Synthesis and biological activity of 1,5-diaryl-3-arylamino-4-carboxymethyl-2,5-dihydro-2-pyrrolones and 1,5-diaryl-4-carboxymethyltetrahydropyrrole-2, 3-diones

Гейн, В. Л.; Попов, А. В.; Kolla, Venkatadri; Попова, Н. А.; Potemkin, K. D.

doi:10.1007/bf00819965

Cited by 31 publications

(9 citation statements)

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“…Besides, 3-amino 1,5-dihydro-2 H -pyrrol-2-ones IV contain the enamine moiety in their structure, and therefore, they are excellent synthetic tools in organic synthesis and have been successfully used as key intermediates for the synthesis of Amaryllidaceae and Sceletium alkaloids . Moreover, γ-lactam derivatives IV can be seen as cyclic α-dehydro α-amino acids, and such skeleton is known to be present in many bioactive compounds as antimicrobials with antibiofilm activity, caspase-3 inhibitors, and analgesics or antipyretics, and it is also the basic structure of 1,2-dithiole annulated antibiotics V …”

Section: Introductionmentioning

confidence: 99%

Brönsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and Fluorine-Derived γ-Lactam Derivatives

et al. 2020

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A Brönsted acid multicomponent reaction between pyruvate derivatives, amines, and aldehydes for the preparation of phosphorus and fluorine substituted γ-lactam derivatives is presented. Depending on the substitution in the resulting 1,5-dihydro-2H-pyrrol-2-one substrates, the reaction provides enol- or enamine-derived γ-lactams. Some enantioselective examples of this reaction are also reported using chiral phosphoric acids as organocatalysts. Moreover, several synthetic applications of γ-lactam derivatives are presented including some examples of highly diastereoselective transformations.

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Section: Introductionmentioning

confidence: 99%

Brönsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and Fluorine-Derived γ-Lactam Derivatives

et al. 2020

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“…Within this family of compounds, the structure of their 3-amino substituted derivatives III (Figure 1) contains the enamine moiety and, in addition to their obvious applications as synthetic intermediates in organic synthesis [14,15], their skeleton is also present in many new bioactive ingredients such as antimicrobials with anti-biofilm activity, caspase-3 inhibitors, antipyretics, or analgesics [16,17,18,19,20]. Moreover, these cyclic α-dehydro α,β-diamino acid derivatives contain the essential structure of dithiopyrrolone antibiotics IV (Figure 1) [21] and are key intermediates for the synthesis of Amaryllidaceae and Sceletium alkaloids [22,23].…”

Section: Introductionmentioning

confidence: 99%

A Brønsted Acid-Catalyzed Multicomponent Reaction for the Synthesis of Highly Functionalized γ-Lactam Derivatives

et al. 2019

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Brønsted acids catalyze a multicomponent reaction of benzaldehyde with amines and diethyl acetylenedicarboxylate to afford highly functionalized γ-lactam derivatives. The reaction consists of a Mannich reaction of an enamine to an imine, both generated in situ, promoted by a phosphoric acid catalyst and a subsequent intramolecular cyclization. The hydrolysis of the cyclic enamine substrate can provide enol derivatives and, moreover, a second attack of the amine on the carboxylate can afford amide derivatives. An optimization of the reaction conditions is presented in order to obtain selectively cyclic enamines that can afford the enol species after selective hydrolysis.

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“…These multicomponent protocols are considered essential tools in diversity-oriented synthesis [ 34 , 35 ] due to the high degree of molecular diversity achieved and, accordingly, they have become a preferential methodology in the field of medicinal chemistry [ 36 , 37 ]. 3-Amino 3-pyrrolin-2-ones can be seen as cyclic α-dehydro α-amino acids, and such skeletons are known to be present in many bioactive molecules, such as antimicrobials with anti-biofilm activity, caspase-3 inhibitors, analgesics, and antipyretics [ 38 , 39 , 40 , 41 , 42 ]. They also represent the basic structure of dithiopyrrolone antibiotics [ 43 ].…”

Section: Introductionmentioning

confidence: 99%

Multicomponent Synthesis of Unsaturated γ-Lactam Derivatives. Applications as Antiproliferative Agents through the Bioisosterism Approach: Carbonyl vs. Phosphoryl Group

et al. 2022

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We report efficient synthetic methodologies for the preparation of 3-amino and 3-hydroxy 3-pyrrolin-2-ones (unsaturated γ-lactams) through a multicomponent reaction of amines, aldehydes and acetylene or pyruvate derivatives. The densely substituted γ-lactam substrates show in vitro cytotoxicity, inhibiting the growth of the carcinoma human tumor cell lines RKO (human colon epithelial carcinoma), SKOV3 (human ovarian carcinoma) and A549 (carcinomic human alveolar basal epithelial cell). In view of the possibilities for the diversity of the substituents that offer a multicomponent, synthetic methodology, an extensive structure–activity profile is presented. In addition, the bioisosteric replacement of the flat ester group by a tetrahedral phosphonate or phosphine oxide moiety in γ-lactam substrates leads to increased growth inhibition activity. Cell morphology analysis and flow cytometry assays indicate that the main pathway by which our compounds induce cytotoxicity is based on the activation of the intracellular apoptotic mechanism.

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Synthesis and biological activity of 1,5-diaryl-3-arylamino-4-carboxymethyl-2,5-dihydro-2-pyrrolones and 1,5-diaryl-4-carboxymethyltetrahydropyrrole-2, 3-diones

Cited by 31 publications

References 1 publication

Brönsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and Fluorine-Derived γ-Lactam Derivatives

Brönsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and Fluorine-Derived γ-Lactam Derivatives

A Brønsted Acid-Catalyzed Multicomponent Reaction for the Synthesis of Highly Functionalized γ-Lactam Derivatives

Multicomponent Synthesis of Unsaturated γ-Lactam Derivatives. Applications as Antiproliferative Agents through the Bioisosterism Approach: Carbonyl vs. Phosphoryl Group

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