5-(4-Piperidin-1-ylmethyl-phenyl)-2,3-dihydro-imidazo[2,1-a]isoquinoline

ID: ALA312225

Cas Number: 115621-81-3

PubChem CID: 9801987

Max Phase: Preclinical

Molecular Formula: C23H25N3

Molecular Weight: 343.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(1): GNF-Pf-429

Canonical SMILES:  C1=C(c2ccc(CN3CCCCC3)cc2)N2CCN=C2c2ccccc21

Standard InChI:  InChI=1S/C23H25N3/c1-4-13-25(14-5-1)17-18-8-10-19(11-9-18)22-16-20-6-2-3-7-21(20)23-24-12-15-26(22)23/h2-3,6-11,16H,1,4-5,12-15,17H2

Standard InChI Key:  WJUGGKGTCAVATA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   -0.3626   -1.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973   -1.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526   -0.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5772   -0.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6219   -1.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2646   -2.5438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0118   -1.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180    0.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104    2.2937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858    2.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5066    0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4386   -1.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991   -2.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5512    1.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9412    0.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2734    1.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565   -2.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364   -1.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004    1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2450    2.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8811   -2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696    2.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250    1.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2710   -1.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596    2.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  3  4  2  0
  5  2  1  0
  2  6  2  0
  7  5  1  0
  8  3  1  0
  9 10  1  0
 10 15  1  0
 11  8  1  0
 12  8  2  0
 13  1  1  0
 14 13  1  0
 15 16  1  0
 11 16  2  0
 17 12  1  0
 18  5  2  0
  7 19  2  0
 20  9  1  0
 21  9  1  0
 22 18  1  0
 23 21  1  0
 24 20  1  0
 25 19  1  0
 26 23  1  0
 14  6  1  0
  7  4  1  0
 15 17  2  0
 25 22  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA312225

   SDZ-62-434 free

2. Alternative Forms:

   

   ALA312225

   5-(4-(Piperidin-1-ylmethyl)phenyl)-2,3-dihydroimidazo[2,1-a]isoquinoline hydrochloride

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: 343.47

Molecular Weight (Monoisotopic): 343.2048

AlogP: 4.25

#Rotatable Bonds: 3

Polar Surface Area: 18.84

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.12

CX LogP: 3.85

CX LogD: 1.95

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.83

Np Likeness Score: -0.61

References

1. Houlihan WJ, Munder PG, Handley DA, Cheon SH, Parrino VA..  (1995)  Antitumor activity of 5-aryl-2,3-dihydroimidazo[2,1-a]isoquinolines.,  38  (2): [PMID:7830265] [10.1021/jm00002a004]

2. Laura Riva, Shuofeng Yuan, Xin Yin, Laura Martin-Sancho, Naoko Matsunaga, Sebastian Burgstaller-Muehlbacher, Lars Pache, Paul P. De Jesus, Mitchell V. Hull, Max Chang, Jasper Fuk-Woo Chan, Jianli Cao, Vincent Kwok-Man Poon, Kristina Herbert, Tu-Trinh Nguyen, Yuan Pu, Courtney Nguyen, Andrey Rubanov, Luis Martinez-Sobrido, Wen-Chun Liu, Lisa Miorin, Kris M. White, Jeffrey R. Johnson, Christopher Benner, Ren Sun, Peter G. Schultz, Andrew Su, Adolfo Garcia-Sastre, Arnab K. Chatterjee, Kwok-Yung Yuen, Sumit K. Chanda.  (2020)  A Large-scale Drug Repositioning Survey for SARS-CoV-2 Antivirals,  [10.1101/2020.04.16.044016]

Source

Source(2):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21