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Usage

Uses

Used in Pharmaceutical Applications:
HNBM is used as a pharmaceutical compound for its antioxidant, anti-inflammatory, and antipyretic activities. Its potential therapeutic applications include the treatment of various diseases such as cancer and diabetes.
Used in Antimicrobial Applications:
In the field of antimicrobials, HNBM is used as an agent to inhibit the growth of certain bacteria and fungi, showcasing its potential in combating infections and contributing to the development of new antimicrobial drugs.
Used in Research and Development:
HNBM is utilized in research and development for further exploration of its full potential in medical and pharmaceutical applications. Ongoing studies aim to uncover additional uses and optimize its effectiveness in various therapeutic areas.

Upstream product

• 936-02-7 2-Hydroxybenzoylhydrazine 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 119-36-8 methyl salicylate 
• 2283-08-1 2-hydroxy-1-naphthalenecarboxylic acid 
• 5386-25-4 1-hydroxymethyl-2-naphthol 
• 69-72-7 salicylic acid 

Relevant academic research and scientific papers

Structure and biological properties of mixed-ligand Cu(II) Schiff base complexes as potential anticancer agents

We synthesized two mixed-ligand Cu(II) complexes containing different aroylhydrazone ligands and a pyridine co-ligand, namely, [Cu(L1)(Py)] (C1) and [Cu(L2)(Py)(Br)] (C2) (L1?= (E)-2-hydroxy-N′-((2-hydroxynaphthalen-1-yl)methylene)benzohydrazide, Py?=?pyr

METHOD OF MODULATING RIBONUCLEOTIDE REDUCTASE

A method of modulating ribonucleotide reductase activity in a neoplastic cell includes administering to the cell an amount of a hydrazone or hydrazine ribonucleotide reductase modulator (RRmod), the amount being effective to inhibit neoplastic cell growth.

Structure-guided design of anti-cancer ribonucleotide reductase inhibitors

Ribonucleotide reductase (RR) catalyses the rate-limiting step of dNTP synthesis, establishing it as an important cancer target. While RR is traditionally inhibited by nucleoside-based antimetabolites, we recently discovered a naphthyl salicyl acyl hydrazone-based inhibitor (NSAH) that binds reversibly to the catalytic site (C-site). Here we report the synthesis and in vitro evaluation of 13 distinct compounds (TP1-13) with improved binding to hRR over NSAH (TP8), with lower KD’s and more predicted residue interactions. Moreover, TP6 displayed the greatest growth inhibiting effect in the Panc1 pancreatic cancer cell line with an IC50 of 0.393 μM. This represents more than a 2-fold improvement over NSAH, making TP6 the most potent compound against pancreatic cancer emerging from the hydrazone inhibitors. NSAH was optimised by the addition of cyclic and polar groups replacing the naphthyl moiety, which occupies the phosphate-binding pocket in the C-site, establishing a new direction in inhibitor design.

Structure-Guided Synthesis and Mechanistic Studies Reveal Sweetspots on Naphthyl Salicyl Hydrazone Scaffold as Non-Nucleosidic Competitive, Reversible Inhibitors of Human Ribonucleotide Reductase

Ribonucleotide reductase (RR), an established cancer target, is usually inhibited by antimetabolites, which display multiple cross-reactive effects. Recently, we discovered a naphthyl salicyl acyl hydrazone-based inhibitor (NSAH or E-3a) of human RR (hRR) binding at the catalytic site (C-site) and inhibiting hRR reversibly. We herein report the synthesis and biochemical characterization of 25 distinct analogs. We designed each analog through docking to the C-site of hRR based on our 2.7 ? X-ray crystal structure (PDB ID: 5TUS). Broad tolerance to minor structural variations preserving inhibitory potency is observed. E-3f (82% yield) displayed an in vitro IC50 of 5.3 ± 1.8 μM against hRR, making it the most potent in this series. Kinetic assays reveal that E-3a, E-3c, E-3t, and E-3w bind and inhibit hRR through a reversible and competitive mode. Target selectivity toward the R1 subunit of hRR is established, providing a novel way of inhibition of this crucial enzyme.

Multiple Hydrogen Bonds Promoted ESIPT and AIE-active Chiral Salicylaldehyde Hydrazide

The simpler, the better! A series of simple and highly fluorescent salicylaldehyde hydrazide molecules (41 samples) have been designed and prepared. Even though these soft materials contain a very small π-conjugated system, they can go through multiple intramolecular and intermolecular hydrogen bonds promoted excited-state intramolecular proton-transfer (ESIPT) to display strong blue, green, yellow, and orange aggregation-induced emission (AIE) with large Stokes shifts (up to 184 nm) and high fluorescence quantum yields (Ф up to 0.20). Unusual mechanochromic fluorescence enhancements are also found in some solid samples. Through coordination, hydrogen and halogen bonds, these flexible molecules can be used as Mg2+ (Ф up to 0.46) probes, universal anion (Ф up to 0.14) and unprotected amino acids (Ф up to 0.16) probes, and chiral diamine (enantiomeric selectivity and Ф up to 0.36 and 0.062, respectively) receptors. Combining their advantages of AIE and biocompatibility, these low cytotoxic dyes have potential application in living cell imaging. Furthermore, the effects of different functional groups on the molecule arrangement, ESIPT, AIE, probe, and chiral recognition properties are also examined, which provide a simple and bright paradigm for the design of multiple-stimuli-responsive smart materials.

METHOD OF MODULATING RIBONUCLEOTIDE REDUCTASE

A method of modulating ribonucleotide reductase activity in a neoplastic cell includes administering to the cell an amount of a ribonucleotide reductase modulator (RRmod), the amount being effective to inhibit neoplastic cell growth.

Synthesis, antioxidant activity and fluorescence properties of novel europium complexes with (E)-2- or 4-hydroxy-N'-[(2-hydroxynaphthalen-1-yl) methylene]benzohydrazide schiff base

Two novel Eu(III) complexes with notable properties have been successfully prepared with hydrazone Schiff base ligands, (E)-2-hydroxy-N'-[(2- hydroxynaphthalen-1-yl)methylene]benzohydrazide (3a) and (E)-4-hydroxy- N'-[(2-hydroxynaphthalen-1-yl)methylene]benzohydrazide (3b). DFT, FMO energy and Mulliken charge distribution studies of the ligands allowed us to hypothesize that their HC=N, >C=O and -OH (naphthyl) groups were involved in coordinating with the Eu3+ ion. The eight coordination sites of the Eu3+ ion were occupied by the three functional groups of the two ligands (3a or 3b) mentioned above and two water molecules. Similar UV, IR and fluorescence spectra indicated the presence of comparable coordination environments for the Eu3+ ion in both complexes. Both the ligands and their complexes exhibited moderate DPPH radical scavenging activity. Moreover, it was found that the Eu(III) complexes exhibited fluorescence properties.