Page last updated: 2024-12-05

benzothiophene

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

Benzothiophene is a heterocyclic aromatic compound with a sulfur atom in the five-membered ring and a benzene ring fused to it. It is a colorless, oily liquid with a characteristic odor. Benzothiophene is commonly found in fossil fuels, particularly in crude oil and coal tar. It is also found in some naturally occurring compounds, such as the antibiotic thiostrepton.

Benzothiophene has been studied for its potential medicinal properties. Some derivatives of benzothiophene have shown activity against various diseases, including cancer, inflammation, and bacterial infections. For example, the benzothiophene derivative tipropidil is used in Japan for treating diabetic retinopathy.

The synthesis of benzothiophene typically involves a cyclization reaction of a thiophenol derivative. This reaction is usually catalyzed by a Lewis acid, such as aluminum chloride or zinc chloride.

Benzothiophene and its derivatives are also important intermediates in the synthesis of various industrial chemicals, such as dyes, pharmaceuticals, and agricultural chemicals. The presence of benzothiophene in fossil fuels can pose environmental concerns, as it is a sulfur-containing compound that can contribute to air pollution. Therefore, the study of benzothiophene and its derivatives is essential for both understanding its potential applications and mitigating its environmental impact.'

Cross-References

ID SourceID
PubMed CID7221
CHEMBL ID87112
CHEBI ID35858
SCHEMBL ID7023
MeSH IDM0232998

Synonyms (59)

Synonym
BIDD:GT0845
CHEBI:35858 ,
CHEMBL87112 ,
EN300-36787
c8h6s
95-15-8
thianaphtene
2,3-benzothiophene
nsc47196
benzothiofuran
thionaphthene
benzothiophen
1-thiaindene
thianaphthene
thianaphthen
nsc-47196
benzo[b]thiophene
1-benzothiophene
inchi=1/c8h6s/c1-2-4-8-7(3-1)5-6-9-8/h1-6
thianaphthene, 95%
thianaphthene, 98%
11095-43-5
benzothiophene
benzo(b)thiophene
B0093
bdbm50167948
A845195
STK053859
AKOS005258172
unii-073790yq2g
einecs 202-395-7
073790yq2g ,
ai3-15523
nsc 47196
FT-0622686
PS-5775
AM20041456
SCHEMBL7023
thianaphthene [mi]
thianapthene
benzo[b]-thiophene
DTXSID2052736
Q-100899
1-benzothiophen
mfcd00005864
benzo[b]thiophene-d6
CS-D1193
GEO-00284
thianaftene
F0001-2267
Q419709
1444206-31-8
mfcd31699976
13730-27-3
SY246286
benzothiophene-5-d
hydrobenzothiophene
A847764
Z370711590

Research Excerpts

Overview

Benzothiophenes are a toxic and relatively recalcitrant fraction of coal-tar creosote.

ExcerptReferenceRelevance
"Benzothiophenes are a toxic and relatively recalcitrant fraction of coal-tar creosote. "( Microbial transformation of benzothiophenes, with carbazole as the auxiliary substrate, by Sphingomonas sp. strain XLDN2-5.
Deng, Z; Gai, Z; Wang, X; Xu, P; Yu, B, 2008
)
2.08

Treatment

ExcerptReferenceRelevance
"The treatment of benzothiophene-based palladacycles with an excess of phosphine ligands in benzene at room temperature selectively afforded trans-bis(phosphine) palladium complexes in good yields."( New cyclopalladated benzothiophenes: a catalyst precursor for the Suzuki coupling of deactivated aryl chlorides.
Bhargava, SK; Kantam, ML; Kennady, PK; Likhar, PR; Racharlawar, SS; Sridhar, B; Subhas, MS, 2010
)
1.01

Toxicity

ExcerptReferenceRelevance
"Treatment plants may be exposed to a whole range of toxic organic and inorganic compounds that may inhibit the removal of organic matter and nitrogen."( Monitoring toxicity of industrial wastewater and specific chemicals to a green alga, nitrifying bacteria and an aquatic bacterium.
Arvin, E; Eilersen, AM; Henze, M, 2004
)
0.32

Bioavailability

ExcerptReferenceRelevance
" The benefits of arzoxifene are attributed to improved bioavailability over raloxifene, whereas the arzoxifene metabolite, desmethylarzoxifene (DMA) is a more potent antiestrogen."( Structural modulation of oxidative metabolism in design of improved benzothiophene selective estrogen receptor modulators.
Ashgodom, RT; Bolton, JL; Choi, Y; Kastrati, I; Lantvit, DD; Overk, CR; Qin, Z; Thatcher, GR; van Breemen, RB, 2009
)
0.59
" A dihydrobenzothiophene series of potent, selective, orally bioavailable LRRK2 inhibitors were identified from a high-throughput screen of the internal Merck sample collection."( Potent, selective and orally bioavailable leucine-rich repeat kinase 2 (LRRK2) inhibitors.
Bilodeau, MT; Chang, RK; Drolet, RE; Greshock, TJ; Kern, JT; Kim, B; Lai, MT; McCauley, JA; Rada, VL; Rajapakse, HA; Renger, JJ; Sanchez, RI; Sanders, JM; Su, H; Sur, SM; Tiscia, HE, 2016
)
0.84
" Moreover, an improved oral bioavailability of the nanotized formulation lowered the dosage at which the pharmacological effect was achieved while avoiding any observable adverse harmful side effects."( Nanotized curcumin-benzothiophene conjugate: A potential combination for treatment of cerebral malaria.
Banerjee, T; Ghosh, A, 2020
)
0.89

Dosage Studied

ExcerptRelevanceReference
" Moreover, an improved oral bioavailability of the nanotized formulation lowered the dosage at which the pharmacological effect was achieved while avoiding any observable adverse harmful side effects."( Nanotized curcumin-benzothiophene conjugate: A potential combination for treatment of cerebral malaria.
Banerjee, T; Ghosh, A, 2020
)
0.89
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
benzothiophene
1-benzothiophenes
[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 (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
EndolysinTequatrovirus T4Kd74.00003.00003.00003.0000AID238119
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID23454Partition coefficient (logP)1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and in vitro LTD4 antagonist activity of bicyclic and monocyclic cyclopentylurethane and cyclopentylacetamide N-arylsulfonyl amides.
AID346025Binding affinity to beta cyclodextrin2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins.
AID238119Dissociation constant against T4 lysozyme mutant L99A2005Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11
Decoys for docking.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (298)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (3.02)18.7374
1990's14 (4.70)18.2507
2000's90 (30.20)29.6817
2010's140 (46.98)24.3611
2020's45 (15.10)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 54.10

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index54.10 (24.57)
Research Supply Index5.72 (2.92)
Research Growth Index5.24 (4.65)
Search Engine Demand Index87.43 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (54.10)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.33%)5.53%
Reviews10 (3.30%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other292 (96.37%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]