2-Allyl-7-chloro-3-thioxo-2,3-dihydro-imidazo[1,5-a]indol-1-one

ID: ALA346212

PubChem CID: 44367100

Max Phase: Preclinical

Molecular Formula: C13H9ClN2OS

Molecular Weight: 276.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCN1C(=O)c2cc3cc(Cl)ccc3n2C1=S

Standard InChI:  InChI=1S/C13H9ClN2OS/c1-2-5-15-12(17)11-7-8-6-9(14)3-4-10(8)16(11)13(15)18/h2-4,6-7H,1,5H2

Standard InChI Key:  NTGAUBPFKPWHRM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    5.7542   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750    0.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -0.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542    0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4875    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4875    1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -1.2042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542    1.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667    1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542    1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542    0.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417    1.6625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  4  2  0
  7  2  1  0
  8  7  1  0
  9  1  2  0
 10  7  2  0
 11  5  2  0
 12  8  2  0
 13  3  1  0
 14 13  1  0
 15 14  2  0
 16 17  2  0
 17 10  1  0
 18 16  1  0
  4  5  1  0
  8  6  1  0
 16 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA346212

   6-Chloro-2-prop-2-enyl-1-sulfanylideneimidazo[1,5-a]indol-3-one

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: 276.75

Molecular Weight (Monoisotopic): 276.0124

AlogP: 3.07

#Rotatable Bonds: 2

Polar Surface Area: 25.24

Molecular Species: ┄

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.30

CX LogD: 3.30

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.62

Np Likeness Score: -1.38

References

1. Voss ME, Carter PH, Tebben AJ, Scherle PA, Brown GD, Thompson LA, Xu M, Lo YC, Yang G, Liu RQ, Strzemienski P, Everlof JG, Trzaskos JM, Decicco CP..  (2003)  Both 5-arylidene-2-thioxodihydropyrimidine-4,6(1H,5H)-diones and 3-thioxo-2,3-dihydro-1H-imidazo[1,5-a]indol-1-ones are light-dependent tumor necrosis factor-alpha antagonists.,  13  (3): [PMID:12565966] [10.1016/s0960-894x(02)00941-1]

Source

Source(1):

• Scientific Literature