5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(Z)-ylidene]-2-mercapto-thiazol-4-one

ID: ALA295739

Chembl Id: CHEMBL295739

Cas Number: 137506-94-6

PubChem CID: 1514885

Max Phase: Preclinical

Molecular Formula: C18H23NO2S2

Molecular Weight: 349.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(/C=C2\SC(=S)NC2=O)cc(C(C)(C)C)c1O

Standard InChI:  InChI=1S/C18H23NO2S2/c1-17(2,3)11-7-10(8-12(14(11)20)18(4,5)6)9-13-15(21)19-16(22)23-13/h7-9,20H,1-6H3,(H,19,21,22)/b13-9-

Standard InChI Key:  WBDPSYDYYOULLK-LCYFTJDESA-N

Alternative Forms

1. Parent:

   

   ALA295739

   (Z)-5-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-thioxo-thiazolidin-4-one

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: 349.52

Molecular Weight (Monoisotopic): 349.1170

AlogP: 4.48

#Rotatable Bonds: 1

Polar Surface Area: 49.33

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.93

CX Basic pKa: ┄

CX LogP: 5.53

CX LogD: 3.70

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -0.83

References

1. Song Y, Connor DT, Doubleday R, Sorenson RJ, Sercel AD, Unangst PC, Roth BD, Gilbertsen RB, Chan K, Schrier DJ, Guglietta A, Bornemeier DA, Dyer RD..  (1999)  Synthesis, structure-activity relationships, and in vivo evaluations of substituted di-tert-butylphenols as a novel class of potent, selective, and orally active cyclooxygenase-2 inhibitors. 1. Thiazolone and oxazolone series.,  42  (7): [PMID:10197959] [10.1021/jm9805081]

2. Unangst PC, Connor DT, Cetenko WA, Sorenson RJ, Sircar JC, Wright CD, Schrier DJ, Dyer RD.  (1993)  Oxazole, thiazole, and imidazole derivatives of 2,6-di-tert-butylphenol as dual 5-lipoxygenase and cyclooxygenase inhibitors,  3  (8): [10.1016/S0960-894X(00)80051-7]

3. Unangst PC, Connor DT, Cetenko WA, Sorenson RJ, Kostlan CR, Sircar JC, Wright CD, Schrier DJ, Dyer RD..  (1994)  Synthesis and biological evaluation of 5-[[3,5-bis(1,1-dimethylethyl)- 4-hydroxyphenyl]methylene]oxazoles, -thiazoles, and -imidazoles: novel dual 5-lipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity.,  37  (2): [PMID:8295221] [10.1021/jm00028a017]

Source

Source(1):

• Scientific Literature