5-{7-[4-(4,5-Dihydro-oxazol-2-yl)-phenoxy]-heptyl}-3-methyl-isoxazole

ID: ALA283639

Chembl Id: CHEMBL283639

Cas Number: 87495-31-6

PubChem CID: 55717

Max Phase: Phase

Molecular Formula: C20H26N2O3

Molecular Weight: 342.44

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Disoxaril | WIN 51,711 | WIN-51711 | DISOXARIL|87495-31-6|Compound IV|Disoxarilum [Latin]|WIN 51711|Disoxarilo [Spanish]|Win-51711|FX8Q9PI4VP|WIN 51,711|CHEBI:3846|3-Methyl-5-(7-(p-2-oxazolin-2-ylphenoxy)heptyl)isoxazole|5-(7-(4-(4,5-Dihydro-2-oxazolyl)phenoxy)heptyl)-3-methylisoxazole|5-(7-(4-(4,5-DIHYDRO-2-OXAZOLYL)PHENOXY)HEPTYL)-3-METHYL ISOXAZOLE|Isoxazole, 5-(7-(4-(4,5-dihydro-2-oxazolyl)phenoxy)heptyl)-3-methyl-|Isoxazole, 5-[7-[4-(4,5-dihydro-2-oxazolyl)phenoxy]heptyl]-3-methyl-|DisoxariShow More

Canonical SMILES:  Cc1cc(CCCCCCCOc2ccc(C3=NCCO3)cc2)on1

Standard InChI:  InChI=1S/C20H26N2O3/c1-16-15-19(25-22-16)7-5-3-2-4-6-13-23-18-10-8-17(9-11-18)20-21-12-14-24-20/h8-11,15H,2-7,12-14H2,1H3

Standard InChI Key:  FKLJPTJMIBLJAV-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

    ALA283639

    DISOXARIL

Associated Targets(Human)

HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RD (1212 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Human rhinovirus sp. (1587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterovirus (1116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rhinovirus A2 (409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rhinovirus B14 (1052 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Echovirus E13 (7 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Poliovirus 1 (1274 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Coxsackievirus B1 (166 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterovirus A71 (1246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Poliovirus 2 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 342.44Molecular Weight (Monoisotopic): 342.1943AlogP: 4.33#Rotatable Bonds: 10
Polar Surface Area: 56.85Molecular Species: NEUTRALHBA: 5HBD:
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 3.99CX LogP: 4.15CX LogD: 4.15
Aromatic Rings: 2Heavy Atoms: 25QED Weighted: 0.60Np Likeness Score: -0.77

References

1. Diana GD, Treasurywala AM, Bailey TR, Oglesby RC, Pevear DC, Dutko FJ..  (1990)  A model for compounds active against human rhinovirus-14 based on X-ray crystallography data.,  33  (5): [PMID:2158559] [10.1021/jm00167a006]
2. Leclerc F, Cedergren R..  (1998)  Modeling RNA-ligand interactions: the Rev-binding element RNA-aminoglycoside complex.,  41  (2): [PMID:9457241] [10.1021/jm970372r]
3. Diana GD, McKinlay MA, Otto MJ, Akullian V, Oglesby C..  (1985)  [[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.,  28  (12): [PMID:2999407] [10.1021/jm00150a025]
4. Diana GD, Oglesby RC, Akullian V, Carabateas PM, Cutcliffe D, Mallamo JP, Otto MJ, McKinlay MA, Maliski EG, Michalec SJ..  (1987)  Structure-activity studies of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating.,  30  (2): [PMID:3027340] [10.1021/jm00385a021]
5. Diana GD, Otto MJ, Treasurywala AM, McKinlay MA, Oglesby RC, Maliski EG, Rossmann MG, Smith TJ..  (1988)  Enantiomeric effects of homologues of disoxaril on the inhibitory activity against human rhinovirus-14.,  31  (3): [PMID:2831362] [10.1021/jm00398a009]
6. Massa S, Artico M, Mai A, Ragno R, Corelli F, Pani A, Marongiu M, Tramontano E, La Colla P.  (1991)  Synthesis of new disoxaril analogues with potent and selective anti-human rhinovirus 14 activity,  (11): [10.1016/S0960-894X(01)81153-7]
7. Klebe G, Abraham U..  (1993)  On the prediction of binding properties of drug molecules by comparative molecular field analysis.,  36  (1): [PMID:8380615] [10.1021/jm00053a009]
8. Massa S, Corelli F, Artico M, Mai A, Ragno R, De Montis A, Loi AG, Corrias S, Marongiu ME, La Colla P..  (1995)  [[[(Thienylcarbonyl)alkyl]oxy]phenyl]- and [[[(pyrrylcarbonyl)alkyl]oxy]phenyl]oxazoline derivatives with potent and selective antihuman rhinovirus activity.,  38  (5): [PMID:7877145] [10.1021/jm00005a007]
9. Spasova M, Philipov S, Nikolaeva-Glomb L, Galabov AS, Milkova Ts..  (2008)  Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.,  16  (15): [PMID:18590964] [10.1016/j.bmc.2008.06.010]
10. Martucci WE, Udier-Blagovic M, Atreya C, Babatunde O, Vargo MA, Jorgensen WL, Anderson KS..  (2009)  Novel non-active site inhibitor of Cryptosporidium hominis TS-DHFR identified by a virtual screen.,  19  (2): [PMID:19059777] [10.1016/j.bmcl.2008.11.054]
11. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 
12. Han X, Sun N, Wu H, Guo D, Tien P, Dong C, Wu S, Zhou HB..  (2016)  Identification and Structure-Activity Relationships of Diarylhydrazides as Novel Potent and Selective Human Enterovirus Inhibitors.,  59  (5): [PMID:26885567] [10.1021/acs.jmedchem.5b01803]
13. Egorova A, Ekins S, Schmidtke M, Makarov V..  (2019)  Back to the future: Advances in development of broad-spectrum capsid-binding inhibitors of enteroviruses.,  178  [PMID:31226653] [10.1016/j.ejmech.2019.06.008]
14. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]