(S)-8-chloro-1-((1r,4r)-4-(pyridin-2-yloxy)cyclohexyl)-5,6-dihydro-4H-benzo[f][1,2,4]triazolo[4,3-a]azepine

ID: ALA4799793

PubChem CID: 162676461

Max Phase: Preclinical

Molecular Formula: C22H23ClN4O

Molecular Weight: 394.91

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Clc1ccc2c(c1)CCCc1nnc([C@H]3CC[C@H](Oc4ccccn4)CC3)n1-2

Standard InChI:  InChI=1S/C22H23ClN4O/c23-17-9-12-19-16(14-17)4-3-5-20-25-26-22(27(19)20)15-7-10-18(11-8-15)28-21-6-1-2-13-24-21/h1-2,6,9,12-15,18H,3-5,7-8,10-11H2/t15-,18-

Standard InChI Key:  XPJLLCAORNNZCL-RZDIXWSQSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   14.6440  -13.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9246  -14.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9181  -14.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6330  -15.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3524  -14.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3569  -14.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6364  -16.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0466  -17.4452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3015  -16.6629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9670  -16.6633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2283  -17.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7823  -18.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9637  -18.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3888  -17.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4864  -16.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1914  -16.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1705  -15.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4454  -15.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7398  -15.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7642  -16.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6455  -12.8809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0156  -15.2120    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.9337  -12.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9393  -11.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2283  -11.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5141  -11.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5152  -12.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2267  -12.8804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7 10  1  0
 11  8  2  0
  8  9  1  0
  9  7  2  0
  4  7  1  1
 10 11  1  0
 11 12  1  0
 10 16  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 21  1  6
 19 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4799793

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.91

Molecular Weight (Monoisotopic): 394.1560

AlogP: 4.91

#Rotatable Bonds: 3

Polar Surface Area: 52.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.06

CX LogP: 4.81

CX LogD: 4.81

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -1.44

References

1. Bozó É,Baska F,Lövei K,Szántó G,Domány-Kovács K,Kurkó D,Szondiné Kordás K,Szokoli T,Bata I.  (2020)  New V1a receptor antagonist. Part 2. Identification and optimization of triazolobenzazepines.,  30  (18.0): [PMID:32731087] [10.1016/j.bmcl.2020.127417]

2. Szeleczky Z, Szakács Z, Bozó É, Baska F, Vukics K, Lévai S, Temesvári K, Vass E, Béni Z, Krámos B, Magdó I, Szántay C, Kóti J, Domány-Kovács K, Greiner I, Bata I..  (2021)  Synthesis and Characterization of New V_1A Antagonist Compounds: The Separation of Four Atropisomeric Stereoisomers.,  64  (14.0): [PMID:34255509] [10.1021/acs.jmedchem.1c00863]

3. Subbaiah MAM, Meanwell NA..  (2021)  Bioisosteres of the Phenyl Ring: Recent Strategic Applications in Lead Optimization and Drug Design.,  64  (19.0): [PMID:34591488] [10.1021/acs.jmedchem.1c01215]

Source

Source(1):

• Scientific Literature