5,6-dimethyl-2-nitro-7-(4-(trifluoromethoxy)benzyl)imidazo[1,2-a]-pyrazin-8(7H)-one

ID: ALA4580469

PubChem CID: 155565862

Max Phase: Preclinical

Molecular Formula: C16H13F3N4O4

Molecular Weight: 382.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(C)n2cc([N+](=O)[O-])nc2c(=O)n1Cc1ccc(OC(F)(F)F)cc1

Standard InChI:  InChI=1S/C16H13F3N4O4/c1-9-10(2)22(15(24)14-20-13(23(25)26)8-21(9)14)7-11-3-5-12(6-4-11)27-16(17,18)19/h3-6,8H,7H2,1-2H3

Standard InChI Key:  RNWJFYKENHDVOH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -0.9991    2.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    1.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2219    1.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5133    0.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4980   -0.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7885   -1.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7711   -3.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8029   -3.6806    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7248   -3.6555    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7566   -4.2679    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1914   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9001   -0.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560   -1.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -2.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6738    1.0851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7008   -0.9930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
  8 14  1  0
 14 15  2  0
 15  5  1  0
  3 16  1  0
 16 17  1  0
 16 18  2  3
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21  2  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 23 27  1  0
 27 21  2  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4580469

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 382.30

Molecular Weight (Monoisotopic): 382.0889

AlogP: 2.97

#Rotatable Bonds: 4

Polar Surface Area: 91.67

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.03

CX LogD: 4.03

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.41

References

1. Jarrad AM, Ang CW, Debnath A, Hahn HJ, Woods K, Tan L, Sykes ML, Jones AJ, Pelingon R, Butler MS, Avery VM, West NP, Karoli T, Blaskovich MAT, Cooper MA..  (2018)  Design, Synthesis, and Biological Evaluation of 2-Nitroimidazopyrazin-one/-es with Antitubercular and Antiparasitic Activity.,  61  (24): [PMID:30468386] [10.1021/acs.jmedchem.8b01578]

2. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of University of Queensland (Australia) compounds,  [10.6019/CHEMBL4513134]

3. Ang CW, Lee BM, Jackson CJ, Wang Y, Franzblau SG, Francisco AF, Kelly JM, Bernhardt PV, Tan L, West NP, Sykes ML, Hinton AO, Bolisetti R, Avery VM, Cooper MA, Blaskovich MAT..  (2022)  Nitroimidazopyrazinones with Oral Activity against Tuberculosis and Chagas Disease in Mouse Models of Infection.,  65  (19.0): [PMID:36111399] [10.1021/acs.jmedchem.2c00972]

Source

Source(2):

• Scientific Literature
• CO-ADD antimicrobial screening data