4-(2-thienyl)butyric acid

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

Description

4-(2-thienyl)butyric acid, also known as 2-thienylbutanoic acid, is an organic compound with the molecular formula C8H10O2S. It is a derivative of butyric acid with a thiophene ring attached to the fourth carbon atom. The compound has been investigated for its potential biological activity and has shown promising results in various studies.

**Synthesis:** 4-(2-thienyl)butyric acid can be synthesized through different methods. One common approach involves the reaction of 2-thienylmagnesium bromide with γ-butyrolactone, followed by acid hydrolysis. Another method utilizes the Friedel-Crafts acylation of thiophene with butyryl chloride in the presence of a Lewis acid catalyst.

**Effects:** Studies have indicated that 4-(2-thienyl)butyric acid exhibits diverse pharmacological effects. It has been reported to possess anti-inflammatory, analgesic, and anti-convulsant properties. Additionally, the compound has shown potential as a neuroprotective agent in animal models of neurological disorders.

**Importance:** 4-(2-thienyl)butyric acid is a promising candidate for drug development due to its potential therapeutic applications. Its anti-inflammatory and neuroprotective effects make it a promising target for treating various diseases, including inflammatory bowel disease, Alzheimer's disease, and Parkinson's disease.

**Studies:** Researchers are actively investigating the mechanisms of action of 4-(2-thienyl)butyric acid and its potential therapeutic applications. Studies have focused on understanding its interactions with specific receptors and enzymes, as well as its effects on cellular signaling pathways. Further research is needed to assess its safety and efficacy in humans.'

4-(2-thienyl)butyric acid : A monocarboxylic acid that is butyric acid bearing a 2-thienyl group at position 4. [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]

Cross-References

ID Source	ID
PubMed CID	78386
CHEMBL ID	1230333
CHEBI ID	40114
SCHEMBL ID	338927
MeSH ID	M0256862

Synonyms (49)

Synonym
BIDD:GT0560
4-(2-thienyl)butyric
4653-11-6
CHEMBL1230333
chebi:40114 ,
vlb4c9g6wy ,
einecs 225-090-0
unii-vlb4c9g6wy
.gamma.-(.alpha.-thienyl)butyric acid
4-(2-thienyl)butanoic acid
2-thiophenebutanoic acid
4-(2-thienyl)butyric acid
4TB ,
inchi=1/c8h10o2s/c9-8(10)5-1-3-7-4-2-6-11-7/h2,4,6h,1,3,5h2,(h,9,10
4-(2-thienyl)butyric acid, 98%
2AY8
DB02434
A1328
2-thiophenebutyric acid
4-thiophen-2-yl-butyric acid
HMS1721F11
4-thiophen-2-ylbutanoic acid
AKOS001046901
4-(thiophen-2-yl)butanoic acid
GEO-02303
gamma-(alpha-thienyl)butyricacid
FT-0635380
EPITOPE ID:167706
SCHEMBL338927
mfcd00005463
SY005888
4-thienylbutyric acid
4-thien-2-ylbutanoic acid
4-(2-thienyl)-butyric acid
4-(2-thiophenyl)butyric acid
4-(2-thienyl)butanoic acid #
J-640130
CS-W020036
AC-29236
J-800134
DTXSID70196868
GS-6648
STL554910
Q27093431
BBL101114
EN300-07300
4-(thiophen-2-yl)butanoicacid
PD008334
Z56951195

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

Role	Description
hapten	Any substance capable of eliciting an immune response only when attached to a large carrier such as a protein. Examples include dinitrophenols; oligosaccharides; peptides; and heavy metals.
[role 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]

Drug Classes (2)

Class	Description
thiophenes	Compounds containing at least one thiophene ring.
monocarboxylic acid	An oxoacid containing a single carboxy group.
[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 (18)

Activation Measurements

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain B, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain A, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain B, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain A, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain B, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain A, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain B, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain A, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain B, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain A, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain B, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain A, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain B, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain A, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain B, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain A, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
Chain B, AROMATIC AMINO ACID AMINOTRANSFERASE	Paracoccus denitrificans	Kd	5,800.0000	280.0000	4,495.0000	6,900.0000	AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (5)

Assay ID	Title	Year	Journal	Article
AID540299	A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis	2010	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21	Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519	A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities	2011	Antiviral research, Sep, Volume: 91, Issue:3	High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1740445	Induction of glucose uptake in mouse C2C12 cells assessed as [3H]2-deoxyglucose uptake preincubated for 16 hrs followed by followed by [3H]2-deoxyglucose addition and measured after 10 mins by liquid scintillation counting method	2020	European journal of medicinal chemistry, Sep-15, Volume: 202	Design, synthesis, and biological evaluation of aryl piperazines with potential as antidiabetic agents via the stimulation of glucose uptake and inhibition of NADH:ubiquinone oxidoreductase.
AID1811	Experimentally measured binding affinity data derived from PDB	1999	Biochemistry, Jan-26, Volume: 38, Issue:4	The active site of Paracoccus denitrificans aromatic amino acid aminotransferase has contrary properties: flexibility and rigidity.
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	1999	Biochemistry, Jan-26, Volume: 38, Issue:4	The active site of Paracoccus denitrificans aromatic amino acid aminotransferase has contrary properties: flexibility and rigidity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	2 (40.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	2 (40.00)	24.3611
2020's	1 (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: 12.87

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.

Metric	This Compound (vs All)
Research Demand Index	12.87 (24.57)
Research Supply Index	1.79 (2.92)
Research Growth Index	4.66 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.87)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	5 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.25	1	aromatic ether; nitrile; polyether; tertiary amino compound
4-phenylbutyric acid 4-phenylbutyric acid: RN refers to the parent cpd. 4-phenylbutyric acid : A monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation.	2	1	monocarboxylic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	1.98	1	diarylmethane
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	2.25	1	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	1.98	1	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	1.98	1	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
5-phenylvaleric acid 5-phenylvaleric acid: from Polygonum salicifolium. 5-phenylpentanoic acid : A monocarboxylic acid that is valeric acid substituted by a phenyl group at the delta-position.	2	1	benzenes; monocarboxylic acid
3-(3,4-dimethoxyphenyl)propanoic acid 3-(3,4-dimethoxyphenyl)propanoic acid : A monocarboxylic acid that is propanoic acid substituted by a 3,4-dimethoxyphenyl group at position 3.	2	1	dimethoxybenzene; monocarboxylic acid

Condition	Indicated	Relationship Strength	Studies	Trials
Encephalitis, Polio [description not available]	0	2.06	1	0
Poliomyelitis An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)	0	2.06	1	0

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