2702-58-1

Usage

Chemical Properties

pale yellow crystalline powder

Synthesis Reference(s)

Synthetic Communications, 12, p. 1139, 1982 DOI: 10.1080/00397918208065981

InChI:InChI=1/C8H6N2O6/c1-16-8(11)5-2-6(9(12)13)4-7(3-5)10(14)15/h2-4H,1H3

Upstream product

• 67-56-1 methanol 
• 99-34-3 3,5-dinitrobenzoic acid 
• 42444-51-9 3,5-dinitrobenzoyl azide 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 1825-61-2 Trimethylmethoxysilane 
• 49791-30-2 3,5-dinitro-benzoyl bromide 
• 4110-35-4 3,5-dinitrobenzonitrile 
• 124-41-4 sodium methylate 
• 931-53-3 Cyclohexyl isocyanide 
• 616-42-2 dimethylsulfite 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 594-09-2 trimethylphosphane 
• 618-95-1 methyl 3-nitrobenzoate 

Downstream Products

• 23218-93-1 3-amino-5-nitro-benzoic acid methyl ester 
• 2900-63-2 3,5-dinitrobenzohydrazide 
• 15573-49-6 3,5-dinitrobenzoate^(1-) 
• 99-34-3 3,5-dinitrobenzoic acid 
• 71466-55-2 1-(1-Adamantyl)-3-methoxycarbonyl-5-nitrobenzol 
• 21903-30-0 methyl 3,5-N,N,N',N'-tetramethylaminobenzoate 
• 618-71-3 ethyl 3,5-dinitrobenzoate 
• 5930-92-7 Ethyl 4-nitropyrrole-2-carboxylate 
• 110842-66-5 N⁽⁴⁾-(4-chlorophenyl)-N⁽¹⁾-(3,5-dinitrobenzoyl)thiosemicarbazide 

Relevant academic research and scientific papers

MECHANISM OF THE REACTION OF 3,5-DINITROBENZONITRILE WITH SODIUM METHOXIDE IN METHANOL.

The reaction of 3,5-dinitrobenzonitrile in a methanolic solution containing a low sodium-methoxide concentration has been reinvestigated. The final product has been found to be methoxy (3,5-dinitrophenyl)methanimine, which is produced by a catalytic reaction. The reaction mechanism has been presented for the formation of the Meisenheimer complexes and the final product in the reaction system. The rate and thermodynamic stabilites for their formation have been discussed on the basis of the LUMO coefficients of 3,5-dinitrobenzonitrile and from the relative potential energies of their formation respectively, considering also the solvent effects.

GENERAL BASE CATALYSES BY α-CYCLODEXTRIN IN THE HYDROLYSES OF ALKYL BENZOATES

The hydrolyses of seven alkyl benzoates are catalyzed by α-cyclodextrin.These results indicate that the general base catalysis by α-cyclodextrin, previously found for the first time in the hydrolysis of 2,2,2-trifluoroethyl 4-nitrobenzoate, is applicable to other alkyl esters.

Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids

The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.

New diarylsulfonamide inhibitors of Leishmania infantum amastigotes

New drugs against visceral leishmaniasis with mechanisms of action differing from existing treatments and with adequate cost, stability, and properties are urgently needed. No antitubulin drug is currently in the clinic against Leishmania infantum, the causative agent of visceral leishmaniasis in the Mediterranean area. We have designed and synthesized a focused library of 350 compounds against the Leishmania tubulin based on the structure-activity relationship (SAR) and sequence differences between host and parasite. The compounds synthesized are accessible, stable, and appropriately soluble in water. We assayed the library against Leishmania promastigotes, axenic, and intracellular amastigotes and found 0, 8, and 16 active compounds, respectively, with a high success rate against intracellular amastigotes of over 10%, not including the cytotoxic compounds. Five compounds have a similar or better potency than the clinically used miltefosine. 14 compounds showed a host-dependent mechanism of action that might be advantageous as it may render them less susceptible to the development of drug resistance. The active compounds cluster in five chemical classes that provide structure-activity relationships for further hit improvement and facilitate series development. Molecular docking is consistent with the proposed mechanism of action, supported by the observed structure-activity relationships, and suggests a potential extension to other Leishmania species due to sequence similarities. A new family of diarylsulfonamides designed against the parasite tubulins is active against Leishmania infantum and represents a new class of potential drugs with favorable cost, stability, and aqueous solubility for the treatment of visceral leishmaniasis (VL). These results could be extended to other clinically relevant species of Leishmania spp.

Discovery of (3-Benzyl-5-hydroxyphenyl)carbamates as new antitubercular agents with potent in vitro and in vivo efficacy

A series of 3-amino-5-benzylphenol derivatives were designed and synthesized. Among them, (3-benzyl-5-hydroxyphenyl)carbamates were found to exert good inhibitory activity against M. tuberculosis H37Ra, H37Rv and clinically isolated multidrug-resistant M. tuberculosis strains (MIC = 0.625-6.25 μg/mL). The privileged compounds 3i and 3l showed moderate cytotoxicity against cell line A549. Compound 3l also exhibited potent in vivo inhibitory activity on a mouse infection model via the oral administration. The results demonstrated 3-hydroxyphenylcarbamates as a class of new antitubercular agents with good potential.

Synthesis and antimicrobial activity of piperine analogues containing 1,2,4-triazole ring

A series 1,2,4-triazole piperine analogues (TP1-TP6) were designed and synthesized. The structures were confirmed using 1H NMR and 13C NMR. Antibacterial study was done using Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative microorganisms (E. coli and Pseudomonas aeruginosa) by disc diffusion method. Compound containing chloro substitution (TP6) showed the highest effect, while compound TP1, TP3, TP4, TP5 showed the moderate activity.

Efficient synthesis of esters through oxone-catalyzed dehydrogenation of carboxylic acids and alcohols

Since esters are important organic synthesis intermediates, an environmentally friendly oxone catalyzed-esterification of carboxylic acids with alcohols has been developed. A series of carboxylic acid esters are obtained in high yield. This strategy requires mild reaction conditions, providing an attractive alternative for the construction of valuable carbonyl esters. Electron-rich and electron-deficient groups are compatible with the standard conditions and a variety of substrates are demonstrated. Moreover, the reaction could easily be adapted to typical prodrugs, drugs and gram-scale synthesis.

Structural design, synthesis and substituent effect of hydrazone-N-acylhydrazones reveal potent immunomodulatory agents

4-(Nitrophenyl)hydrazone derivatives of N-acylhydrazone were synthesized and screened for suppress lymphocyte proliferation and nitrite inhibition in macrophages. Compared to an unsubstituted N-acylhydrazone, active compounds were identified within initial series when hydroxyl, chloride and nitro substituents were employed. Structure-activity relationship was further developed by varying the position of these substituents as well as attaching structurally-related substituents. Changing substituent position revealed a more promising compound series of anti-inflammatory agents. In contrast, an N-methyl group appended to the 4-(nitrophenyl)hydrazone moiety reduced activity. Anti-inflammatory activity of compounds is achieved by modulating IL-1β secretion and prostaglandin E2 synthesis in macrophages and by inhibiting calcineurin phosphatase activity in lymphocytes. Compound SintMed65 was advanced into an acute model of peritonitis in mice, where it inhibited the neutrophil infiltration after being orally administered. In summary, we demonstrated in great details the structural requirements and the underlying mechanism for anti-inflammatory activity of a new family of hydrazone-N-acylhydrazone, which may represent a valuable medicinal chemistry direction for the anti-inflammatory drug development in general.

Design, synthesis, and biological evaluation of m-amidophenol derivatives as a new class of antitubercular agents

A series of m-amidophenol derivatives (6a-6l, 7a-7q, 9a, 9b, 12a-12c, 14 and 15) were designed and synthesized. Their antitubercular activities were evaluated in vitro against M. tuberculosis strains H37Ra and H37Rv and clinically isolated multidrug-resistant M. tuberculosis strains. Ten compounds displayed minimal inhibitory concentrations (MICs) against M. tuberculosis H37Ra below 2.5 μg mL?1 and 6g was the most active compound (MIC = 0.625 μg mL?1). Compounds 6g and 7a also showed potent inhibitory activity against M. tuberculosis H37Rv (MIC = 0.39 μg mL?1) and several clinically isolated multidrug-resistant M. tuberculosis strains (MIC = 0.39-3.125 μg mL?1). The compounds did not show inhibitory activity against normal Gram-positive and Gram-negative bacteria. They exhibited low cytotoxicity against HepG2 and RAW264.7 cell lines. The results demonstrated m-amidophenol as an attractive scaffold for the development of new antitubercular agents.

S-substituted 3,5-dinitrophenyl 1,3,4-oxadiazole-2-thiols and tetrazole-5-thiols as highly efficient antitubercular agents

Two new classes of antitubercular agents, namely 5-alkylsulfanyl-1-(3,5-dinitrophenyl)-1H-tetrazoles and 2-alkylsulfanyl-5-(3,5-dinitrophenyl)-1,3,4-oxadiazoles, and their structure-activity relationships are described. These compounds possessed excellent activity against Mycobacterium tuberculosis, including the clinically isolated multidrug (MDR) and extensively drug-resistant (XDR) strains, with no cross resistance with first or second-line anti-TB drugs. The minimum inhibitory concentration (MIC) values of the most promising compounds reached 0.03 μM. Furthermore, these compounds had a highly selective antimycobacterial effect because they were completely inactive against 4 gram positive and 4 gram negative bacteria and eight fungal strains and had low in vitro toxicity for four mammalian cell lines, including hepatic cell lines HepG2 and HuH7. Although the structure-activity relationship study showed that the presence of two nitro groups is highly beneficial for antimycobacterial activity, the analogues with a trifluoromethyl group instead of one of the nitro groups maintained a high antimycobacterial activity, which indicates the possibility for further structural optimization of this class of antitubercular agents.