4'-(p-toluenesulfonamide)-3,4-dihydroxy chalcone

ID: ALA199829

Chembl Id: CHEMBL199829

PubChem CID: 11668680

Max Phase: Preclinical

Molecular Formula: C22H19NO5S

Molecular Weight: 409.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)Nc2ccc(C(=O)/C=C/c3ccc(O)c(O)c3)cc2)cc1

Standard InChI:  InChI=1S/C22H19NO5S/c1-15-2-10-19(11-3-15)29(27,28)23-18-8-6-17(7-9-18)20(24)12-4-16-5-13-21(25)22(26)14-16/h2-14,23,25-26H,1H3/b12-4+

Standard InChI Key:  XCEAUELSIXURQB-UUILKARUSA-N

Alternative Forms

1. Parent:

   

   ALA199829

   Sulfonamide chalcone, 5

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: 409.46

Molecular Weight (Monoisotopic): 409.0984

AlogP: 4.10

#Rotatable Bonds: 6

Polar Surface Area: 103.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.78

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 4.15

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.32

Np Likeness Score: -0.57

References

1. Seo WD, Kim JH, Kang JE, Ryu HW, Curtis-Long MJ, Lee HS, Yang MS, Park KH..  (2005)  Sulfonamide chalcone as a new class of alpha-glucosidase inhibitors.,  15  (24): [PMID:16202584] [10.1016/j.bmcl.2005.08.087]

2. Campo VL, Sesti-Costa R, Carneiro ZA, Silva JS, Schenkman S, Carvalho I..  (2012)  Design, synthesis and the effect of 1,2,3-triazole sialylmimetic neoglycoconjugates on Trypanosoma cruzi and its cell surface trans-sialidase.,  20  (1): [PMID:22154559] [10.1016/j.bmc.2011.11.022]

3. Mahapatra DK, Bharti SK, Asati V..  (2015)  Chalcone scaffolds as anti-infective agents: structural and molecular target perspectives.,  101  [PMID:26188621] [10.1016/j.ejmech.2015.06.052]

4. Chen Z, Marcé P, Resende R, Alzari PM, Frasch AC, van den Elsen JMH, Crennell SJ, Watts AG..  (2018)  The synthesis and kinetic evaluation of aryl α-aminophosphonates as novel inhibitors of T. cruzi trans-sialidase.,  158  [PMID:30199703] [10.1016/j.ejmech.2018.08.089]

5.  (2013)  Method for screening anti-cancer compounds inhibiting function of TM4SF5 and anti-cancer composition containing chalcone compounds, 

6. Luthra T,Banothu V,Adepally U,Kumar K,M S,Chakrabarti S,Maddi SR,Sen S.  (2020)  Discovery of novel pyrido-pyrrolidine hybrid compounds as alpha-glucosidase inhibitors and alternative agent for control of type 1 diabetes.,  188  [PMID:31927314] [10.1016/j.ejmech.2020.112034]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data