4-Amino-3,5-dichloro-N-((R)-9-methyl-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-3-yl)-benzamide

ID: ALA125671

Chembl Id: CHEMBL125671

PubChem CID: 10648358

Max Phase: Preclinical

Molecular Formula: C25H20Cl2N4O2

Molecular Weight: 479.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c3c(c1)C(c1ccccc1)=N[C@@H](NC(=O)c1cc(Cl)c(N)c(Cl)c1)C(=O)N3CC2

Standard InChI:  InChI=1S/C25H20Cl2N4O2/c1-13-9-15-7-8-31-22(15)17(10-13)21(14-5-3-2-4-6-14)29-23(25(31)33)30-24(32)16-11-18(26)20(28)19(27)12-16/h2-6,9-12,23H,7-8,28H2,1H3,(H,30,32)/t23-/m0/s1

Standard InChI Key:  IQZZOLVGBYWFIM-QHCPKHFHSA-N

Alternative Forms

1. Parent:

   

   ALA125671

   4-amino-3,5-dichloro-N-[(11R)-6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl]benzamide

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: 479.37

Molecular Weight (Monoisotopic): 478.0963

AlogP: 4.38

#Rotatable Bonds: 3

Polar Surface Area: 87.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.77

CX LogP: 4.68

CX LogD: 4.68

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.55

Np Likeness Score: -0.55

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