(1S,4S)-2-methyl-5-(6-phenylpyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptane

ID: ALA1082655

PubChem CID: 15462089

Max Phase: Preclinical

Molecular Formula: C16H18N4

Molecular Weight: 266.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2C[C@H]1CN2c1ccc(-c2ccccc2)nn1

Standard InChI:  InChI=1S/C16H18N4/c1-19-10-14-9-13(19)11-20(14)16-8-7-15(17-18-16)12-5-3-2-4-6-12/h2-8,13-14H,9-11H2,1H3/t13-,14-/m0/s1

Standard InChI Key:  GJYSEBOVCLZXAI-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   10.8179  -11.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6337  -11.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0403  -10.6788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6337   -9.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8179   -9.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4044  -10.6788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8535  -10.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2611  -11.3885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0758  -11.3908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4886  -10.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0775   -9.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2607   -9.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5886  -10.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8116  -10.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8116   -9.1463    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6274  -12.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3152  -10.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7281  -11.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5557  -11.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9715  -10.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5536   -9.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7273   -9.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
  6 13  1  0
  5 14  1  0
  2 14  1  0
  5 15  1  1
  2 16  1  1
  1  2  1  0
 17 18  2  0
  1  6  1  0
 18 19  1  0
  2  3  1  0
 19 20  2  0
  3  4  1  0
 20 21  1  0
  4  5  1  0
 21 22  2  0
 22 17  1  0
 10 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1082655

   (1S,4S)-2-methyl-5-(6-phenylpyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptane

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: 266.35

Molecular Weight (Monoisotopic): 266.1531

AlogP: 2.04

#Rotatable Bonds: 2

Polar Surface Area: 32.26

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.69

CX LogP: 2.37

CX LogD: 1.90

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.83

Np Likeness Score: -0.90

References

1. Li T, Bunnelle WH, Ryther KB, Anderson DJ, Malysz J, Helfrich R, Grønlien JH, Håkerud M, Peters D, Schrimpf MR, Gopalakrishnan M, Ji J..  (2010)  Syntheses and structure-activity relationship (SAR) studies of 2,5-diazabicyclo[2.2.1]heptanes as novel alpha7 neuronal nicotinic receptor (NNR) ligands.,  20  (12): [PMID:20472430] [10.1016/j.bmcl.2010.04.105]

2. Beinat C, Reekie T, Banister SD, O'Brien-Brown J, Xie T, Olson TT, Xiao Y, Harvey A, O'Connor S, Coles C, Grishin A, Kolesik P, Tsanaktsidis J, Kassiou M..  (2015)  Structure-activity relationship studies of SEN12333 analogues: determination of the optimal requirements for binding affinities at α7 nAChRs through incorporation of known structural motifs.,  95  [PMID:25827398] [10.1016/j.ejmech.2015.03.025]

Source

Source(1):

• Scientific Literature