8-Chloro-11-(4-methyl-piperazin-1-yl)-dibenzo[b,f][1,4]thiazepine (isoclothiapine)

ID: ALA67284

Cas Number: 5747-55-7

PubChem CID: 9928073

Max Phase: Preclinical

Molecular Formula: C18H18ClN3S

Molecular Weight: 343.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(C2=Nc3cc(Cl)ccc3Sc3ccccc32)CC1

Standard InChI:  InChI=1S/C18H18ClN3S/c1-21-8-10-22(11-9-21)18-14-4-2-3-5-16(14)23-17-7-6-13(19)12-15(17)20-18/h2-7,12H,8-11H2,1H3

Standard InChI Key:  KPQVFXHERXUYEX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    3.5328  -22.1253    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1816  -21.2797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667  -22.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6726  -21.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4234  -20.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588  -20.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7442  -19.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9923  -20.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606  -20.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8354  -22.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419  -22.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6497  -23.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0498  -24.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8464  -24.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2350  -23.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1904  -22.0818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6027  -22.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4228  -22.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8368  -22.0836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4246  -21.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5983  -21.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6633  -22.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7774  -18.8133    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
  4  5  2  0
 11 12  1  0
  5  2  1  0
 12 13  2  0
  5  6  1  0
 13 14  1  0
  3 10  1  0
 14 15  2  0
 15 10  1  0
  6  7  2  0
  3 16  1  0
 16 17  1  0
 11  1  1  0
  7  8  1  0
  2  3  2  0
  8  9  2  0
  9  4  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
  4  1  1  0
  7 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA67284

   ISOCLOTHIAPINE

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: 343.88

Molecular Weight (Monoisotopic): 343.0910

AlogP: 4.13

#Rotatable Bonds: ┄

Polar Surface Area: 18.84

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.27

CX LogP: 4.15

CX LogD: 3.91

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.72

Np Likeness Score: -1.09

References

1. Liégeois JF, Bruhwyler J, Damas J, Nguyen TP, Chleide EM, Mercier MG, Rogister FA, Delarge JE..  (1993)  New pyridobenzodiazepine derivatives as potential antipsychotics: synthesis and neurochemical study.,  36  (15): [PMID:8101877] [10.1021/jm00067a009]

2. Warawa EJ, Migler BM, Ohnmacht CJ, Needles AL, Gatos GC, McLaren FM, Nelson CL, Kirkland KM..  (2001)  Behavioral approach to nondyskinetic dopamine antagonists: identification of seroquel.,  44  (3): [PMID:11462978] [10.1021/jm000242+]

3. Liégeois JF, Rogister FA, Bruhwyler J, Damas J, Nguyen TP, Inarejos MO, Chleide EM, Mercier MG, Delarge JE..  (1994)  Pyridobenzoxazepine and pyridobenzothiazepine derivatives as potential central nervous system agents: synthesis and neurochemical study.,  37  (4): [PMID:7907148] [10.1021/jm00030a011]

4. 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]

5. Vischer HF, Hulshof JW, Hulscher S, Fratantoni SA, Verheij MH, Victorina J, Smit MJ, de Esch IJ, Leurs R..  (2010)  Identification of novel allosteric nonpeptidergic inhibitors of the human cytomegalovirus-encoded chemokine receptor US28.,  18  (2): [PMID:20031418] [10.1016/j.bmc.2009.11.060]

Source

Source(1):

• Scientific Literature