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1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole

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

Description

1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole: intermediate in the synthesis of imidazolineoxyl N-oxides; partial structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID2733503
CHEMBL ID388065
CHEBI ID90702
MeSH IDM0212538

Synonyms (13)

Synonym
2-(4-carboxyphenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide . potassium salt
1,3-dtcti
corboxy-ptio
chebi:90702 ,
CHEMBL388065
2-(4-carboxyphenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide
1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole
145757-47-7
1h-imidazol-1-yloxy, 2-(4-carboxyphenyl)-4,5-dihydro-4,4,5,5-tetramethyl-, 3-oxide
FT-0623488
[2-(4-carboxyphenyl)-4,4,5,5-tetramethyl-3-oxo-4,5-dihydro-1h-3lambda(5)-imidazol-1-yl]oxidanyl
CS-0014215
HY-18734

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" These results demonstrate that (a) reduction in the availability of glucose and intracellular glutathione renders the cells more vulnerable to the cytotoxic effects of NO donors, (b) in this model of cytotoxicity, long-lived NO donors were more cytotoxic than short-lived NO donors, (c) the differential effects of N-acetylcysteine on S-nitroso-N-acetylpenicillamine-induced and bacterial lipopolysaccharide-mediated cytotoxicity support the existence of other toxic species different from NO or NO-related compounds with a potent cytotoxic activity in immunostimulated macrophages, and (d) other non-protein thiols like N-acetylcysteine may substitute for glutathione as a major component of the cellular antioxidant defense system."( The protective role of thiols against nitric oxide-mediated cytotoxicity in murine macrophage J774 cells.
Herman, AG; Matthys, KE; Zamora, R, 1997
)
0.3

Bioavailability

ExcerptReferenceRelevance
" We tested the hypothesis that endothelial dysfunction, either produced by injury or simulated pharmacologically by reducing the bioavailability of NO, results in elevated Ca2+ channel availability (ngmax=maximum conductance/cell capacitance) in smooth muscle cells isolated from the vessel."( Functional integrity of endothelium determines Ca2+ channel availability in smooth muscle: involvement of nitric oxide.
Li, X; Simard, JM, 2000
)
0.31

Dosage Studied

ExcerptRelevanceReference
" ODQ (1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one), a potent and selective inhibitor of soluble guanylyl cyclase (sGC), did not significantly affect relaxant actions of ONOO-, but ODQ markedly attenuated SIN-1-elicited relaxation with a rightward shift in the dose-response curve and an unaltered maximal response."( Comparative vasodilation of peroxynitrite and 3-morpholinosydnonimine.
Trakranrungsie, N; Will, JA, 2001
)
0.31
"5 h after permanent middle cerebral artery occlusion, to evaluate the dose-response effects."( Delayed treatment with carboxy-PTIO permits a 4-h therapeutic window of opportunity and prevents against ischemia-induced energy depletion following permanent focal cerebral ischemia in mice.
Chen, HY; Chen, TY; Hung, YC; Lee, EJ; Wu, TS, 2009
)
0.35
" In each case, the dose-response curve for N(2)O was progressively shifted to the right by increasing the dose of each pretreatment drug."( Involvement of a NO-cyclic GMP-PKG signaling pathway in nitrous oxide-induced antinociception in mice.
Chung, E; Ohgami, Y; Quock, LP; Quock, RM; Zhang, Y, 2011
)
0.37
" Further, comparative analysis of CNP with Chitosan revealed that the very small dosage of CNP performed at par with recommended dose of Chitosan for downy mildew management."( Chitosan nanoparticles having higher degree of acetylation induce resistance against pearl millet downy mildew through nitric oxide generation.
Chen, JY; Dai, XF; Gupta, VK; Kalagatur, NK; Mocan, A; Mudili, V; Prasanth, KVH; Satyanarayana, NR; Satyavati, T; Siddaiah, CN; Singh, BP; Srivastava, RK, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
radical scavengerA role played by a substance that can react readily with, and thereby eliminate, radicals.
apoptosis inhibitorAny substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
[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 (3)

ClassDescription
organic radical
benzoic acidA compound comprising a benzene ring core carrying a carboxylic acid substituent.
imidazolinesDiazoline compounds having the nitrogen atoms at the 1- and 3-positions and a double bond at an unspecified position.
[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]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID761782Inhibition of tyrosinase in SNP-stimulated mouse B16F10 cells at 16 uM incubated for 1 hr prior to SNP challenge measured after 48 hrs (Rvb = 198.83 +/- 11.46%)2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
The inhibitory effect of a synthetic compound, (Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione (MHY498), on nitric oxide-induced melanogenesis.
AID761786Antimelanogenic activity in mouse B16F10 cells assessed as reduction in SNP-induced phosphorylated CREB level at 16 uM by Western blotting analysis2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
The inhibitory effect of a synthetic compound, (Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione (MHY498), on nitric oxide-induced melanogenesis.
AID761790Inhibition of SNP-induced NO production in mouse B16F10 cells assessed as decrease of intracellular cGMP level at 16 uM incubated for 1 hr prior to SNP challenge measured after 30 mins by EIA relative to control2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
The inhibitory effect of a synthetic compound, (Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione (MHY498), on nitric oxide-induced melanogenesis.
AID761779Antimelanogenic activity in mouse B16F10 cells assessed as reduction of SNP-induced melanin level at 16 uM incubated for 1 hr prior to SNP challenge measured after 48 hrs (Rvb = 282.59 +/- 47.06%)2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
The inhibitory effect of a synthetic compound, (Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione (MHY498), on nitric oxide-induced melanogenesis.
AID761781Inhibition of tyrosinase in mouse B16F10 cells at 30 uM incubated for 1 hr prior to SNP challenge measured after 48 hrs (Rvb = 198.83 +/- 11.46%)2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
The inhibitory effect of a synthetic compound, (Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione (MHY498), on nitric oxide-induced melanogenesis.
AID287075Inhibitory ratio on NOR1-induced NO activation in human Chang liver cells assessed as nitric oxide scavenging activity relative to NOR12007Journal of natural products, May, Volume: 70, Issue:5
Cucurbitane glycosides from the fruits of Siraitia gros venorii and their inhibitory effects on Epstein-Barr virus activation.
AID288766Scavenging activity against NO generation in human Chang liver cells assessed as inhibition of NOR1-activation at 350 nM relative to NOR12007Journal of natural products, Jun, Volume: 70, Issue:6
Cancer chemopreventive effects of cycloartane-type and related triterpenoids in in vitro and in vivo models.
AID378962Scavenging activity against (+/-)-(E)-methyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide-induced NO generation in human Chang liver cells2006Journal of natural products, Jan, Volume: 69, Issue:1
Chalcones and other compounds from the exudates of Angelica keiskei and their cancer chemopreventive effects.
AID358972Antioxidant activity assessed as nitric oxide radical scavenging activity2002Journal of natural products, May, Volume: 65, Issue:5
Parasitenone, a new epoxycyclohexenone related to gabosine from the marine-derived fungus Aspergillus parasiticus.
AID761794Inhibition of SNP-induced NO production in mouse B16F10 cells at 16 uM incubated 1 hr prior to SNP challenge measured after 48 hrs by Griess assay (Rvb = 237.84 +/- 4.12%)2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
The inhibitory effect of a synthetic compound, (Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione (MHY498), on nitric oxide-induced melanogenesis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (284)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's69 (24.30)18.2507
2000's107 (37.68)29.6817
2010's99 (34.86)24.3611
2020's9 (3.17)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (0.34%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other289 (99.66%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]