7-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-4H-benzo[1,4]oxazin-3-one

ID: ALA346389

Chembl Id: CHEMBL346389

Cas Number: 200195-01-3

PubChem CID: 9885114

Max Phase: Preclinical

Molecular Formula: C19H20ClN3O2

Molecular Weight: 357.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1COc2cc(CN3CCN(c4ccc(Cl)cc4)CC3)ccc2N1

Standard InChI:  InChI=1S/C19H20ClN3O2/c20-15-2-4-16(5-3-15)23-9-7-22(8-10-23)12-14-1-6-17-18(11-14)25-13-19(24)21-17/h1-6,11H,7-10,12-13H2,(H,21,24)

Standard InChI Key:  UFFHNEZNXKJHFB-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA346389

   7-((4-(4-Chlorophenyl)piperazin-1-yl)methyl)-4H-1,4-benzoxazin-3-one

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: 357.84

Molecular Weight (Monoisotopic): 357.1244

AlogP: 2.99

#Rotatable Bonds: 3

Polar Surface Area: 44.81

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.62

CX Basic pKa: 7.33

CX LogP: 3.04

CX LogD: 2.77

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.92

Np Likeness Score: -1.64

References

1. Belliotti TR, Wustrow DJ, Brink WA, Zoski KT, Shih YH, Whetzel SZ, Georgic LM, Corbin AE, Akunne HC, Heffner TG, Pugsley TA, Wise LD..  (1999)  A series of 6- and 7-piperazinyl- and -piperidinylmethylbenzoxazinones with dopamine D4 antagonist activity: discovery of a potential atypical antipsychotic agent.,  42  (25): [PMID:10602703] [10.1021/jm990277d]

2. Lindsley CW, Hopkins CR..  (2017)  Return of D4 Dopamine Receptor Antagonists in Drug Discovery.,  60  (17): [PMID:28489950] [10.1021/acs.jmedchem.7b00151]

3. Giorgioni G, Del Bello F, Pavletić P, Quaglia W, Botticelli L, Cifani C, Micioni Di Bonaventura E, Micioni Di Bonaventura MV, Piergentili A..  (2021)  Recent findings leading to the discovery of selective dopamine D₄ receptor ligands for the treatment of widespread diseases.,  212  [PMID:33422983] [10.1016/j.ejmech.2020.113141]

Source

Source(1):

• Scientific Literature