ID: ALA571992

Max Phase: Preclinical

Molecular Formula: C25H34N6S

Molecular Weight: 450.66

Molecule Type: Small molecule

Representations

Synonyms (1): D-301
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCN(CCN1CCN(c2nccc3ccccc23)CC1)[C@H]1CCc2nc(N)sc2C1

Standard InChI:  InChI=1S/C25H34N6S/c1-2-11-30(20-7-8-22-23(18-20)32-25(26)28-22)15-12-29-13-16-31(17-14-29)24-21-6-4-3-5-19(21)9-10-27-24/h3-6,9-10,20H,2,7-8,11-18H2,1H3,(H2,26,28)/t20-/m0/s1

Standard InChI Key:  SNMHDHJEXUFVCO-FQEVSTJZSA-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: 450.66

Molecular Weight (Monoisotopic): 450.2566

AlogP: 3.67

#Rotatable Bonds: 7

Polar Surface Area: 61.52

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.64

CX LogP: 4.27

CX LogD: 2.04

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.59

Np Likeness Score: -1.56

References

1. Ghosh B, Antonio T, Zhen J, Kharkar P, Reith ME, Dutta AK..  (2010)  Development of (S)-N6-(2-(4-(isoquinolin-1-yl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]-thiazole-2,6-diamine and its analogue as a D3 receptor preferring agonist: potent in vivo activity in Parkinson's disease animal models.,  53  (3): [PMID:20038106] [10.1021/jm901184n]

2. Ghosh B, Antonio T, Gopishetty B, Reith M, Dutta A..  (2010)  Further delineation of hydrophobic binding sites in dopamine D(2)/D(3) receptors for N-4 substituents on the piperazine ring of the hybrid template 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-ol.,  18  (15): [PMID:20605099] [10.1016/j.bmc.2010.06.025]

3. Johnson M, Antonio T, Reith ME, Dutta AK..  (2012)  Structure-activity relationship study of N⁶-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine analogues: development of highly selective D3 dopamine receptor agonists along with a highly potent D2/D3 agonist and their pharmacological characterization.,  55  (12): [PMID:22642365] [10.1021/jm300268s]

4. Gopishetty B, Zhang S, Kharkar PS, Antonio T, Reith M, Dutta AK..  (2013)  Modification of agonist binding moiety in hybrid derivative 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-1-ol/-2-amino versions: impact on functional activity and selectivity for dopamine D2/D3 receptors.,  21  (11): [PMID:23623679] [10.1016/j.bmc.2013.03.059]

Source

Source(1):

• Scientific Literature