6-(Naphthalene-2-sulfinyl)-quinazoline-2,4-diamine

ID: ALA6979

Chembl Id: CHEMBL6979

Cas Number: 51123-77-4

PubChem CID: 328136

Max Phase: Preclinical

Molecular Formula: C18H14N4OS

Molecular Weight: 334.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2cc([S+]([O-])c3ccc4ccccc4c3)ccc2n1

Standard InChI:  InChI=1S/C18H14N4OS/c19-17-15-10-14(7-8-16(15)21-18(20)22-17)24(23)13-6-5-11-3-1-2-4-12(11)9-13/h1-10H,(H4,19,20,21,22)

Standard InChI Key:  QSWGIUCUSOBPPC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA6979

   6-Naphthalen-2-ylsulfinylquinazoline-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: 334.40

Molecular Weight (Monoisotopic): 334.0888

AlogP: 3.11

#Rotatable Bonds: 2

Polar Surface Area: 100.88

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.77

CX LogP: 2.84

CX LogD: 2.75

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.55

Np Likeness Score: -0.42

References

1. Ghose AK, Crippen GM..  (1983)  Combined distance geometry analysis of dihydrofolate reductase inhibition by quinazolines and triazines.,  26  (7): [PMID:6864738] [10.1021/jm00361a012]

2. Crippen GM..  (1980)  Quantitative structure-activity relationships by distance geometry: systematic analysis of dihydrofolate reductase inhibitors.,  23  (6): [PMID:7392027] [10.1021/jm00180a004]

3. Battershell C, Malhotra D, Hopfinger AJ..  (1981)  Inhibition of dihydrofolate reductase: structure-activity correlations of quinazolines based upon molecular shape analysis.,  24  (7): [PMID:7277385] [10.1021/jm00139a009]

4. Ghose AK, Crippen GM..  (1982)  Quantitative structure-activity relationship by distance geometry: quinazolines as dihydrofolate reductase inhibitors.,  25  (8): [PMID:7120278] [10.1021/jm00350a003]

5. Ghose AK, Crippen GM..  (1984)  General distance geometry three-dimensional receptor model for diverse dihydrofolate reductase inhibitors.,  27  (7): [PMID:6737433] [10.1021/jm00373a016]

6. Elslager EF, Hutt MP, Jacob P, Johnson J, Temporelli B, Werbel LM, Worth DF, Rane L..  (1979)  Folate antagonists. 15. 2,3-Diamino-6-(2-naphthylsulfonyl)quinazoline and related 2,4-diamino-6-[(phenyl and naphthyl)sulfinyl and sulfonyl]quinazolines, a potent new class of antimetabolites with phenomenal antimalarial activity.,  22  (10): [PMID:117107] [10.1021/jm00196a019]

7. Fukunaga JY, Hansch C, Steller EE..  (1976)  Inhibition of dihydrofolate reductase. Structure-activity correlations of quinazolines.,  19  (5): [PMID:1271401] [10.1021/jm00227a006]

8. Hansch C, Fukunaga JY, Jow PY..  (1977)  Quantitative structure-activity relationships of antimalarial and dihydrofolate reductase inhibition by quinazolines and 5-substituted benzyl-2,4-diaminopyrimidines.,  20  (1): [PMID:319234] [10.1021/jm00211a020]

Source

Source(1):

• Scientific Literature