2-Chloro-5-ethyl-8-fluoro-11-(4-methylpiperazin-1-yl)-5Hdibenzo[b,e][1,4]diazepine

ID: ALA3609330

PubChem CID: 91808045

Max Phase: Preclinical

Molecular Formula: C20H22ClFN4

Molecular Weight: 372.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1c2ccc(F)cc2N=C(N2CCN(C)CC2)c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C20H22ClFN4/c1-3-26-18-6-4-14(21)12-16(18)20(25-10-8-24(2)9-11-25)23-17-13-15(22)5-7-19(17)26/h4-7,12-13H,3,8-11H2,1-2H3

Standard InChI Key:  NQBRFDSRSGHBBK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    4.7970   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1241    0.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0183    1.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3486   -1.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6509    1.9313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1246    1.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5854    0.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2272   -0.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -1.3706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4672   -0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7943    0.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    1.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3330    0.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215   -1.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730   -1.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2718    0.4439    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802    0.5079    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310    3.2812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0344    3.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    4.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9775    5.9128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4779    5.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435    4.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5546    6.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8563   -2.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1889   -3.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  7  2  0
  8  4  2  0
  4  1  1  0
  5  6  2  0
  6 11  1  0
  5  7  1  0
  8  9  1  0
  9 10  1  0
  7  8  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  2 16  1  0
 13 17  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  6 18  1  0
 21 24  1  0
  9 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3609330

   2-Chloro-5-Ethyl-8-Fluoro-11-(4-Methylpiperazin-1-Yl)-Dibenzodiazepine

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: 372.88

Molecular Weight (Monoisotopic): 372.1517

AlogP: 4.28

#Rotatable Bonds: 1

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: 7.28

CX LogP: 4.12

CX LogD: 3.88

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: -1.22

References

1. Karpov AS, Amiri P, Bellamacina C, Bellance MH, Breitenstein W, Daniel D, Denay R, Fabbro D, Fernandez C, Galuba I, Guerro-Lagasse S, Gutmann S, Hinh L, Jahnke W, Klopp J, Lai A, Lindvall MK, Ma S, Möbitz H, Pecchi S, Rummel G, Shoemaker K, Trappe J, Voliva C, Cowan-Jacob SW, Marzinzik AL..  (2015)  Optimization of a Dibenzodiazepine Hit to a Potent and Selective Allosteric PAK1 Inhibitor.,  6  (7): [PMID:26191365] [10.1021/acsmedchemlett.5b00102]

Source

Source(1):

• Scientific Literature