phenyl vinyl sulfone profile

Phenyl vinyl sulfone (PVS) is a versatile building block in organic synthesis. It is commonly used as an electrophilic synthon, participating in various reactions such as Michael additions and Diels-Alder reactions. Its synthesis typically involves the reaction of benzene with sulfuryl chloride followed by treatment with vinyl magnesium bromide. PVS exhibits interesting biological activities, acting as a potent inhibitor of certain enzymes and displaying antimicrobial properties. The compound's unique structure and reactivity have made it a subject of extensive study in fields like medicinal chemistry and materials science. Its potential applications in drug discovery and polymer synthesis are being explored. '

phenyl vinyl sulfone: RN and structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	79664
CHEMBL ID	165058
SCHEMBL ID	13341764
SCHEMBL ID	45672
MeSH ID	M0500585

Synonym
(vinylsulfonyl)benzene
5535-48-8
nsc-35394
uri 744
nsc35394
sulfone, phenyl vinyl
benzene, (ethenylsulfonyl)-
phenyl vinyl sulfone
phenyl vinyl sulfone, 99%
(ethenylsulfonyl)benzene
bdbm50125084
AKOS005146278
CHEMBL165058 ,
vinylsulfonylbenzene
ethenesulfonyl-benzene
P0982
ethenylsulfonylbenzene
A24646
(vinylsulfonyl)benzene;sulfone, phenyl vinyl
STK695234
EN300-65394
unii-31973457vy
einecs 226-890-2
phenyl vinyl sulphone
31973457vy ,
nsc 35394
(ethenesulfonyl)benzene
phenylvinylsultone
FT-0602583
AM20040709
uri-744
ethenyl phenyl sulfone
phenyl vinyl sulfone [mi]
SCHEMBL13341764
CS-M1815
SCHEMBL45672
phenylvinylsulphone
phenyl vinylsulfone
ethenesulfonylbenzene
SY019515
mfcd00007554
Q-101907
(vinyl sulfonyl) benzene
(vinylsulfonyl)benzene #
DTXSID50203903
Z1020737978
AS-17307
Q27256031
O10233

Excerpt	Reference	Relevance
"Phenyl vinyl sulfone is a synthetic inhibitor of cysteine protease and has antihelminthic and antiprotozoal properties. "	( Fasciola gigantica: evaluation of the effect of phenyl vinyl sulfone in vitro. Fahmy, ZH; Helmy, MM; Sabry, HY, 2008)	2.04

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Class A sortase SrtA	Staphylococcus aureus	IC50 (µMol)	736.0000	0.3000	2.8600	5.9000	AID1167597; AID419045
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay ID	Title	Year	Journal	Article
AID1890237	Inhibition of methicillin-susceptible Staphylococcus aureus ATCC 29213 bacterial cell adhesion to fibronectin at 0.1 mg/ml followed by compound addition on fibronectin precoated plate measured after 2 hrs by crystal violet dye based analysis	2022	Bioorganic & medicinal chemistry letters, 05-01, Volume: 63	Antibacterial activity evaluation of vinyl sulfones against global predominant methicillin-resistant Staphylococcus aureus USA300.
AID419045	Inhibition of 6-His tagged Staphylococcus aureus recombinant sortase delta N24 expressed in Escherichia coli BL21 (DE3)	2009	Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7	Probing of the cis-5-phenyl proline scaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureus sortase SrtA isoform.
AID1167597	Inhibition of Staphylococcus aureus sortase A using dabcyl-QALPETGEE-edans as substrate incubated for 1 hr prior to substrate addition measured at 1 min interval for 1 hr by FRET analysis	2014	Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21	Discovery and structure-activity relationship studies of irreversible benzisothiazolinone-based inhibitors against Staphylococcus aureus sortase A transpeptidase.
AID1687067	Inhibition of recombinant cathepsin B (unknown origin) endopeptidase activity expressed in Escherichia coli assessed as residual activity at 100 uM using Z-RR-AMC as substrate preincubated for 30 mins under shaking in presence of 5 mM cysteine followed by	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	A road map for prioritizing warheads for cysteine targeting covalent inhibitors.
AID89966	In vitro inhibition of inducible vascular cell adhesion molecule-1 (VCAM-1) expression in Human aortic endothelial cells (HAEC)	2003	Bioorganic & medicinal chemistry letters, Feb-24, Volume: 13, Issue:4	Lead discovery of alpha,beta-unsaturated sulfones from a combinatorial library as inhibitors of inducible VCAM-1 expression.
AID1167601	Cytotoxicity against Swiss mouse NIH/3T3 cells after 48 hrs by MTT assay	2014	Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21	Discovery and structure-activity relationship studies of irreversible benzisothiazolinone-based inhibitors against Staphylococcus aureus sortase A transpeptidase.
AID1687066	Inhibition of Escherichia coli MurA assessed as residual activity at 100 uM using UNAG and PEP as substrate preincubated for 30 mins in presence of UNAG followed by PEP addition and measured after 15 mins in presence of 5 mM cysteine by malachite green co	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	A road map for prioritizing warheads for cysteine targeting covalent inhibitors.
AID1687069	Inhibition of recombinant cathepsin X (unknown origin) expressed in Pichia pastoris assessed as residual activity at 100 uM using Abz-Fek(Dnp)-OH as substrate preincubated for 30 mins under shaking in presence of 5 mM cysteine followed by substrate additi	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	A road map for prioritizing warheads for cysteine targeting covalent inhibitors.
AID1687065	Inhibition of Escherichia coli MurA assessed as residual activity at 100 uM using UNAG and PEP as substrate preincubated for 30 mins in presence of UNAG followed by PEP addition and measured after 15 mins by malachite green colorimetric assay relative to	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	A road map for prioritizing warheads for cysteine targeting covalent inhibitors.
AID1687068	Inhibition of recombinant cathepsin B (unknown origin) exopeptidase activity expressed in Escherichia coli assessed as residual activity at 100 uM using Abz-GIVRAK(Dnp)-OH as substrate preincubated for 30 mins under shaking in presence of 5 mM cysteine fo	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	A road map for prioritizing warheads for cysteine targeting covalent inhibitors.
AID1687063	Inhibition of Staphylococcus aureus MurA expressed in Escherichia coli using UNAG and PEP as substrate preincubated for 30 mins in presence of UNAG followed by PEP addition and measured after 15 mins by malachite green colorimetric assay	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	A road map for prioritizing warheads for cysteine targeting covalent inhibitors.
AID1687062	Inhibition of Escherichia coli MurA using UNAG and PEP as substrate preincubated for 30 mins in presence of UNAG followed by PEP addition and measured after 15 mins by malachite green colorimetric assay	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	A road map for prioritizing warheads for cysteine targeting covalent inhibitors.
AID1167598	Antibacterial activity against Staphylococcus aureus ATCC 25904 after 24 hrs by broth dilution method	2014	Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21	Discovery and structure-activity relationship studies of irreversible benzisothiazolinone-based inhibitors against Staphylococcus aureus sortase A transpeptidase.
AID1687064	Inhibition of Staphylococcus aureus MurA expressed in Escherichia coli assessed as residual activity at 100 uM using UNAG and PEP as substrate preincubated for 30 mins in presence of UNAG followed by PEP addition and measured after 15 mins by malachite gr	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	A road map for prioritizing warheads for cysteine targeting covalent inhibitors.
AID1902022	Inhibition of tau K18 domain (unknown origin) assessed as inhibition of heparin-induced aggregation by measuring protein aggregation rate at 10 uM by thioflavin-T fluorescence assay relative to control	2022	European journal of medicinal chemistry, Mar-05, Volume: 231	A covalent strategy to target intrinsically disordered proteins: Discovery of novel tau aggregation inhibitors.
AID1167599	Antibacterial activity against Staphylococcus epidermidis ATCC 12228 after 24 hrs by broth dilution method	2014	Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21	Discovery and structure-activity relationship studies of irreversible benzisothiazolinone-based inhibitors against Staphylococcus aureus sortase A transpeptidase.
AID1167600	Antibacterial activity against Escherichia coli ATCC 25922 after 24 hrs by broth dilution method	2014	Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21	Discovery and structure-activity relationship studies of irreversible benzisothiazolinone-based inhibitors against Staphylococcus aureus sortase A transpeptidase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	10 (50.00)	29.6817
2010's	7 (35.00)	24.3611
2020's	3 (15.00)	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	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	20 (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
benzyl isothiocyanate benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma	2.17	1	benzenes; isothiocyanate	antibacterial drug
phenacyl bromide phenacyl bromide: structure. phenacyl bromide : An alpha-bromoketone that is acetophenone substituted by a bromo group at position 2.	2.17	1	acetophenones; alpha-bromoketone	metabolite
divinyl sulfone divinyl sulfone: cross-linking reagent for agarose gels. divinyl sulfone : A sulfone compound having two S-vinyl substituents.	2.01	1	sulfone	cross-linking reagent
phenylisothiocyanate phenylisothiocyanate: structure. phenyl isothiocyanate : An isothiocyanate having a phenyl group attached to the nitrogen; used for amino acid sequencing in the Edman degradation.	2.17	1	isothiocyanate	allergen; reagent
4-methylbenzenethiol 4-methylbenzenethiol: structure in first source	2.17	1
maleimide [no description available]	2.13	1	dicarboximide; maleimides	EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
2-chloroacetanilide [no description available]	2.17	1
Berberine chloride (TN) [no description available]	2.05	1	organic molecular entity
1,2-benzisothiazoline-3-one 1,2-benzisothiazoline-3-one: a preservative in water-based solutions such as paints, cutting fluids, printing inks, cleaning agents, polyvinyl chloride gloves, etc.. benzo[d]isothiazol-3-one : An organic heterobicyclic compound based on a fused 1,2-thiazole and benzene bicyclic ring skeleton, with the S atom positioned adjacent to one of the positions of ring fusion.	2.17	1	organic heterobicyclic compound; organonitrogen heterocyclic compound	disinfectant; drug allergen; environmental contaminant; platelet aggregation inhibitor; sensitiser; xenobiotic
methyl vinyl sulfone [no description available]	2.01	1
alkenes [no description available]	2.02	1
vanadates Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.	2.11	1	trivalent inorganic anion; vanadium oxoanion	EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
amantadine hydrochloride [no description available]	2.1	1	hydrochloride	antiviral agent; dopamine agonist; NMDA receptor antagonist
2-bromo-4'-nitroacetophenone [no description available]	2.17	1
1H-1lambda~6~-benzo[b]thiophene-1,1-dione [no description available]	2.01	1	benzenoid aromatic compound
n-benzylmaleimide [no description available]	2.17	1
ethyl 2-butynoate [no description available]	2.17	1
ethylphenylpropiolate ethylphenylpropiolate: structure	2.17	1
tris(2-carboxyethyl)phosphine tris(2-carboxyethyl)phosphine: water-soluble reagent which irreversibly reduces disulfides to thiols at room temperature & is active below neutral pH; used for quantitation of iodine and iodate. TCEP : A tertiary phosphine in which phosphane is substituted with three 2-carboxyethyl groups. It is a commonly used reducing agent.	2.13	1	phosphine derivative; tricarboxylic acid	reducing agent
topsentin a topsentin A: number of carbony group = 1 for topsentin A and no carbonyl group for nortopsentin B and D; structure in first source	2.05	1
isoaaptamine isoaaptamine: structure in first source	2.05	1
fosfomycin Fosfomycin: An antibiotic produced by Streptomyces fradiae.. fosfomycin : A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.	2.17	1	epoxide; phosphonic acids	antimicrobial agent; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor
vinyl sulfonamide vinyl sulfonamide: structure in first source	2.41	1
dimethyl fumarate [no description available]	2.17	1	diester; enoate ester; methyl ester	antipsoriatic; immunomodulator
crotononitrile crotononitrile: RN given refers to cpd without isomeric designation	2.17	1	nitrile
morin morin: a light yellowish pigment found in the wood of old fustic (Chlorophora tinctoria). morin : A pentahydroxyflavone that is 7-hydroxyflavonol bearing three additional hydroxy substituents at positions 2' 4' and 5.	2.05	1	7-hydroxyflavonol; pentahydroxyflavone	angiogenesis modulating agent; anti-inflammatory agent; antibacterial agent; antihypertensive agent; antineoplastic agent; antioxidant; EC 5.99.1.2 (DNA topoisomerase) inhibitor; hepatoprotective agent; metabolite; neuroprotective agent
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	2.11	1	1-O-acyl-sn-glycero-3-phosphocholine
bay 11-7082 (E)-3-tosylacrylonitrile : A nitrile that is acrylonitrile in which the hydrogen located beta,trans to the cyano group is replaced by a tosyl group. It is an inhibitor of cytokine-induced IkappaB-alpha phosphorylation in cells.	2.41	1	nitrile; sulfone	apoptosis inducer; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; non-steroidal anti-inflammatory drug; platelet aggregation inhibitor
lyoniside daucosterol : A steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa.	2.05	1	beta-D-glucoside; monosaccharide derivative; steroid saponin	plant metabolite

Condition	Relationship Strength	Studies
Infections, Staphylococcal [description not available]	2.58	2
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2.58	2
Degenerative Diseases, Central Nervous System [description not available]	2.41	1
Tauopathies Neurodegenerative disorders involving deposition of abnormal tau protein isoforms (TAU PROTEINS) in neurons and glial cells in the brain. Pathological aggregations of tau proteins are associated with mutation of the tau gene on chromosome 17 in patients with ALZHEIMER DISEASE; DEMENTIA; PARKINSONIAN DISORDERS; progressive supranuclear palsy (SUPRANUCLEAR PALSY, PROGRESSIVE); and corticobasal degeneration.	2.41	1
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	2.41	1
Blastocystis hominis Infections [description not available]	2.13	1
Malignant Melanoma [description not available]	2.11	1
Angiogenesis, Pathologic [description not available]	2.11	1
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	2.11	1
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	2.03	1
Actinomycetales Infections Infections with bacteria of the order ACTINOMYCETALES.	2.03	1

phenyl vinyl sulfone

Description

Cross-References

Synonyms (49)

Research Excerpts

Overview

Protein Targets (1)

Inhibition Measurements

Bioassays (17)

Research

Studies (20)

Market Indicators

Research Demand Index: 28.72

Study Types

phenyl vinyl sulfone

Description

Cross-References

Synonyms (49)

Research Excerpts

Overview

Protein Targets (1)

Inhibition Measurements

Bioassays (17)

Research

Studies (20)

Market Indicators

Research Demand Index: 28.72

Study Types

Related Drugs (29)

Related Conditions (11)