(2E)-1-(2,5-dimethoxyphenyl)-3-(quinoxalin-6-yl)prop-2-en-1-one

ID: ALA1938885

PubChem CID: 57328005

Max Phase: Preclinical

Molecular Formula: C19H16N2O3

Molecular Weight: 320.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(C(=O)/C=C/c2ccc3nccnc3c2)c1

Standard InChI:  InChI=1S/C19H16N2O3/c1-23-14-5-8-19(24-2)15(12-14)18(22)7-4-13-3-6-16-17(11-13)21-10-9-20-16/h3-12H,1-2H3/b7-4+

Standard InChI Key:  BTPRTQBGYFRKOB-QPJJXVBHSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -5.3223   -5.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3234   -5.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6086   -6.2610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6104   -4.6080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950   -5.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -5.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1790   -6.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639   -5.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4687   -5.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1846   -4.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7568   -4.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398   -5.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3278   -4.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -4.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3329   -3.7597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3897   -5.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1059   -6.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -5.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -4.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0944   -4.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0858   -3.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -7.0508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3983   -7.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7960   -3.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 11 12  2  0
  5  6  1  0
 12 13  1  0
  3  6  2  0
 13 14  1  0
  6  7  1  0
 13 15  2  0
  1  2  2  0
 14 16  2  0
  7  8  2  0
 16 17  1  0
  5  4  2  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  4  1  1  0
 19 20  2  0
 20 14  1  0
  9 10  2  0
 20 21  1  0
 10  5  1  0
 17 22  1  0
 22 23  1  0
  9 11  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1938885

   (E)-1-(2,5-dimethoxyphenyl)-3-quinoxalin-6-ylprop-2-en-1-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: 320.35

Molecular Weight (Monoisotopic): 320.1161

AlogP: 3.54

#Rotatable Bonds: 5

Polar Surface Area: 61.31

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.72

CX LogP: 2.90

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.53

Np Likeness Score: -0.38

References

1. Mielcke TR, Mascarello A, Filippi-Chiela E, Zanin RF, Lenz G, Leal PC, Chiaradia LD, Yunes RA, Nunes RJ, Battastini AM, Morrone FB, Campos MM..  (2012)  Activity of novel quinoxaline-derived chalcones on in vitro glioma cell proliferation.,  48  [PMID:22209415] [10.1016/j.ejmech.2011.12.023]

2. Kumar Sahoo S, Maddipatla S, Nageswara Rao Gajula S, Naiyaz Ahmad M, Kaul G, Nanduri S, Sonti R, Dasgupta A, Chopra S, Madhavi Yaddanapudi V..  (2022)  Identification of nitrofuranylchalcone tethered benzoxazole-2-amines as potent inhibitors of drug resistant Mycobacterium tuberculosis demonstrating bactericidal efficacy.,  64  [PMID:35487101] [10.1016/j.bmc.2022.116777]

Source

Source(1):

• Scientific Literature