1-(3,4-Dimethoxyphenyl)-3-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea

ID: ALA566563

Cas Number: 1072801-42-3

PubChem CID: 25022550

Max Phase: Preclinical

Molecular Formula: C16H22N4O2S

Molecular Weight: 334.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=S)NCCCn2cncc2C)cc1OC

Standard InChI:  InChI=1S/C16H22N4O2S/c1-12-10-17-11-20(12)8-4-7-18-16(23)19-13-5-6-14(21-2)15(9-13)22-3/h5-6,9-11H,4,7-8H2,1-3H3,(H2,18,19,23)

Standard InChI Key:  AYTMAWUKURFAAB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -5.0721    0.1758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2464    0.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9695    0.9372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6294    1.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3064    0.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2572    1.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5420    0.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8299    1.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1105    0.9633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    1.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3211    0.9760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4058    2.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332    1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492    0.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519    2.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7368    2.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4550    1.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0205    2.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1729    0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1772    0.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1656    2.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8834    2.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6127    2.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 10 12  2  0
  3  6  1  0
 11 13  1  0
 13 14  2  0
 15 16  1  0
  6  7  1  0
  2  3  1  0
  7  8  1  0
  3  4  1  0
 13 18  1  0
 14 17  1  0
 17 15  2  0
 16 18  2  0
  8  9  1  0
 17 19  1  0
  4  5  2  0
 19 20  1  0
  9 10  1  0
 15 21  1  0
  5  1  1  0
 21 22  1  0
 10 11  1  0
  4 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA566563

   1-(3,4-Dimethoxyphenyl)-3-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea

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: 334.45

Molecular Weight (Monoisotopic): 334.1463

AlogP: 2.59

#Rotatable Bonds: 7

Polar Surface Area: 60.34

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.48

CX Basic pKa: 7.33

CX LogP: 1.84

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -1.80

References

1. Buchholz M, Hamann A, Aust S, Brandt W, Böhme L, Hoffmann T, Schilling S, Demuth HU, Heiser U..  (2009)  Inhibitors for human glutaminyl cyclase by structure based design and bioisosteric replacement.,  52  (22): [PMID:19863057] [10.1021/jm900969p]

2. Tran PT, Hoang VH, Thorat SA, Kim SE, Ann J, Chang YJ, Nam DW, Song H, Mook-Jung I, Lee J, Lee J..  (2013)  Structure-activity relationship of human glutaminyl cyclase inhibitors having an N-(5-methyl-1H-imidazol-1-yl)propyl thiourea template.,  21  (13): [PMID:23643900] [10.1016/j.bmc.2013.04.005]

3. Hoang VH, Tran PT, Cui M, Ngo VT, Ann J, Park J, Lee J, Choi K, Cho H, Kim H, Ha HJ, Hong HS, Choi S, Kim YH, Lee J..  (2017)  Discovery of Potent Human Glutaminyl Cyclase Inhibitors as Anti-Alzheimer's Agents Based on Rational Design.,  60  (6): [PMID:28234463] [10.1021/acs.jmedchem.7b00098]

4. Hoang VH, Ngo VTH, Cui M, Manh NV, Tran PT, Ann J, Ha HJ, Kim H, Choi K, Kim YH, Chang H, Macalino SJY, Lee J, Choi S, Lee J..  (2019)  Discovery of Conformationally Restricted Human Glutaminyl Cyclase Inhibitors as Potent Anti-Alzheimer's Agents by Structure-Based Design.,  62  (17): [PMID:31411468] [10.1021/acs.jmedchem.9b00751]

5. Van Manh N, Hoang VH, Ngo VTH, Ann J, Jang TH, Ha JH, Song JY, Ha HJ, Kim H, Kim YH, Lee J, Lee J..  (2021)  Discovery of highly potent human glutaminyl cyclase (QC) inhibitors as anti-Alzheimer's agents by the combination of pharmacophore-based and structure-based design.,  226  [PMID:34536669] [10.1016/j.ejmech.2021.113819]

6. Van Manh N, Hoang VH, Ngo VTH, Kang S, Jeong JJ, Ha HJ, Kim H, Kim YH, Ann J, Lee J..  (2022)  Discovery of potent indazole-based human glutaminyl cyclase (QC) inhibitors as Anti-Alzheimer's disease agents.,  244  [PMID:36265279] [10.1016/j.ejmech.2022.114837]

Source

Source(1):

• Scientific Literature