Synthesis, characterization and evaluation of cytotoxic and antioxidant activities of dihydropyrimidone substituted pyrrole derivatives

Khalilpour, Asieh; Asghari, Sakineh

doi:10.1007/s00044-017-2041-4

Cited by 17 publications

(10 citation statements)

References 32 publications

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“…Thirteen DHPMs derivatives were selected with good activity against anticancer. All the structures are attached in Table S3 [ 20 , 35 , 36 ]. The final pharmacophore models were achieved with follow operations, including a population size value of 20, a maximum generation value of 100 and the value of molecular required hitting was 8.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Anticancer Activities Evaluation of Compounds Derived from 3,4-Dihydropyrimidin-2(1H)-one

Liu

Zhang

et al. 2019

Molecules

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3,4-dihydropyrimidin-2(1H)-one compounds (DHPMs) possess extensive biological activities and are mainly prepared via Biginelli reaction and N-alkylation. In the present study, selective alkylation of N1 was investigated by using tetrabutylammonium hydroxide. In vitro cytotoxicity study on all synthesized compounds demonstrated that introduction of the aryl chain in the R3 as well as the low electron-donating group in the R1 of DHPMs contributed to the anti-proliferative potency. A larger value of the partition coefficient (Log P) and suitable polar surface area (PSA) values were both found to be important in order to maintain the antitumor activity. The results from in vivo study indicated the great potential of compound 3d to serve as a lead compound for novel anti-tumor drugs to treat glioma. Pharmacophore study regarding the structure-activity relations of DHPMs were also conducted. Our results here could provide a guide for the design of novel bioactive 3,4-dihydropyrimidin-2(1H)-one compounds.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Anticancer Activities Evaluation of Compounds Derived from 3,4-Dihydropyrimidin-2(1H)-one

Liu

Zhang

et al. 2019

Molecules

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“…These products demonstrated moderate to good cytotoxicity against HeLa cancer cell lines (Scheme 5). [14] Nikomanesh, et al in 2017 demonstrated a simple and efficient method for the synthesis of polyfunctionalized pyrroles 18 through four-component reaction of PPh 3 15, ammonium acetate 16, dialkylacetylene dicarboxylate 1 and arylglyoxals 17 in CH 3 CN at room temperature. The corresponding products 18 were obtained in excellent yields (Scheme 6).…”

Section: Pyrrolesmentioning

confidence: 99%

“…These products demonstrated moderate to good cytotoxicity against HeLa cancer cell lines (Scheme 5). [14] …”

Section: Synthesis Of Five‐membered Rings With One Heteroatom Includingmentioning

confidence: 99%

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

2022

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Dialkyl acetylenedicarboxylates (DAAD) are the class of acetylenic compounds that are broadly used in organic synthesis in a noticeable quantity. Their wide application has made them an important moiety in heterocyclic compounds and drug discovery programs. Dialkyl acetylenedicarboxylate is a di-ester in which the ester groups are conjugated with a carbon-carbon triple bond. As such, the molecule is very electrophilic, and is broadly used as a dienophile in various cycloaddition reactions, for example the Diels-Alder reaction. In addition, it is a strong Michael acceptor. Due the importance of dialkyl acetylenedicarboxylate in organic synthesis, we are trying to show the applications of this compound in the synthesis of different heterocycles using multicomponent reactions. In this review, we show recent advances (2016)(2017)(2018)(2019)(2020)(2021)(2022) for the synthesis of various heterocycles that have different ring sizes (five, six and seven membered, Spiro and fused heterocycles), using DAAD via multicomponent reactions.

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“…Due to the fact of its aromatic structure, pyrrole can react with various electrophiles, leading to a wide variety of compounds with biological potential, some of them having a crucial role in life processes. Numerous pyrrole derivatives have been reported to have various biological activities [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ], especially anticancer properties [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

New Pyrrole Derivatives as Promising Biological Agents: Design, Synthesis, Characterization, In Silico, and Cytotoxicity Evaluation

Ivan

Bărbuceanu

Hotnog

et al. 2022

IJMS

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The current study describes the synthesis, physicochemical characterization and cytotoxicity evaluation of a new series of pyrrole derivatives in order to identify new bioactive molecules. The new pyrroles were obtained by reaction of benzimidazolium bromide derivatives with asymmetrical acetylenes in 1,2-epoxybutane under reflux through the Huisgen [3 + 2] cycloaddition of several ylide intermediates to the corresponding dipolarophiles. The intermediates salts were obtained from corresponding benzimidazole with bromoacetonitrile. The structures of the newly synthesized compounds were confirmed by elemental analysis, spectral techniques (i.e., IR, 1H-NMR and 13C-NMR) and single-crystal X-ray analysis. The cytotoxicity of the synthesized compounds was evaluated on plant cells (i.e., Triticum aestivum L.) and animal cells using aquatic crustaceans (i.e., Artemia franciscana Kellogg and Daphnia magna Straus). The potential antitumor activity of several of the pyrrole derivatives was studied by performing in vitro cytotoxicity assays on human adenocarcinoma-derived cell lines (i.e., LoVo (colon), MCF-7 (breast), and SK-OV-3 (ovary)) and normal human umbilical vein endothelial cells (HUVECs). The obtained results of the cytotoxicity assessment indicated that the tested compounds had nontoxic activity on Triticum aestivum L., while on Artemia franciscana Kellogg nauplii, only compounds 2c and 4c had moderate toxicity. On Daphnia magna, 4b and 4c showed high toxicity; 2a, 2b, and 2c moderate to high toxicity; only 4a and 4d were nontoxic. The compound-mediated cytotoxicity assays showed that several pyrrole compounds demonstrated dose- and time-dependent cytotoxic activity against all tested tumor cell lines, the highest antitumor properties being achieved by 4a and its homologue 4d, especially against LoVo colon cells.

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Synthesis, characterization and evaluation of cytotoxic and antioxidant activities of dihydropyrimidone substituted pyrrole derivatives

Cited by 17 publications

References 32 publications

Synthesis, Characterization, and Anticancer Activities Evaluation of Compounds Derived from 3,4-Dihydropyrimidin-2(1H)-one

Synthesis, Characterization, and Anticancer Activities Evaluation of Compounds Derived from 3,4-Dihydropyrimidin-2(1H)-one

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

New Pyrrole Derivatives as Promising Biological Agents: Design, Synthesis, Characterization, In Silico, and Cytotoxicity Evaluation

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