Page last updated: 2024-12-08

1,4-dimethyl-6-nitro-9H-carbazole

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

1,4-dimethyl-6-nitro-9H-carbazole is an organic compound with the chemical formula C14H12N2O2. Here's a breakdown of its structure and significance:

**Structure:**

* **Carbazole core:** The molecule is based on the carbazole structure, a tricyclic aromatic compound. This core consists of three fused rings: two benzene rings and a five-membered pyrrole ring.
* **Substituents:** The core carbazole is modified with the following substituents:
* **Methyl groups (CH3):** Two methyl groups are attached at positions 1 and 4 on the carbazole ring.
* **Nitro group (NO2):** A nitro group is attached at position 6 on the carbazole ring.
* **Hydrogen atom:** A hydrogen atom is attached at position 9, giving the molecule its 9H designation.

**Importance in Research:**

1,4-dimethyl-6-nitro-9H-carbazole has gained significant research interest due to its potential applications in various fields, including:

* **Organic Electronics:**
* **Organic semiconductors:** This molecule exhibits semiconductor properties, making it useful in the development of organic transistors, solar cells, and other organic electronic devices.
* **Charge transport:** The presence of the nitro group enhances electron-withdrawing capabilities, leading to improved charge transport properties.
* **Organic light-emitting diodes (OLEDs):** Carbazole derivatives like this are used in OLED technology for their ability to emit light efficiently.

* **Materials Science:**
* **Polymer chemistry:** Carbazole derivatives are employed as monomers in the synthesis of polymers with specific properties, such as conductivity, fluorescence, and thermal stability.
* **Metal-organic frameworks (MOFs):** Carbazole-based ligands can be used to synthesize MOFs with interesting properties, like gas storage and catalysis.

* **Medicinal Chemistry:**
* **Drug discovery:** The nitrogen atom in the carbazole core and the electron-withdrawing nature of the nitro group make this molecule a potential pharmacophore for developing new drugs.
* **Antimicrobial activity:** Some carbazole derivatives exhibit antimicrobial activity against bacteria and fungi.

**Ongoing Research:**

Researchers are continuously exploring the potential of 1,4-dimethyl-6-nitro-9H-carbazole and related compounds for various applications. These include:

* **Tuning electronic properties:** Exploring modifications to the carbazole core and substituents to optimize its conductivity and charge transport properties.
* **Developing novel materials:** Synthesizing new carbazole-based polymers and MOFs with enhanced functionality.
* **Identifying biological targets:** Investigating the interaction of this molecule with various biological targets to develop potential therapeutic agents.

**Note:** While this compound shows promise in various research areas, further research is needed to fully understand its potential and develop practical applications.

Cross-References

ID SourceID
PubMed CID154436
CHEMBL ID1484180
CHEBI ID108495
SCHEMBL ID15202149

Synonyms (16)

Synonym
1,4-dimethyl-6-nitro-9h-carbazole
smr000126250
MLS000541392
9h-carbazole, 1,4-dimethyl-6-nitro-
5,8-dimethyl-3-nitrocarbazole
CHEBI:108495
AKOS005081577
NCGC00246582-01
133591-38-5
ccris 8641
HMS2342G16
CHEMBL1484180
12W-0853
SCHEMBL15202149
Q27187383
DTXSID20158193
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
carbazoles
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency6.30960.044717.8581100.0000AID485341
Chain A, Ferritin light chainEquus caballus (horse)Potency50.11875.623417.292931.6228AID485281
glp-1 receptor, partialHomo sapiens (human)Potency12.58930.01846.806014.1254AID624417
TDP1 proteinHomo sapiens (human)Potency16.46870.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency18.85410.180013.557439.8107AID1460; AID1468
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency12.58930.28189.721235.4813AID2326
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency10.32250.00419.984825.9290AID504444
importin subunit beta-1 isoform 1Homo sapiens (human)Potency35.48135.804836.130665.1308AID540263
snurportin-1Homo sapiens (human)Potency35.48135.804836.130665.1308AID540263
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency79.43280.050127.073689.1251AID588590
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency35.48130.00798.23321,122.0200AID2551
VprHuman immunodeficiency virus 1Potency39.81071.584919.626463.0957AID651644
lamin isoform A-delta10Homo sapiens (human)Potency35.48130.891312.067628.1838AID1487
TAR DNA-binding protein 43Homo sapiens (human)Potency2.51191.778316.208135.4813AID652104
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
negative regulation of protein phosphorylationTAR DNA-binding protein 43Homo sapiens (human)
mRNA processingTAR DNA-binding protein 43Homo sapiens (human)
RNA splicingTAR DNA-binding protein 43Homo sapiens (human)
negative regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
regulation of protein stabilityTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of insulin secretionTAR DNA-binding protein 43Homo sapiens (human)
response to endoplasmic reticulum stressTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of protein import into nucleusTAR DNA-binding protein 43Homo sapiens (human)
regulation of circadian rhythmTAR DNA-binding protein 43Homo sapiens (human)
regulation of apoptotic processTAR DNA-binding protein 43Homo sapiens (human)
negative regulation by host of viral transcriptionTAR DNA-binding protein 43Homo sapiens (human)
rhythmic processTAR DNA-binding protein 43Homo sapiens (human)
regulation of cell cycleTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA destabilizationTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA stabilizationTAR DNA-binding protein 43Homo sapiens (human)
nuclear inner membrane organizationTAR DNA-binding protein 43Homo sapiens (human)
amyloid fibril formationTAR DNA-binding protein 43Homo sapiens (human)
regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
double-stranded DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
RNA bindingTAR DNA-binding protein 43Homo sapiens (human)
mRNA 3'-UTR bindingTAR DNA-binding protein 43Homo sapiens (human)
protein bindingTAR DNA-binding protein 43Homo sapiens (human)
lipid bindingTAR DNA-binding protein 43Homo sapiens (human)
identical protein bindingTAR DNA-binding protein 43Homo sapiens (human)
pre-mRNA intronic bindingTAR DNA-binding protein 43Homo sapiens (human)
molecular condensate scaffold activityTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
intracellular non-membrane-bounded organelleTAR DNA-binding protein 43Homo sapiens (human)
nucleusTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
perichromatin fibrilsTAR DNA-binding protein 43Homo sapiens (human)
mitochondrionTAR DNA-binding protein 43Homo sapiens (human)
cytoplasmic stress granuleTAR DNA-binding protein 43Homo sapiens (human)
nuclear speckTAR DNA-binding protein 43Homo sapiens (human)
interchromatin granuleTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
chromatinTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.56 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]