Synthesis and in vitro antimycobacterial potential of novel hydrazones of eugenol

Rohane, Sachin H.; Chauhan, Ashlesha; Fuloria, Neeraj Kumar; Fuloria, Shivkanya

doi:10.1016/j.arabjc.2019.09.004

Cited by 43 publications

(41 citation statements)

References 7 publications

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“…Novel hydrazide-hydrazones synthesized from eugenol were tested for antimycobacterial potential. Among synthesized derivatives, compound 38 possessed the highest sensitivity against M. tuberculosis H37Rv at 25 µg/mL level (Figure 30) [40]. Gürsoy et al, in 2020, obtained novel thiazole derivatives with antitubercular activity.…”

Section: Antimycobacterial Activitymentioning

confidence: 99%

“…The authors discovered that compounds bearing methoxy groups in the phenyl ring attached to the 1,3-oxazole scaffold displayed better activity compared to the other compounds (Figure 32). Synthesized substances (40,41) were tested in vitro for cytotoxicity in human embryonic kidney (HEK-293T) cells and did not display changes in cytotoxicity as compared with vehicle (DMSO) [42].…”

Section: Antimycobacterial Activitymentioning

confidence: 99%

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Updated Information on Antimicrobial Activity of Hydrazide–Hydrazones

Popiołek

2021

IJMS

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Hydrazide–hydrazones possess a wide spectrum of bioactivity, including antibacterial, antitubercular, antifungal, anticancer, anti-inflammatory, anticonvulsant, antidepressant, antiviral, and antiprotozoal properties. This review is focused on the latest scientific reports regarding antibacterial, antimycobacterial, and antifungal activities of hydrazide–hydrazones published between 2017 and 2021. The molecules and their chemical structures presented in this article are the most active derivatives, with discussed activities having a hydrazide–hydrazone moiety as the main scaffold or as a side chain. Presented information constitute a concise summary, which may be used as a practical guide for further design of new molecules with antimicrobial activity.

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Section: Antimycobacterial Activitymentioning

confidence: 99%

Section: Antimycobacterial Activitymentioning

confidence: 99%

Updated Information on Antimicrobial Activity of Hydrazide–Hydrazones

Popiołek

2021

IJMS

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“…and M. tuberculosis [32]. Its hydrazone derivatives were studied by molecular docking against the enoyl-ACP reductase as a molecular target, and validated by in vitro assay, which showed a docking score of −10.393 kcal/mol with minimum inhibitory activity at 25µg/mL [31,33].…”

Section: Introductionmentioning

confidence: 99%

Acetyleugenol from Acacia nilotica (L.) Exhibits a Strong Antibacterial Activity and Its Phenyl and Indole Analogues Show a Promising Anti-TB Potential Targeting PknE/B Protein Kinases

Abdulhamid

Awad

Ahmed

et al. 2021

Microbiology Research

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Acetyleugenol is a phytochemical compound with broad effects against infectious diseases and tumors. Here, we extracted, characterized, and elucidated the structure of acetyeugenol, for the first time, from the leaves of Acacia nilotica (L.)—a well-known medicinal plant. The broad antibacterial potential of acetyleugenol was first confirmed against seven bacterial clinical isolates, which reveal a strong activity against Proteus sp., Salmonella typhi, Staphylococcus aureus, and Streptococcus pneumonia with similar or better zone of inhibition comparing to that of the control amoxicillin. To further investigate its effect against Mycobacterium tuberculosis, acetyleugenol and its indole and phenyl analogues were subjected to molecular docking experiments against two potential tuberculosis drug targets—MtPknE and MtPknB Ser/Thr protein kinases. The results reveal that all of the analogs have improved docking scores compared to the acetyleugenol. The indole analogues EUG-1 and EUG-3 were more effective with better docking scores for MtPknE with −11.08 and −10.05 kcal/mol, respectively. Similar results were obtained for the MtPknB. In contrast, only the EUG-2 phenyl analogue has given rise to similar docking scores for both targets. This opens the door for further comprehensive studies on these acetyleugenol analogues with in vitro and in vivo experiments to validate and get more insights into their mechanisms of action.

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“…Grinding methods are appealing eco-friendly techniques for efficient organic synthesis with many advantages, such as: mild reaction conditions, easy separation and purifications [ 2 , 3 ], high efficiency and selectivity [ 4 ], and environmental acceptability [ 5 ]. In the meantime, hydrazone is an effective nucleus because hydrazine-containing compounds (R 1 R 2 C=NNH-R 3 ) offer a wide range of biological activities, including anticholinesterase [ 6 ], antimycobacterial [ 7 ], anti - cancer [ 8 ], antibacterial, anti-inflammatory, anti-viral, antifungal, anti-tubercular, analgesic, muscle relaxants, and antihistamines [ 9 , 10 , 11 , 12 ]. Hydrazones possessing an azometine -NHN=CH- proton constitute an important class of compounds for new drug development.…”

Section: Introductionmentioning

confidence: 99%

Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro)

et al. 2020

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A novel series of some hydrazones bearing thiazole moiety were generated via solvent-drop grinding of thiazole carbohydrazide 2 with various carbonyl compounds. Also, dehydrative-cyclocondensation of 2 with active methylene compounds or anhydrides gave the respective pyarzole or pyrazine derivatives. The structures of the newly synthesized compounds were established based on spectroscopic evidences and their alternative syntheses. Additionally, the anti-viral activity of all the products was tested against SARS-CoV-2 main protease (Mpro) using molecular docking combined with molecular dynamics simulation (MDS). The average binding affinities of the compounds 3a, 3b, and 3c (–8.1 ± 0.33 kcal/mol, –8.0 ± 0.35 kcal/mol, and –8.2 ± 0.21 kcal/mol, respectively) are better than that of the positive control Nelfinavir (–6.9 ± 0.51 kcal/mol). This shows the possibility of these three compounds to effectively bind to SARS-CoV-2 Mpro and hence, contradict the virus lifecycle.

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Synthesis and in vitro antimycobacterial potential of novel hydrazones of eugenol

Cited by 43 publications

References 7 publications

Updated Information on Antimicrobial Activity of Hydrazide–Hydrazones

Updated Information on Antimicrobial Activity of Hydrazide–Hydrazones

Acetyleugenol from Acacia nilotica (L.) Exhibits a Strong Antibacterial Activity and Its Phenyl and Indole Analogues Show a Promising Anti-TB Potential Targeting PknE/B Protein Kinases

Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro)

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