Synthesis, characterization, and in vitro anticancer evaluation of 2-substituted 5-arylsulfonyl-1,3-oxazole-4-carbonitriles

Kachaeva, Maryna; Pilyo, Stepan; Zhirnov, Victor; Броварец, В. С.

doi:10.1007/s00044-018-2265-y

Cited by 20 publications

(19 citation statements)

References 10 publications

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“… The preparation of sulfanyl derivatives 7‐11 involves treatment of 2‐acylamino‐3,3‐dichloroacrylonitriles 1‐4 with arenethiols in the presence of triethylamine to obtain 2‐acylamino‐3,3‐bis (arylsulphanyl)acrylonitriles, which can be cyclized in the presence of silver carbonate to form 5‐arylsulphanyl‐1,3‐oxazole‐4‐carbonitriles 7‐11 . The latter were converted into the corresponding sulfonyl derivatives 12‐16 by oxidation with hydrogen peroxide …”

Section: Resultsmentioning

confidence: 99%

“…Compounds 12 , 14‐16 , 19 , and 20 satisfied the predetermined threshold inhibition criteria of the NCI‐60 One‐Dose Screening were tested against the panels of 60 cancer cell lines of NCI of the five‐dose assay for anticancer activity against each cancer cell line …”

Section: Resultsmentioning

confidence: 99%

“…The latter were converted into the corresponding sulfonyl derivatives 12-16 by oxidation with hydrogen peroxide. [46] 4-Cyano-1,3-oxazole-5-sulfonyl amides 19-22 have been synthesized according to the procedure [35] from sulfonyl chlorides 17 or 18 [47] by refluxing with appropriate amine and excess of triethylamine (Scheme 2).…”

Section: Chemistrymentioning

confidence: 99%

“…One-Dose Screening were tested against the panels of 60 cancer cell lines of NCI of the five-dose assay for anticancer activity against each cancer cell line. [46] Compound 12 showed GI 50 values ranging from 0.41μM (non-small cell lung cancer NCI-H522 cell line) to 37.3μM (CNS Cancer SNB-19 cell line), TGI-from 1.67μM (non-small cell lung cancer NCI-H522 cell line) to 75.9μM (CNS Cancer SF-395 cell line), and LC 50 -from 6.0μM (renal cancer RXF-393 cell line) to 83.9μM (nonsmall cell lung cancer A549/ATCC cell line). LC 50 for leukemia panel, EKVX, HOP-62, and NCI-H226 (lung cancer), SF-295 and SNB-19 (CNS cancer), NCI/ADR-RES and SK-OV-3 (ovarian cancer), HS-578T and T-47D (breast cancer) exceeded 100μM.…”

Section: -Arylsulfonylmentioning

confidence: 99%

“…General procedure for the synthesis of compounds 12, 14-16 [46] Solution of appropriate 5-arylsulfanyl-1,3-oxazole-4-carbonitrile 7-11 (0.01 mol) in glacial acetic acid (20 ml) was heated to reflux. Three portions of 30% H 2 O 2 of 2 ml each were added during 2 h. The mixture was kept at room temperature for 8 h. The residue was triturated with water to give a crude product which was separated, recrystallized, and dried at 70-80°C.…”

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Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Kachaeva

Hodyna

Obernikhina

et al. 2019

Journal of Heterocyclic Chem

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A series of new 1,3‐oxazole derivatives, containing in position 5 both donor and acceptor substituents were synthesized. These substances were considered as potentially active anticancer pharmacophores in the human tumor cell line panel derived from nine cancer types, including lung, colon, melanoma, renal, ovarian, brain, leukemia, breast, and prostate. Primary in vitro one‐dose anticancer screening was shown that compounds with acceptor substituents (such as –C(O)OMe, –CN) in the position 5 inhibit the growth of most cell lines, and compounds with donor substituents (such as –NHR, −SR) in the position 5 do not practically inhibit the growth of cancer cell lines. It can be assumed that the pharmacological activity of 1,3‐oxazole derivatives depends on donor/acceptor nature of the substituents in position 5. It was proposed to evaluate the donor/acceptor ability of 1,3‐oxazole derivatives using the special parameter φ0, which takes into account the relative position of the boundary levels (HOMO end LUMO). The quantum‐chemical modeling was performed; the special parameter φ0 for 1,3‐oxazole derivatives correlates with the experimental results. Quantum‐chemical calculations of the special parameter φ0 allow modeling the pharmacological activity of 1,3‐oxazole derivatives by introducing donor or acceptor substituents at position 2 or 5. This work may be useful for chemists to develop a target synthesis of potential biologically active compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: -Arylsulfonylmentioning

confidence: 99%

mentioning

confidence: 99%

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Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Kachaeva

Hodyna

Obernikhina

et al. 2019

Journal of Heterocyclic Chem

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Divergent Synthesis of C5‐Heteroatom Substituted Oxazoles

2022

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C,O‐Chelated organotin(IV) derivatives as potential anticancer agents: Synthesis, characterization, and cytotoxic activity

Someşan

Vieriu

Crăciun

et al. 2022

Applied Organom Chemis

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Organotin(IV) chemistry is nowadays in a continuous expansion due to the biological and medicinal potential found for some of these species. Within this study, the cytotoxic activity of several organotin(IV) compounds was investigated on two lung cancer cell lines (H522 and SK‐MES‐1) and on a normal lung cell line in order to have an overview of the toxicity and the selectivity of these derivatives. Moreover, the synthetic protocols, as well as the structural particularities of the novel organotin(IV) species, are also discussed. Hydrolysis of [2‐{(CH2O)2CR}C6H4]2SnPh2 [R = H (1), Me (2)] with p‐toluenesulfonic acid as a proton source afford the expected derivatives [2‐(O═CR)C6H4]2SnPh2 [R = H (3), Me (4)]. When hydrochloric acid is used in these reactions, a chlorine‐phenyl exchange took place in addition to the removal of the acetal fragments and the following products [2‐(O═CR)C6H4]2SnPhCl [R = H (5), Me (6)] were isolated. Treatment of 5 with 2 equiv of 3‐aminomethylpyridine in neat affords the imino(aryl)tin compound 2‐(3′‐PyCH2N═CH)C6H4]2SnPhCl (7). The reaction between 6 and potassium nicotinate allows the isolation of the organotin(IV) carboxylate [2‐{O═C (CH3)}C6H4]2SnPh[O(O)CC5H4N‐3] (8). Compounds 1–8 were characterized by multinuclear NMR spectroscopy in solution, mass spectrometry, and IR spectroscopy, and their molecular structures were confirmed by X‐ray diffraction analysis. Compounds 1–8 were investigated for their antitumoral effects on Homo sapiens lung cancer cell lines (H522 and SK‐MES‐1) and on a normal bronchial epithelial cell line, BEAS‐2B.

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Synthesis, characterization, and in vitro anticancer evaluation of 2-substituted 5-arylsulfonyl-1,3-oxazole-4-carbonitriles

Cited by 20 publications

References 10 publications

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Divergent Synthesis of C5‐Heteroatom Substituted Oxazoles

C,O‐Chelated organotin(IV) derivatives as potential anticancer agents: Synthesis, characterization, and cytotoxic activity

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