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[ CAS No. 22720-75-8 ] {[proInfo.proName]}

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Chemical Structure| 22720-75-8
Chemical Structure| 22720-75-8
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Product Citations

Product Citations

Kosmalski, Tomasz ; Hetmann, Anna ; Studzinska, Renata , et al. DOI: PubMed ID:

Abstract: Chemotherapy is one of the most commonly used methods of cancer disease treatment. Due to the acquisition of drug resistance and the possibility of cancer recurrence, there is an urgent need to search for new mols. that would be more effective in destroying cancer cells. In this study, 1-(benzofuran-2-yl)ethan-1-one oxime and 26 oxime ethers containing heterocyclic, alicyclic or aromatic moiety were screened for their cytotoxicity against HeLa cancer cell line. The most promising derivatives with potential antitumor activity were 2-(cyclohexylideneaminoxy)acetic acid (18) and (E)-acetophenone O-2-morpholinoethyl oxime (22), which reduced the viability of HeLa cells below 20% of control at concentrations of 100-250 μg/mL. Some oxime ethers, namely thiazole and benzothiophene derivatives (24-27), also reduced HeLa cell viability at similar concentrations but with lower efficiency. Further cytotoxicity evaluation confirmed the specific toxicity of (E)-acetophenone O-2-morpholinoethyl oxime (22) against A-549, Caco-2, and HeLa cancer cells, with an EC50 around 7 μg/mL (30 μM). The most potent and specific compound was (E)-1-(benzothiophene-2-yl)ethanone O-4-methoxybenzyl oxime (27), which was selective for Caco-2 (with EC50 116 μg/mL) and HeLa (with EC50 28 μg/mL) cells. Considering the bioavailability parameters, the tested derivatives meet the criteria for good absorption and permeation. The presented results allow us to conclude that oxime ethers deserve more scientific attention and further research on their chemotherapeutic activity.

Keywords: anti-cancer therapy ; benzofuran derivatives ; cytotoxicity ; human cancer cells ; oxime ethers ; thiophene derivatives

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Product Details of [ 22720-75-8 ]

CAS No. :22720-75-8 MDL No. :MFCD00090217
Formula : C10H8OS Boiling Point : No data available
Linear Structure Formula :- InChI Key :SGSGCQGCVKWRNM-UHFFFAOYSA-N
M.W : 176.24 Pubchem ID :89805
Synonyms :

Calculated chemistry of [ 22720-75-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.02
TPSA : 45.31 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 3.1
Log Po/w (MLOGP) : 2.11
Log Po/w (SILICOS-IT) : 3.96
Consensus Log Po/w : 2.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.29
Solubility : 0.0911 mg/ml ; 0.000517 mol/l
Class : Soluble
Log S (Ali) : -3.57
Solubility : 0.047 mg/ml ; 0.000267 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.67
Solubility : 0.0372 mg/ml ; 0.000211 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 22720-75-8 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302 Packing Group:
GHS Pictogram:
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