1443321-11-6

Basic information

• Product Name: N′-[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]-3-(2-methyl-1H-benzimidazol-1-yl)propanehydrazide)
• Synonyms: 2-[(2-Hydroxy-1-naphthalenyl)methylene]hydrazide-2-methyl-1H-Benzimidazole-1-propanoic acid;Divin;N′-[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]-3-(2-methyl-1H-benzimidazol-1-yl)propanehydrazide);(E)-N-((2-hydroxynaphthalen-1-yl)methylene)-3-(2-methyl-1H-benzo[d]imidazol-1-yl)propanehydrazide
• CAS NO: 1443321-11-6
• Molecular Formula: C22H20N4O2
• Molecular Weight: 372.42
• Mol File: 1443321-11-6.mol
• Article Data: 1

Chemical Properties

• Appearance: white to beige/
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble20mg/mL, clear
• PKA: 7.89±0.50(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: N′-[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]-3-(2-methyl-1H-benzimidazol-1-yl)propanehydrazide)(CAS DataBase Reference)
• NIST Chemistry Reference: N′-[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]-3-(2-methyl-1H-benzimidazol-1-yl)propanehydrazide)(1443321-11-6)
• EPA Substance Registry System: N′-[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]-3-(2-methyl-1H-benzimidazol-1-yl)propanehydrazide)(1443321-11-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1443321-11-6(Hazardous Substances Data)

Usage

Description

N′-[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]-3-(2-methyl-1H-benzimidazol-1-yl)propanehydrazide) is a complex organic compound characterized by its unique molecular structure. It is a derivative of hydrazides, which are known for their diverse applications in various fields due to their reactivity and ability to form chelates with metal ions.
Used in Pharmaceutical Industry:
N′-[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]-3-(2-methyl-1H-benzimidazol-1-yl)propanehydrazide) is used as a pharmaceutical candidate for the development of new drugs targeting bacterial infections. Its application is based on its ability to chelate iron, cobalt, and copper, which are essential for bacterial growth and division. By chelating these metals, the compound arrests the late stages of cytokinesis in bacteria, blocking the physical process of constriction in dividing cells without affecting FtsZ. This mechanism of action can potentially lead to the development of new antibiotics or adjuvant therapies to combat antibiotic resistance.
Used in Research Applications:
In addition to its potential pharmaceutical applications, N′-[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]-3-(2-methyl-1H-benzimidazol-1-yl)propanehydrazide) can also be used in research settings to study the effects of metal chelation on bacterial cell division and the role of metal ions in cytokinesis. N′-[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]-3-(2-methyl-1H-benzimidazol-1-yl)propanehydrazide) can serve as a valuable tool for understanding the molecular mechanisms underlying bacterial growth and the development of antibiotic resistance.
Used in Material Science:
The unique structure and metal-chelating properties of N′-[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]-3-(2-methyl-1H-benzimidazol-1-yl)propanehydrazide) may also find applications in material science, particularly in the development of new materials with antimicrobial properties. By incorporating this compound into various materials, it may be possible to create surfaces or coatings that inhibit bacterial growth, which could have applications in healthcare, food packaging, and other industries where controlling microbial contamination is important.

References

1) Eun?et al.?(2013)?Divin: A small molecule inhibitor of bacterial divisome assembly; J. Am. Chem. Soc.?135?9768 2) Santos?et al.?(2018)?Small Molecule Chelators Reveal That Iron Starvation Inhibits Late Stages of Bacterial Cytokinesis; ACS Chem. Biol.?13?235

Upstream product

• 138942-42-4 methyl-3-(2-methyl-1H-1,3-benzodiazol-1-yl)propanoate 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 

Relevant articles and documents

Structure-activity studies of divin: An inhibitor of bacterial cell division

We describe the synthesis and structure-activity relationship (SAR) studies of divin, a small molecule that blocks bacterial division by perturbing the assembly of proteins at the site of cell septation. The bacteriostatic mechanism of action of divin is distinct from other reported inhibitors of bacterial cell division and provides an opportunity for assessing the therapeutic value of a new class of antimicrobial agents. We demonstrate a convenient synthetic route to divin and its analogues, and describe compounds with a 10-fold increase in solubility and a 4-fold improvement in potency. Divin analogues produce a phenotype that is identical to divin, suggesting that their biological activity comes from a similar mechanism of action. Our studies indicate that the 2-hydroxynaphthalenyl hydrazide portion of divin is essential for its activity and that alterations and substitution to the benzimidazole ring can increase its potency. The SAR study provides a critical opportunity to isolate drug resistant mutants and synthesize photoaffinity probes to determine the cellular target and biomolecular mechanism of divin.