2-(6-chloro-2-methoxyacridin-9-ylamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

ID: ALA4465089

PubChem CID: 155531010

Max Phase: Preclinical

Molecular Formula: C22H16ClN3OS

Molecular Weight: 405.91

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2nc3cc(Cl)ccc3c(Nc3sc4c(c3C#N)CCC4)c2c1

Standard InChI:  InChI=1S/C22H16ClN3OS/c1-27-13-6-8-18-16(10-13)21(15-7-5-12(23)9-19(15)25-18)26-22-17(11-24)14-3-2-4-20(14)28-22/h5-10H,2-4H2,1H3,(H,25,26)

Standard InChI Key:  LHKPZIDFFKVKSB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    4.8852  -18.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8841  -19.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5921  -20.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5903  -18.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2990  -18.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2997  -19.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0082  -20.1912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0027  -18.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7118  -18.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7154  -19.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4277  -20.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1369  -19.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1293  -18.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4164  -18.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1760  -20.1963    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.8331  -18.5312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5447  -18.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9983  -17.7377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2885  -17.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1962  -16.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412  -17.6725    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7976  -15.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4010  -15.4229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9911  -17.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3953  -16.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419  -15.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955  -16.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1878  -16.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  2 15  1  0
 13 16  1  0
 16 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  2  0
 20 25  1  0
 24 21  1  0
 21 19  1  0
 22 23  3  0
 20 22  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4465089

   ---

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: 405.91

Molecular Weight (Monoisotopic): 405.0703

AlogP: 6.22

#Rotatable Bonds: 3

Polar Surface Area: 57.94

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.96

CX Basic pKa: 7.51

CX LogP: 6.34

CX LogD: 5.99

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -1.69

References

1. Prasher P, Sharma M..  (2018)  Medicinal chemistry of acridine and its analogues.,  9  (10): [PMID:30429967] [10.1039/C8MD00384J]

2. Pathania S, Narang RK, Rawal RK..  (2019)  Role of sulphur-heterocycles in medicinal chemistry: An update.,  180  [PMID:31330449] [10.1016/j.ejmech.2019.07.043]

3. Duvauchelle V, Meffre P, Benfodda Z..  (2022)  Recent contribution of medicinally active 2-aminothiophenes: A privileged scaffold for drug discovery.,  238  [PMID:35696863] [10.1016/j.ejmech.2022.114502]

Source

Source(1):

• Scientific Literature