Synthesis and antimicrobial activity of some new hydrazone-bridged thiazole-pyrrole derivatives

Yurttaş, Leyla; Özkay, Yusuf; Kaplancıklı, Zafer Asım; Tunalı, Yağmur; Karaca, Hülya

doi:10.3109/14756366.2012.688043

Cited by 51 publications

(34 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All the synthesized compounds were characterized by their FT-IR, 1 H-NMR, GC Mass spectroscopy. FT-IR spectra were recorded in KBr on Bruker FT-IR instrument (Germany), 1 H-NMR spectra were recorded on Bruker Avance 1 H-NMR spectrometer (Germany), at 400 MHz in DMSO-d6, by using varian instrument using TMS as internal standard and chemical shift values are given in ppm downfield to TMS (tetramethylsilane), GC Mass were recorded on GCMS-QP-5050 Schimadzu (Japan), and Perkin Elmer 2400 Series II CHN Elemental Analyzer. The standard drugs norfloxacin, ketoconazole, and ibuprofen were obtained as gift sample from Wockhardt Ltd., Aurangabad, India.…”

Section: Experimental Materials and Methodsmentioning

confidence: 99%

“…Despite the many chemotherapeutics available, the emergence of old and new antibiotic-resistant bacterial strains, mutations in microbial genomes, the incorrect use of antibiotics has been thoroughly demonstrated to greatly increase the development of resistant genotypes has generated a substantial need for new classes of anti-bacterial agents [1][2]. Various 2-thioxo-1,3-thiazol have been extensively investigated due to their application in different areas of biological activity such as antimicrobial [2][3], hypoglycemic [4], anti-inflammatory and analgesic agents [5], antidiabetic [6], antihyperglycemic [7].…”

Section: Introductionmentioning

confidence: 99%

“…Above mentioned facts prompted us to synthesis a series of N-(4-(aryl)-2-thioxo-1,3-thiazol-3(2H)-yl)pyridine-4-carboxamide compounds having antimicrobial and anti-inflammatory activity. The structures of the compounds were confirmed by FT-IR, 1 H-NMR, GC-mass spectroscopy and elemental analysis data studies; their antibacterial, antifungal, and antiinflammatory activities were performed by MIC (Minimum Inhibitory Concentration) method.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Some N-(4-(Aryl)-2-Thioxo-1,3-Thiazol-3(2H)-yl)Pyridine-4- Carboxamide as Antimicrobial and Anti-inflammatory Agents

Rajurkar¹

2015

Med Cherm

View full text Add to dashboard Cite

Section: Experimental Materials and Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Some N-(4-(Aryl)-2-Thioxo-1,3-Thiazol-3(2H)-yl)Pyridine-4- Carboxamide as Antimicrobial and Anti-inflammatory Agents

Rajurkar¹

2015

Med Cherm

View full text Add to dashboard Cite

“…Obtained from general procedure C as a dark solid, yield 99%; mp 126°C (lit. 125°C [47] (11,(49)(50)(51).…”

mentioning

confidence: 99%

Synthesis of a Sugar-Based Thiosemicarbazone Series and Structure-Activity Relationship versus the Parasite Cysteine Proteases Rhodesain, Cruzain, and Schistosoma mansoni Cathepsin B1

Fonseca

Cruz

Villela

et al. 2015

Antimicrob Agents Chemother

View full text Add to dashboard Cite

gThe pressing need for better drugs against Chagas disease, African sleeping sickness, and schistosomiasis motivates the search for inhibitors of cruzain, rhodesain, and Schistosoma mansoni CB1 (SmCB1), the major cysteine proteases from Trypanosoma cruzi, Trypanosoma brucei, and S. mansoni, respectively. Thiosemicarbazones and heterocyclic analogues have been shown to be both antitrypanocidal and inhibitory against parasite cysteine proteases. A series of compounds was synthesized and evaluated against cruzain, rhodesain, and SmCB1 through biochemical assays to determine their potency and structure-activity relationships (SAR). This approach led to the discovery of 6 rhodesain, 4 cruzain, and 5 SmCB1 inhibitors with 50% inhibitory concentrations (IC 50 s) of <10 M. Among the compounds tested, the thiosemicarbazone derivative of peracetylated galactoside (compound 4i) was discovered to be a potent rhodesain inhibitor (IC 50 ‫؍‬ 1.2 ؎ 1.0 M). The impact of a range of modifications was determined; removal of thiosemicarbazone or its replacement by semicarbazone resulted in virtually inactive compounds, and modifications in the sugar also diminished potency. Compounds were also evaluated in vitro against the parasites T. cruzi, T. brucei, and S. mansoni, revealing active compounds among this series. N ew drugs for parasitic diseases are urgently needed, but these globally important infections are often "neglected" because they most commonly afflict poor and marginalized communities. Current therapies are limited by poor efficacy, toxicity, high costs, and parasite resistance. Chagas disease, African sleeping sickness, and schistosomiasis are examples of diseases for which new therapies are needed (1, 2). Among the most studied and exploited molecular targets for these diseases are cysteine proteases. These enzymes have essential roles in parasite nutrition, immune evasion, host cell invasion, and metacyclogenesis (3-6). Indeed, the cysteine proteases cruzain, rhodesain, and Schistosoma mansoni CB1 (SmCB1) from Trypanosoma cruzi, Trypanosoma brucei, and S. mansoni, respectively, are validated molecular targets and have been the subject of numerous medicinal chemistry projects (7-17) that have yielded trypanocidal inhibitors, both in parasite culture and in animal models of infection (13,15,(18)(19)(20)(21).The diverse inhibitors of these enzymes comprise compound classes which bind noncovalently (11, 12) and scaffolds containing a "warhead" that binds covalently to the catalytic cysteine. Within the latter category, vinylsulfones (8,(22)(23)(24)(25), oxy-methyl ketones (7, 26), nitriles (16), epoxides, and thiosemicarbazones (13-15, 27-29) have been described previously. Thiosemicarbazones present as advantages their low molecular weight, low cost of synthesis, and nonpeptidic nature (27). Greenbaum and coworkers synthesized and evaluated the cysteine protease inhibitory and antiparasitic activities of a library of thiosemicarbazones, with promising results (13). According to those authors, the thiosemicarbazones are...

show abstract

“…Heterocyclic compounds containing thiazole moiety were found to exhibit a wide spectrum of biological activities such as antioxidant (8), antitubercular (9,10), diuretic (11), antischizophrenia (12), antibacterial (13,14), anti-inflammatory (15), anti-HIV (16), antihypertensive (17), antiallergic (18), hypnotic (19), analgesic (20), antitumor and cytotoxic (21,22). Thiazole moiety is present in many drugs such as thiamine (vitamin B 1 ), penicillin (antibiotic), sulfathiazole (antibacterial drug), 2-(4-chlorophenyl)thiazole-4-ylacetic (anti-inflammatory agent), thiabendazole [2-(4-thiazolyl)benzimidazole] (anthelmintic and fungicide), and niridazole [1-(5-nitro-2-thiazolyl)-2-imidazolidinone] (schistosomicidal agent) (23,24).…”

mentioning

confidence: 99%

Synthesis and cytotoxicity evaluation of thiazole derivatives obtained from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene- 3-carbonitrile

2017

View full text Add to dashboard Cite

Synthesis and antimicrobial activity of some new hydrazone-bridged thiazole-pyrrole derivatives

Cited by 51 publications

References 21 publications

Synthesis of Some N-(4-(Aryl)-2-Thioxo-1,3-Thiazol-3(2H)-yl)Pyridine-4- Carboxamide as Antimicrobial and Anti-inflammatory Agents

Synthesis of Some N-(4-(Aryl)-2-Thioxo-1,3-Thiazol-3(2H)-yl)Pyridine-4- Carboxamide as Antimicrobial and Anti-inflammatory Agents

Synthesis of a Sugar-Based Thiosemicarbazone Series and Structure-Activity Relationship versus the Parasite Cysteine Proteases Rhodesain, Cruzain, and Schistosoma mansoni Cathepsin B1

Synthesis and cytotoxicity evaluation of thiazole derivatives obtained from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene- 3-carbonitrile

Contact Info

Product

Resources

About