[(4aS,8aR)-4-(4-Amino-6,7-dimethoxy-quinazolin-2-yl)-octahydro-quinoxalin-1-yl]-furan-2-yl-methanone

ID: ALA342062

Chembl Id: CHEMBL342062

PubChem CID: 9824384

Max Phase: Preclinical

Molecular Formula: C23H27N5O4

Molecular Weight: 437.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2nc(N3CCN(C(=O)c4ccco4)[C@@H]4CCCC[C@@H]43)nc(N)c2cc1OC

Standard InChI:  InChI=1S/C23H27N5O4/c1-30-19-12-14-15(13-20(19)31-2)25-23(26-21(14)24)28-10-9-27(16-6-3-4-7-17(16)28)22(29)18-8-5-11-32-18/h5,8,11-13,16-17H,3-4,6-7,9-10H2,1-2H3,(H2,24,25,26)/t16-,17+/m1/s1

Standard InChI Key:  XBRXTUGRUXGBPX-SJORKVTESA-N

Alternative Forms

1. Parent:

   

   ALA342062

   [(4aS,8aR)-4-(4-amino-6,7-dimethoxyquinazolin-2-yl)-2,3,4a,5,6,7,8,8a-octahydroquinoxalin-1-yl]-(furan-2-yl)methanone

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: 437.50

Molecular Weight (Monoisotopic): 437.2063

AlogP: 3.10

#Rotatable Bonds: 4

Polar Surface Area: 106.95

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.21

CX LogP: 3.06

CX LogD: 2.85

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.66

Np Likeness Score: -0.82

References

1. Giardinà D, Crucianelli M, Romanelli R, Leonardi A, Poggesi E, Melchiorre C..  (1996)  Synthesis and biological profile of the enantiomers of [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)-cis-octahydroquinoxalin- 1-yl]furan-2-ylmethanone (cyclazosin), a potent competitive alpha 1B- adrenoceptor antagonist.,  39  (23): [PMID:8917649] [10.1021/jm960510x]

2. Sagratini G, Buccioni M, Marucci G, Poggesi E, Skorski M, Costanzi S, Giardinà D..  (2018)  Chiral analogues of (+)-cyclazosin as potent α1B-adrenoceptor selective antagonist.,  26  (12): [PMID:29784274] [10.1016/j.bmc.2018.05.023]

Source

Source(1):

• Scientific Literature