The Diverse Biological Activity of Recently Synthesized Nitro Compounds

Abstract

The search for new and efficient pharmaceuticals is a constant struggle for medicinal chemists. New substances are needed in order to treat different pathologies affecting the health of humans and animals, and these new compounds should be safe, effective and have the fewest side effects possible. Some functional groups are known for having biological activity; in this matter, the nitro group (NO2) is an efficient scaffold when synthesizing new bioactive molecules. Nitro compounds display a wide spectrum of activities that include antineoplastic, antibiotic, antihypertensive, antiparasitic, tranquilizers and even herbicides, among many others. Most nitro molecules exhibit antimicrobial activity, and several of the compounds mentioned in this review may be further studied as lead compounds for the treatment of H. pylori, P. aeruginosa, M. tuberculosis and S. mutans infections, among others. The NO2 moiety triggers redox reactions within cells causing toxicity and the posterior death of microorganisms, not only bacteria but also multicellular organisms such as parasites. The same effect may be present in humans as well, so the nitro groups can be considered both a pharmacophore and a toxicophore at the same time. The role of the nitro group itself also has a deep effect on the polarity and electronic properties of the resulting molecules, and hence favors interactions with some amino acids in proteins. For these reasons, it is fundamental to analyze the recently synthesized nitro molecules that show any potential activity in order to develop new pharmacological treatments that enhance human health.

Synthesis and Biological Evaluation of Some Hydrazide-Hydrazone Derivatives as Anticancer Agents

“…It has been determined that the nitro group of the compounds at the para and meta position shows higher efficiency than the ortho position due to the steric effect. 23,24 On the other hand, compound 3h has a pyrrole ring as a heteroaromatic ring in its structure and showed the highest cytotoxic activity against all cancer cell lines selectively, regardless of the above-mentioned structure-activity relationship.…”

Nitrostilbenes: Synthesis and Biological Evaluation as Potential Anti-Influenza Virus Agents

“…These compounds contain a nitro group at the R4 position. Recently, Saúl Noriega et al conducted a large analysis on the role of nitro function in medicinal chemistry [40]. The nitro group has a high electron-withdrawing ability by means of both resonance and inductive properties, [41] affecting the biological and pharmacokinetic profiles.…”

Intramolecular Hydrogen Bonding Effect on the Electron-Transfer Thermodynamics of a Series of o-Nitrobenzyl Alcohol Derivatives

“…5,7 The ultimate biological effect of nitro-containing compound will depend both on their relative stability and their reactivity against the specific biological target; therefore, incorporating a nitro group into a drug or bioactive agent can be a double-edged sword. 4,5 An increasing number of nitro-containing drugs is under development due to its promising leads in medicinal chemistry, owing to their antineoplastic, 6 antibiotic or antiparasitic activities, 8−11 and among other beneficial effects. 12,13 The specificity of the interaction with biomolecular targets and their therapeutic activity has been directly related with their capacity of forming hydrogen bonds.…”

“…The nitro group plays a preponderant role in a wide range of applications, ranging from material sciences , to medicinal chemistry , due to its unique ability to interact with biomolecules in various forms. Its electrophilic nature causes electrophilic sites that may interact with biological nucleophiles, such as proteins, enzymes, amino acids, or nucleic acids. ,, This group can be involved in non-covalent interactions, such as intra- and inter-molecular hydrogen bonding, or an enzymatic in vivo electron uptake, giving rise to highly reactive reduced compounds. , The ultimate biological effect of nitro-containing compound will depend both on their relative stability and their reactivity against the specific biological target; therefore, incorporating a nitro group into a drug or bioactive agent can be a double-edged sword. , …”