8-Chloro-5-methyl-11-(4-methyl-piperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine

ID: ALA266723

PubChem CID: 11724853

Max Phase: Preclinical

Molecular Formula: C19H21ClN4

Molecular Weight: 340.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(C2=Nc3cc(Cl)ccc3N(C)c3ccccc32)CC1

Standard InChI:  InChI=1S/C19H21ClN4/c1-22-9-11-24(12-10-22)19-15-5-3-4-6-17(15)23(2)18-8-7-14(20)13-16(18)21-19/h3-8,13H,9-12H2,1-2H3

Standard InChI Key:  XQIPQCHREHNRDI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.7542   -6.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875   -5.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -4.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2250   -5.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -4.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -7.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -5.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -8.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -7.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -7.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -8.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -8.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -5.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -5.5125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -9.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5375   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3500   -4.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA266723

   8-Chloro-5-methyl-11-(4-methyl-piperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine

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: 340.86

Molecular Weight (Monoisotopic): 340.1455

AlogP: 3.75

#Rotatable Bonds: ┄

Polar Surface Area: 22.08

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.35

CX LogP: 3.62

CX LogD: 3.35

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: -0.81

References

1. de Paulis T, Betts CR, Smith HE, Mobley PL, Manier DH, Sulser F..  (1981)  Synthesis of clozapine analogues and their affinity for clozapine and spiroperidol binding sites in rat brain.,  24  (9): [PMID:7288815] [10.1021/jm00141a001]

2. Phillips ST, de Paulis T, Baron BM, Siegel BW, Seeman P, Van Tol HH, Guan HC, Smith HE..  (1994)  Binding of 5H-dibenzo[b,e][1,4]diazepine and chiral 5H-dibenzo[a,d]cycloheptene analogues of clozapine to dopamine and serotonin receptors.,  37  (17): [PMID:8064797] [10.1021/jm00043a008]

3. Smits RA, Lim HD, Stegink B, Bakker RA, de Esch IJ, Leurs R..  (2006)  Characterization of the histamine H4 receptor binding site. Part 1. Synthesis and pharmacological evaluation of dibenzodiazepine derivatives.,  49  (15): [PMID:16854056] [10.1021/jm051008s]

Source

Source(1):

• Scientific Literature