6-[(2,5-Dimethoxy-phenylamino)-methyl]-pyrido[3,2-d]pyrimidine-2,4-diamine

ID: ALA52947

Chembl Id: CHEMBL52947

Cas Number: 164596-23-0

PubChem CID: 457778

Max Phase: Preclinical

Molecular Formula: C16H18N6O2

Molecular Weight: 326.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(NCc2ccc3nc(N)nc(N)c3n2)c1

Standard InChI:  InChI=1S/C16H18N6O2/c1-23-10-4-6-13(24-2)12(7-10)19-8-9-3-5-11-14(20-9)15(17)22-16(18)21-11/h3-7,19H,8H2,1-2H3,(H4,17,18,21,22)

Standard InChI Key:  PIKOPKOXFNIUMO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA52947

   6-[(2,5-Dimethoxyanilino)methyl]pyrido[3,2-d]pyrimidine-2,4-diamine

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: 326.36

Molecular Weight (Monoisotopic): 326.1491

AlogP: 1.82

#Rotatable Bonds: 5

Polar Surface Area: 121.20

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.21

CX LogP: 1.17

CX LogD: 1.17

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: -0.92

References

1. Gangjee A, Zhu Y, Queener SF, Francom P, Broom AD..  (1996)  Nonclassical 2,4-diamino-8-deazafolate analogues as inhibitors of dihydrofolate reductases from rat liver, Pneumocystis carinii, and Toxoplasma gondii.,  39  (9): [PMID:8627607] [10.1021/jm950918e]

2. Rosowsky A, Forsch RA, Queener SF..  (1995)  2,4-Diaminopyrido[3,2-d]pyrimidine inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii.,  38  (14): [PMID:7629801] [10.1021/jm00014a014]

3. Gangjee A, Lin X..  (2005)  CoMFA and CoMSIA analyses of Pneumocystis carinii dihydrofolate reductase, Toxoplasma gondii dihydrofolate reductase, and rat liver dihydrofolate reductase.,  48  (5): [PMID:15743188] [10.1021/jm040153n]

4. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

5. Shah K, Queener S, Cody V, Pace J, Gangjee A..  (2019)  Development of substituted pyrido[3,2-d]pyrimidines as potent and selective dihydrofolate reductase inhibitors for pneumocystis pneumonia infection.,  29  (15): [PMID:31176699] [10.1016/j.bmcl.2019.06.004]

Source

Source(1):

• Scientific Literature