cytotoxic activity study of novel 2-(Aryldiazenyl)-3-methyl-1h-benzo[g]indole derivatives

A novel series of 2-(aryldiazenyl)-3-methyl-1H-benzo[g]indole derivatives (3a–f) were prepared through the cyclization of the corresponding arylamidrazones, employing polyphosphoric acid (PPA) as a cyclizing agent. All of the compounds (3a–f) were characterized using1H NMR,13C NMR, MS, elemental analysis, and melting point techniques. The synthesized compounds were evaluated for cytotoxic activity against diverse human cancer cell lines by the National Cancer Institute. While all of the screened compounds were found to be cytotoxic at a 10 μM concentration, two of them (2c) and (3c) were subjected to five dose screens and showed a significant cytotoxicity and selectivity.

Synthesis and structure-activity relationship; exploration of some potent anti-cancer phenyl amidrazone derivatives

Background: Amidrazones have been reported to have significant anti-tumor properties against several cancer cell lines. Objectives: The current project aims to profile the structure-anticancer activity relationship of phenyl-amidrazons. Methods: Fifteen p

Spectral characterization, CT-DNA binding, DFT/B3LYP, molecular docking and antitumor studies for new nano-sized VO(II)-hydrazonoyl complexes

New hydrazonoyl chloride derivatives were prepared and characterized. Their VO(II) complexes were isolated after adjusting reaction medium to slightly basic by 0.5?g acetate. Neutral tridentate mode is a general coordination feature of ligands towards bin

Synthesis, in vitro and in Silico studies of some novel 5-nitrofuran-2-yl hydrazones as antimicrobial and antitubercular agents

In this study, we synthesized two series of novel 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e in addition to a third series of thiophene-2-carbohydrazides 23a-g to develop potent antimicrobial and/or antitubercular agents. The newly synthesized compounds were evaluated in vitro for their antimicrobial and antimycobacterial activities. Most of the 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e displayed variable activity against Aspergillus fumigates, Staphylococcus aureus, Streptococcus pneumonia, Bacillis subtilis, Salmonella typhimurium, Klebsiella pneumonia, Escherichia coli and Mycobacterium tuberculosis. The sulfonamide derivative 21f exhibited superior potency and broad-spectrum antimicrobial activity with minimum inhibitory concentration (MIC)=0.06-0.98 μg/mL and antimycobacterial activity with MIC=3.9 μg/mL. The 5-nitrofuran-2-carbohydrazides 21a, b, g, h and 22a-c exhibited significant antibacterial activity with MIC values in the range of 0.12-7.81 μg/mL. The significances of the 5-nitrofuran moiety and sulfonamide function were explored via the structure-activity relationship (SAR) study. In addition, docking studies revealed that the p-amino benzoic acid (PABA) and binding pockets of the dihydropteroate synthase (DHPS) were successfully occupied by compound 21f. Furthermore, two quantitative structure-activity relationship (QSAR) models were built to explore the structural requirements which controlled the activity.

A facile one-pot synthesis of model diethyl 6,6'-dioxotetrahydro-5,5'-bi(1, 2,4-triazine)-5,5'-dicarboxylates

The reaction of diethyl aminomalonate with nitrile imine 1,3-dipolar species 1a,b follows a stereospecific path to deliver the racemic tetrahydro-6,6'-dioxo-5,5'-bi(1,2,4-triazine)-5,5'-dicarboxylates 4a,b, whilst the corresponding diastereomeric meso forms (5R, 5'S) could not be detected in the reaction product. Structural assignments for these novel heterocyclic dimers are based on microanalytical and spectral (MS, NMR) data, and further confirmed by X-ray diffraction analysis of single crystal for 4a.

Synthesis, antitumor activity, and electrochemical behavior of some piperazinyl amidrazones

New piperazinyl amidrazones have been synthesized by direct interaction of the corresponding aryl hydrazones with the appropriate piperazine. On the basis of preliminary screening data for these new compounds, the antitumor activity of 1-(4-methylpiperazi

Reaction of nitrilimines with alkoxycarbonyl-hydrazines: Synthesis of 6-acetyl-4-aryl-2-ethoxycarbonyl-1,2,3,4-tetrahydro-s-tetrazines

Nitrilimines 2 are found to react with alkoxycarbonylhydrazines 3-5 to afford the acyclic adducts 6-8. 6c is oxidized upon heating with charcoal in refluxing toluene to the corresponding formazan 9c. Compounds 8 cyclize upon heating with charcoal in reflu

HETEROCYCLES FROM NITRILE IMINES. PART IV. CHIRAL 4,5-DIHYDRO-1,2,4-TRIAZIN-6-ONES

The reaction of nitrile imines (II) with α-amino esters (III) proceeds with no detectable racemization and constitutes a convenient synthetic route to 4,5-dihydro-1,2,4-triazin-6-ones (IV).Permangamate oxidation of heterocycles (IV) affords the corresponding 1,2,4-triazin-6-ones (V).The reaction of (II) with β-amino esters gives the respective acyclic amidrazone adducts (VI).