Solvent-Free Synthesis of Carboxylic Acids and Amide Analogs of CAPE (Caffeic Acid Phenethyl Ester) under Infrared Irradiation Conditions

Martínez-Soriano, Pablo A.; Macías‐Pérez, José Roberto; Velázquez, Ana María; Camacho-Enriquez, Brígida del Carmen; Pretelín-Castillo, Gustavo; Ruiz-Sánchez, Mónica B.; Abrego-Reyes, Víctor H.; Villa‐Treviño, Saúl; Ángeles, Enrique

doi:10.4236/gsc.2015.52011

Cited by 4 publications

(4 citation statements)

References 35 publications

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“…(1) and derivatives (2-5) (Figure 1) has particularly increased, once they have showed several potential therapeutic activities, such as anti-inflammatory, antioxidant, antiviral, antibacterial, and antifungal. Likewise, multiple anticancer activities by inhibiting the growth of mammary (MCF-7) and prostatic (PC-3) neoplastic cells by inducing apoptosis (Gunia-Krzyżak et al, 2018;Pontiki et al, 2014;Jitareanu et al, 2013;Martínez-Soriano et al, 2015;Imai et al, 2019). Fonte: Jitareanu et al, (2013); Gunia-Krzyżak et al, (2018).…”

Section: Bioactivity Of Cinnamic Acid and Its Derivativesmentioning

confidence: 99%

“…In recent decades, it was found that CAD's from natural sources have anti-cancer, antioxidant and others related potential activity (Jitareanu et al, 2013;Martínez-Soriano et al, 2015;Zeng & Lai, 2019). Studies revealed that these biological activities were related to the cinnamoyl nucleus, present in the structure of this class of compounds, and hydroxyl groups, the latter being crucial for the elimination of free radicals and ROS, minimizing the oxidation of low-density lipoprotein (LDL) (Jitareanu et al, 2013;Martínez-Soriano et al, 2015).…”

Section: Antioxidant Activitymentioning

confidence: 99%

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Synthesis, applications and Structure-Activity Relationship (SAR) of cinnamic acid derivatives: a review

França¹,

Correia²,

Castro³

et al. 2021

RSD

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The article aims to analyze the progress of the evolution of cinnamic acid derivatives through a bibliographic review, describing the main synthetic routes in obtaining this class, as well as remarkable biological applications and application of the structure-activity relationship (SAR) as a strategy for design pharmacologically active molecules. The methodology used consists of reading and analyzing articles, whose approach is descriptive, with data being collected regarding the therapeutic potential of derivatives of cinnamic acid and its relationship with structural scaffolding, as well as the most widely used synthetic approaches. As a result, it was observed that cinnamic acid and its derivatives from natural sources can be synthesized in appreciable quantities with varied synthetic routes, as well as being candidates for therapeutic agents, since they have several therapeutic applications against diabetes, infectious and degenerative diseases, among others, in addition to presenting activity such as pest control, which has attracted the attention of academic and industrial researchers. These compounds are highly versatile since their activity is intrinsically associated with the mode of interaction between the structure and its molecular target. However, in nature they are obtained in small quantities, therefore, the development of new approaches of synthetic methodologies to obtain such compounds in substantial quantities and linked to medicinal chemistry can contribute to the development of very effective bioactive molecules in comparison with their precursors.

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Section: Bioactivity Of Cinnamic Acid and Its Derivativesmentioning

confidence: 99%

Section: Antioxidant Activitymentioning

confidence: 99%

Synthesis, applications and Structure-Activity Relationship (SAR) of cinnamic acid derivatives: a review

França¹,

Correia²,

Castro³

et al. 2021

RSD

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“…In the last 10 years, interest in CA and its derivatives (esters, amides, aldehydes and alcohols) [ 5 ] has increased because of its many pharmacological activities, such as antituberculosis [ 6 , 7 , 8 , 9 ], antiviral [ 10 ], anticancer [ 11 , 12 , 13 , 14 , 15 , 16 ], mammary (MCF-7) and prostate (PC-3) inhibition, neoplastic cell growth, apoptosis inducement [ 17 , 18 , 19 ], anticholesterolemic [ 20 , 21 , 22 , 23 ], cardioprotective [ 24 ], antioxidant [ 25 , 26 , 27 , 28 ], anti-inflammatory [ 2 , 29 , 30 , 31 , 32 ], hepatoprotective [ 33 , 34 , 35 ], antidiabetic [ 36 , 37 , 38 ], antimalarial [ 39 ], anxiolytic [ 40 ], central nervous system depressant [ 41 ], neuroprotective [ 42 , 43 , 44 , 45 , 46 ], larvicidal agent [ 47 , 48 , 49 , 50 , 51 ], anti-leishmania [ 52 ], cosmetic […”

Section: Introductionmentioning

confidence: 99%

Synthetic Cinnamides and Cinnamates: Antimicrobial Activity, Mechanism of Action, and In Silico Study

et al. 2023

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The severity of infectious diseases associated with the resistance of microorganisms to drugs highlights the importance of investigating bioactive compounds with antimicrobial potential. Therefore, nineteen synthetic cinnamides and cinnamates having a cinnamoyl nucleus were prepared and submitted for the evaluation of antimicrobial activity against pathogenic fungi and bacteria in this study. To determine the minimum inhibitory concentration (MIC) of the compounds, possible mechanisms of antifungal action, and synergistic effects, microdilution testing in broth was used. The structures of the synthesized products were characterized with FTIR spectroscopy, 1 H-NMR, 13 C-NMR, and HRMS. Derivative 6 presented the best antifungal profile, suggesting that the presence of the butyl substituent potentiates its biological response (MIC = 626.62 μM), followed by compound 4 (672.83 μM) and compound 3 (726.36 μM). All three compounds were fungicidal, with MFC/MIC ≤ 4. For mechanism of action, compounds 4 and 6 directly interacted with the ergosterol present in the fungal plasmatic membrane and with the cell wall. Compound 18 presented the best antibacterial profile (MIC = 458.15 μM), followed by compound 9 (550.96 μM) and compound 6 (626.62 μM), which suggested that the presence of an isopropyl group is important for antibacterial activity. The compounds were bactericidal, with MBC/MIC ≤ 4. Association tests were performed using the Checkerboard method to evaluate potential synergistic effects with nystatin (fungi) and amoxicillin (bacteria). Derivatives 6 and 18 presented additive effects. Molecular docking simulations suggested that the most likely targets of compound 6 in C. albicans were caHOS2 and caRPD3, while the most likely target of compound 18 in S. aureus was saFABH. Our results suggest that these compounds could be used as prototypes to obtain new antimicrobial drugs.

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“…The following supporting information can be downloaded at: , Spectroscopic data of compounds [ 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 ].…”

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confidence: 99%

Antileishmanial Activity of Cinnamic Acid Derivatives against Leishmania infantum

et al. 2023

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Leishmania infantum is the etiological agent of visceral leishmaniasis (VL) in South America, the Mediterranean basin, and West and Central Asia. The most affected country, Brazil, reported 4297 VL cases in 2017. L. infantum is transmitted by female phlebotomine sand flies during successive blood meals. There are no validated vaccines to prevent the infection and the treatment relies on drugs that often present severe side effects, which justify the efforts to find new antileishmanial drugs. Cinnamic acid derivatives have shown several pharmacological activities, including antiparasitic action. Therefore, in the present study, the biological evaluation of cinnamic acid and thirty-four derivatives against L. infantum is reported. The compounds were prepared by several synthesis methods and characterized by spectroscopic techniques and high-resolution mass spectrometry. The results revealed that compound 32 (N-(4-isopropylbenzyl)cinnamamide) was the most potent antileishmanial agent (IC50 = 33.71 μM) with the highest selectivity index (SI > 42.46), followed by compound 15 (piperonyl cinnamate) with an IC50 = 42.80 μM and SI > 32.86. Compound 32 was slightly less potent and nineteen times more selective for the parasite than amphotericin B (MIC = 3.14 uM; SI = 2.24). In the molecular docking study, the most likely target for the compound in L. infantum was aspartyl aminopeptidase, followed by aldehyde dehydrogenase, mitochondrial. The data obtained show the antileishmanial potential of this class of compounds and may be used in the search for new drug candidates against Leishmania species.

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Solvent-Free Synthesis of Carboxylic Acids and Amide Analogs of CAPE (Caffeic Acid Phenethyl Ester) under Infrared Irradiation Conditions

Cited by 4 publications

References 35 publications

Synthesis, applications and Structure-Activity Relationship (SAR) of cinnamic acid derivatives: a review

Synthesis, applications and Structure-Activity Relationship (SAR) of cinnamic acid derivatives: a review

Synthetic Cinnamides and Cinnamates: Antimicrobial Activity, Mechanism of Action, and In Silico Study

Antileishmanial Activity of Cinnamic Acid Derivatives against Leishmania infantum

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