3,6-diamino-2-(3-chlorobenzoyl)-4-(2-chlorophenyl)thieno[2,3-b]pyridine-5-carbonitrile

ID: ALA2313853

Chembl Id: CHEMBL2313853

PubChem CID: 51039273

Max Phase: Preclinical

Molecular Formula: C21H12Cl2N4OS

Molecular Weight: 439.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c(N)nc2sc(C(=O)c3cccc(Cl)c3)c(N)c2c1-c1ccccc1Cl

Standard InChI:  InChI=1S/C21H12Cl2N4OS/c22-11-5-3-4-10(8-11)18(28)19-17(25)16-15(12-6-1-2-7-14(12)23)13(9-24)20(26)27-21(16)29-19/h1-8H,25H2,(H2,26,27)

Standard InChI Key:  BXLXOBIMRFZEAE-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2313853

   3,6-Diamino-2-(3-chlorobenzoyl)-4-(2-chlorophenyl)thieno[2,3-b]pyridine-5-carbonitrile

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: 439.33

Molecular Weight (Monoisotopic): 438.0109

AlogP: 5.54

#Rotatable Bonds: 3

Polar Surface Area: 105.79

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.89

CX LogD: 5.89

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: -1.70

References

1. Fugel W, Oberholzer AE, Gschloessl B, Dzikowski R, Pressburger N, Preu L, Pearl LH, Baratte B, Ratin M, Okun I, Doerig C, Kruggel S, Lemcke T, Meijer L, Kunick C..  (2013)  3,6-Diamino-4-(2-halophenyl)-2-benzoylthieno[2,3-b]pyridine-5-carbonitriles are selective inhibitors of Plasmodium falciparum glycogen synthase kinase-3.,  56  (1): [PMID:23214499] [10.1021/jm301575n]

2. Galal KA, Truong A, Kwarcinski F, de Silva C, Avalani K, Havener TM, Chirgwin ME, Merten E, Ong HW, Willis C, Abdelwaly A, Helal MA, Derbyshire ER, Zutshi R, Drewry DH..  (2022)  Identification of Novel 2,4,5-Trisubstituted Pyrimidines as Potent Dual Inhibitors of Plasmodial PfGSK3/PfPK6 with Activity against Blood Stage Parasites In Vitro.,  65  (19.0): [PMID:36166733] [10.1021/acs.jmedchem.2c00996]

Source

Source(1):

• Scientific Literature