6-Propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol

ID: ALA27559

Cas Number: 114033-65-7

PubChem CID: 10333842

Max Phase: Preclinical

Molecular Formula: C19H21NO

Molecular Weight: 279.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (R)-OH-N-propylnoraporphine | CHEMBL27559|(R)-OH-N-propylnoraporphine|SCHEMBL1203699|BDBM84636|NPA-11-OH-R,(+)|PD129363|114033-65-7

Canonical SMILES:  CCCN1CCc2cccc3c2[C@H]1Cc1cccc(O)c1-3

Standard InChI:  InChI=1S/C19H21NO/c1-2-10-20-11-9-13-5-3-7-15-18(13)16(20)12-14-6-4-8-17(21)19(14)15/h3-8,16,21H,2,9-12H2,1H3/t16-/m1/s1

Standard InChI Key:  WZJSIHGOLMMBAL-MRXNPFEDSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -5.1938    2.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1951    1.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4844    3.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710    2.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343    1.8140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336    2.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0541    3.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0558    1.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7718    1.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4847    1.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0528    0.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    0.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4855    0.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    0.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2008   -0.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826   -1.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7717   -0.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9113    0.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226    1.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6246    0.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9127    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3469    0.9924    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 11  1  0
  9 10  2  0
 10 13  1  0
 12 11  1  0
  4  3  2  0
 12 13  2  0
  4  7  1  0
 13 14  1  0
  8  5  1  0
 14 15  2  0
  5  6  1  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  8  9  1  0
 14 18  1  0
  3  1  1  0
  5 19  1  0
  4  9  1  0
 19 20  1  0
  1  2  2  0
 20 21  1  0
  2 10  1  0
  8 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA27559

   (R)-OH-N-propylnoraporphine

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: 279.38

Molecular Weight (Monoisotopic): 279.1623

AlogP: 3.92

#Rotatable Bonds: 2

Polar Surface Area: 23.47

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.73

CX Basic pKa: 8.39

CX LogP: 4.09

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.90

Np Likeness Score: 0.83

References

1. Gao Y, Zong R, Campbell A, Kula NS, Baldessarini RJ, Neumeyer JL..  (1988)  Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine.,  31  (7): [PMID:3385732] [10.1021/jm00402a024]

2. Neumeyer JL, Arana GW, Law SJ, Lamont JS, Kula NS, Baldessarini RJ..  (1981)  Aporphines, 36. Dopamine receptor interactions of trihydroxyaporphines. Synthesis, radioreceptor binding, and striatal adenylate cyclase stimulation of 2,10,11-trihydroxyaporphines in comparison with other hydroxylated aporphines.,  24  (12): [PMID:7310821] [10.1021/jm00144a014]

3. Neumeyer JL, Gao YG, Kula NS, Baldessarini RJ..  (1991)  R and S enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue.,  34  (1): [PMID:1671415] [10.1021/jm00105a005]

4. Hedberg MH, Linnanen T, Jansen JM, Nordvall G, Hjorth S, Unelius L, Johansson AM..  (1996)  11-substituted (R)-aporphines: synthesis, pharmacology, and modeling of D2A and 5-HT1A receptor interactions.,  39  (18): [PMID:8784448] [10.1021/jm960189i]

5. Zhang A, Zhang Y, Branfman AR, Baldessarini RJ, Neumeyer JL..  (2007)  Advances in development of dopaminergic aporphinoids.,  50  (2): [PMID:17228858] [10.1021/jm060959i]

6. Si YG, Gardner MP, Tarazi FI, Baldessarini RJ, Neumeyer JL..  (2008)  Synthesis and dopamine receptor affinities of N-alkyl-11-hydroxy-2-methoxynoraporphines: N-alkyl substituents determine D1 versus D2 receptor selectivity.,  51  (4): [PMID:18251489] [10.1021/jm701045j]

7. Si YG, Gardner MP, Tarazi FI, Baldessarini RJ, Neumeyer JL..  (2008)  Synthesis and binding studies of 2-O- and 11-O-substituted N-alkylnoraporphines.,  18  (14): [PMID:18585036] [10.1016/j.bmcl.2008.06.016]

8. Si YG, Choi YK, Gardner MP, Tarazi FI, Baldessarini RJ, Neumeyer JL..  (2009)  Synthesis and neuropharmacological evaluation of esters of R(-)-N-alkyl-11-hydroxy-2-methoxynoraporphines.,  19  (1): [PMID:19058967] [10.1016/j.bmcl.2008.11.025]

9. Liu Z, Chen X, Sun P, Yu L, Zhen X, Zhang A..  (2008)  N-Propylnoraporphin-11-O-yl carboxylic esters as potent dopamine D(2) and serotonin 5-HT(1A) receptor dual ligands.,  16  (18): [PMID:18783955] [10.1016/j.bmc.2008.08.056]

10. Liu Z, Zhang H, Ye N, Zhang J, Wu Q, Sun P, Li L, Zhen X, Zhang A..  (2010)  Synthesis of dihydrofuroaporphine derivatives: identification of a potent and selective serotonin 5-HT 1A receptor agonist.,  53  (3): [PMID:20041669] [10.1021/jm9015763]

11. Sromek AW, Si YG, Zhang T, George SR, Seeman P, Neumeyer JL..  (2011)  Synthesis and Evaluation of Fluorinated Aporphines: Potential Positron Emission Tomography Ligands for D2 Receptors,  2  (3): [PMID:21666830] [10.1021/ml1001689]

12. Zhang H, Ye N, Zhou S, Guo L, Zheng L, Liu Z, Gao B, Zhen X, Zhang A..  (2011)  Identification of N-propylnoraporphin-11-yl 5-(1,2-dithiolan-3-yl)pentanoate as a new anti-Parkinson's agent possessing a dopamine D2 and serotonin 5-HT1A dual-agonist profile.,  54  (13): [PMID:21591752] [10.1021/jm200347t]

Source

Source(1):

• Scientific Literature