4-{4-(3-Methoxybenzoylamino)-2-methylphenoxy}phenol

ID: ALA2441094

Chembl Id: CHEMBL2441094

PubChem CID: 60165333

Max Phase: Preclinical

Molecular Formula: C21H19NO4

Molecular Weight: 349.39

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1cccc(C(=O)Nc2ccc(Oc3ccc(O)cc3)c(C)c2)c1

Standard InChI:  InChI=1S/C21H19NO4/c1-14-12-16(22-21(24)15-4-3-5-19(13-15)25-2)6-11-20(14)26-18-9-7-17(23)8-10-18/h3-13,23H,1-2H3,(H,22,24)

Standard InChI Key:  IBNFBUZURJLOIX-UHFFFAOYSA-N

Associated Targets(Human)

AR Tclin Androgen Receptor (11781 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGR Tclin Progesterone receptor (8562 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LNCaP (8286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CWR22R (2180 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Ar Androgen Receptor (399 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SC-3 (21 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: NoAvailability: 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: 349.39Molecular Weight (Monoisotopic): 349.1314AlogP: 4.75#Rotatable Bonds: 5
Polar Surface Area: 67.79Molecular Species: NEUTRALHBA: 4HBD: 2
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 9.70CX Basic pKa: CX LogP: 4.62CX LogD: 4.62
Aromatic Rings: 3Heavy Atoms: 26QED Weighted: 0.70Np Likeness Score: -1.00

References

1. Yamada A, Fujii S, Mori S, Kagechika H..  (2013)  Design and Synthesis of 4-(4-Benzoylaminophenoxy)phenol Derivatives As Androgen Receptor Antagonists.,  (10): [PMID:24900588] [10.1021/ml4001744]
2. Yamada A, Kazui Y, Yoshioka H, Tanatani A, Mori S, Kagechika H, Fujii S..  (2016)  Development of N-(4-Phenoxyphenyl)benzenesulfonamide Derivatives as Novel Nonsteroidal Progesterone Receptor Antagonists.,  (12): [PMID:27994732] [10.1021/acsmedchemlett.6b00184]
3. Yoshioka H, Yamada A, Nishiyama Y, Kagechika H, Hashimoto Y, Fujii S..  (2017)  Development of nonsteroidal glucocorticoid receptor modulators based on N-benzyl-N-(4-phenoxyphenyl)benzenesulfonamide scaffold.,  25  (13): [PMID:28506584] [10.1016/j.bmc.2017.04.032]
4. Kazui Y, Fujii S, Yamada A, Ishigami-Yuasa M, Kagechika H, Tanatani A..  (2018)  Structure-activity relationship of novel (benzoylaminophenoxy)phenol derivatives as anti-prostate cancer agents.,  26  (18): [PMID:30228001] [10.1016/j.bmc.2018.09.008]
5. Xiang W, Wang S..  (2022)  Therapeutic Strategies to Target the Androgen Receptor.,  65  (13.0): [PMID:35786895] [10.1021/acs.jmedchem.2c00716]

Source