(2R,2'S)-2-(1'-Methyl-2'-pyrrolidinyl)-7-hydroxy-1,4-benzodioxane

ID: ALA1917231

PubChem CID: 56643499

Max Phase: Preclinical

Molecular Formula: C13H17NO3

Molecular Weight: 235.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCC[C@H]1[C@@H]1COc2ccc(O)cc2O1

Standard InChI:  InChI=1S/C13H17NO3/c1-14-6-2-3-10(14)13-8-16-11-5-4-9(15)7-12(11)17-13/h4-5,7,10,13,15H,2-3,6,8H2,1H3/t10-,13-/m0/s1

Standard InChI Key:  OHYANMWFAIMESB-GWCFXTLKSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   12.7843   -6.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7843   -7.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4964   -7.9464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4964   -6.2963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2085   -6.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2069   -7.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9178   -7.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6310   -7.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6286   -6.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9169   -6.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0702   -6.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0648   -5.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2786   -5.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7979   -5.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2873   -6.5592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0374   -7.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3417   -6.2954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1967   -7.2964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6510   -5.7087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  9 10  2  0
 10  5  1  0
 11 12  1  0
  1  2  1  0
  5  6  2  0
  1  4  1  0
  6  7  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  1 11  1  0
  2  3  1  0
 15 16  1  0
  7  8  2  0
  9 17  1  0
  3  6  1  0
  1 18  1  6
  8  9  1  0
 11 19  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1917231

   (3R)-3-[(2S)-1-methylpyrrolidin-2-yl]-2,3-dihydro-1,4-benzodioxin-6-ol

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: 235.28

Molecular Weight (Monoisotopic): 235.1208

AlogP: 1.63

#Rotatable Bonds: 1

Polar Surface Area: 41.93

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: 8.38

CX LogP: 1.58

CX LogD: 0.69

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.80

Np Likeness Score: 1.29

References

1. Bolchi C, Gotti C, Binda M, Fumagalli L, Pucci L, Pistillo F, Vistoli G, Valoti E, Pallavicini M..  (2011)  Unichiral 2-(2'-pyrrolidinyl)-1,4-benzodioxanes: the 2R,2'S diastereomer of the N-methyl-7-hydroxy analogue is a potent α4β2- and α6β2-nicotinic acetylcholine receptor partial agonist.,  54  (21): [PMID:21942635] [10.1021/jm200937t]

2. Bolchi C, Valoti E, Gotti C, Fasoli F, Ruggeri P, Fumagalli L, Binda M, Mucchietto V, Sciaccaluga M, Budriesi R, Fucile S, Pallavicini M..  (2015)  Chemistry and Pharmacology of a Series of Unichiral Analogues of 2-(2-Pyrrolidinyl)-1,4-benzodioxane, Prolinol Phenyl Ether, and Prolinol 3-Pyridyl Ether Designed as α4β2-Nicotinic Acetylcholine Receptor Agonists.,  58  (16): [PMID:26225816] [10.1021/acs.jmedchem.5b00904]

3. Bavo F,Pallavicini M,Gotti C,Appiani R,Moretti M,Colombo SF,Pucci S,Viani P,Budriesi R,Renzi M,Fucile S,Bolchi C.  (2020)  Modifications at C(5) of 2-(2-Pyrrolidinyl)-Substituted 1,4-Benzodioxane Elicit Potent α4β2 Nicotinic Acetylcholine Receptor Partial Agonism with High Selectivity over the α3β4 Subtype.,  63  (24): [PMID:33325696] [10.1021/acs.jmedchem.0c01150]

4. Appiani R, Pallavicini M, Hamouda AK, Bolchi C..  (2022)  Pyrrolidinyl benzofurans and benzodioxanes: Selective α4β2 nicotinic acetylcholine receptor ligands with different activity profiles at the two receptor stoichiometries.,  65  [PMID:35346843] [10.1016/j.bmcl.2022.128701]

Source

Source(1):

• Scientific Literature