(2R,4S)-2-[2-(4-Chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[{(4-hydroxyphenyl)thio}methyl]-1,3-dioxolane

ID: ALA208047

Chembl Id: CHEMBL208047

PubChem CID: 25143073

Max Phase: Preclinical

Molecular Formula: C22H23ClN2O3S

Molecular Weight: 430.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(SC[C@@H]2CO[C@@](CCc3ccc(Cl)cc3)(Cn3ccnc3)O2)cc1

Standard InChI:  InChI=1S/C22H23ClN2O3S/c23-18-3-1-17(2-4-18)9-10-22(15-25-12-11-24-16-25)27-13-20(28-22)14-29-21-7-5-19(26)6-8-21/h1-8,11-12,16,20,26H,9-10,13-15H2/t20-,22+/m0/s1

Standard InChI Key:  YSVCQFYCUWODIY-RBBKRZOGSA-N

Alternative Forms

1. Parent:

   

   ALA208047

   Imidazole-dioxolane, 9

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: 430.96

Molecular Weight (Monoisotopic): 430.1118

AlogP: 4.78

#Rotatable Bonds: 8

Polar Surface Area: 56.51

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.39

CX Basic pKa: 6.43

CX LogP: 5.13

CX LogD: 5.10

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: -0.41

References

1. Vlahakis JZ, Kinobe RT, Nakatsu K, Szarek WA, Crandall IE..  (2006)  Anti-Plasmodium activity of imidazole-dioxolane compounds.,  16  (9): [PMID:16495054] [10.1016/j.bmcl.2006.01.122]

2. Vlahakis JZ, Hum M, Rahman MN, Jia Z, Nakatsu K, Szarek WA..  (2009)  Synthesis and evaluation of imidazole-dioxolane compounds as selective heme oxygenase inhibitors: effect of substituents at the 4-position of the dioxolane ring.,  17  (6): [PMID:19268600] [10.1016/j.bmc.2009.01.078]

3. Intagliata S, Salerno L, Ciaffaglione V, Leonardi C, Fallica AN, Carota G, Amata E, Marrazzo A, Pittalà V, Romeo G..  (2019)  Heme Oxygenase-2 (HO-2) as a therapeutic target: Activators and inhibitors.,  183  [PMID:31550661] [10.1016/j.ejmech.2019.111703]

Source

Source(1):

• Scientific Literature