ID: ALA128168

Max Phase: Preclinical

Molecular Formula: C17H18N2O

Molecular Weight: 266.34

Molecule Type: Small molecule

Representations

Synonyms (1): Biphenyline
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(Oc1ccccc1-c1ccccc1)C1=NCCN1

Standard InChI:  InChI=1S/C17H18N2O/c1-13(17-18-11-12-19-17)20-16-10-6-5-9-15(16)14-7-3-2-4-8-14/h2-10,13H,11-12H2,1H3,(H,18,19)

Standard InChI Key:  OGOLMGZJNRNULQ-UHFFFAOYSA-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: 266.34

Molecular Weight (Monoisotopic): 266.1419

AlogP: 3.12

#Rotatable Bonds: 4

Polar Surface Area: 33.62

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.27

CX LogP: 3.10

CX LogD: 1.34

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.92

Np Likeness Score: -0.22

References

1. Gentili F, Bousquet P, Brasili L, Caretto M, Carrieri A, Dontenwill M, Giannella M, Marucci G, Perfumi M, Piergentili A, Quaglia W, Rascente C, Pigini M..  (2002)  Alpha2-adrenoreceptors profile modulation and high antinociceptive activity of (S)-(-)-2-[1-(biphenyl-2-yloxy)ethyl]-4,5-dihydro-1H-imidazole.,  45  (1): [PMID:11754577] [10.1021/jm0110082]

2. Gentili F, Ghelfi F, Giannella M, Piergentili A, Pigini M, Quaglia W, Vesprini C, Crassous PA, Paris H, Carrieri A..  (2004)  alpha 2-adrenoreceptors profile modulation. 2. Biphenyline analogues as tools for selective activation of the alpha 2C-subtype.,  47  (25): [PMID:15566287] [10.1021/jm0408215]

3. Crassous PA, Cardinaletti C, Carrieri A, Bruni B, Di Vaira M, Gentili F, Ghelfi F, Giannella M, Paris H, Piergentili A, Quaglia W, Schaak S, Vesprini C, Pigini M..  (2007)  Alpha2-adrenoreceptors profile modulation. 3.1 (R)-(+)-m-nitrobiphenyline, a new efficient and alpha2C-subtype selective agonist.,  50  (16): [PMID:17630725] [10.1021/jm061487a]

4. Gentili F, Cardinaletti C, Vesprini C, Carrieri A, Ghelfi F, Farande A, Giannella M, Piergentili A, Quaglia W, Laurila JM, Huhtinen A, Scheinin M, Pigini M..  (2008)  Alpha2-adrenoreceptors profile modulation. 4. From antagonist to agonist behavior.,  51  (14): [PMID:18578476] [10.1021/jm800250z]

5. Del Bello F, Mattioli L, Ghelfi F, Giannella M, Piergentili A, Quaglia W, Cardinaletti C, Perfumi M, Thomas RJ, Zanelli U, Marchioro C, Dal Cin M, Pigini M..  (2010)  Fruitful adrenergic α(2C)-agonism/α(2A)-antagonism combination to prevent and contrast morphine tolerance and dependence.,  53  (21): [PMID:20925410] [10.1021/jm100977d]

6. Del Bello F, Bargelli V, Cifani C, Gratteri P, Bazzicalupi C, Diamanti E, Giannella M, Mammoli V, Matucci R, Micioni Di Bonaventura MV, Piergentili A, Quaglia W, Pigini M..  (2015)  Antagonism/Agonism modulation to build novel antihypertensives selectively triggering i1-imidazoline receptor activation.,  6  (5): [PMID:26005521] [10.1021/acsmedchemlett.5b00115]

7. Dosa PI, Amin EA..  (2016)  Tactical Approaches to Interconverting GPCR Agonists and Antagonists.,  59  (3): [PMID:26390077] [10.1021/acs.jmedchem.5b00982]

Source

Source(1):

• Scientific Literature