4-{2-[2-(4-Chloro-phenyl)-ethyl]-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethylsulfanyl}-phenylamine

ID: ALA421109

PubChem CID: 9867329

Max Phase: Preclinical

Molecular Formula: C22H24ClN3O2S

Molecular Weight: 429.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(SC[C@@H]2CO[C@@](CCc3ccc(Cl)cc3)(Cn3ccnc3)O2)cc1

Standard InChI:  InChI=1S/C22H24ClN3O2S/c23-18-3-1-17(2-4-18)9-10-22(15-26-12-11-25-16-26)27-13-20(28-22)14-29-21-7-5-19(24)6-8-21/h1-8,11-12,16,20H,9-10,13-15,24H2/t20-,22+/m0/s1

Standard InChI Key:  VYNIUBZKEWJOJP-RBBKRZOGSA-N

Molfile:  

     RDKit          2D

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   -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
   -7.7025   -3.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3084   -4.8243    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8003   -4.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4079   -6.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8994   -6.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7834   -5.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1759   -3.9349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6845   -3.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9766   -5.4342    0.0000 N   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  6
 13 14  1  0
  1 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 16 20  1  0
 19 20  2  0
  3 21  1  6
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 23 28  1  0
 27 28  2  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA421109

   Imidazole-dioxolane, 5

2. Alternative Forms:

   

   ALA421109

   4-[[(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methylsulfanyl]aniline;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: 429.97

Molecular Weight (Monoisotopic): 429.1278

AlogP: 4.66

#Rotatable Bonds: 8

Polar Surface Area: 62.30

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.43

CX LogP: 4.61

CX LogD: 4.57

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: -0.60

References

1. Walker KA, Kertesz DJ, Rotstein DM, Swinney DC, Berry PW, So OY, Webb AS, Watson DM, Mak AY, Burton PM..  (1993)  Selective inhibition of mammalian lanosterol 14 alpha-demethylase: a possible strategy for cholesterol lowering.,  36  (15): [PMID:8340925] [10.1021/jm00067a022]

2. Vlahakis JZ, Kinobe RT, Bowers RJ, Brien JF, Nakatsu K, Szarek WA..  (2005)  Synthesis and evaluation of azalanstat analogues as heme oxygenase inhibitors.,  15  (5): [PMID:15713406] [10.1016/j.bmcl.2004.12.075]

3. 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]

4. 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