Synthesis and antimycobacterial evaluation of new trans-cinnamic acid hydrazide derivatives

Carvalho, Samir A.; Silva, Edson F. da; Souza, Marcus V. N. de; Lourenço, Maria Cristina S.; Vicente, Felipe R.

doi:10.1016/j.bmcl.2007.11.091

Cited by 115 publications

(47 citation statements)

References 10 publications

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“…The 1 H-Nucleic Magnetic Resonance (NMR) spectra were recorded at 300 MHz on a Bruker AM 300 spectrometer (Bruker Analytische Messtechnik GmbH, Rheinstetten, Germany) in CDCl 3 or DMSO using tetramethylsilane as an internal standard unless otherwise stated. 13 C-NMR spectra were obtained at 75.5 MHz on a Bruker AM 300 spectrometer in CDCl 3 or DMSO solutions with tetramethylsilane as internal reference unless otherwise stated. Chemical shifts are expressed in δ (ppm) and coupling constants J in Hz.…”

Section: Materials and Instrumentsmentioning

confidence: 99%

“…Additionally, trans-cinnamic acid derivatives, both isolated from plant sources or synthesized, are well known for their antioxidant [10], antitumor [11], antimicrobial [12] and antimycobacterial properties [13]. Cinnamic acid derivatives, especially those combining the cinnamoyl moiety with hydroxyl groups, present strong free radical scavenging properties.…”

Section: Introductionmentioning

confidence: 99%

“…The pure final products were recrystallized from ethanol/water. IR, 1 H-NMR, 13 C-NMR and elemental analysis were used for the confirmation of the synthesized compounds structures (Table 1). Scheme 1.…”

Section: Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

et al. 2014

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Cinnamic acids have been identified as interesting compounds with antioxidant, anti-inflammatory and cytotoxic properties. In the present study, simple cinnamic acids were synthesized by Knoevenagel condensation reactions and evaluated for the above biological activities. Compound 4ii proved to be the most potent LOX inhibitor. Phenylsubstituted acids showed better inhibitory activity against soybean LOX, and it must be noted that compounds 4i and 3i with higher lipophilicity values resulted less active than compounds 2i and 1i. The compounds have shown very good activity in different antioxidant assays. The antitumor properties of these derivatives have been assessed by their 1/IC 50 inhibitory values in the proliferation of HT-29, A-549, OAW-42, MDA-MB-231, HeLa and MRC-5 normal cell lines. The compounds presented low antitumor activity considering the IC 50 values attained for the cell lines, with the exception of compound 4ii. Molecular docking studies were carried out on cinnamic acid derivative 4ii and were found to be in accordance with our experimental biological results.

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Section: Materials and Instrumentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

et al. 2014

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“…These key cinnamyl alcohols are produced through two successive enzyme-catalyzed reductions starting from the corresponding cinnamyl SCoA-esters. In recent years, transcinnamic acid derivatives have also attracted much attention due to their antioxidative (Chung & Shin, 2007), antitumor (De et al, 2011a) and antimicrobial (Naz et al, 2006;Carvalho et al, 2008) properties.…”

Section: Fig 2 Cinnamic Acid and Its Natural Phenolic-analoguesmentioning

confidence: 99%

“…trans-Cinnamic acid hydrazide derivatives were presented as potential antituberculosis agents (Carvalho et al 2008). The authors designed and explored the introduction of the trans-cinnamic moiety into isoniazid (11) core structure to ameliorate its activity.…”

Section: Cinnamic Acid Hydrazide Thioester and Other Derivativesmentioning

confidence: 99%

Cinnamic Derivatives in Tuberculosis

De¹,

Veau²,

Bedos‐Belval³

et al. 2012

Understanding Tuberculosis - New Approaches to Fighting Against Drug Resistance

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Synthesis, Bioactivity Evaluation,3D‐QSAR, and Molecular Docking of Novel Pyrazole‐4‐carbohydrazides as Potential Fungicides Targeting Succinate Dehydrogenase

et al. 2021

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Main observation and conclusion To screen novel antifungal agents targeting the succinate dehydrogenase (SDH), a series of pyrazole‐4‐carbohydrazides were rationally designed, synthesized, and characterized under the guidance of the structures of succinate dehydrogenase inhibitors (SDHIs). Bioassay results in vitro indicated that most of the target compounds exhibited excellent activity against Rhizoctonia solani (R. solani), Fusarium graminearum (F. graminearum), Botrytis cinerea (B. cinerea) and Colletotrichum capsica (C. cinerea). Compounds 7d, 7l, 7t and 7x were identified as the most promoting candidates, and their anti‐F. graminearum EC50 values were as low as 0.56, 0.47, 0.46 and 0.49 μg/mL, respectively, presenting the similar antifungal activity as that of the commonly used fungicide carbendazim (0.43 μg/mL). The 3D‐QSAR models were built for a systematic structure‐activity relationship profile to explore more potent pyrazole‐4‐carbohydrazides as novel fungicides. Molecular docking of 7d, 7l and 7r with SDH was performed to reveal the binding modes in active pocket and analyze the interactions between the molecules and the SDH protein.

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Synthesis and antimycobacterial evaluation of new trans-cinnamic acid hydrazide derivatives

Cited by 115 publications

References 10 publications

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

Cinnamic Derivatives in Tuberculosis

Synthesis, Bioactivity Evaluation,3D‐QSAR, and Molecular Docking of Novel Pyrazole‐4‐carbohydrazides as Potential Fungicides Targeting Succinate Dehydrogenase

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