Novel N‐Substituted ((1H‐indol‐3‐yl)methylene)benzohydrazides and ((1H‐indol‐3‐yl)methylene)‐2‐phenylhydrazines: Synthesis and Antiplatelet Aggregation Activity

Kalhor, Nadia; Mardani, Matin; Abdollahzadeh, Sepideh; Vakof, Mona; Zadeh, Marjan Esfahani; Tehrani, Kamaleddin Haj Mohammad Ebrahim; Kobarfard, Farzad; Mohebbi, Shohreh

doi:10.1002/bkcs.10531

Cited by 7 publications

(5 citation statements)

References 20 publications

(32 reference statements)

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“…As described in study conducted by Kalhor et al . ( 26 ), the synthesis of N -benzylated of isatin with different substitutions was done in acetonitrile including potassium carbonate as a weak base ( Scheme 1 ). The final thiosemicarbazone derivatives were prepared through reacting N-substituted isatins with thiosemicarbazide ( Scheme 2 ).…”

Section: Discussionmentioning

confidence: 99%

Discovery of novel isatin-based thiosemicarbazones: synthesis, antibacterial, antifungal, and antimycobacterial screening

et al. 2020

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Background and purpose: A group of thiosemicarbazones were prepared and their structures were confirmed by spectroscopic methods such as IR and H-NMR, mass spectrometry and also analytical method like elemental analysis. The synthesized semicarbazones were then assessed for their inhibitory activity against bacterial strains including Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus epidermidis, Bacillus cereus, Salmonella species, Enterobacter faecalis, methicillin-resistant Staphylococcus aureus , and fungi such as Candida albicans and Aspergillus niger . Experimental approach: The schiff bases of isatin ( 2a - j ) were prepared by a condensation reaction between thiosemicarbazide and substituted N-aryl isatins leading to the desired thiosemicarbazones with exquisite purity. Findings / Results: The results disclosed that all compounds have noticeable inhibitory activity. Compounds 2a , 2b , 2c , 2g , and 2h were among the most potent derivatives against Gram negative bacteria and fungi. Besides, the activity of theses compounds were tested against Mycobacterium bovis bacillus Calmette-Guerin ( M. bovis BCG). The antimycobacterial activity indicated compounds 2e and 2j are highly active against M. bovis BCG (minimum inhibitory concentration < 3.9 μg/mL). Among fluorinated structures, compounds 2a and 2j showed the best activities against M. bovis BCG. Conclusion and implications: To sum up, amongst the 10 synthesized compounds, fluorinated derivatives exhibited remarkable activities against both gram negative strains and candida albicans microorganism. Therefore, they should be considered as a clue for further modifications in next investigations. Furthermore, inserting a small/medium size halogen atom with electron-withdrawing and lipophilic properties increases anti- salmonella activity of these compounds and moreover 2-halogenated semithiocarbazones presented promising antimycobacterial activity.

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Section: Discussionmentioning

confidence: 99%

Discovery of novel isatin-based thiosemicarbazones: synthesis, antibacterial, antifungal, and antimycobacterial screening

et al. 2020

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“…Furthermore, antiplatelet activity of N -benzylidene-carbohydrazide-1H-pyrazolo [3,4-b]pyridine derivatives have been reported [22]. A variety of indole hydrazone derivatives such as indole N-acylhydrazones [23,24], indole-3-carboxaldehyde phenylhydrazones [25], N-1 substituted indolehydrazones [26], indole-3-carbaldehyde, and indole-2-carbaldehayde hydrazones [27] have been previously synthesized in our research group. Some of these reported derivatives exhibited remarkable antiplatelet activity.…”

Section: Anti-platelet Activitymentioning

confidence: 99%

Synthesis of Imine Congeners of Resveratrol and Evaluation of Their Anti-Platelet Activity

Bigdeli

Sabbaghan

Esfahanizadeh

et al. 2018

Molbank

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Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a cardioprotective phytochemical occurring in many plant products. In this study, a new series of imine congeners of resveratrol has been synthesized in which the imine moiety replaced the double bond in the structure of resveratrol. In addition, the in vitro antiplatelet activity of these resveratrol derivatives has been evaluated against adenosine diphosphate (ADP), arachidonic acid (AA), and collagen as platelet aggregation inducers. In general, the synthesized compounds were active as antiplatelet agents, and, therefore, the imine functional group may be considered as an effective replacement for a double bond in resveratrol for developing new and promising antiplatelet drugs.

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“…Over the past years, our research team started several studies with emphasis on the chemical structures bearing hydrazine moiety as potential antiplatelet agents. Intriguingly, we discovered that hydrazones of substituted phenyl reveal a notable inhibition of AA-induced platelet aggregation with IC 50 values comparable to that of indomethacin as a standard inhibitor ( 11 12 13 ).…”

Section: Introductionmentioning

confidence: 95%

Novel N-substituted indole hydrazones as potential antiplatelet agents: synthesis, biological evaluations, and molecular docking studies

et al. 2022

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Background and purpose: Antiplatelet agents can diminish the chance of coronary heart diseases due to the prevention of unusual clotting in the arteries by inhibiting platelet aggregation and avoiding the formation of a blood clot. This mechanism can help to prevent ischemic stroke likewise. To improve the activity of these drugs and reduce their side effects, further studies are required. Experimental approach: Based on the previous studies representing the promising antiplatelet activity of indole hydrazones, a series of their homologs containing twenty-one compounds were prepared in two steps. First, alkylation reaction on the nitrogen of the indole ring, and second, chiff base formation by condensation of a primary amine and N-substituted indole-3 carbaldehyde. Consequently, their platelet anti-aggregation activity was evaluated based on the Born turbidimetric method. Findings/Results: Most of the compounds exhibited noticeable activity against platelet aggregation induced by arachidonic acid. Amongst them, two compounds 2e and 2f showed higher activity with IC 50 values that made comparable to indomethacin and acetylsalicylic acid as standard drugs and had no toxicity on platelets. Conclusion and implications: The synthesized compounds exhibited promising activity against arachidonic acid-induced aggregation; however, none of them showed noticeable antiplatelet activity induced by adenosine di-phosphate. Chemical structure comparison of the prepared derivatives indicated the existence of a lipophilic medium-sized group on the phenyl ring increased their activity. In addition, the docking studies confirmed this hydrophobic interaction in the lipophilic pocket of cyclooxygenase-1 enzyme suggesting that hydrophobicity of this region plays a pivotal role in the anti-platelet activity of these compounds. To prove this finding, the enzymatic evaluation with the target enzyme is required.

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Novel N‐Substituted ((1H‐indol‐3‐yl)methylene)benzohydrazides and ((1H‐indol‐3‐yl)methylene)‐2‐phenylhydrazines: Synthesis and Antiplatelet Aggregation Activity

Abstract: Novel Antiplatelet N‐1 substituted indole‐hydrazones.

Cited by 7 publications

References 20 publications

Discovery of novel isatin-based thiosemicarbazones: synthesis, antibacterial, antifungal, and antimycobacterial screening

Discovery of novel isatin-based thiosemicarbazones: synthesis, antibacterial, antifungal, and antimycobacterial screening

Synthesis of Imine Congeners of Resveratrol and Evaluation of Their Anti-Platelet Activity

Novel N-substituted indole hydrazones as potential antiplatelet agents: synthesis, biological evaluations, and molecular docking studies

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