Compounds > 4',6-dichloroflavan
Page last updated: 2024-12-07

4',6-dichloroflavan

Description

4',6-dichloroflavan: antirhinovirus cpd; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID126331
CHEMBL ID29441
SCHEMBL ID4461737
MeSH IDM0097560

Synonyms (16)

Synonym
73110-56-2
6-chloro-2-(4-chlorophenyl)chromane
bw683c
4',6-dichloroflavan
2h-1-benzopyran, 6-chloro-2-(4-chlorophenyl)-3,4-dihydro-
bw-683c
brn 5750146
6,4'-dichloroflavan
bw 683c
2h-1-benzopyran, 3,4-dihydro-6-chloro-2-(4-chlorophenyl)-
3,4-dihydro-6-chloro-2-(4-chlorophenyl)-2h-1-benzopyran
CHEMBL29441
SCHEMBL4461737
6-chloro-2-(4-chlorophenyl)-3,4-dihydro-2h-1-benzopyran
DTXSID80993860
6,4'-dichloroflavan; bw 683c; bw 683c77

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Mice dosed orally with 200 mg/kg of 1c or 1h exhibited serum levels well in excess of each compound's MIC50, indicating that some analogues have the potential to be orally effective drugs."( 3,4-Dihydro-2-phenyl-2H-pyrano[2,3-b]pyridines with potent antirhinovirus activity.
Bargar, TM; Daniel, JK; Dulworth, JK; Kenny, MT; Massad, R; Sargent, RN; Wilson, T, 1986)		0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID200189In vitro activity against Rhinovirus type 1B by plaque inhibition assay.1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
9-Benzyl-6-(dimethylamino)-9H-purines with antirhinovirus activity.
AID200199In vitro anti-picornavirus activity against Rhinovirus type-2.1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Isoxazoles with antipicornavirus activity.
AID511348Antiviral activity against Human enterovirus 71 infected in human Hep2 cells at maximum non-cytotoxic concentration after 3 days by plaque reduction assay2010Bioorganic & medicinal chemistry, Sep-01, Volume: 18, Issue:17
New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders.
AID1063591Cytotoxicity against human HeLa cells assessed as reduction in cell viability after 3 days by XTT assay2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Synthesis and anti-rhinovirus activity of novel 3-[2-(pyridinyl)vinyl]substituted -2H-chromenes and -4H-chromen-4-ones.
AID86997Concentration required to reduce Rhino virus type 9 induced plaque formation in HeLa cell culture to 50% of control1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
3,4-Dihydro-2-phenyl-2H-pyrano[2,3-b]pyridines with potent antirhinovirus activity.
AID1063586Antiviral activity against HRV 1B infected in human HeLa cells assessed as reduction in plaque number at maximum non-cytotoxic concentration after 3 days by neutral red assay2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Synthesis and anti-rhinovirus activity of novel 3-[2-(pyridinyl)vinyl]substituted -2H-chromenes and -4H-chromen-4-ones.
AID424993Therapeutic index, ratio of TC50 for human HeLa Ohio cells to IC50 for HRV1B infected in human HeLa Ohio cells2009Bioorganic & medicinal chemistry, May-15, Volume: 17, Issue:10
Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives.
AID86992Concentration required to reduce Rhino virus type 1A induced plaque formation in HeLa cell culture to 50% of control1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
3,4-Dihydro-2-phenyl-2H-pyrano[2,3-b]pyridines with potent antirhinovirus activity.
AID199858In vitro antiviral activity against Rhinovirus type-21985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID1439647Antiviral activity against HRV 14 infected in human HeLa cells up to MNCC after 72 hrs by plaque reduction assay2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors.
AID1439635Antiviral activity against HRV 1B infected in human HeLa cells after 72 hrs by plaque reduction assay2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors.
AID86823Lowest concentration at which the effect on HeLa cell colony formation became apparent.1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
3,4-Dihydro-2-phenyl-2H-pyrano[2,3-b]pyridines with potent antirhinovirus activity.
AID86994Concentration required to reduce Rhino virus type 64 induced plaque formation in HeLa cell culture to 50% of control1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
3,4-Dihydro-2-phenyl-2H-pyrano[2,3-b]pyridines with potent antirhinovirus activity.
AID162259In vitro anti-picornavirus activity against Poliovirus type-2.1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Isoxazoles with antipicornavirus activity.
AID103315Compound was tested for anti-rhinovirus type 1B activity in a plaque inhibition assay using monolayers of M-HeLa cells1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Synthesis and structure-activity relationships of 2-substituted-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purines with antirhinovirus activity.
AID634250Therapeutic index, ratio of TC50 for human HeLa cells to IC50 for Human rhinovirus 1B infected in human HeLa cells2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Design, synthesis and in vitro evaluation of novel chroman-4-one, chroman, and 2H-chromene derivatives as human rhinovirus capsid-binding inhibitors.
AID511347Antiviral activity against Human enterovirus 71 infected in human Hep2 cells after 2 days by plaque reduction assay2010Bioorganic & medicinal chemistry, Sep-01, Volume: 18, Issue:17
New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders.
AID1439634Cytotoxicity against human HeLa cells assessed as reduction in cell viability by XTT assay2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors.
AID424987Cytotoxicity against human HeLa Ohio cells after 3 days by XTT assay2009Bioorganic & medicinal chemistry, May-15, Volume: 17, Issue:10
Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives.
AID332519Antiviral activity against Rhinovirus 1B infected in human HeLa cells assessed as reduction in plaque formation per plate after 72 hrs1994Journal of natural products, May, Volume: 57, Issue:5
Isolation of antirhinoviral sesquiterpenes from ginger (Zingiber officinale).
AID1063590Antiviral activity against HRV 1B infected in human HeLa cells assessed as reduction in plaque number after 3 days by neutral red assay2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Synthesis and anti-rhinovirus activity of novel 3-[2-(pyridinyl)vinyl]substituted -2H-chromenes and -4H-chromen-4-ones.
AID1063589Selectivity index, ratio of CC50 for human HeLa cells to IC50 for HRV 1B infected in human HeLa cells2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Synthesis and anti-rhinovirus activity of novel 3-[2-(pyridinyl)vinyl]substituted -2H-chromenes and -4H-chromen-4-ones.
AID1439636Selectivity index, ratio of CC50 for human HeLa cells to IC50 for HRV 1B infected in human HeLa cells2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors.
AID511340Cytotoxicity against human HeLa cells assessed as maximum non-cytotoxic concentration after 3 days by XTT assay2010Bioorganic & medicinal chemistry, Sep-01, Volume: 18, Issue:17
New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders.
AID634248Cytotoxicity against human HeLa cells after 3 days by XTT based ELISA reader2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Design, synthesis and in vitro evaluation of novel chroman-4-one, chroman, and 2H-chromene derivatives as human rhinovirus capsid-binding inhibitors.
AID200198Evaluated for inhibitory activity against rhinovirus type 51990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Antirhinovirus activity of 6-anilino-9-benzyl-2-chloro-9H-purines.
AID634249Antiviral activity against Human rhinovirus 1B infected in human HeLa cells assessed as inhibition of virus induced-plaque formation after 3 days by neutral red-based plaque reduction assay2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Design, synthesis and in vitro evaluation of novel chroman-4-one, chroman, and 2H-chromene derivatives as human rhinovirus capsid-binding inhibitors.
AID200197Evaluated for inhibitory activity against rhinovirus type 41990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Antirhinovirus activity of 6-anilino-9-benzyl-2-chloro-9H-purines.
AID511341Antiviral activity against Human rhinovirus 1B infected in human HeLa cells after 3 days by plaque reduction assay2010Bioorganic & medicinal chemistry, Sep-01, Volume: 18, Issue:17
New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders.
AID115933In vitro antiviral activity against mice infected intracerebrally with Poliovirus type-2; Inactive1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID200195Evaluated for inhibitory activity against rhinovirus type 21990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Antirhinovirus activity of 6-anilino-9-benzyl-2-chloro-9H-purines.
AID1439633Cytotoxicity against human HeLa cells assessed as changes in morphology after 3 days by microscopic method2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors.
AID424989Antiviral activity against HRV 1B infected in human HeLa Ohio cells assessed as reduction in viral plaque formation after 3 days by neutral red uptake assay2009Bioorganic & medicinal chemistry, May-15, Volume: 17, Issue:10
Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives.
AID511344Antiviral activity against Human rhinovirus 14 infected in human HeLa cells at maximum non-cytotoxic concentration after 3 days by plaque reduction assay2010Bioorganic & medicinal chemistry, Sep-01, Volume: 18, Issue:17
New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders.
AID634247Cytotoxicity against human HeLa cells after 3 days by microscopic analysis2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Design, synthesis and in vitro evaluation of novel chroman-4-one, chroman, and 2H-chromene derivatives as human rhinovirus capsid-binding inhibitors.
AID634254Antiviral activity against Human rhinovirus 14 infected in human HeLa cells assessed as inhibition of virus induced-plaque formation at 25 uM after 3 days by neutral red-based plaque reduction assay2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Design, synthesis and in vitro evaluation of novel chroman-4-one, chroman, and 2H-chromene derivatives as human rhinovirus capsid-binding inhibitors.
AID511339Cytotoxicity against human HeLa cells after 3 days by XTT assay2010Bioorganic & medicinal chemistry, Sep-01, Volume: 18, Issue:17
New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders.
AID511346Cytotoxicity against human Hep2 cells assessed as maximum non-cytotoxic concentration after 3 days by XTT assay2010Bioorganic & medicinal chemistry, Sep-01, Volume: 18, Issue:17
New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders.
AID200192Inhibitory activity against rhinovirus type 1B1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Antirhinovirus activity of 6-anilino-9-benzyl-2-chloro-9H-purines.
AID424991Antiviral activity against HRV 14 infected in human HeLa Ohio cells assessed as reduction in viral plaque formation after 3 days by neutral red uptake assay2009Bioorganic & medicinal chemistry, May-15, Volume: 17, Issue:10
Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives.
AID424988Cytotoxicity against human HeLa Ohio cells assessed as maximal non-cytotoxic concentration after 3 days by XTT assay2009Bioorganic & medicinal chemistry, May-15, Volume: 17, Issue:10
Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (65.38)18.7374
1990's3 (11.54)18.2507
2000's1 (3.85)29.6817
2010's4 (15.38)24.3611
2020's1 (3.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.12

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 Index11.12 (24.57)
Research Supply Index3.43 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.12)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (11.11%)5.53%
Reviews3 (11.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (77.78%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetic acid
Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.		1.9610monocarboxylic acidantimicrobial food preservative;
Daphnia magna metabolite;
food acidity regulator;
protic solvent
win 52035
Win 52035: structure given in first source		1.9610aromatic ether
win 52084
Win 52084: structure given in first source; RN given refers to (+-)-isomer; RN for cpd without isomeric designation not available 7/89		1.9610aromatic ether
ciprofloxacin
Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.		3.0610aminoquinoline;
cyclopropanes;
fluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone;
zwitterion		antibacterial drug;
antiinfective agent;
antimicrobial agent;
DNA synthesis inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
environmental contaminant;
topoisomerase IV inhibitor;
xenobiotic
chloroform
Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.		1.9610chloromethanes;
one-carbon compound		carcinogenic agent;
central nervous system drug;
inhalation anaesthetic;
non-polar solvent;
refrigerant
isoxazoles
Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.		3.7630isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
neutral red
Neutral Red: A vital dye used as an indicator and biological stain. Various adverse effects have been observed in biological systems.. neutral red : A hydrochloride obtained by combining the free base of neutral red with one equivalent of hydrochloric acid. Neutral red acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0.		1.9610hydrochlorideacid-base indicator;
dye;
two-colour indicator
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		1.9610benzenes;
phenyl acetates
arildone
[no description available]		1.9610methoxybenzenes
amifloxacin
amifloxacin: structure in UD		3.0610quinolines
disoxaril
disoxaril: antipicornavirus agent		3.9840aromatic ether
rmi 15731
RMI 15731: structure		3.7530
r 61837
R 61837: antirhinovirus cpd; structure given in first source		2.3820
chalcone
trans-chalcone : The trans-isomer of chalcone.		6.9291chalconeEC 3.2.1.1 (alpha-amylase) inhibitor
sodium dodecyl sulfate
Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.		1.9610organic sodium saltdetergent;
protein denaturant
quercetin
[no description available]		2.37207-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
pachypodol
pachypodol: new flavonoid isolated from Pachypodanthium confine; from Chinese herb Agastache folium; structure. pachypodol : A trimethoxyflavone that is quercetin in which the hydroxy groups at position 3, 7 and 3' are replaced by methoxy groups. It has been isolated from Combretum quadrangulare and Euodia elleryana.		2.3720dihydroxyflavone;
trimethoxyflavone		antiemetic;
plant metabolite
viroxime
[no description available]		9.1650
ro 09-0410
Ro 09-0410: structure given in first source		11.6871
ConditionIndicatedRelationship StrengthStudiesTrials
Infections, Picornaviridae
[description not available]		03.8140
Catarrh
Inflammation of a mucous membrane with increased flow of mucous in humans or animals. Catarrh is used mostly in a historical context.		06.5743
Common Cold
A catarrhal disorder of the upper respiratory tract, which may be viral or a mixed infection. It generally involves a runny nose, nasal congestion, and sneezing.		06.5743
Hepatitis B Virus Infection
[description not available]		04.2711
Hepatitis B
INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.		04.2711
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