Compounds > 5-methyl-4-[(3-methyl-5-oxo-1,2-dihydropyrazol-4-yl)-[1-(1-naphthalenylmethyl)-3-indolyl]methyl]-1,2-dihydropyrazol-3-one

Page last updated: 2024-08-01 04:20:48

5-methyl-4-[(3-methyl-5-oxo-1,2-dihydropyrazol-4-yl)-[1-(1-naphthalenylmethyl)-3-indolyl]methyl]-1,2-dihydropyrazol-3-one

Description

5-methyl-4-[(3-methyl-5-oxo-1,2-dihydropyrazol-4-yl)-[1-(1-naphthalenylmethyl)-3-indolyl]methyl]-1,2-dihydropyrazol-3-one : no description available [CHeBI]

Cross-References

ID Source	ID
PubMed CID	4240836
CHEMBL ID	1560141
CHEBI ID	107349

Synonyms (17)

Synonym
AN-698/42027015
4-{(5-hydroxy-3-methyl-1h-pyrazol-4-yl)[1-(1-naphthylmethyl)-1h-indol-3-yl]methyl}-3-methyl-1h-pyrazol-5-ol
MLS000539683 ,
smr000162433
STK113025
4,4'-{[1-(naphthalen-1-ylmethyl)-1h-indol-3-yl]methanediyl}bis(3-methyl-1h-pyrazol-5-ol)
CHEBI:107349
AKOS000364789
5-methyl-4-[(3-methyl-5-oxo-1,2-dihydropyrazol-4-yl)-[1-(naphthalen-1-ylmethyl)indol-3-yl]methyl]-1,2-dihydropyrazol-3-one
HMS2287F13
CHEMBL1560141
bdbm83905
5-methyl-4-[(3-methyl-5-oxo-1,2-dihydropyrazol-4-yl)-[1-(1-naphthalenylmethyl)-3-indolyl]methyl]-1,2-dihydropyrazol-3-one
4-[(3-keto-5-methyl-3-pyrazolin-4-yl)-[1-(1-naphthylmethyl)indol-3-yl]methyl]-5-methyl-3-pyrazolin-3-one
cid_4240836
5-methyl-4-[(3-methyl-5-oxidanylidene-1,2-dihydropyrazol-4-yl)-[1-(naphthalen-1-ylmethyl)indol-3-yl]methyl]-1,2-dihydropyrazol-3-one
Q27185649

Drug Classes (1)

Class	Description
naphthalenes	Any benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.

Protein Targets (37)

Potency Measurements

Protein	Taxonomy	Measurement	Average (mM)	Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASE	Homo sapiens (human)	Potency	11.2202	AID485290
Chain A, Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	5.6101	AID2451
Chain A, Ferritin light chain	Equus caballus (horse)	Potency	15.8489	AID485281
Nrf2	Homo sapiens (human)	Potency	15.8489	AID624171
glp-1 receptor, partial	Homo sapiens (human)	Potency	10.0000	AID624417
USP1 protein, partial	Homo sapiens (human)	Potency	14.1254	AID743255
GLS protein	Homo sapiens (human)	Potency	11.2202	AID624170
TDP1 protein	Homo sapiens (human)	Potency	7.7536	AID686978; AID686979
Microtubule-associated protein tau	Homo sapiens (human)	Potency	13.8914	AID1460; AID1468
Smad3	Homo sapiens (human)	Potency	35.4813	AID588855
aldehyde dehydrogenase 1 family, member A1	Homo sapiens (human)	Potency	0.3162	AID1030
nonstructural protein 1	Influenza A virus (A/WSN/1933(H1N1))	Potency	12.5893	AID2326
bromodomain adjacent to zinc finger domain 2B	Homo sapiens (human)	Potency	7.9433	AID504333
IDH1	Homo sapiens (human)	Potency	29.0929	AID686970
euchromatic histone-lysine N-methyltransferase 2	Homo sapiens (human)	Potency	44.6684	AID504332
Bloom syndrome protein isoform 1	Homo sapiens (human)	Potency	31.6228	AID2528
lysosomal alpha-glucosidase preproprotein	Homo sapiens (human)	Potency	17.6470	AID2100
chromobox protein homolog 1	Homo sapiens (human)	Potency	28.1838	AID540317
thyroid hormone receptor beta isoform a	Homo sapiens (human)	Potency	7.9433	AID1469
serine/threonine-protein kinase PLK1	Homo sapiens (human)	Potency	7.5193	AID720504
DNA polymerase eta isoform 1	Homo sapiens (human)	Potency	44.6684	AID588591
lethal(3)malignant brain tumor-like protein 1 isoform I	Homo sapiens (human)	Potency	7.9433	AID485360
geminin	Homo sapiens (human)	Potency	23.1093	AID624296; AID624297
DNA dC->dU-editing enzyme APOBEC-3G isoform 1	Homo sapiens (human)	Potency	22.3872	AID602310
DNA dC->dU-editing enzyme APOBEC-3F isoform a	Homo sapiens (human)	Potency	35.4813	AID602313
Polyunsaturated fatty acid lipoxygenase ALOX15B	Homo sapiens (human)	Potency	3.9811	AID881
Rap guanine nucleotide exchange factor 3	Homo sapiens (human)	Potency	89.1251	AID720709
Histamine H2 receptor	Cavia porcellus (domestic guinea pig)	Potency	3.9811	AID881

Inhibition Measurements

Protein	Taxonomy	Measurement	Average (mM)	Bioassay(s)
Apoptotic peptidase activating factor 1	Homo sapiens (human)	IC50	59.6500	AID588524; AID588538
protein artemis isoform a	Homo sapiens (human)	IC50	12.5000	AID720701
caspase-9 isoform alpha precursor	Homo sapiens (human)	IC50	13.5000	AID588574
caspase-3 isoform a preproprotein	Homo sapiens (human)	IC50	13.5000	AID588574
hypothetical protein SA1422	Staphylococcus aureus subsp. aureus N315	IC50	10.7950	AID624317; AID651709
sentrin-specific protease 8	Homo sapiens (human)	IC50	4.3400	AID624322; AID651559

Other Measurements

Protein	Taxonomy	Measurement	Average (mM)	Bioassay(s)
aryl hydrocarbon receptor nuclear translocator	Homo sapiens (human)	AC50	19.8600	AID651703
jumonji domain containing 2C, partial	Homo sapiens (human)	AC50	11.4100	AID488835
transforming acidic coiled-coil-containing protein 3	Homo sapiens (human)	AC50	19.8600	AID651703

Bioassays (7)

Assay ID	Title	Year	Journal	Article
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression	2022	The Journal of biological chemistry, 08, Volume: 298, Issue:8 ISSN: 1083-351X
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13ISSN: 1934-9300	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 ISSN: 1552-4922	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1 ISSN: 1557-8127	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13ISSN: 1934-9300	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 ISSN: 1552-4922	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1 ISSN: 1557-8127	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7 ISSN: 1945-7170	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13ISSN: 1934-9300	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 ISSN: 1552-4922	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1 ISSN: 1557-8127	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7 ISSN: 1945-7170	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845	Primary qHTS for Inhibitors of ATXN expression	2022	The Journal of biological chemistry, 08, Volume: 298, Issue:8 ISSN: 1083-351X

Research

Studies (5)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	1 (20.00)	29.6817
2010's	3 (60.00)	24.3611
2020's	1 (20.00)	2.80

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%

Substance	Classes	Roles	Relationship Strength
naphthalene	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component	low
2-(6-methoxy-2-naphthalenyl)propanoic acid	naphthalenes		low
N-(2-aminoethyl)-5-chloro-1-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
butenafine	naphthalenes; tertiary amine	antifungal drug; EC 1.14.13.132 (squalene monooxygenase) inhibitor	low
hydroxy-2-naphthalenyl-methyl phosphonic acid trisacetoxymethylester	acetate ester; naphthalenes; organic phosphonate	tyrosine kinase inhibitor	low
1-(2-naphthalenyl)-3-[(phenylmethyl)-propan-2-ylamino]-1-propanone	naphthalenes		low
1-(2-naphthalenyl)-2-propen-1-one	naphthalenes		low
ml 9	naphthalenes; sulfonic acid derivative		low
w 12	naphthalenes; sulfonic acid derivative		low
n-(4-aminobutyl)-5-chloro-2-naphthalenesulfonamide	naphthalenes; organochlorine compound; primary amino compound; sulfonamide		low
n-(6-aminohexyl)-1-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
nafoxidine	benzenes; naphthalenes; ring assembly		low
nafronyl	naphthalenes		low
naphazoline	naphthalenes		low
pronethalol	naphthalenes		low
propranolol	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic	low
sc-10	naphthalenes; sulfonic acid derivative		low
N,6,6-trimethyl-N-(1-naphthalenylmethyl)-1-hept-2-en-4-ynamine	naphthalenes		low
carbaryl	carbamate ester; naphthalenes	acaricide; agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant growth retardant	low
naphthaleneacetamide	naphthalenes; primary carboxamide	synthetic auxin	low
1-naphthylphenylamine	naphthalenes		low
2-naphthalenethiol	naphthalenes		low
2-methoxynaphthalene	naphthalenes		low
bromelia	naphthalenes		low
neozone	naphthalenes		low
benzo(j)fluoranthene	naphthalenes		low
benzo(k)fluoranthene	naphthalenes		low
chlornaphazin	naphthalenes		low
methallenestril	naphthalenes		low
1,5-naphthylene di-isocyanate	naphthalenes		low
nitrosocarbaryl	carbamate ester; naphthalenes; nitroso compound	carcinogenic agent; mutagen	low
devrinol	aromatic ether; monocarboxylic acid amide; naphthalenes		low
2,6-diisopropylnaphthalene	naphthalenes	agrochemical; plant growth retardant	low
nadoxolol	naphthalenes		low
naftifine	allylamine antifungal drug; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; sterol biosynthesis inhibitor	low
tolrestat	naphthalenes	EC 1.1.1.21 (aldehyde reductase) inhibitor	low
lonapalene	naphthalenes; organochlorine compound		low
fananserin	naphthalenes; sulfonic acid derivative		low
aptiganel	naphthalenes		low
5-Aminoacenaphthene	naphthalenes		low
dapoxetine	naphthalenes		low
2-naphthyl sulfate	aryl sulfate; naphthalenes		low
bexarotene	benzoic acids; naphthalenes; retinoid	antineoplastic agent	low
1,8-bis(dimethylamino)naphthalene	naphthalenes		low
1-(1,2-dihydroacenaphthylen-5-yl)ethanone	naphthalenes		low
1,1,6-trimethyl-1,2-dihydronaphthalene	naphthalenes		low
11-(dansylamino)undecanoic acid	naphthalenes; sulfonic acid derivative		low
5-(dimethylamino)-n-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
n-(6-phenylhexyl)-5-chloro-1-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
xaliproden hydrochloride	naphthalenes		low
xaliproden	(trifluoromethyl)benzenes; naphthalenes; tertiary amino compound; tetrahydropyridine	serotonergic agonist	low
1-naphthylacetylspermine	naphthalenes		low
cinacalcet	(trifluoromethyl)benzenes; naphthalenes; secondary amino compound	calcimimetic; P450 inhibitor	low
birb 796	aromatic ether; morpholines; naphthalenes; pyrazoles; ureas	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; immunomodulator	low
5-(2-naphthalenylmethylidene)-1,3-diazinane-2,4,6-trione	naphthalenes		low
6,11-dioxo-12-naphtho[2,3-b]indolizinecarboxylic acid ethyl ester	naphthalenes		low
acetic acid (4-acetyloxy-6,7-dimethyl-5,8-dihydronaphthalen-1-yl) ester	naphthalenes		low
korupensamine-b	isoquinolines; naphthalenes		low
dioncophylline a	biaryl; isoquinoline alkaloid; isoquinolines; methoxynaphthalene; methylnaphthalenes; naphthalenes	antifungal agent; antimalarial; metabolite; molluscicide	low
1-[(4-fluoro-1-naphthalenyl)sulfonyl]piperidine	naphthalenes; sulfonic acid derivative		low
6-tert-butylnaphthalene-2,3-dicarbonitrile	naphthalenes		low
5-(diethylsulfamoyl)-3-hydroxy-2-naphthalenecarboxylic acid	naphthalenes; sulfonic acid derivative		low
2,6-dimethyl-4-[1-(2-naphthalenylsulfonyl)-4-piperidinyl]morpholine	naphthalenes; sulfonic acid derivative		low
1,3-dimethyl-6-(1-naphthalenyl)pyrrolo[3,4-d]pyrimidine-2,4-dione	naphthalenes		low
5-(4-methyl-1-piperidinyl)-2-(1-naphthalenylmethyl)-4-oxazolecarbonitrile	naphthalenes		low
5-[2-(3,4-dimethoxyphenyl)ethylamino]-2-(1-naphthalenylmethyl)-4-oxazolecarbonitrile	naphthalenes		low
3-methyl-6-(1-naphthalenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole	naphthalenes; triazolothiadiazole		low
N-(1,2-dihydroacenaphthylen-5-yl)methanesulfonamide	naphthalenes		low
N,N-diethyl-2-oxo-1H-benzo[cd]indole-6-sulfonamide	naphthalenes; sulfonic acid derivative		low
spiro[1,3-dihydroperimidine-2,1'-cycloheptane]	naphthalenes		low
2-(3-nitrophenyl)-2,3-dihydro-1H-perimidine	naphthalenes		low
2-phenylmethoxy-1-naphthalenecarboxaldehyde	naphthalenes		low
alpha-naphthyl thiourea	naphthalenes		low
4-[(2-methoxy-1-naphthalenyl)methyl]thiomorpholine	naphthalenes		low
N-(3-methoxyphenyl)-2-benzo[cd]indolamine	naphthalenes		low
LSM-21110	naphthalenes; sulfonic acid derivative		low
4-[(6-methoxy-2-naphthalenyl)sulfonyl]morpholine	naphthalenes; sulfonic acid derivative		low
LSM-28278	naphthalenes		low
4-(2-naphthalenylmethyl)-1-piperazinecarboxylic acid ethyl ester	naphthalenes		low
6-(4-morpholinyl)naphthalene-2,3-dicarbonitrile	naphthalenes		low
N-(1-naphthalenyl)-4-(phenylmethyl)-1-piperazinecarboxamide	naphthalenes		low
3,5-dimethyl-1-[(7-methyl-2-naphthalenyl)sulfonyl]pyrazole	naphthalenes; sulfonic acid derivative		low
2-methyl-N-(2-naphthalenyl)-3-furancarboxamide	naphthalenes		low
4-chloro-N-(2-pyridinyl)-1-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
3-(2-benzo[cd]indolylamino)benzoic acid	naphthalenes		low
4-(2-naphthalenyloxymethyl)-2-thiazolamine	naphthalenes		low
1-(1-naphthalenylmethoxy)benzotriazole	naphthalenes		low
3-chloro-4,5-dimethoxy-N-(1-naphthalenylmethyl)benzamide	naphthalenes		low
1-[[2-(4-chlorophenyl)-1-oxoethyl]amino]-3-(1-naphthalenyl)urea	naphthalenes		low
1-methyl-N-(2-naphthalenyl)-5-benzotriazolecarboxamide	naphthalenes		low
N-(1-naphthalenyl)-5-pyridin-4-yl-1,3,4-thiadiazol-2-amine	naphthalenes		low
1-methyl-2-oxo-N-(2-pyridinyl)-6-benzo[cd]indolesulfonamide	naphthalenes; sulfonic acid derivative		low
pyrabactin	naphthalenes; organobromine compound; pyridines; sulfonamide	abscisic acid receptor agonist; hormone; plant growth regulator	low
1-ethyl-2-oxo-N-(2-pyridinylmethyl)-6-benzo[cd]indolesulfonamide	naphthalenes; sulfonic acid derivative		low
N-[(1,2-dihydroacenaphthylen-5-ylamino)-sulfanylidenemethyl]-2-phenoxyacetamide	naphthalenes		low
1-(4-bromophenyl)-4-[1-naphthalenyl(oxo)methyl]-3-pyrazolecarboxylic acid ethyl ester	carbonyl compound; naphthalenes		low
1-(1,2,3-benzothiadiazol-5-yl)-3-(1-naphthalenyl)urea	naphthalenes		low
1-(4-methylphenyl)sulfonyl-4-(2-naphthalenylsulfonyl)-1,4-diazepane	naphthalenes; sulfonic acid derivative		low
N2,N2-dimethyl-6-[[[1-(1-naphthalenyl)-5-tetrazolyl]thio]methyl]-1,3,5-triazine-2,4-diamine	naphthalenes		low
terbinafine	acetylenic compound; allylamine antifungal drug; enyne; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor; sterol biosynthesis inhibitor	low
1-ethyl-N-[3-(4-morpholinyl)propyl]-2-oxo-6-benzo[cd]indolesulfonamide	naphthalenes; sulfonic acid derivative		low
N-[4-(4-morpholinyl)phenyl]-2-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
4-fluorobenzoic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
4-bromobenzoic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
2-benzofurancarboxylic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
N-(5-methyl-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-2-yl)-2-(2-naphthalenyloxy)acetamide	naphthalenes		low
thiocyanic acid [2-(1-naphthalenyl)-2-oxoethyl] ester	naphthalenes		low
2-[2-(1-naphthalenyloxy)ethylthio]pyrimidine	naphthalenes		low
N-[2-(1-naphthalenyl)-1,3-benzoxazol-5-yl]-1H-1,2,4-triazole-5-carboxamide	naphthalenes		low
N-(2-naphthalenyl)-2-[[6-[[[2-(2-naphthalenylamino)-2-oxoethyl]thio]methyl]-2-pyridinyl]methylthio]acetamide	naphthalenes		low
1-(1-naphthalenylmethyl)-3-phenylurea	naphthalenes		low
N'-(3,4-dihydro-2H-pyrrol-5-yl)-2-(2-naphthalenylamino)acetohydrazide	naphthalenes		low
N-butyl-N-methyl-2-benzo[cd]indolamine	naphthalenes		low
N-(5-methyl-3-isoxazolyl)-2-(2-naphthalenylthio)acetamide	naphthalenes		low
LSM-19724	naphthalenes; sulfonic acid derivative		low
N-(3-chloro-2-quinoxalinyl)-2-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
2-(2-naphthalenylsulfonylamino)acetic acid [2-(2,5-dimethyl-1-phenyl-3-pyrrolyl)-2-oxoethyl] ester	naphthalenes; sulfonic acid derivative		low
5-(1-naphthalenylamino)-3H-1,3,4-thiadiazole-2-thione	naphthalenes		low
4-(3,5-dichloro-4-pyridinyl)-N-(1-naphthalenyl)-1,4-diazepane-1-carboxamide	naphthalenes		low
2-(1-naphthalenyl)-N-[2,2,2-trichloro-1-[[(2-chloroanilino)-sulfanylidenemethyl]amino]ethyl]acetamide	naphthalenes		low
acetic acid [4-[acetyl-(4-chlorophenyl)sulfonylamino]-1-naphthalenyl] ester	naphthalenes		low
2,2-dibromo-1-methyl-N-(2-naphthalenyl)-1-cyclopropanecarboxamide	naphthalenes		low
N'-[2-(1-naphthalenyloxy)-1-oxoethyl]-2-oxolanecarbohydrazide	naphthalenes		low
N-[3-(3,5-dimethyl-1-pyrazolyl)-2-hydroxypropyl]-N-(4-methylphenyl)-2-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
1-[2-furanyl(oxo)methyl]-6-(1-pyrrolidinylsulfonyl)-2-benzo[cd]indolone	naphthalenes; sulfonic acid derivative		low
2-(2-bromophenyl)-2,3-dihydro-1H-perimidine	naphthalenes		low
acetic acid [1-[(3-nitrophenyl)-(1-oxopentylamino)methyl]-2-naphthalenyl] ester	naphthalenes		low
4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]-2-butyn-1-ol	naphthalenes		low
N-(2-methoxyethyl)-1-methyl-2-oxo-6-benzo[cd]indolesulfonamide	naphthalenes; sulfonic acid derivative		low
3-(5-methyl-2-furanyl)-5-[1-(2-naphthalenylsulfonyl)-3-piperidinyl]-1,2,4-oxadiazole	naphthalenes; sulfonic acid derivative		low
(7-methoxy-4,5-dihydrobenzo[g][1,2]benzoxazol-3-yl)-(4-morpholinyl)methanone	naphthalenes		low
1-(1-naphthalenyl)-3-[3-(1-pyrrolidinyl)propyl]urea	naphthalenes		low
N-[3-(1-imidazolyl)propyl]-7-methoxy-4,5-dihydrobenzo[g][1,2]benzoxazole-3-carboxamide	naphthalenes		low
7-methoxy-4,5-dihydro-2H-benzo[g]indazole-3-carboxylic acid	naphthalenes		low
(1R,2R)-2-[(R)-(diphenylphosphorylamino)-phenylmethyl]-N-(2-naphthalenyl)-1-cyclopropanecarboxamide	naphthalenes		low
5-methyl-N-[(S)-[(1S,2R)-1-methyl-2-[(2R)-1-(2-naphthalenylamino)-1-oxopropan-2-yl]cyclopropyl]-phenylmethyl]-3-isoxazolecarboxamide	naphthalenes		low
2,5-dimethyl-N-[(S)-[(1S,2R)-1-methyl-2-[(2R)-1-(2-naphthalenylamino)-1-oxopropan-2-yl]cyclopropyl]-phenylmethyl]-3-pyrazolecarboxamide	naphthalenes		low
2,3-dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline	naphthalenes; sulfonic acid derivative		low
2-(1-naphthalenyl)acetic acid [2-[4-chloro-3-(dimethylsulfamoyl)anilino]-2-oxoethyl] ester	naphthalenes		low
1,1-dimethyl-3-[3-(4-morpholinyl)propyl]-3-(1-naphthalenylmethyl)urea	naphthalenes		low
N-(4-ethoxyphenyl)sulfonyl-N-(2-oxo-5-benzo[g][1,3]benzoxathiolyl)-2-furancarboxamide	naphthalenes		low
N-[2-(3,4-dimethoxyphenyl)ethyl]-4-dimethoxyphosphoryl-2-(1-naphthalenyl)-5-oxazolamine	naphthalenes		low
4-[4-dimethoxyphosphoryl-2-(1-naphthalenyl)-5-oxazolyl]morpholine	naphthalenes		low
2-amino-1-(dimethylamino)-4-(1-naphthalenyl)-5-oxo-7-phenyl-4,6,7,8-tetrahydroquinoline-3-carbonitrile	naphthalenes; quinolines		low
4-[4-diethoxyphosphoryl-2-(1-naphthalenyl)-5-oxazolyl]morpholine	naphthalenes		low
2-[(1-methyl-2-imidazolyl)thio]-1-(2-naphthalenyl)ethanone	naphthalenes		low
2-(1-naphthalenyl)-4-quinolinecarboxylic acid [1-[(1,5-dimethyl-3-oxo-2-phenyl-4-pyrazolyl)amino]-1-oxopropan-2-yl] ester	naphthalenes; quinolines		low
N-(1-dibutoxyphosphoryl-4-oxo-1-naphthalenyl)benzenesulfonamide	naphthalenes		low
4-dimethoxyphosphoryl-2-(1-naphthalenyl)-N-(phenylmethyl)-5-oxazolamine	naphthalenes		low
4-chlorobenzoic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
4-amino-5-cyano-2-(1-naphthalenylmethylthio)-3-azaspiro[5.5]undeca-2,4-diene-1-carboxamide	naphthalenes		low
N-[[[2-(2-naphthalenyloxy)-1-oxopropyl]hydrazo]-sulfanylidenemethyl]-2-furancarboxamide	naphthalenes		low
(4-chloro-1-ethyl-3-pyrazolyl)-[3-(2-hydroxyphenyl)-5-(2-naphthalenyl)-3,4-dihydropyrazol-2-yl]methanone	naphthalenes		low
N-(4-methoxyphenyl)sulfonyl-N-(2-oxo-5-benzo[g][1,3]benzoxathiolyl)-2-furancarboxamide	naphthalenes		low
4-(2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl)benzoic acid	benzoic acids; naphthalenes; retinoid	antineoplastic agent; retinoic acid receptor agonist; teratogenic agent	low
cgp 71683 a	naphthalenes; sulfonic acid derivative		low
bedaquiline	aromatic ether; naphthalenes; organobromine compound; quinolines; tertiary alcohol; tertiary amino compound	antitubercular agent; ATP synthase inhibitor	low
6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2h-pyran-2-one	naphthalenes		low
2-methyl-5-[(2-oxo-1H-benzo[cd]indol-6-yl)sulfonylamino]-3-benzofurancarboxylic acid butyl ester	naphthalenes; sulfonic acid derivative		low
N'-(1-methyl-4-pyrazolo[3,4-d]pyrimidinyl)-2-(1-naphthalenyl)acetohydrazide	naphthalenes		low
1-(3-ethylphenyl)-3-(1-naphthalenyl)thiourea	naphthalenes		low
ws-5995 c	benzenes; naphthalenes; ring assembly		low
np 031112	benzenes; naphthalenes; thiadiazolidine	anti-inflammatory agent; apoptosis inducer; EC 2.7.11.26 (tau-protein kinase) inhibitor; neuroprotective agent	low
(6-methoxy-2-naphthalenyl)-[1-[(2-methyl-5-thiazolyl)methyl]-3-piperidinyl]methanone	naphthalenes		low
1,2-dihydroacenaphthylen-5-yl-[1-[(6-methyl-2-pyridinyl)methyl]-3-piperidinyl]methanone	naphthalenes		low
1,2-dihydroacenaphthylen-5-yl-[1-(2-pyridinylmethyl)-3-piperidinyl]methanone	naphthalenes		low
1-[3-[(6-methoxy-2-naphthalenyl)-oxomethyl]-1-piperidinyl]-2-[(5-methyl-1,3,4-oxadiazol-2-yl)thio]ethanone	naphthalenes		low
4-[[(4S)-2-amino-3-[2-(1-naphthalenyl)ethyl]-4,5-dihydroimidazol-4-yl]methyl]phenol	naphthalenes		low
[5-[(4-methoxy-1-naphthalenyl)oxymethyl]-3-isoxazolyl]-(4-methoxy-1-piperidinyl)methanone	naphthalenes		low
GRL-0617	benzamides; naphthalenes; secondary carboxamide; substituted aniline	anticoronaviral agent; protease inhibitor	low
N-(1-naphthalenylmethyl)-2-thiophenecarboxamide	naphthalenes		low
(1-(4-(naphthalen-2-yl)pyrimidin-2-yl)piperidin-4-yl)methanamine	naphthalenes		low
N-[4-cyano-2-(1-naphthalenyl)-5-oxazolyl]acetamide	naphthalenes		low
2-[(4-methylphenyl)methylthio]-5-(1-naphthalenyl)-1,3,4-oxadiazole	naphthalenes		low
5-amino-2-(1-naphthalenyl)-4-oxazolecarbonitrile	naphthalenes		low
4-(dimethylamino)benzoic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
1H-imidazole-5-carboxylic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
N-[(2R,3S)-5-[(2S)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl-[(1-naphthalenylamino)-oxomethyl]amino]methyl]-6-oxo-2,3,4,7-tetrahydro-1,5-benzoxazonin-9-yl]-2-phenylacetamide	naphthalenes		low
KOM70144	acetamides; benzamides; naphthalenes; secondary carboxamide	anticoronaviral agent; protease inhibitor	low
lesinurad	aryl sulfide; cyclopropanes; monocarboxylic acid; naphthalenes; organobromine compound; triazoles	uricosuric drug	low
difenacoum	benzenes; naphthalenes; ring assembly		low
bromfenacoum	benzenes; naphthalenes; ring assembly		low
flocoumafen	benzenes; naphthalenes; ring assembly		low
abt-333	aromatic ether; naphthalenes; pyrimidone; sulfonamide	antiviral drug; nonnucleoside hepatitis C virus polymerase inhibitor	low

Condition	Indicated	Studies	First Year	Last Year	Average Age	Relationship Strength	Trials	pre-1990	1990's	2000's	2010's	post-2020
Inflammation	0	1	2010	2010	14.0	high	0	0	0	1	0	0
Innate Inflammatory Response	0	1	2010	2010	14.0	high	0	0	0	1	0	0