N-(4-chlorophenyl)-N-methyl-3-(4-(methylcarbamoyl)phenyl)imidazo[1,2-a]pyrazine-6-carboxamide

ID: ALA3325608

Cas Number: 1513879-19-0

PubChem CID: 90157166

Product Number: K413526, Order Now?

Max Phase: Preclinical

Molecular Formula: C22H18ClN5O2

Molecular Weight: 419.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1ccc(-c2cnc3cnc(C(=O)N(C)c4ccc(Cl)cc4)cn23)cc1

Standard InChI:  InChI=1S/C22H18ClN5O2/c1-24-21(29)15-5-3-14(4-6-15)19-11-26-20-12-25-18(13-28(19)20)22(30)27(2)17-9-7-16(23)8-10-17/h3-13H,1-2H3,(H,24,29)

Standard InChI Key:  TYMFFISSODJRDV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    8.9123   -8.4136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8472  -10.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2064   -9.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7833   -9.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6273   -9.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2035   -8.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7878   -9.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6242   -8.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0474   -8.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3330   -8.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2999  -10.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3267   -7.5924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0120   -7.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5342   -8.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9091   -7.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7552   -8.4038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5880   -9.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4940  -10.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2396  -10.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7844   -8.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4922   -8.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5308   -7.3291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7530   -7.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4959  -10.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0361   -7.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5553  -11.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0118  -12.3735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3555  -11.9288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6123  -12.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748  -10.0587    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 23 25  1  0
  6  1  1  0
 22 23  2  0
 23 16  1  0
 17  7  1  0
 16 14  1  0
  4 18  1  0
 24 11  2  0
 14  7  1  0
 14 13  2  0
  8  5  2  0
 13 22  1  0
  3  6  1  0
 18  3  2  0
  1 15  1  0
  1  8  1  0
 11  2  1  0
 25 12  2  0
  2 17  2  0
  9 16  1  0
 21 20  1  0
 19 24  1  0
  8 10  1  0
  7 19  2  0
 10  9  2  0
 12 10  1  0
  6 21  2  0
 20  4  2  0
 11 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
  4 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3325608

   KDU691

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: 419.87

Molecular Weight (Monoisotopic): 419.1149

AlogP: 3.69

#Rotatable Bonds: 4

Polar Surface Area: 79.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.48

CX LogP: 2.13

CX LogD: 2.13

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -1.60

References

1. Zou B, Nagle A, Chatterjee AK, Leong SY, Tan LJ, Sim WL, Mishra P, Guntapalli P, Tully DC, Lakshminarayana SB, Lim CS, Tan YC, Abas SN, Bodenreider C, Kuhen KL, Gagaring K, Borboa R, Chang J, Li C, Hollenbeck T, Tuntland T, Zeeman AM, Kocken CH, McNamara C, Kato N, Winzeler EA, Yeung BK, Diagana TT, Smith PW, Roland J..  (2014)  Lead optimization of imidazopyrazines: a new class of antimalarial with activity on Plasmodium liver stages.,  5  (8): [PMID:25147620] [10.1021/ml500244m]

2. Kandepedu N, Gonzàlez Cabrera D, Eedubilli S, Taylor D, Brunschwig C, Gibhard L, Njoroge M, Lawrence N, Paquet T, Eyermann CJ, Spangenberg T, Basarab GS, Street LJ, Chibale K..  (2018)  Identification, Characterization, and Optimization of 2,8-Disubstituted-1,5-naphthyridines as Novel Plasmodium falciparum Phosphatidylinositol-4-kinase Inhibitors with in Vivo Efficacy in a Humanized Mouse Model of Malaria.,  61  (13): [PMID:29889526] [10.1021/acs.jmedchem.8b00648]

3. Liang X,Jiang Z,Huang Z,Li F,Chen C,Hu C,Wang W,Hu Z,Liu Q,Wang B,Wang L,Qi Z,Liu J,Jiang L,Liu Q.  (2020)  Discovery of 6'-chloro-N-methyl-5'-(phenylsulfonamido)-[3,3'-bipyridine]-5-carboxamide (CHMFL-PI4K-127) as a novel Plasmodium falciparum PI(4)K inhibitor with potent antimalarial activity against both blood and liver stages of Plasmodium.,  188  [PMID:31911293] [10.1016/j.ejmech.2019.112012]

Source

Source(1):

• Scientific Literature