ID: ALA8758

Max Phase: Preclinical

Molecular Formula: C22H18BrF2O4P

Molecular Weight: 495.26

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(c1ccccc1)C(Cc1ccc(C(F)(F)P(=O)(O)O)c(Br)c1)c1ccccc1

Standard InChI:  InChI=1S/C22H18BrF2O4P/c23-20-14-15(11-12-19(20)22(24,25)30(27,28)29)13-18(16-7-3-1-4-8-16)21(26)17-9-5-2-6-10-17/h1-12,14,18H,13H2,(H2,27,28,29)

Standard InChI Key:  WDTMVBQZDFMOIK-UHFFFAOYSA-N

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

Properties

Molecular Weight: 495.26

Molecular Weight (Monoisotopic): 494.0094

AlogP: 5.89

#Rotatable Bonds: 7

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.49

CX Basic pKa:

CX LogP: 5.46

CX LogD: 2.71

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.32

Np Likeness Score: -0.16

References

1. Dufresne C, Roy P, Wang Z, Asante-Appiah E, Cromlish W, Boie Y, Forghani F, Desmarais S, Wang Q, Skorey K, Waddleton D, Ramachandran C, Kennedy BP, Xu L, Gordon R, Chan CC, Leblanc Y..  (2004)  The development of potent non-peptidic PTP-1B inhibitors.,  14  (4): [PMID:15013019] [10.1016/j.bmcl.2003.11.048]

2. Han Y, Belley M, Bayly CI, Colucci J, Dufresne C, Giroux A, Lau CK, Leblanc Y, McKay D, Therien M, Wilson MC, Skorey K, Chan CC, Scapin G, Kennedy BP..  (2008)  Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor.,  18  (11): [PMID:18477508] [10.1016/j.bmcl.2008.04.064]

3. Combs AP..  (2010)  Recent advances in the discovery of competitive protein tyrosine phosphatase 1B inhibitors for the treatment of diabetes, obesity, and cancer.,  53  (6): [PMID:20000419] [10.1021/jm901090b]

4. Basu S, Prasad UV, Barawkar DA, De S, Palle VP, Menon S, Patel M, Thorat S, Singh UP, Das Sarma K, Waman Y, Niranjan S, Pathade V, Gaur A, Reddy S, Ansari S..  (2012)  Discovery of novel and potent heterocyclic carboxylic acid derivatives as protein tyrosine phosphatase 1B inhibitors.,  22  (8): [PMID:22424978] [10.1016/j.bmcl.2012.02.070]

5. Zhang R, Yu R, Xu Q, Li X, Luo J, Jiang B, Wang L, Guo S, Wu N, Shi D..  (2017)  Discovery and evaluation of the hybrid of bromophenol and saccharide as potent and selective protein tyrosine phosphatase 1B inhibitors.,  134  [PMID:28395151] [10.1016/j.ejmech.2017.04.004]

6. Meanwell NA..  (2018)  Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.,  61  (14): [PMID:29400967] [10.1021/acs.jmedchem.7b01788]

7. Kousaxidis A, Petrou A, Lavrentaki V, Fesatidou M, Nicolaou I, Geronikaki A..  (2020)  Aldose reductase and protein tyrosine phosphatase 1B inhibitors as a promising therapeutic approach for diabetes mellitus.,  207  [PMID:32871344] [10.1016/j.ejmech.2020.112742]

Source

Source(1):

• Scientific Literature