2-(4-bromophenyl)quinazolin-4(3H)-one

ID: ALA2058057

Chembl Id: CHEMBL2058057

PubChem CID: 135421564

Max Phase: Preclinical

Molecular Formula: C14H9BrN2O

Molecular Weight: 301.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(-c2ccc(Br)cc2)nc2ccccc12

Standard InChI:  InChI=1S/C14H9BrN2O/c15-10-7-5-9(6-8-10)13-16-12-4-2-1-3-11(12)14(18)17-13/h1-8H,(H,16,17,18)

Standard InChI Key:  NRCCYFAMXZIJSC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2058057

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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: 301.14

Molecular Weight (Monoisotopic): 299.9898

AlogP: 3.35

#Rotatable Bonds: 1

Polar Surface Area: 45.75

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.12

CX Basic pKa: 4.56

CX LogP: 3.40

CX LogD: 3.33

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.75

Np Likeness Score: -1.02

References

1. Mulakayala N, Kandagatla B, Ismail, Rapolu RK, Rao P, Mulakayala C, Kumar CS, Iqbal J, Oruganti S..  (2012)  InCl3-catalysed synthesis of 2-aryl quinazolin-4(3H)-ones and 5-aryl pyrazolo[4,3-d]pyrimidin-7(6H)-ones and their evaluation as potential anticancer agents.,  22  (15): [PMID:22749421] [10.1016/j.bmcl.2012.06.003]

2. Nathubhai A, Haikarainen T, Hayward PC, Muñoz-Descalzo S, Thompson AS, Lloyd MD, Lehtiö L, Threadgill MD..  (2016)  Structure-activity relationships of 2-arylquinazolin-4-ones as highly selective and potent inhibitors of the tankyrases.,  118  [PMID:27163581] [10.1016/j.ejmech.2016.04.041]

3. Wei M, Chai WM, Wang R, Yang Q, Deng Z, Peng Y..  (2017)  Quinazolinone derivatives: Synthesis and comparison of inhibitory mechanisms on α-glucosidase.,  25  (4): [PMID:28110817] [10.1016/j.bmc.2016.09.042]

4. Mohd Siddique MU, McCann GJ, Sonawane VR, Horley N, Gatchie L, Joshi P, Bharate SB, Jayaprakash V, Sinha BN, Chaudhuri B..  (2017)  Quinazoline derivatives as selective CYP1B1 inhibitors.,  130  [PMID:28259840] [10.1016/j.ejmech.2017.02.032]

5. Brown CE, Kong T, Bordón C, Yolken R, Jones-Brando L, McNulty J..  (2018)  One-pot, multicomponent synthesis of 2,3-disubstituted quinazolin-ones with potent and selective activity against Toxoplasma gondii.,  28  (9): [PMID:29598911] [10.1016/j.bmcl.2018.03.036]

6. Sonawane V, Mohd Siddique MU, Jadav SS, Sinha BN, Jayaprakash V, Chaudhuri B..  (2019)  Cink4T, a quinazolinone-based dual inhibitor of Cdk4 and tubulin polymerization, identified via ligand-based virtual screening, for efficient anticancer therapy.,  165  [PMID:30665142] [10.1016/j.ejmech.2019.01.011]

7. Pieterse L, van der Walt MM, Terre'Blanche G..  (2020)  C2-substituted quinazolinone derivatives exhibit A₁ and/or A_2A adenosine receptor affinities in the low micromolar range.,  30  (16): [PMID:32631506] [10.1016/j.bmcl.2020.127274]

8. Damale MG, Pathan SK, Shinde DB, Patil RH, Arote RB, Sangshetti JN..  (2020)  Insights of tankyrases: A novel target for drug discovery.,  207  [PMID:32877803] [10.1016/j.ejmech.2020.112712]

Source

Source(1):

• Scientific Literature