2-[7-(Benzyloxy)-10-methyl-5,10-dihydropyrrolo[1,2-b]isoquinolin-10-yl]acetonitrile

ID: ALA4871294

PubChem CID: 164620306

Max Phase: Preclinical

Molecular Formula: C22H20N2O

Molecular Weight: 328.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(CC#N)c2ccc(OCc3ccccc3)cc2Cn2cccc21

Standard InChI:  InChI=1S/C22H20N2O/c1-22(11-12-23)20-10-9-19(25-16-17-6-3-2-4-7-17)14-18(20)15-24-13-5-8-21(22)24/h2-10,13-14H,11,15-16H2,1H3

Standard InChI Key:  RORQQJFZIBMPGR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   10.4832  -23.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8959  -24.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3043  -23.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7772  -24.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7761  -25.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4841  -26.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4823  -24.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1909  -24.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1943  -25.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9067  -26.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1215  -23.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6169  -24.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6186  -25.6432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4060  -25.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8910  -25.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4033  -24.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9387  -23.6829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0680  -26.0528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3606  -25.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6526  -26.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9460  -25.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2384  -26.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373  -26.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9497  -27.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6543  -26.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8  2  1  0
  9 10  1  0
 10 13  1  0
 12  2  1  0
  3 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  2  0
 11 17  3  0
  5 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4871294

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 328.42

Molecular Weight (Monoisotopic): 328.1576

AlogP: 4.65

#Rotatable Bonds: 4

Polar Surface Area: 37.95

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.38

CX LogD: 4.38

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -0.26

References

1. Barbolla I, Hernández-Suárez L, Quevedo-Tumailli V, Nocedo-Mena D, Arrasate S, Dea-Ayuela MA, González-Díaz H, Sotomayor N, Lete E..  (2021)  Palladium-mediated synthesis and biological evaluation of C-10b substituted Dihydropyrrolo[1,2-b]isoquinolines as antileishmanial agents.,  220  [PMID:33901901] [10.1016/j.ejmech.2021.113458]

Source

Source(1):

• Scientific Literature