2-[2-(4-chlorophenyl)ethyl]-2-[1H-imidazol-1-yl)methyl]-1,3-dioxolane

ID: ALA495072

PubChem CID: 11500273

Max Phase: Preclinical

Molecular Formula: C15H17ClN2O2

Molecular Weight: 292.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc(CCC2(Cn3ccnc3)OCCO2)cc1

Standard InChI:  InChI=1S/C15H17ClN2O2/c16-14-3-1-13(2-4-14)5-6-15(19-9-10-20-15)11-18-8-7-17-12-18/h1-4,7-8,12H,5-6,9-11H2

Standard InChI Key:  NPIOYRIZNLPLDH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2073   -4.4014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2131   -3.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4656   -1.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9978   -2.2972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907   -5.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901   -6.0072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4476   -7.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9794   -7.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2335   -6.4934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2407   -5.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  4  5  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  6 11  1  0
 10 11  2  0
  7 12  1  0
 10 13  1  0
  1 14  1  0
 13 14  1  0
  1 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 16 20  1  0
 19 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA495072

   1-({2-[2-(4-Chlorophenyl)ethyl]-1,3-Dioxolan-2-Yl}methyl)-1h-Imidazole

2. Alternative Forms:

   

   ALA495072

   1-[[2-(2-(4-Chlorophenyl)ethyl)-1,3-dioxolan-2-yl]methyl]imidazole hydrochloride

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: 292.77

Molecular Weight (Monoisotopic): 292.0979

AlogP: 2.91

#Rotatable Bonds: 5

Polar Surface Area: 36.28

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.43

CX LogP: 3.21

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.85

Np Likeness Score: -0.71

References

1. Rahman MN, Vlahakis JZ, Szarek WA, Nakatsu K, Jia Z..  (2008)  X-ray crystal structure of human heme oxygenase-1 in complex with 1-(adamantan-1-yl)-2-(1H-imidazol-1-yl)ethanone: a common binding mode for imidazole-based heme oxygenase-1 inhibitors.,  51  (19): [PMID:18798608] [10.1021/jm800505m]

2. Salerno L, Amata E, Romeo G, Marrazzo A, Prezzavento O, Floresta G, Sorrenti V, Barbagallo I, Rescifina A, Pittalà V..  (2018)  Potholing of the hydrophobic heme oxygenase-1 western region for the search of potent and selective imidazole-based inhibitors.,  148  [PMID:29454190] [10.1016/j.ejmech.2018.02.007]

3. Salerno L, Floresta G, Ciaffaglione V, Gentile D, Margani F, Turnaturi R, Rescifina A, Pittalà V..  (2019)  Progress in the development of selective heme oxygenase-1 inhibitors and their potential therapeutic application.,  167  [PMID:30784878] [10.1016/j.ejmech.2019.02.027]

Source

Source(1):

• Scientific Literature