Isoquinoline-3-carboxylic acid ((R)-9-methoxy-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-3-yl)-amide

ID: ALA126581

Chembl Id: CHEMBL126581

PubChem CID: 10552011

Max Phase: Preclinical

Molecular Formula: C28H22N4O3

Molecular Weight: 462.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c3c(c1)C(c1ccccc1)=N[C@@H](NC(=O)c1cc4ccccc4cn1)C(=O)N3CC2

Standard InChI:  InChI=1S/C28H22N4O3/c1-35-21-13-19-11-12-32-25(19)22(15-21)24(17-7-3-2-4-8-17)30-26(28(32)34)31-27(33)23-14-18-9-5-6-10-20(18)16-29-23/h2-10,13-16,26H,11-12H2,1H3,(H,31,33)/t26-/m0/s1

Standard InChI Key:  OOBZIRLXBADNBG-SANMLTNESA-N

Alternative Forms

1. Parent:

   

   ALA126581

   N-[(11R)-6-methoxy-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl]isoquinoline-3-carboxamide

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: 462.51

Molecular Weight (Monoisotopic): 462.1692

AlogP: 3.74

#Rotatable Bonds: 4

Polar Surface Area: 83.89

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.18

CX LogP: 3.79

CX LogD: 3.79

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.50

Np Likeness Score: -0.33

References

1. Pascal Y, Andrianjara CR, Auclair E, Avenel N, Bertin B, Calvet A, Féru F, Lardon S, Moodley I, Ouagued M, Payne A, Pruniaux MP, Szilagyi C..  (2000)  Synthesis and structure-activity relationships of 4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indoles: novel PDE4 inhibitors.,  10  (1): [PMID:10636238] [10.1016/s0960-894x(99)00573-9]

2. Burnouf C, Auclair E, Avenel N, Bertin B, Bigot C, Calvet A, Chan K, Durand C, Fasquelle V, Féru F, Gilbertsen R, Jacobelli H, Kebsi A, Lallier E, Maignel J, Martin B, Milano S, Ouagued M, Pascal Y, Pruniaux MP, Puaud J, Rocher MN, Terrasse C, Wrigglesworth R, Doherty AM..  (2000)  Synthesis, structure-activity relationships, and pharmacological profile of 9-amino-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6, 7,1-hi]indoles: discovery of potent, selective phosphodiesterase type 4 inhibitors.,  43  (25): [PMID:11123995] [10.1021/jm000315p]

Source

Source(1):

• Scientific Literature