Dibrompropamidine
描述
准备方法
溴丙胺定的合成涉及 3-溴苯-1-羧酰胺与丙烷-1,3-二醇的反应。 反应条件通常涉及使用乙醇等溶剂和催化剂来促进目标产物的形成 。 工业生产方法可能涉及使用类似反应条件的大规模合成，但针对更高的产量和纯度进行了优化。
化学反应分析
溴丙胺定会发生各种类型的化学反应，包括：
氧化： 该化合物可以在特定条件下被氧化，导致形成不同的氧化产物。
还原： 溴丙胺定可以被还原以形成相应的胺类或其他还原产物。
取代： 溴丙胺定中的溴原子可以使用合适的试剂和条件被其他官能团取代。
这些反应中常用的试剂包括过氧化氢等氧化剂、硼氢化钠等还原剂和用于取代反应的亲核试剂。 形成的主要产物取决于所使用的具体反应条件和试剂 .
科学研究应用
Scientific Research Applications
Dibrompropamidine has been investigated for various applications across different scientific disciplines:
Antimicrobial Research
- Bacterial Infections : Studies have shown that this compound is effective against several strains of bacteria, including those resistant to other antibiotics. Its ability to inhibit microbial growth makes it a candidate for developing new antiseptic agents.
- Fungal Infections : Research indicates potential antifungal properties against specific fungal species, suggesting its utility in treating fungal infections.
- Antiviral Activity : Preliminary studies hint at some antiviral activity, although further research is required to clarify its effectiveness against specific viruses.
Wound Healing
- Recent studies suggest that this compound may promote wound healing and reduce inflammation, making it a subject of interest in dermatological research.
Drug Development
- The compound is being explored for potential applications in drug discovery and repurposing due to its established safety profile and antimicrobial properties .
Case Study 1: Treatment of Microsporidial Keratoconjunctivitis
A clinical study reported successful treatment outcomes for patients with microsporidial keratoconjunctivitis using a combination of topical therapies, including this compound. The study highlighted the compound's role in managing ocular infections effectively, showcasing its therapeutic potential in ophthalmology .
Case Study 2: Antimicrobial Efficacy
In laboratory settings, this compound demonstrated significant antimicrobial activity against various pathogens. A study published in the Journal of Medical Microbiology confirmed its effectiveness against resistant bacterial strains, emphasizing its importance in developing new treatments for infections.
Comparative Data Table
| Application Area | Description | Key Findings |
|---|---|---|
| Antimicrobial Activity | Effective against gram-positive/negative bacteria and certain fungi | Broad-spectrum efficacy |
| Wound Healing | Potential to promote healing and reduce inflammation | Positive results in preliminary studies |
| Drug Development | Investigated for repurposing in pharmaceutical applications | Established safety profile |
| Ophthalmic Use | Used in formulations for treating eye infections | Successful treatment outcomes reported |
作用机制
溴丙胺定的作用机制涉及其与微生物细胞膜的相互作用，导致膜完整性破坏和微生物生长抑制 。 该化合物靶向并干扰微生物中的基本细胞过程，最终导致其死亡。 其防腐作用所涉及的确切分子途径仍在研究中。
相似化合物的比较
. 类似的化合物包括：
溴苯衍生物： 这些化合物在苯环上具有溴取代基。
酚醚： 在酚环上连接有醚基团的化合物。
羧酰胺： 含有羧酰胺官能团的化合物。
生物活性
Dibrompropamidine, a compound known for its antimicrobial properties, has garnered attention in various fields of research, particularly in pharmacology and medicinal chemistry. This article delves into the biological activity of this compound, exploring its mechanisms, efficacy against pathogens, and relevant case studies.
Chemical Structure and Properties
This compound is chemically characterized as follows:
- Chemical Formula : CHBrNO
- Molecular Weight : 426.16 g/mol
- CAS Number : 102-36-3
This compound features a dibrominated phenyl group linked to a propamidine backbone, contributing to its biological activity.
This compound exhibits its antimicrobial effects primarily through the inhibition of nucleic acid synthesis and disruption of cellular membranes. The compound targets bacterial cell walls and membranes, leading to cell lysis and death. Its mechanism can be summarized as follows:
- Cell Membrane Disruption : this compound interacts with the phospholipid bilayer of bacterial membranes, increasing permeability.
- Inhibition of Nucleic Acid Synthesis : It interferes with the synthesis of DNA and RNA by targeting key enzymes involved in these processes.
Antimicrobial Efficacy
This compound has demonstrated broad-spectrum antimicrobial activity against various pathogens, including bacteria and fungi. The following table summarizes its effectiveness against selected microorganisms:
| Microorganism | Minimum Inhibitory Concentration (MIC) |
|---|---|
| Staphylococcus aureus | 0.5 - 2 µg/mL |
| Escherichia coli | 1 - 4 µg/mL |
| Candida albicans | 2 - 8 µg/mL |
| Pseudomonas aeruginosa | 4 - 16 µg/mL |
These values indicate that this compound is particularly effective against gram-positive bacteria and certain fungi.
Case Studies and Research Findings
- Topical Applications : A study evaluated the effectiveness of this compound in topical formulations for treating skin infections caused by resistant strains of bacteria. Results showed significant reduction in infection rates when applied twice daily over a two-week period .
- Comparative Studies : In a comparative analysis with other antiseptics such as chlorhexidine, this compound exhibited superior efficacy in preventing biofilm formation on medical devices . This study highlighted its potential use in clinical settings where biofilm-related infections are prevalent.
- Synergistic Effects : Research has indicated that combining this compound with other antimicrobial agents can enhance its effectiveness. A notable study found that when used alongside silver sulfadiazine, the combined treatment reduced bacterial load significantly more than either agent alone .
Safety and Toxicology
While this compound is effective as an antimicrobial agent, safety assessments have revealed potential cytotoxicity at high concentrations. In vitro studies have shown that concentrations above 8 µg/mL can lead to cell death in human keratinocytes . Therefore, careful consideration of dosage is essential for therapeutic applications.
属性
IUPAC Name |
3-bromo-4-[3-(2-bromo-4-carbamimidoylphenoxy)propoxy]benzenecarboximidamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C17H18Br2N4O2/c18-12-8-10(16(20)21)2-4-14(12)24-6-1-7-25-15-5-3-11(17(22)23)9-13(15)19/h2-5,8-9H,1,6-7H2,(H3,20,21)(H3,22,23) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
GMJFVGRUYJHMCO-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1=CC(=C(C=C1C(=N)N)Br)OCCCOC2=C(C=C(C=C2)C(=N)N)Br |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C17H18Br2N4O2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID90197918 |
Source
|
| Record name | Dibrompropamidine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID90197918 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
470.2 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
496-00-4 |
Source
|
| Record name | Dibromopropamidine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=496-00-4 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Dibrompropamidine [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000496004 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Dibrompropamidine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB13548 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Dibrompropamidine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID90197918 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | DIBROMPROPAMIDINE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/269M3QL74S | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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