N-((R)-9-Methyl-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-3-yl)-isonicotinamide

ID: ALA111925

Chembl Id: CHEMBL111925

Cas Number: 179024-48-7

PubChem CID: 9865514

Max Phase: Preclinical

Molecular Formula: C24H20N4O2

Molecular Weight: 396.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: CI-1018 | CI-1018|Y4O6325SYW|PD-168787|179024-48-7|UNII-Y4O6325SYW|CHEMBL111925|DTXSID0047248|(+)-CI-1018|CI-1018, (+)-|4-Pyridinecarboxamide, N-((3R)-3,4,6,7-tetrahydro-9-methyl-4-oxo-1-phenylpyrrolo(3,2,1-jk)(1,4)benzodiazepin-3-yl)-|4-Pyridinecarboxamide, N-(3,4,6,7-tetrahydro-9-methyl-4-oxo-1-phenylpyrrolo(3,2,1-jk)(1,4)benzodiazepin-3-yl)-, (R)-|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]pyridine-4-carboxamide|N-[(R)-9-METHYL-4-OXO-1-PShow More⌵

Canonical SMILES:  Cc1cc2c3c(c1)C(c1ccccc1)=N[C@@H](NC(=O)c1ccncc1)C(=O)N3CC2

Standard InChI:  InChI=1S/C24H20N4O2/c1-15-13-18-9-12-28-21(18)19(14-15)20(16-5-3-2-4-6-16)26-22(24(28)30)27-23(29)17-7-10-25-11-8-17/h2-8,10-11,13-14,22H,9,12H2,1H3,(H,27,29)/t22-/m0/s1

Standard InChI Key:  KYFWUBJMTHVBIF-QFIPXVFZSA-N

Alternative Forms

1. Parent:

   

   ALA111925

   4-Pyridinecarboxamide, N-((3R)-3,4,6,7-tetrahydro-9-methyl-4-oxo-1-phenylpyrrolo(3,2,1-jk)(1,4)benzodiazepin-3-yl)-

Molecule Features

Natural Product: Yes

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: 396.45

Molecular Weight (Monoisotopic): 396.1586

AlogP: 2.89

#Rotatable Bonds: 3

Polar Surface Area: 74.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.87

CX Basic pKa: 3.35

CX LogP: 3.09

CX LogD: 3.09

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.74

Np Likeness Score: -0.48

References

1. Devillers I, Pevet I, Jacobelli H, Durand C, Fasquelle V, Puaud J, Gaudillière B, Idrissi M, Moreau F, Wrigglesworth R..  (2004)  New substituted triaza-benzo[cd]azulen-9-ones as promising phosphodiesterase-4 inhibitors.,  14  (12): [PMID:15149695] [10.1016/j.bmcl.2004.03.067]

2. 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]

3. 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]

4. Kodimuthali A, Jabaris SS, Pal M..  (2008)  Recent advances on phosphodiesterase 4 inhibitors for the treatment of asthma and chronic obstructive pulmonary disease.,  51  (18): [PMID:18686943] [10.1021/jm800582j]

5. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays