7h-dibenzo(c,g)carbazole profile

7H-Dibenzo[c,g]carbazole is a tricyclic aromatic hydrocarbon with a carbazole core. It has been synthesized through various methods, including the condensation of 2-aminobiphenyl with 1,2-dichloroethane and the reaction of dibenzofuran with phenylhydrazine. This compound exhibits fluorescence properties and has been investigated for its potential applications in organic electronics, particularly in organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs). The compound's unique electronic structure and high thermal stability make it an attractive candidate for these applications. Furthermore, 7H-Dibenzo[c,g]carbazole has been explored for its potential biological activity, including its ability to inhibit the growth of certain cancer cell lines. Research efforts continue to explore its potential in various fields, including materials science, organic chemistry, and medicinal chemistry.'
```

ID Source	ID
PubMed CID	9134
CHEBI ID	82312
SCHEMBL ID	492860
MeSH ID	M0061280

Synonym
dibenzo(c,g)carbazole
7h-dibenzo(c,g)carbazole
3,4,5,6-dibenzocarbazole
7-aza-7h-dibenzo(c,g)fluorene
ccris 209
einecs 205-895-3
hsdb 5098
brn 0213015
nsc 87519
3,4:5,6-dibenzocarbazole
nsc-87519
wln: t d6 c6 b566 mmj
3,5,6-dibenzocarbazole
nsc87519
7h-dibenzo[c,g]carbazole
3,5,6-dibenzcarbazol
194-59-2
3,5,6-dibenzcarbazole
7-aza-7h-dibenzo[c,g]fluorene
7h-db(c,g)c
NCIOPEN2_005134
inchi=1/c20h13n/c1-3-7-15-13(5-1)9-11-17-19(15)20-16-8-4-2-6-14(16)10-12-18(20)21-17/h1-12,21h
stjxcdgcxvzhdu-uhfffaoysa-
C19221
unii-9shh23m02s
unii-szf1oji89d
szf1oji89d ,
FT-0614184
AKOS015913990
7h-dibenzo(c,g)carbazole [hsdb]
7h-dibenzo(c,g)carbazole [iarc]
CHEBI:82312
DTXSID9059755
SCHEMBL492860
3,4,5,6-dibenzcarbazole
3,4,5,6-dibenzcarbazol
D4473
7h-dibenzo[c,g]carbazole, bcr(r) certified reference material
mfcd00215941
c20h13n
dibenzo[c,g]carbazole
12-azapentacyclo[11.8.0.02,11.03,8.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaene
DS-6628
Q26841191
OL10172
CS-0078865
SY056348
A904282
SB66864

Excerpt	Reference	Relevance
" These results suggest that human liver cell lines differ markedly in the ability to metabolize DBC to toxic species and that DBC-induced apoptosis is only observed in cells that produce detectable metabolites and DBC-DNA adducts."	( In vitro toxicity of 7H-dibenzo[c,g]carbazole in human liver cell lines. Mitchell, K; O'Brien, T; Schneider, J; Warshawsky, D, 2002)	0.31
" Photoactivation-induced conversion of harmless chemical compounds to toxic photoproducts associated with reactive oxygen species generation may substantially amplify the adverse health effects of UVA radiation and contribute to increased incidence of skin cancer."	( Ultraviolet A radiation potentiates the cytotoxic and genotoxic effects of 7 H-dibenzo[c,g]carbazole and its methyl derivatives. Bábelová, A; Frecer, V; Gábelová, A; Kozics, K; Sedlačková, E; Šelc, M; Srančíková, A, 2015)	0.42

Excerpt	Reference	Relevance
" Differences in DBC uptake were not observed in any of the cell lines, suggesting that bioavailability was not a limiting factor."	( In vitro toxicity of 7H-dibenzo[c,g]carbazole in human liver cell lines. Mitchell, K; O'Brien, T; Schneider, J; Warshawsky, D, 2002)	0.31

Excerpt	Relevance	Reference
" The dosage was 25 micromol/kg body weight of each substance, administered on 5 occasions with an interval of 12-14 days."	( DNA adduct formation and persistence in liver and extrahepatic tissues of northern pike (Esox lucius) following oral exposure to benzo[a]pyrene, benzo[k]fluoranthene and 7H-dibenzo[c,g]carbazole. Balk, L; Ericson, G; Noaksson, E, 1999)	0.3
" There was a distinct time- and dose-response of stable DBC-DNA adducts detected by (32)P-post-labeling."	( One-electron oxidation is not a major route of metabolic activation and DNA binding for the carcinogen 7H-dibenzo[c,g]carbazole in vitro and in mouse liver and lung. Dowty, HV; LaDow, K; Talaska, G; Warshawsky, D; Xue, W, 2000)	0.31

Class	Description
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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	16 (29.09)	18.7374
1990's	18 (32.73)	18.2507
2000's	15 (27.27)	29.6817
2010's	5 (9.09)	24.3611
2020's	1 (1.82)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (3.17%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	61 (96.83%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	1.98	1	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	1.99	1	diatomic iodine	nutrient
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	1.99	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	2.38	2	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	9.18	17	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
safrole Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.	1.96	1	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	1.96	1	mitomycin	alkylating agent; antineoplastic agent
1,2,5,6-dibenzanthracene 1,2,5,6-dibenzanthracene: RN given refers to parent cpd	2.06	1	ortho-fused polycyclic arene	mutagen
2-acetylaminofluorene 2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.	7.37	2	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
benz(a)anthracene benz(a)anthracene: 4 fused rings of which one is angular in contrast to the linear NAPHTHACENES. tetraphene : An angular ortho-fused polycyclic arene consisting of four fused benzene rings.	1.98	1	ortho-fused polycyclic arene; tetraphenes
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.38	2	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
carbazole carbazole: structure in first source	3.35	1	carbazole
4-biphenylamine 4-biphenylamine: used in detection of sulfates, & as a carcinogen in cancer research; RN given refers to parent cpd; structure. biphenyl-4-amine : An aminobiphenyl that is biphenyl substituted by an amino group at position 4.	2.03	1	aminobiphenyl	carcinogenic agent
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	1.98	1	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
dibenzo(a,i)pyrene [no description available]	2.06	1	ortho- and peri-fused polycyclic arene
dibenzo(a,h)pyrene dibenzo(a,h)pyrene: structure given in first source	2.06	1	ortho- and peri-fused polycyclic arene
indeno(1,2,3-cd)pyrene indeno(1,2,3-cd)pyrene: structure in first source	2.06	1	pyrenes
benzo(j)fluoranthene benzo(j)fluoranthene: dihydrodiol metabolites identified as mutagens; structure given in first source	2.06	1	naphthalenes
benzo(b)fluoranthene benzo[b]fluoranthene : An ortho- and peri-fused polycyclic arene that consists of a benzene ring fused with a acephenanthrylene ring.	2.06	1	ortho- and peri-fused polycyclic arene	mutagen
benzo(k)fluoranthene [no description available]	2.71	3	naphthalenes
dibenzacridine dibenzacridine: RN given refers to dibenz(a,j)acridine	4.34	6
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	4.34	6	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
5-methylchrysene 5-methylchrysene: methylchrysenes in tobacco smoke are suspected to contribute to tumorigenicity of this inhalant; RN given refers to unlabeled cpd; structure	2.06	1	carbopolycyclic compound
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	1.98	1	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	1.98	1	benzenes; phenyl acetates
n-methyl-7h-dibenzo(c,g)carbazole N-methyl-7H-dibenzo(c,g)carbazole: structure given in first source	3.5	8
5,9-dimethyldibenzo(c,g)carbazole 5,9-dimethyldibenzo(c,g)carbazole: structure given in first source	3.41	7
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	2	1	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	3.23	6

Condition	Relationship Strength	Studies
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	3.17	1
Hepatocellular Carcinoma [description not available]	2.44	2
Cancer of Liver [description not available]	2.91	4
Chromosome-Defective Micronuclei [description not available]	3.12	5
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.44	2
Liver Neoplasms Tumors or cancer of the LIVER.	2.91	4
Experimental Hepatoma [description not available]	3.24	6
EHS Tumor [description not available]	2.7	3
Benign Neoplasms [description not available]	2.06	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.06	1
Genetic Predisposition [description not available]	2.03	1
Experimental Neoplasms [description not available]	2.37	2
Cancer of Lung [description not available]	3.59	3
Cancer of Skin [description not available]	3.37	7
Lung Neoplasms Tumors or cancer of the LUNG.	3.59	3
Skin Neoplasms Tumors or cancer of the SKIN.	3.37	7
Adenoma, Basal Cell [description not available]	2.9	1
Adenoma A benign epithelial tumor with a glandular organization.	2.9	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	1.99	1
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2	1
Hepatoblastoma A malignant neoplasm occurring in young children, primarily in the liver, composed of tissue resembling embryonal or fetal hepatic epithelium, or mixed epithelial and mesenchymal tissues. (Stedman, 25th ed)	2	1
Papilloma, Squamous Cell [description not available]	1.98	1
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	1.98	1

7h-dibenzo(c,g)carbazole

Cross-References

Synonyms (49)

Research Excerpts

Toxicity

Bioavailability

Dosage Studied

Drug Classes (1)

Research

Studies (55)

Market Indicators

Research Demand Index: 10.22

Study Types