(E)-3-(4-Bromo-phenyl)-1-(2-hydroxy-phenyl)-propenone

ID: ALA89988

Chembl Id: CHEMBL89988

Cas Number: 65786-14-3

PubChem CID: 5372941

Max Phase: Preclinical

Molecular Formula: C15H11BrO2

Molecular Weight: 303.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(Br)cc1)c1ccccc1O

Standard InChI:  InChI=1S/C15H11BrO2/c16-12-8-5-11(6-9-12)7-10-15(18)13-3-1-2-4-14(13)17/h1-10,17H/b10-7+

Standard InChI Key:  RBCJPKVEKWAARH-JXMROGBWSA-N

Alternative Forms

1. Parent:

   

   ALA89988

   2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxyphenyl)-

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 303.15

Molecular Weight (Monoisotopic): 301.9942

AlogP: 4.05

#Rotatable Bonds: 3

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.19

CX Basic pKa: ┄

CX LogP: 5.01

CX LogD: 4.59

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.69

Np Likeness Score: 0.08

References

1. Stoyanov EV, Champavier Y, Simon A, Basly JP..  (2002)  Efficient liquid-phase synthesis of 2'-hydroxychalcones.,  12  (19): [PMID:12217354] [10.1016/s0960-894x(02)00553-x]

2. Cabrera M, Simoens M, Falchi G, Lavaggi ML, Piro OE, Castellano EE, Vidal A, Azqueta A, Monge A, de Ceráin AL, Sagrera G, Seoane G, Cerecetto H, González M..  (2007)  Synthetic chalcones, flavanones, and flavones as antitumoral agents: biological evaluation and structure-activity relationships.,  15  (10): [PMID:17383189] [10.1016/j.bmc.2007.03.031]

3. Tran TD, Park H, Kim HP, Ecker GF, Thai KM..  (2009)  Inhibitory activity of prostaglandin E2 production by the synthetic 2'-hydroxychalcone analogues: Synthesis and SAR study.,  19  (6): [PMID:19233646] [10.1016/j.bmcl.2009.02.001]

4. Cabrera M, Lavaggi ML, Croce F, Celano L, Thomson L, Fernández M, Pintos C, Raymondo S, Bollati M, Monge A, López de Ceráin A, Piro OE, Cerecetto H, González M..  (2010)  Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers.,  18  (14): [PMID:20639112] [10.1016/j.bmc.2010.05.033]

5. Dias TA, Duarte CL, Lima CF, Proença MF, Pereira-Wilson C..  (2013)  Superior anticancer activity of halogenated chalcones and flavonols over the natural flavonol quercetin.,  65  [PMID:23771043] [10.1016/j.ejmech.2013.04.064]

6. Kupcewicz B, Jarzęcki AA, Małecka M, Krajewska U, Rozalski M..  (2014)  Cytotoxic activity of substituted chalcones in terms of molecular electronic properties.,  24  (17): [PMID:25091929] [10.1016/j.bmcl.2014.07.027]

7. Cabrera M, Mastandrea I, Otero G, Cerecetto H, González M..  (2016)  In vivo phase II-enzymes inducers, as potential chemopreventive agents, based on the chalcone and furoxan skeletons.,  24  (8): [PMID:26970663] [10.1016/j.bmc.2016.02.041]

8.  (2016)  7  (12): [10.1039/C6MD00456C]

Source

Source(1):

• Scientific Literature