Synthesis of novel imidazo[2,1-b][1,3,4]thiadiazoles appended to sydnone as anticancer agents

Gireesh, Tegginamath; Kamble, Ravindra R.; Taj, Tasneem; Kattimani, Pramod P.; Meti, Gangadhar Y.

doi:10.1007/s00044-012-0441-z

Cited by 20 publications

(6 citation statements)

References 21 publications

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“…Besides being used as an anthelmintic drug, the fact that these compounds are bio‐isostere of Tetramisole and its enantiomers Levamisole and Dexamisole, that are used as regulating and strengthening elements for immune system, has caused the anti‐cancer activity studies to focus on imidazo[2,1‐ b ][1,3,4]thiadiazole derivatives . It was reported that, apart from their biological activities, imidazo[2,1‐ b ][1,3,4]thiadiazole and their heterocyclic derivatives are also preferred in different industrial fields such as dye production .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

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Ece

et al. 2017

Molecular Informatics

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In this study, a novel series of phenyl substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives were synthesized, characterized and explored for antibacterial activity against Gram-negative Escherichia coli, Gram-positive Staphylococcus aureus and Bacillus subtilis and antifungal activity against Candida albicans. Most of the synthesized compounds exhibited remarkable antimicrobial activities, some of which being ten times more potent than positive controls. The most promising compound showed excellent activity with MIC value of 0.03 μg/ml against both S. aureus and B. subtilis (MIC values of positive compound Chloramphenicol are 0.4 μg/ml and 0.85 μg/ml, respectively). Furthermore, structure-activity relationship was also investigated with the help of computational tools. Some physicochemical and ADME properties of the compounds were calculated too. The combination of electronic structure calculations performed at PM6 level and molecular docking simulations using Glide extra-precision mode showed that the hydrophobic nature of keto aryl ring with no electron withdrawing substituents at para position enhances activity while electron-donating substituents at the second aryl ring is detrimental to activity.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

Tahtacı

Karacık

Ece

et al. 2017

Molecular Informatics

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“…The range of MIC was 34 to 44 µg/mL for Aspergillus niger and 32 to 48 µg/mL for Candida albicans (Table-3). In this study, the anticancer activity of the synthesized compounds was evaluated by determining LC50, TGI, and GI50 values in µg/mL using sulforhodamine-B dye method 30 . The compounds 4(f) possessing LC50 value >80; TGI value >80 and GI50 = 24.0 µg/mL and 4(g) with LC50 value >80; TGI value >80 and GI50 = 28.1 µg/mL showed good anticancer activity while 4(a), 4(b) and 4(c) exhibited the moderate activity with same values of LC50 >80; TGI values >80 but the GI50 values 35.4, 39.3, 46.8 µg/mL respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The structure-anticancer activity relationship was discovered from data that the ability of substituent at para position to withdraw or donate electrons to the phenyl ring of thiadiazoles is an essential part in such anticancer heterocyclic compounds 30,31 . When an electron releasing group was substituted at the para position such as hydroxyl group in the phenyl ring (compound 4f) which showed prominent anticancer activity on MCF-7 cell line.…”

Section: Resultsmentioning

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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“…They were discovered in 1935 by Earl and Mackney 1 and their mesoionic structure was assigned in 1949 by Baker and Ollis. 2 Sydnones present an array of biological properties such as antibacterial, 3,5 antifungal, 3,5 antimicrobial, [4][5][6] anticancer, 5,7 antiproliferative, 8 anti-HIV, 8 anti-inflammatory and analgesic activities. 9 Sydnones ( Figure 1) undergo two main chemical reactions, namely 1,3-dipolar cycloaddition to form pyrazoles and electrophilic substitution at C-4.…”

Section: Introductionmentioning

confidence: 99%

1,3-Dipolar cycloaddition between acetylenic dipolarophiles and sydnone-N-ylides as bis(1,3-dipoles)

et al. 2015

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Synthesis of novel imidazo[2,1-b][1,3,4]thiadiazoles appended to sydnone as anticancer agents

Cited by 20 publications

References 21 publications

Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

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

1,3-Dipolar cycloaddition between acetylenic dipolarophiles and sydnone-N-ylides as bis(1,3-dipoles)

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