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2-Styryl-4,5-dihydro-1H-imidazole

ID: ALA275970

PubChem CID: 6455104

Max Phase: Preclinical

Molecular Formula: C11H12N2

Molecular Weight: 172.23

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  C(=C/c1ccccc1)\C1=NCCN1

Standard InChI:  InChI=1S/C11H12N2/c1-2-4-10(5-3-1)6-7-11-12-8-9-13-11/h1-7H,8-9H2,(H,12,13)/b7-6+

Standard InChI Key:  IGISUADTPSLENQ-VOTSOKGWSA-N

Molfile:  

     RDKit          2D

 13 14  0  0  0  0  0  0  0  0999 V2000
   -2.0083    1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083    2.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    1.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375    1.7333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250    1.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375    2.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958    2.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5833    1.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0958    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5833   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0958    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  3  2  0
  6  5  1  0
  7  2  1  0
  8  4  1  0
  9  6  2  0
 10  6  1  0
 11  9  1  0
 12 10  2  0
 13 12  1  0
  8  7  1  0
 11 13  2  0
M  END

Alternative Forms

  1. Parent:

    ALA275970

    TRACIZOLINE

Associated Targets(Human)

NISCH Tclin Nischarin (304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase (395 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Adra2c Adrenergic receptor alpha-2 (3313 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Maob Monoamine oxidase (439 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nisch Nischarin (241 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 172.23Molecular Weight (Monoisotopic): 172.1000AlogP: 1.70#Rotatable Bonds: 2
Polar Surface Area: 24.39Molecular Species: BASEHBA: 2HBD: 1
#RO5 Violations: HBA (Lipinski): 2HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 10.10CX LogP: 1.73CX LogD: -0.51
Aromatic Rings: 1Heavy Atoms: 13QED Weighted: 0.72Np Likeness Score: 0.06

References

1. Baurin N, Vangrevelinghe E, Morin-Allory L, Mérour JY, Renard P, Payard M, Guillaumet G, Marot C..  (2000)  3D-QSAR CoMFA study on imidazolinergic I(2) ligands: a significant model through a combined exploration of structural diversity and methodology.,  43  (6): [PMID:10737743] [10.1021/jm991124t]
2. Touzeau F, Arrault A, Guillaumet G, Scalbert E, Pfeiffer B, Rettori MC, Renard P, Mérour JY..  (2003)  Synthesis and biological evaluation of new 2-(4,5-dihydro-1H-imidazol-2-yl)-3,4-dihydro-2H-1,4-benzoxazine derivatives.,  46  (10): [PMID:12723959] [10.1021/jm021050c]
3. Gentili F, Bousquet P, Brasili L, Dontenwill M, Feldman J, Ghelfi F, Giannella M, Piergentili A, Quaglia W, Pigini M..  (2003)  Imidazoline binding sites (IBS) profile modulation: key role of the bridge in determining I1-IBS or I2-IBS selectivity within a series of 2-phenoxymethylimidazoline analogues.,  46  (11): [PMID:12747788] [10.1021/jm021113r]
4. Quaglia W, Bousquet P, Pigini M, Carotti A, Carrieri A, Dontenwill M, Gentili F, Giannella M, Maranca F, Piergentili A, Brasili L..  (1999)  2-(2-Phenylcyclopropyl)imidazolines: reversed enantioselective interaction at I(1) and I(2) imidazoline receptors.,  42  (15): [PMID:10425083] [10.1021/jm991049m]
5. Glennon RA, Grella B, Tyacke RJ, Lau A, Westaway J, Hudson AL..  (2004)  Binding of an imidazopyridoindole at imidazoline I2 receptors.,  14  (2): [PMID:14698196] [10.1016/j.bmcl.2003.09.092]
6. Gentili F, Pizzinat N, Ordener C, Marchal-Victorion S, Maurel A, Hofmann R, Renard P, Delagrange P, Pigini M, Parini A, Giannella M..  (2006)  3-[5-(4,5-dihydro-1H-imidazol-2-yl)-furan-2-yl]phenylamine (Amifuraline), a promising reversible and selective peripheral MAO-A inhibitor.,  49  (18): [PMID:16942031] [10.1021/jm060605r]
7. Nicolotti O, Carotti A, Carrieri A, Pigini M, Gentili F, Brasili L, Giannella M, Quaglia W, Piergentili A, Bousquet P, Dontenwill M.  (2004)  Alpha2-Adrenergic Receptors in Intestinal Epithelial Cells: Mechanisms of Signaling, Role, and Regulation,  13  (3): [10.1007/s00044-004-0023-9]
8. Vucicevic J, Srdic-Rajic T, Pieroni M, Laurila JM, Perovic V, Tassini S, Azzali E, Costantino G, Glisic S, Agbaba D, Scheinin M, Nikolic K, Radi M, Veljkovic N..  (2016)  A combined ligand- and structure-based approach for the identification of rilmenidine-derived compounds which synergize the antitumor effects of doxorubicin.,  24  (14): [PMID:27265687] [10.1016/j.bmc.2016.05.043]
9. Giusepponi ME, Cifani C, Micioni Di Bonaventura MV, Mattioli L, Hudson A, Diamanti E, Del Bello F, Giannella M, Mammoli V, Paoletti CD, Piergentili A, Pigini M, Quaglia W..  (2016)  Combined Interactions with I1-, I2-Imidazoline Binding Sites and α2-Adrenoceptors To Manage Opioid Addiction.,  (10): [PMID:27774136] [10.1021/acsmedchemlett.6b00290]
10. Abás S, Rodríguez-Arévalo S, Bagán A, Griñán-Ferré C, Vasilopoulou F, Brocos-Mosquera I, Muguruza C, Pérez B, Molins E, Luque FJ, Pérez-Lozano P, de Jonghe S, Daelemans D, Naesens L, Brea J, Loza MI, Hernández-Hernández E, García-Sevilla JA, García-Fuster MJ, Radan M, Djikic T, Nikolic K, Pallàs M, Callado LF, Escolano C..  (2020)  Bicyclic α-Iminophosphonates as High Affinity Imidazoline I2 Receptor Ligands for Alzheimer's Disease.,  63  (7): [PMID:32150414] [10.1021/acs.jmedchem.9b02080]

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