BROQUINALDOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H7Br2NO
Molecular Weight	316.977
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NC2=C(C=C1)C(Br)=CC(Br)=C2O

InChI

InChIKey=BNACJQWJZKPAPV-UHFFFAOYSA-N

InChI=1S/C10H7Br2NO/c1-5-2-3-6-7(11)4-8(12)10(14)9(6)13-5/h2-4,14H,1H3

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27018907 | https://www.ncbi.nlm.nih.gov/pubmed/24269165 | https://www.ncbi.nlm.nih.gov/pubmed/22170715

Broquinaldol is a halogenated derivative of quinoline and a member of the class of compounds known as halogenated phenazines. Broquinaldol and related compounds have demonstrated efficacy against antibiotic-tolerant bacterial biofilms and Mycobacterium tuberculosis. Against several bacterial strains, broquinaldol had a minimum inhibitory concentration of 0.78 microM. Broquinaldol was also identified as having antiproliferative activity against thyroid cancer cells in vitro.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24269165 https://www.ncbi.nlm.nih.gov/pubmed/27018907	Primary		Basic research	Unknown Approved Use Unknown
Thyroid cancer 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22170715	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antimicrobial activities of some amino derivatives of 5,7-dibromo-2-methyl-8-hydroxyquinoline.	2000 Feb	10706397
Quantitative high-throughput drug screening identifies novel classes of drugs with anticancer activity in thyroid cancer cells: opportunities for repurposing.	2012 Mar	22170715
Preparation of 8-hydroxyquinoline derivatives as potential antibiotics against Staphylococcus aureus.	2014 Jan 1	24269165
Structure-Activity Relationships of a Diverse Class of Halogenated Phenazines That Targets Persistent, Antibiotic-Tolerant Bacterial Biofilms and Mycobacterium tuberculosis.	2016 Apr 28	27018907

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Bromoquinaldol and other related compounds were screened for antibacterial properties against a panel of pathogenic bacteria, including: S. aureus, S. epidermidis, Enterococcus faecium, Acinetobacter baumannii, Pseudomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli. Minimum Inhibitory concentration was determined by the broth dilution method and included a bacterial inoculation with 10^5 bacterial cells prepared from fresh log phase cultures. The tested concentration range for Bromoquinaldol was 0.10 to 100 microM. Bromoquinaldol showed a MIC of 0.78 microM for most bacterial strains, and 25 microM against antibiotic-resistant M. tuberculosis.

Name

Type

Language

BROQUINALDOL

Official Name

English

5,7-DIBROMO-2-METHYL-8-QUINOLINOL

Systematic Name

English

Broquinaldol [WHO-DD]

Common Name

English

broquinaldol [INN]

Common Name

English

NSC-85838

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C254