4-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-furan-2-carbonitrile

ID: ALA138059

Chembl Id: CHEMBL138059

Cas Number: 304854-47-5

PubChem CID: 9921530

Max Phase: Preclinical

Molecular Formula: C15H12N2O3

Molecular Weight: 268.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)OC(=O)Nc2ccc(-c3coc(C#N)c3)cc21

Standard InChI:  InChI=1S/C15H12N2O3/c1-15(2)12-6-9(10-5-11(7-16)19-8-10)3-4-13(12)17-14(18)20-15/h3-6,8H,1-2H3,(H,17,18)

Standard InChI Key:  IJSGDARRCNDONL-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA138059

   4-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-furan-2-carbonitrile

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: 268.27

Molecular Weight (Monoisotopic): 268.0848

AlogP: 3.62

#Rotatable Bonds: 1

Polar Surface Area: 75.26

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.64

CX Basic pKa: ┄

CX LogP: 2.84

CX LogD: 2.84

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.86

Np Likeness Score: 0.35

References

1. Zhang P, Terefenko EA, Fensome A, Wrobel J, Winneker R, Lundeen S, Marschke KB, Zhang Z..  (2002)  6-Aryl-1,4-dihydro-benzo[d][1,3]oxazin- 2-ones: a novel class of potent, selective, and orally active nonsteroidal progesterone receptor antagonists.,  45  (20): [PMID:12238914] [10.1021/jm025555e]

2. Fensome A, Bender R, Chopra R, Cohen J, Collins MA, Hudak V, Malakian K, Lockhead S, Olland A, Svenson K, Terefenko EA, Unwalla RJ, Wilhelm JM, Wolfrom S, Zhu Y, Zhang Z, Zhang P, Winneker RC, Wrobel J..  (2005)  Synthesis and structure-activity relationship of novel 6-aryl-1,4-dihydrobenzo[d][1,3]oxazine-2-thiones as progesterone receptor modulators leading to the potent and selective nonsteroidal progesterone receptor agonist tanaproget.,  48  (16): [PMID:16078826] [10.1021/jm050358b]

Source

Source(1):

• Scientific Literature