Synthesis, characterization and molecular docking studies of novel S-substituted phenacyl-1,3,4-thiadiazole-thiol derivatives as antimicrobial agents

Kerur, Shashidhar; Alagawadi, K. R.; Zhu, Hai‐Liang; Manvi, Fakkirappa

doi:10.5155/eurjchem.3.3.293-297.613

Cited by 4 publications

(3 citation statements)

References 11 publications

(5 reference statements)

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“…The 1,3,4‐thiadiazole moiety is one of those compounds at the apex of chemists attention owing to its biological and pharmaceutical importance. A literature survey shows that 1,3,4‐thiadiazole derivatives exhibit antimicrobial , anti‐inflammatory , antitumor , antihyperlipidemic , anticonvulsant , antiviral , antioxidant , antifungal , antitubercular , and antidepressant activities . In addition, 1,3,4‐thiadiazole has important technological uses as corrosion and oxidation inhibitors , metal complexation agents , and in analytical fields .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Polyfunctionally Substituted Heterocyclic Compounds Derived from 5‐Cinnamoylamino‐2‐Cyanomethyl‐1,3,4‐Thiadiazole

Mahmoud

El‐Shahawi

El-Azm

et al. 2017

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Cinnamoyl isothiocyanate 1 was reacted with 2-cyanoethanoic acid hydrazide 2 to afford 1-cyanoacetyl-4-substituted thiosemicarbazide 3, which on treatment with a mixture of glacial acetic acid and acetic anhydride gave the desired 5-cinnamoylamino-2-cyanomethyl-1,3,4-thiadiazole 4. Compound 4 was subjected to react with aromatic aldehydes, phenylisothiocyanate, carbon disulphide, and arylidene malononitrile to give coumarin 5, thiazolidines 8,9, and 1,3,4-thiadiazolo[3,2-a]pyridine 13 derivatives. The structures of all synthesized compounds were ascertained by spectral and analytical data. Antimicrobial activity of some of prepared compounds was investigated, and compounds 7, 8 were found to exhibit the highest strength.Scheme 3. Synthesis of the 1,3,4-thiadiazole derivatives 7 and 8.Scheme 2. Synthesis of 2-(2-Oxo-2H-chromen-3-yl)-5-cinnamoylamino-1,3,4-thiadiazole.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Polyfunctionally Substituted Heterocyclic Compounds Derived from 5‐Cinnamoylamino‐2‐Cyanomethyl‐1,3,4‐Thiadiazole

Mahmoud

El‐Shahawi

El-Azm

et al. 2017

Journal of Heterocyclic Chem

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“…The 1,3,4-thiadiazole moiety is one of those compounds at the apex of chemists attention owing to its biological and pharmaceutical importance. A literature survey shows that 1,3,4-thiadiazole derivatives exhibit antimicrobial [14][15][16][17][18], anti-inflammatory [18,19], antitumor [20][21][22][23], antihyperlipidemic [24], anticonvulsant [25,26], antiviral [27], antioxidant [28], antifungal [29,30], antitubercular [31,32] and antide-pressant activities [33]. In addition, 1,3,4-thiadiazole have important technological uses as corrosion and oxidation inhibitors [34], metal complexation agents [35,36] and in analytical fields [37].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Polyfunctionally Substituted Heterocyclic Compounds Derived From 5-Cinnamoylamino-2-Cyanomethyl-1,3,4-Thiadiazole

Mahmoud

El‐Shahawi

El-Azm

et al. 2016

Al-Azhar Bulletin of Science

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Cinnamoyl isothiocyanate 1 was reacted with 2-cyanoethanoic acid hydrazide 2 to afford 1-cyanoacetyl-4-substituted thiosemicarbazide 3 which on treatment with a mixture of glacial acetic acid and acetic anhydride gave the desired 5-cinnamoylamino-2-cyanomethyl-1,3,4-thiadiazole 4. Compound 4 was subjected to react with aromatic aldehydes, phenylisothiocyanate, carbon disulphide and arylidene malononitrile to give coumarin 5, thiazolidines 8,9 and 1,3,4-thiadiazolo[3,2-a]pyridine 13 derivatives. The structures of all synthesized compounds were ascertained by spectral and analytical data.

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“…5-Phenyl-1,3,4-thiadiazole is familiar group of bioactive compounds with numerous pharmacological activities 4 . Various pharmacological activities reported for 1,3,4-thiadiazole analogues are anticancer [5][6][7] antimicrobial [8][9][10] , antitubercular 11,12 , anti-inflammatory 13 , analgesic 14 , anticonvulsant 15 , antihypertensive 16 , diuretic 17 , local anesthetic 18 and antioxidant activities 19 .Hence, it is envisaged to synthesize 1,3,4-thiadiazole analogs and screened them for antimicrobial and anticancer activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial and Anticancer Activities of 5-(4-Substituted-Phenyl)-1,3,4- Thiadiazole-2-Amines

2017

Rasayan J Chem

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A series of 5-(4-substituted phenyl)-1,3,4-thiadiazole-2-amines (4a-h) were prepared from dehydrocyclization of 4-substituted benzoyl thiosemicarbazides (3a-h) using concentrated sulphuric acid. The chemical structures of compounds were elucidated by Infra-red, NMR, Mass spectral and elemental analyses. Antibacterial activities of these compounds against Staphylococcus aureus, Bacillus substilis, Eschereria coli and Pseudomonas aeruginosa using Ciprofloxacin while antifungal activities against Aspergillus niger and Candida albicans using Fluconazole as standard drugs were performed. Minimum inhibitory concentrations and anticancer activity of potent compounds was determined. The results indicate that compounds 4(a), 4(b) and 4(c) possess significant antibacterial activity whereas compounds 4(f) and 4(g) possess significant antifungal activity among the series of synthesized thiadiazoles comparing with standard drugs. Further, the results of anticancer studies on breast cancer cell line suggested that some potent antimicrobials i.e. 4(c), 4(f) and 4(g) associated with moderate to good anticancer activity. Thus, it may be found that synthesized compounds have good antibacterial activity and moderate antifungal activity. However, these compounds could be further screened for the antibacterial activities against a battery of bacteria to achieve their broad spectrum profile and also used to screen cytotoxic effect against other cancer cell lines.

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Synthesis, characterization and molecular docking studies of novel S-substituted phenacyl-1,3,4-thiadiazole-thiol derivatives as antimicrobial agents

Cited by 4 publications

References 11 publications

Synthesis and Antimicrobial Activity of Polyfunctionally Substituted Heterocyclic Compounds Derived from 5‐Cinnamoylamino‐2‐Cyanomethyl‐1,3,4‐Thiadiazole

Synthesis and Antimicrobial Activity of Polyfunctionally Substituted Heterocyclic Compounds Derived from 5‐Cinnamoylamino‐2‐Cyanomethyl‐1,3,4‐Thiadiazole

Synthesis of Polyfunctionally Substituted Heterocyclic Compounds Derived From 5-Cinnamoylamino-2-Cyanomethyl-1,3,4-Thiadiazole

Synthesis, Antimicrobial and Anticancer Activities of 5-(4-Substituted-Phenyl)-1,3,4- Thiadiazole-2-Amines

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