7,8-dimethoxy-10-(4-nitrobenzyl)-10-(trifluoromethyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline

ID: ALA4870516

PubChem CID: 164621120

Max Phase: Preclinical

Molecular Formula: C22H19F3N2O4

Molecular Weight: 432.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(Cc1ccc([N+](=O)[O-])cc1)(C(F)(F)F)c1cccn1C2

Standard InChI:  InChI=1S/C22H19F3N2O4/c1-30-18-10-15-13-26-9-3-4-20(26)21(22(23,24)25,17(15)11-19(18)31-2)12-14-5-7-16(8-6-14)27(28)29/h3-11H,12-13H2,1-2H3

Standard InChI Key:  FLTMIGGNHIHYGT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.2439  -11.8022    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.9589  -11.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2486  -10.9793    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.3747  -12.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7861  -11.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2407  -12.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2395  -13.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9527  -13.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9509  -12.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6646  -12.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6680  -13.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3856  -13.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6092  -11.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0216  -12.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8439  -12.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2542  -11.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8361  -10.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0150  -10.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1009  -12.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1026  -13.3618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8958  -13.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3843  -12.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8930  -12.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5277  -12.1266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5263  -13.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5275  -11.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5256  -14.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0804  -11.3823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4889  -10.6676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4950  -12.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3684  -10.6807    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  2  1  0
  5  4  1  0
  6  7  2  0
  7  8  1  0
  8 11  2  0
 10  9  2  0
  9  6  1  0
 10 11  1  0
 10  4  1  0
 11 12  1  0
 12 20  1  0
 19  4  1  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  2  0
  6 24  1  0
  7 25  1  0
 24 26  1  0
 25 27  1  0
 28 29  2  0
 28 30  1  0
 16 28  1  0
  2 31  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4870516

   ---

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: 432.40

Molecular Weight (Monoisotopic): 432.1297

AlogP: 4.87

#Rotatable Bonds: 5

Polar Surface Area: 66.53

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.19

CX LogD: 5.19

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -0.44

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