Quinolines, Isoquinolines, Angustureine, and Congeneric Alkaloids — Occurrence, Chemistry, and Biological Activity

Díaz, Gaspar; Miranda, Izabel Luzia; Diaz, Marisa Alves Nogueira

doi:10.5772/59819

Cited by 23 publications

(22 citation statements)

References 54 publications

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“…The effect of a heteroaromatic amine moiety on the γ-lactam structure was also studied. In this context, quinoline scaffold plays an important role in drug development [ 66 , 67 ] and many of their derivatives have shown their potential as anticancer agents [ 68 ] such as well-known camptothecin and their derivatives [ 69 ]. However, although an improvement in the cytotoxic activity and selectivity in the A549 cell line was observed in 2-quinolinylamine substituted lactam 12a with respect to other similar derivatives, like p -toluidine, p -anisidine, p -chloroaniline, and p -bromoaniline substituted lactams 4g , 6b , 7 , and 8a ( Table 2 , Entry 11 vs. Table 1 , Entries 7 and Table 2 , Entries 2, 4 and 5), m -chloroaniline, o -fluoroaniline, and m -trifluoromethylaniline substituted substrates 9 , 10 and 11b proved to be superior to 2-quinolinylamine derivative 12a in this respect ( Table 2 , Entries 7, 8 and 10 vs. Table 2 , Entry 11).…”

Section: Resultsmentioning

confidence: 99%

A Multicomponent Protocol for the Synthesis of Highly Functionalized γ-Lactam Derivatives and Their Applications as Antiproliferative Agents

et al. 2021

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An efficient synthetic methodology for the preparation of 3-amino 1,5-dihydro-2H-pyrrol-2-ones through a multicomponent reaction of amines, aldehydes, and pyruvate derivatives is reported. In addition, the densely substituted lactam substrates show in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell lines HEK293 (human embryonic kidney), MCF7 (human breast adenocarcinoma), HTB81 (human prostate carcinoma), HeLa (human epithelioid cervix carcinoma), RKO (human colon epithelial carcinoma), SKOV3 (human ovarian carcinoma), and A549 (carcinomic human alveolar basal epithelial cell). Given the possibilities in the diversity of the substituents that offer the multicomponent synthetic methodology, an extensive structure-activity profile is presented. In addition, both enantiomers of phosphonate-derived γ-lactam have been synthesized and isolated and a study of the cytotoxic activity of the racemic substrate vs. its two enantiomers is also presented. 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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Section: Resultsmentioning

confidence: 99%

A Multicomponent Protocol for the Synthesis of Highly Functionalized γ-Lactam Derivatives and Their Applications as Antiproliferative Agents

et al. 2021

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“…This group of chemicals is divided in true alkaloids, protoalkaloid, polyamine alkaloids, peptide and cyclopeptide alkaloids and pseudoalkaloids [33]. Dragendorff reagent has been used to detect tertiary and quaternary alkaloids [34,35,36]. Tyramine, as well as N-methylthyramine, are classified as primary alkaloids and were detected in our study by the specific protocol developed by Davet et al [7].…”

Section: Discussionmentioning

confidence: 99%

Cereus jamacaru D.C. Hydroalcoholic Extract Promotes Anti-Cytotoxic and Antitumor Activity

et al. 2018

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Cereus jamacaru D.C. (mandacaru) is a cactus used as food and in the traditional medicine. In the present study, hydroalcoholic extract of C. jamacaru was evaluated for its chemical composition, antioxidant activity, cytotoxic and anti-cytotoxic effects in human lymphocytes and sarcoma 180 cells in vitro by MTT assay and antitumoral, mutagenic and cytotoxic effects on mice sarcoma-induced in vivo. Phytochemical characterization showed positive reactions for coumarin, flavanol and tyramine and total flavonoid content of 0.51 µg/mL. C. jamacaru showed antioxidant activity following DPPH (EC50 = 427.74 µg/mL), ABTS (EC50 = 270.57 µg/mL) and Fe2+ chelating ions assays (EC50 = 41.18 µg/mL). C. jamacaru induced significant decrease of sarcoma 180 viability at 24 h and 48 h of treatment, did not induce cytotoxicity in human lymphocytes and inhibits the cytotoxicity of cisplatin in vitro. Following in vivo assays, C. jamacaru promoted tumor reduction (86.07% of tumor inhibition), without inducing mutagenic or cytotoxic damage on mice blood cells. We propose that phenolic and alkaloid compounds in the extract are related to antioxidant activity, increasing its ability in metal chelating activity and promoting anti-cytotoxic activity against cisplatin, as well as these compounds may act on the cell cycle of the tumor cells in vitro and in vivo, leading to anticancer effects and tumor reduction.

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“…Alkaloids are group of naturally occurring chemical compounds which mostly contain basic nitrogen atoms [15]. In other word, alkaloids are nitrogenous secondary metabolites heterocyclic derivatives of amino acids or by the transamination process which confers basic characters [21]. The group includes some related compounds with neutral and even weakly acidic properties.…”

Section: Alkaloidsmentioning

confidence: 99%

Phytochemical Compositions in Some Nigerian Medicinal Plants and Their Pharmacological Properties: A Review

Kutama¹,

Abdulkadir²,

Kwalli³

et al. 2018

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Nigeria is naturally blessed with both savannah and tropical rainforests vegetation and these offer a wide distribution of plants believed to possesses secondary metabolites which are responsible for treating or curing various diseases. Several researches have been carried out in order to explore and identify the chemical compositions responsible for various pharmacological activities in Nigerian medicinal plants. This paper discussed the meaning and historical development of medicinal plants. A brief account of phytochemicals (alkaloids and flavonoids) were also given. The plants presented in this paper confirmed the pharmacological activities of these plants and includes;

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Quinolines, Isoquinolines, Angustureine, and Congeneric Alkaloids — Occurrence, Chemistry, and Biological Activity

Cited by 23 publications

References 54 publications

A Multicomponent Protocol for the Synthesis of Highly Functionalized γ-Lactam Derivatives and Their Applications as Antiproliferative Agents

A Multicomponent Protocol for the Synthesis of Highly Functionalized γ-Lactam Derivatives and Their Applications as Antiproliferative Agents

Cereus jamacaru D.C. Hydroalcoholic Extract Promotes Anti-Cytotoxic and Antitumor Activity

Phytochemical Compositions in Some Nigerian Medicinal Plants and Their Pharmacological Properties: A Review

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