Synthesis and anticancer evaluation of some new hydrazone derivatives of 2,6-dimethylimidazo[2,1-b][1,3,4]thiadiazole-5-carbohydrazide

Terzioglu, Nalan; Gürsoy, Aysel

doi:10.1016/s0223-5234(03)00138-7

Cited by 297 publications

(127 citation statements)

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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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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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“…properties such as anticancer [1], antitubercular [2], antibacterial [3], antifungal [4], anticonvulsant, analgesic [5] and antisecretory [6] activities. They have been reported to selectively inhibit several therapeutic receptors and enzymes, extending their applications in modern drug design.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 5-{[2-(4-fluorobenzyl)-6-arylimidazo[2,1-b] [1,3,4]thiadiazol-5-yl]methylene}thiazolidine-2,4-diones as potent Antidiabetic agents

Badiger¹

2015

IJSEA

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“…19) It is well-known that tricyclazole, a triazolo [3,4-b]benzothiazole derivative, is applied mainly as a commercial fungicide to control Pyricularia oryzae. 13) In line with our continuous e orts to synthesize bioactive lead compounds for crop protection, the title compounds were designed by introducing a hydrazone pharmacophore into the benzothiazole sca old. Our original strategy is depicted in Fig.…”

Section: Introductionmentioning

confidence: 99%

“…It is also reported that hydrazones possess a diverse range of bioactivities in the medicinal and agrochemical elds, such as anticancer, 13) anti-in ammatory, 14) antimicrobial, 15) herbicidal, 16) fungicidal 17) and insecticidal 18) activities. In addition, hydrazones are very useful starting materials in many reactions in the synthesis of various bioactive molecules.…”

Section: Introductionmentioning

confidence: 99%

“…Its favorable bioactivity has prompted widespread studies on benzothiazole derivatives in the past two decades. For example, a number of benzothiazole derivatives are shown to have antitumor, 6) antimicrobial, 7) antifungal, 8) anthelmintic, 9) anti-in ammatory, 10) cardiovascular 11) and antitubercular 12) activities.It is also reported that hydrazones possess a diverse range of bioactivities in the medicinal and agrochemical elds, such as anticancer, 13) anti-in ammatory, 14) antimicrobial, 15) herbicidal, 16) fungicidal 17) and insecticidal 18) activities. In addition, hydrazones are very useful starting materials in many reactions in the synthesis of various bioactive molecules.…”

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confidence: 99%

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Synthesis and fungicidal activity of hydrazones containing 4-methylbenzo[d]thiazole moiety

2012

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A new series of hydrazone derivatives containing 4-methylbenzo [d]thiazole moiety was synthesized. e structures of the title compounds were characterized by 1 H NMR, FTIR, MS and elemental analysis. Fungicidal activities of the title compounds were investigated. e results indicated that some of these compounds exhibit excellent fungicidal activities. © Pesticide Science Society of Japan Keywords: hydrazone, benzothiazole, synthesis, fungicidal activity. IntroductionSulfur-and nitrogen-linked heterocyclic compounds have received considerable attention in recent years because of their pharmacological and pesticidal importance. [1][2][3][4][5] Benzothiazole is one of the oldest and potent heterocyclic compounds displaying interesting medicinal and agricultural activities. Its favorable bioactivity has prompted widespread studies on benzothiazole derivatives in the past two decades. For example, a number of benzothiazole derivatives are shown to have antitumor, 6) antimicrobial, 7) antifungal, 8) anthelmintic, 9) anti-in ammatory, 10) cardiovascular 11) and antitubercular 12) activities.It is also reported that hydrazones possess a diverse range of bioactivities in the medicinal and agrochemical elds, such as anticancer, 13) anti-in ammatory, 14) antimicrobial, 15) herbicidal, 16) fungicidal 17) and insecticidal 18) activities. In addition, hydrazones are very useful starting materials in many reactions in the synthesis of various bioactive molecules. 19) It is well-known that tricyclazole, a triazolo [3,4-b]benzothiazole derivative, is applied mainly as a commercial fungicide to control Pyricularia oryzae. 13) In line with our continuous e orts to synthesize bioactive lead compounds for crop protection, the title compounds were designed by introducing a hydrazone pharmacophore into the benzothiazole sca old. Our original strategy is depicted in Fig. 1. Materials and Methods InstrumentsMelting points were determined using an X-4 apparatus without calibration. 1 H NMR spectra were measured on a Bruker ADVANCE III instrument (500 MHz) using TMS as an internal standard and deuterochloroform as a solvent. FT-IR spectra were recorded on a NICOLET 6700 instrument. Mass spectra were recorded on a ermo Scienti c ITQ 1100TM and erm LCQ TM Deca XP plus instrument. Elemental analyses were performed on a Vario EL elemental analyzer. Synthesis of compoundsAll starting materials were used as purchased or of analytic grade purity. Analytical TLC was performed on silica gel GF254. e title compounds were synthesized according to the route shown in Fig. 2. 2-Hydrazino-4-methylbenzo [d]thiazole was prepared according to the reference. 20) o-Toluidine (0.2 mol) was added to water and warmed with dilute hydrochloric acid (10 mL) until a clear solution was obtained. Ammonium thiocyanate (0.22 mol) dissolved in water (50 mL), then added this solution gradually. e reaction mixture boiled at 100-110°C for 8 hr and evaporated to less than half the volume. It was then cooled to get the precipitate of compound 2, which was ltered, washed wit...

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Synthesis and anticancer evaluation of some new hydrazone derivatives of 2,6-dimethylimidazo[2,1-b][1,3,4]thiadiazole-5-carbohydrazide

Cited by 297 publications

References 11 publications

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

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

Synthesis of novel 5-{[2-(4-fluorobenzyl)-6-arylimidazo[2,1-b] [1,3,4]thiadiazol-5-yl]methylene}thiazolidine-2,4-diones as potent Antidiabetic agents

Synthesis and fungicidal activity of hydrazones containing 4-methylbenzo[d]thiazole moiety

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