2-(3,4-Dichlorophenyl)-1-((4aS,8S,8aS)-8-(pyrrolidin-1-yl)-octahydroquinoxalin-1(2H)-yl)ethanone

ID: ALA4069231

PubChem CID: 117697800

Max Phase: Preclinical

Molecular Formula: C20H27Cl2N3O

Molecular Weight: 396.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(Cl)c(Cl)c1)N1CCN[C@H]2CCC[C@H](N3CCCC3)[C@H]21

Standard InChI:  InChI=1S/C20H27Cl2N3O/c21-15-7-6-14(12-16(15)22)13-19(26)25-11-8-23-17-4-3-5-18(20(17)25)24-9-1-2-10-24/h6-7,12,17-18,20,23H,1-5,8-11,13H2/t17-,18-,20-/m0/s1

Standard InChI Key:  LWDJYEJRZVMWMH-BJLQDIEVSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   20.1084  -11.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4201  -12.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9127  -13.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1104  -12.9871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0854  -13.9780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3899  -14.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4205  -15.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1463  -15.6228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8460  -15.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5718  -15.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2714  -15.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2409  -14.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5108  -13.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8154  -14.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4790  -13.0966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1266  -12.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8404  -11.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0117  -11.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7860  -12.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6185  -11.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3075  -10.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4897  -10.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9840  -10.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2978  -11.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8094  -13.5310    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.8388  -16.0143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.1754   -9.4682    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.1620  -10.7825    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  5  1  0
  9 14  1  0
 13 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
  1 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24  1  1  0
 14 25  1  1
  9 26  1  1
 22 27  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4069231

   1-[(4aS,8S,8aS)-8-pyrrolidin-1-yl-3,4,4a,5,6,7,8,8a-octahydro-2H-quinoxalin-1-yl]-2-(3,4-dichlorophenyl)ethanone

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: 396.36

Molecular Weight (Monoisotopic): 395.1531

AlogP: 3.35

#Rotatable Bonds: 3

Polar Surface Area: 35.58

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.41

CX LogP: 3.38

CX LogD: 1.35

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: -0.48

References

1. Soeberdt M, Molenveld P, Storcken RP, Bouzanne des Mazery R, Sterk GJ, Autar R, Bolster MG, Wagner C, Aerts SN, van Holst FR, Wegert A, Tangherlini G, Frehland B, Schepmann D, Metze D, Lotts T, Knie U, Lin KY, Huang TY, Lai CC, Ständer S, Wünsch B, Abels C..  (2017)  Design and Synthesis of Enantiomerically Pure Decahydroquinoxalines as Potent and Selective κ-Opioid Receptor Agonists with Anti-Inflammatory Activity in Vivo.,  60  (6): [PMID:28218838] [10.1021/acs.jmedchem.6b01868]

2. Tangherlini G, Kalinin DV, Schepmann D, Che T, Mykicki N, Ständer S, Loser K, Wünsch B..  (2019)  Development of Novel Quinoxaline-Based κ-Opioid Receptor Agonists for the Treatment of Neuroinflammation.,  62  (2): [PMID:30543421] [10.1021/acs.jmedchem.8b01609]

Source

Source(1):

• Scientific Literature