3-(3,4-Difluoro-phenyl)-4-(4-methanesulfonyl-phenyl)-5H-furan-2-one

ID: ALA18264

Chembl Id: CHEMBL18264

Cas Number: 162011-83-8

PubChem CID: 127923

Max Phase: Preclinical

Molecular Formula: C17H12F2O4S

Molecular Weight: 350.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1ccc(C2=C(c3ccc(F)c(F)c3)C(=O)OC2)cc1

Standard InChI:  InChI=1S/C17H12F2O4S/c1-24(21,22)12-5-2-10(3-6-12)13-9-23-17(20)16(13)11-4-7-14(18)15(19)8-11/h2-8H,9H2,1H3

Standard InChI Key:  INRQTVDUZFESAO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA18264

   3-(3,4-Difluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2(5H)-furanone

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: 350.34

Molecular Weight (Monoisotopic): 350.0424

AlogP: 2.84

#Rotatable Bonds: 3

Polar Surface Area: 60.44

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.10

CX Basic pKa: ┄

CX LogP: 2.85

CX LogD: 2.85

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -0.63

References

1. Riendeau D, Salem M, Styhler A, Ouellet M, Mancini JA, Li CS..  (2004)  Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2.,  14  (5): [PMID:14980665] [10.1016/j.bmcl.2003.12.047]

2. Prasit P, Wang Z, Brideau C, Chan CC, Charleson S, Cromlish W, Ethier D, Evans JF, Ford-Hutchinson AW, Gauthier JY, Gordon R, Guay J, Gresser M, Kargman S, Kennedy B, Leblanc Y, Léger S, Mancini J, O'Neill GP, Ouellet M, Percival MD, Perrier H, Riendeau D, Rodger I, Zamboni R..  (1999)  The discovery of rofecoxib, [MK 966, Vioxx, 4-(4'-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2-inhibitor.,  9  (13): [PMID:10406640] [10.1016/s0960-894x(99)00288-7]

3. Smith ND, Reger TS, Payne J, Zunic J, Lorrain D, Correa L, Stock N, Cramer M, Chen W, Yang J, Prasit P, Munoz B..  (2005)  Water soluble prodrug of a COX-2 selective inhibitor suitable for intravenous administration in models of cerebral ischemia.,  15  (13): [PMID:15936193] [10.1016/j.bmcl.2005.05.002]

4. Blouin M, Han Y, Burch J, Farand J, Mellon C, Gaudreault M, Wrona M, Lévesque JF, Denis D, Mathieu MC, Stocco R, Vigneault E, Therien A, Clark P, Rowland S, Xu D, O'Neill G, Ducharme Y, Friesen R..  (2010)  The discovery of 4-{1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic acid (MK-2894), a potent and selective prostaglandin E2 subtype 4 receptor antagonist.,  53  (5): [PMID:20163116] [10.1021/jm901771h]

5. Husain A, Khan SA, Iram F, Iqbal MA, Asif M..  (2019)  Insights into the chemistry and therapeutic potential of furanones: A versatile pharmacophore.,  171  [PMID:30909021] [10.1016/j.ejmech.2019.03.021]

Source

Source(1):

• Scientific Literature