Compounds > 6-chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinolin-4(1h)-one
Page last updated: 2024-11-13

6-chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinolin-4(1h)-one

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Description

6-Chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinolin-4(1H)-one: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID67016608
CHEMBL ID2431810
SCHEMBL ID1394397
MeSH IDM000610680

Synonyms (25)

Synonym
6-chloro-7-methoxy-2-methyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1h-quinolin-4-one
elq-300
CHEMBL2431810
6-chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy) phenyl) quinolin-4(1h)-one
6-chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinolin-4(1h)-one
SCHEMBL1394397
1354745-52-0
gtpl10021
elq300
HY-13836
Q15410945
elq300; elq 300
BCP30856
SB17071
BS-45982
CS-0007966
N17034
endochin-like quinolone-300
6-chloro-7-methoxy-2-methyl-3-{4-[4-(trifluoromethoxy)phenoxy]phenyl}quinolin-4(1h)-one
4(1h)-quinolinone, 6-chloro-7-methoxy-2-methyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-
6-chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)-4(1h)-quinolinone
brc5ye92rx ,
4(1h)-quinolinone, 6-chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)-
unii-brc5ye92rx
DTXSID001045320

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"To improve the solubility and oral bioavailability of a novel antimalarial agent ELQ-331(a prodrug of ELQ-300), spray-dried dispersions (SDD) and a self-emulsifying drug delivery system (SEDDS) were developed."( Improving solubility and oral bioavailability of a novel antimalarial prodrug: comparing spray-dried dispersions with self-emulsifying drug delivery systems.
Frueh, L; Green, C; Liu, M; Mutyam, SK; Nilsen, A; Potharaju, S; Pou, S; Riscoe, MK; Shankar, G; Winter, R, 2020)		0.56

Dosage Studied

ExcerptRelevanceReference
" In our monotherapy assessments, we found that ATV functioned as a single-dose curative compound in suppressive tests whereas ELQ-300 demonstrated a unique cumulative dosing effect that successfully blocked recrudescence even in a high-parasitemia acute infection model."( Atovaquone and ELQ-300 Combination Therapy as a Novel Dual-Site Cytochrome bc1 Inhibition Strategy for Malaria.
Forquer, IP; Kelly, JX; Li, Y; Morrisey, JM; Nilsen, A; Pou, S; Riscoe, MK; Smilkstein, MJ; Stickles, AM; Vaidya, AB; Winter, RW, 2016)		0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID1625271Antimalarial activity against atovaquone-resistant Plasmodium falciparum TM90C2B2016Journal of medicinal chemistry, 06-23, Volume: 59, Issue:12
Antimalarial Chemotherapy: Natural Product Inspired Development of Preclinical and Clinical Candidates with Diverse Mechanisms of Action.
AID1140157Inhibition of human cytochrome bc1 complex derived from HEK293 cell mitochondria using 50 uM decylubiquinol as substrate2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1625270Inhibition of Plasmodium falciparum NDH2 expressed in HEK293 cells by spectrophotometric analysis2016Journal of medicinal chemistry, 06-23, Volume: 59, Issue:12
Antimalarial Chemotherapy: Natural Product Inspired Development of Preclinical and Clinical Candidates with Diverse Mechanisms of Action.
AID1140155Antimalarial activity against atovaquone-resistant clinical isolate Plasmodium falciparum TM90-C2B infected in human red blood cells assessed as suppression of parasitemia after 72 hrs by SYBR Green I-based fluorescence method2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1140159Antimalarial activity against Plasmodium yoelii MR4 MRA-428 infected in mouse CF1 assessed as dose required to achieve cure measured as 30 days survival administered through oral gavage once daily for 4 days2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1140154Antimalarial activity against multidrug-resistant Plasmodium falciparum Dd2 MRA-156 infected in human red blood cells assessed as suppression of parasitemia after 72 hrs by SYBR Green I-based fluorescence method2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1412517Antimalarial activity against Plasmodium berghei infected in mouse by Thompson test2018MedChemComm, Mar-01, Volume: 9, Issue:3
Recent updates in the discovery and development of novel antimalarial drug candidates.
AID1604218Antiparasitic activity against Plasmodium falciparum infected in mouse2019European journal of medicinal chemistry, Nov-01, Volume: 181New dimensions in the field of antimalarial research against malaria resurgence.
AID1140158Antimalarial activity against Plasmodium yoelii MR4 MRA-428 infected in mouse CF1 assessed as reduction on parasite burden administered through oral gavage once daily for 4 days2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1140156Cytotoxicity against human HepG2 cells after 24 hrs incubation by Alamar Blue assay2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1604213Antiparasitic activity against Plasmodium falciparum infected in human PBMC2019European journal of medicinal chemistry, Nov-01, Volume: 181New dimensions in the field of antimalarial research against malaria resurgence.
AID1604219Antiparasitic activity against Plasmodium falciparum infected in SCID mouse2019European journal of medicinal chemistry, Nov-01, Volume: 181New dimensions in the field of antimalarial research against malaria resurgence.
AID1604209Antiparasitic activity against Plasmodium falciparum 3D72019European journal of medicinal chemistry, Nov-01, Volume: 181New dimensions in the field of antimalarial research against malaria resurgence.
AID1140153Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 MRA-285 infected in human red blood cells assessed as suppression of parasitemia after 72 hrs by SYBR Green I-based fluorescence method2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1375191Resistance index, ratio of IC50 for drug-resistant Plasmodium falciparum Dd2 harboring CytB Ile22Leu mutant to IC50 for wild type Plasmodium falciparum Dd22018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
Identification of Fast-Acting 2,6-Disubstituted Imidazopyridines That Are Efficacious in the in Vivo Humanized Plasmodium falciparum NODscidIL2Rγ
AID1625269Antimalarial activity against Plasmodium falciparum 3D72016Journal of medicinal chemistry, 06-23, Volume: 59, Issue:12
Antimalarial Chemotherapy: Natural Product Inspired Development of Preclinical and Clinical Candidates with Diverse Mechanisms of Action.
AID1140161Metabolic stability in human liver microsomes2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1625267Antimalarial activity against blood stage Plasmodium yoelii infected in mouse administered qd through oral gavage for 4 days2016Journal of medicinal chemistry, 06-23, Volume: 59, Issue:12
Antimalarial Chemotherapy: Natural Product Inspired Development of Preclinical and Clinical Candidates with Diverse Mechanisms of Action.
AID1849714Antimalarial activity against Plasmodium falciparum Dd22021European journal of medicinal chemistry, Jan-15, Volume: 210An insight into the recent development of the clinical candidates for the treatment of malaria and their target proteins.
AID1375190Antimalarial activity against wild type Plasmodium falciparum Dd22018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
Identification of Fast-Acting 2,6-Disubstituted Imidazopyridines That Are Efficacious in the in Vivo Humanized Plasmodium falciparum NODscidIL2Rγ
AID1140160Metabolic stability in rat liver microsomes2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1140164Selectivity ratio of IC50 for human cytochrome bc1 complex to EC50 for Plasmodium falciparum cytochrome bc1 complex2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1849717Cytotoxicity against human HepG2 cells2021European journal of medicinal chemistry, Jan-15, Volume: 210An insight into the recent development of the clinical candidates for the treatment of malaria and their target proteins.
AID1604220Antiparasitic activity against Plasmodium falciparum2019European journal of medicinal chemistry, Nov-01, Volume: 181New dimensions in the field of antimalarial research against malaria resurgence.
AID772528Solubility of the compound at pH 6.82013Journal of medicinal chemistry, Oct-24, Volume: 56, Issue:20
Cell-based medicinal chemistry optimization of high-throughput screening (HTS) hits for orally active antimalarials. Part 1: challenges in potency and absorption, distribution, metabolism, excretion/pharmacokinetics (ADME/PK).
AID1849719Antimalarial activity against Plasmodium falciparum Tm90-C2B2021European journal of medicinal chemistry, Jan-15, Volume: 210An insight into the recent development of the clinical candidates for the treatment of malaria and their target proteins.
AID772529Antimicrobial activity against clinical isolates of Plasmodium falciparum2013Journal of medicinal chemistry, Oct-24, Volume: 56, Issue:20
Cell-based medicinal chemistry optimization of high-throughput screening (HTS) hits for orally active antimalarials. Part 1: challenges in potency and absorption, distribution, metabolism, excretion/pharmacokinetics (ADME/PK).
AID1140163Inhibition of cytochrome bc1 complex isolated from trophozoite stage Plasmodium falciparum2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1604203Antiparasitic activity against Plasmodium falciparum D62019European journal of medicinal chemistry, Nov-01, Volume: 181New dimensions in the field of antimalarial research against malaria resurgence.
AID1140165Antimalarial activity against Plasmodium falciparum TM93-C1088 assessed as suppression of parasitemia after 72 hrs by SYBR Green I-based fluorescence method2014Journal of medicinal chemistry, May-08, Volume: 57, Issue:9
Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers.
AID1849720In vivo antimalarial activity against Plasmodium yoelii infected in mouse2021European journal of medicinal chemistry, Jan-15, Volume: 210An insight into the recent development of the clinical candidates for the treatment of malaria and their target proteins.
AID1375182Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring CytB Ile22Leu mutant2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
Identification of Fast-Acting 2,6-Disubstituted Imidazopyridines That Are Efficacious in the in Vivo Humanized Plasmodium falciparum NODscidIL2Rγ
AID1625268Inhibition of Plasmodium falciparum cytochrome bc1 expressed in HEK293 cells by spectrophotometric analysis2016Journal of medicinal chemistry, 06-23, Volume: 59, Issue:12
Antimalarial Chemotherapy: Natural Product Inspired Development of Preclinical and Clinical Candidates with Diverse Mechanisms of Action.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's13 (81.25)24.3611
2020's3 (18.75)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.70

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.

MetricThis Compound (vs All)
Research Demand Index11.70 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.70)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (31.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (68.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
fosmidomycin
fosmidomycin: from Streptomyces lavendulae; RN given refers to parent cpd; structure in second source. fosmidomycin : Propylphosphonic acid in which one of the hydrogens at position 3 is substituted by a formyl(hydroxy)amino group. An antibiotic obtained from Streptomyces lavendulae, it specifically inhibits DXP reductoisomerase (EC 1.1.1.267), a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis.		3.2310hydroxamic acid;
phosphonic acids		antimicrobial agent;
bacterial metabolite;
EC 1.1.1.267 (1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitor
iodine
Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..		2.1110diatomic iodinenutrient
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		4.740aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
primaquine
Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.		3.4110aminoquinoline;
aromatic ether;
N-substituted diamine		antimalarial
carbostyril
Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.		3.7690monohydroxyquinoline;
quinolone		bacterial xenobiotic metabolite
ethyl acetoacetate
ethyl acetoacetate: RN given refers to unlabeled parent cpd. ethyl acetoacetate : An ethyl ester resulting from the formal condensation of the carboxy group of acetoacetic acid with ethanol.		2.1110ethyl esterantibacterial agent;
flavouring agent;
plant metabolite
pamaquine
pamaquine: structure; RN given refers to parent cpd		3.4110aminoquinoline
erythromycin
Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.		3.2310cyclic ketone;
erythromycin
clopidol
pharmcoccide: Russian drug; no other info available 1/1/79		3.1810chloropyridine
pentaquine
pentaquine: RN given refers to parent cpd		3.4110
mefloquine
(-)-(11S,2'R)-erythro-mefloquine : An optically active form of [2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol having (-)-(11S,2'R)-erythro-configuration. An antimalarial agent, used in racemic form, which acts as a blood schizonticide; its mechanism of action is unknown.		3.3110[2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanolantimalarial
quinocide
quinocide: Russian drug; RN given refers to parent cpd; structure		3.4110
coptisine
coptisine: RN given refers to parent cpd		3.4110alkaloidmetabolite
atovaquone
Atovaquone: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.. atovaquone : A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position.		4.1540hydroxy-1,2-naphthoquinone
3-heptyl-4-hydroxy-7-methoxy-2-methylquinoline
3-heptyl-4-hydroxy-7-methoxy-2-methylquinoline: structure given in first source		2.110
wr 99210
BRL 6231: RN given refers to parent cpd; NM & N1 refer to HCl; synonym BRL 51084 refers to (mono-HBr); structure		3.2710
3-(n-acetyl-n-hydroxy)aminopropylphosphonic acid
3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid: from Streptomyces rubellomurinus sp. nov.; interferes with bacterial cell wall synthesis; structure in first source		3.2310phosphonoacetic acid
ferruginol
ferruginol: structure in first source. ferruginol : An abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12.		3.3110abietane diterpenoid;
carbotricyclic compound;
meroterpenoid;
phenols		antibacterial agent;
antineoplastic agent;
plant metabolite;
protective agent
clindamycin
Clindamycin: An antibacterial agent that is a semisynthetic analog of LINCOMYCIN.. clindamycin : A carbohydrate-containing antibiotic that is the semisynthetic derivative of lincomycin, a natural antibiotic.		3.2310
zithromax
Azithromycin: A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.. azithromycin : A macrolide antibiotic useful for the treatment of bacterial infections.		3.2310macrolide antibioticantibacterial drug;
environmental contaminant;
xenobiotic
proguanil
Proguanil: A biguanide compound which metabolizes in the body to form cycloguanil, an anti-malaria agent.. proguanil : A biguanide compound which has isopropyl and p-chlorophenyl substituents on the terminal N atoms. A prophylactic antimalarial drug, it works by inhibiting the enzyme dihydrofolate reductase, which is involved in the reproduction of the malaria parasites Plasmodium falciparum and P. vivax within the red blood cells.		2.5820biguanides;
monochlorobenzenes		antimalarial;
antiprotozoal drug;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor
artesunate
artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether		2.1710artemisinin derivative;
cyclic acetal;
dicarboxylic acid monoester;
hemisuccinate;
semisynthetic derivative;
sesquiterpenoid		antimalarial;
antineoplastic agent;
ferroptosis inducer
arterolane
arterolane: a trioxolane with antimalarial activity; structure in first source. arterolane : An oxaspiro compound that is dispiro[cyclohexane-1,3'-[1,2,4]trioxolane-5',2''-tricyclo[3.3.1.1(3,7)]decane] substituted by a 2-[(2-amino-2-methylpropyl)amino]-2-oxoethyl group at position 4s. Its maleic acid salt is used as an antimalarial drug in combination with piperaquine.		3.2310
oz 439
artefenomel: an antimalarial ozonide; structure in first source		4.220
nitd 609
NITD 609: an antimalarial and coccidiostat; structure in first source		5.0340
kaf156
ganaplacide: antimalarial		3.4110
sj733
SJ733: antimalarial; structure in first source		3.6820
ConditionIndicatedRelationship StrengthStudiesTrials
Plasmodium falciparum Malaria
[description not available]		03.4220
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		03.4220
Infections, Plasmodium
[description not available]		05.1260
Malaria
A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.		05.1260
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1710
Parasitemia
The presence of parasites (especially malarial parasites) in the blood. (Dorland, 27th ed)		02.1310