6-Methyl-5-(3,4,5-trimethoxy-benzyl)-pyrimidine-2,4-diamine

ID: ALA325533

Chembl Id: CHEMBL325533

Cas Number: 21822-27-5

PubChem CID: 9972300

Max Phase: Preclinical

Molecular Formula: C15H20N4O3

Molecular Weight: 304.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cc2c(C)nc(N)nc2N)cc(OC)c1OC

Standard InChI:  InChI=1S/C15H20N4O3/c1-8-10(14(16)19-15(17)18-8)5-9-6-11(20-2)13(22-4)12(7-9)21-3/h6-7H,5H2,1-4H3,(H4,16,17,18,19)

Standard InChI Key:  KUPCMNHSRONILW-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA325533

   6-Methyl-5-(3,4,5-trimethoxybenzyl)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: 304.35

Molecular Weight (Monoisotopic): 304.1535

AlogP: 1.57

#Rotatable Bonds: 5

Polar Surface Area: 105.51

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.88

CX LogP: 1.42

CX LogD: 0.83

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.86

Np Likeness Score: -0.15

References

1. Sirichaiwat C, Intaraudom C, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y..  (2004)  Target guided synthesis of 5-benzyl-2,4-diamonopyrimidines: their antimalarial activities and binding affinities to wild type and mutant dihydrofolate reductases from Plasmodium falciparum.,  47  (2): [PMID:14711307] [10.1021/jm0303352]

2. Roth B, Strelitz JZ, Rauckman BS..  (1980)  2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 2. C-Alkylation of pyrimidines with Mannich bases and application to the synthesis of trimethoprim and analogues.,  23  (4): [PMID:6991692] [10.1021/jm00178a007]

3. Dunn WJ, Hopfinger AJ, Catana C, Duraiswami C..  (1996)  Solution of the conformation and alignment tensors for the binding of trimethoprim and its analogs to dihydrofolate reductase: 3D-quantitative structure-activity relationship study using molecular shape analysis, 3-way partial least-squares regression, and 3-way factor analysis.,  39  (24): [PMID:8941396] [10.1021/jm960491r]

4. Roth B, Aig E, Lane K, Rauckman BS..  (1980)  2,4-Diamino-5-benzylpyrimidines as antibacterial agents. 4. 6-Substituted trimethoprim derivatives from phenolic Mannich intermediates. Application to the synthesis of trimethoprim and 3,5-dialkylbenzyl analogues.,  23  (5): [PMID:6991695] [10.1021/jm00179a012]

5. Hopfinger AJ..  (1981)  Inhibition of dihydrofolate reductase: structure-activity correlations of 2,4-diamino-5-benzylpyrimidines based upon molecular shape analysis.,  24  (7): [PMID:7277386] [10.1021/jm00139a010]

6. 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]

Source

Source(1):

• Scientific Literature