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

ID: ALA424135

Chembl Id: CHEMBL424135

PubChem CID: 462112

Max Phase: Preclinical

Molecular Formula: C16H18N6O2

Molecular Weight: 326.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(NCc2cnc3nc(N)nc(N)c3c2)c1

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

Standard InChI Key:  YSSYHMDWUMVMEA-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA424135

   6-[(2,5-Dimethoxyanilino)methyl]pyrido[2,3-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: 3.76

CX LogP: 1.03

CX LogD: 1.03

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: -0.92

References

1. Gangjee A, Adair OO, Queener SF..  (2003)  Synthesis and biological evaluation of 2,4-diamino-6-(arylaminomethyl)pyrido[2,3-d]pyrimidines as inhibitors of Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase and as antiopportunistic infection and antitumor agents.,  46  (23): [PMID:14584957] [10.1021/jm030312n]

2. 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