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Table 3: Antifungal activity of 1,3,4-thiadiazole derivatives
AB - A series of 5-substituted-2-phenyl-1, 3, 4-thiadiazole were prepared by the reaction of different substituted benzoylisothiocyanate with 5-amino -2-phenyl -1, 3, 4-thiadiazole. The target molecules were characterized by CHNS analysis, IR, NMR and mass spectra. All these new compounds were screened for antibacterial and antifungal activity. Some of those compounds had promising antimicrobial activity.
of phenyl hydrazine on cyclization with different aromatic carboxylic acid in POCl3 gives 2-(substituted phenyl)-5- (2-phenylhydrazinyl)-1,3,4-thiadiazole. 1,3,4-thiadiazole constitute a unique class of nitrogen and sulphur containing five member heterocycle. During the last years considerable evidence has also accumulated to demonstrate the efficacy of 1,3,4-thiadiazole including antifungal , , anticonvulsant , insecticidal, anti bacterial, anti inflammatory and other biological effects. All the compounds were characterized on the basis of IR and 1HNMR spectral data & were screened for antimicrobial activity.
Volume 39 (2016) Issue 4 Pages 502-515
The progress achieved in the synthesis of heterocyclic compounds with biological potential is due to improvement of the methodological study of tested substances too. It is known that many 1,3,4-thiadiazole derivatives have biological activity, with their , , , , antidepressive and cardiotonic action being notable. Recent research has also established for these heterocycles an activity. Taking these data into account, in the present study, some new 1,3,4-thiadiazole derivatives having a phenylhydrazine moiety have been synthesized and their structure confirmed by elemental and spectral (FT-IR, 1H-NMR, MS) analyses [-].
All melting points were determined on a Melt-Temp R apparatus equipped with a digital thermometer and are uncorrected. The IR spectra were measured as potassium bromide pellets on a Digilab Scimitar Series FT-IR Spectrophotometer; the wave numbers are given in cm-1. The 1H-NMR spectra were recorded in DMSO-d6 or CD3COCD3 solutions on Bruker ARX-300 spectrometer at ambient temperature. Chemical shifts were recorded as δ values in parts per millions (ppm) and were indirectly referenced to tetramethylsilane via residual solvent signal (2.49 for 1H). MS spectra were obtained using an instrument produced by Agilent Technologies, Wilmington, DE, USA. The instrument, Accurate Mass Q-TOF LC/MS 6520 was operated via the manufacture’s software, Mass Hunter. Samples were dissolved in acetonitrile/water mixture (95/5 v/v) to obtain a concentration of 10 μg/mL and 0.05 mL were directly injected into the electrospray source using the auto sampler at a rate of 0.05 ml/min. The instrument was operated in High resolution mode with an acquisition rate of 4 GHz. The source voltage was set at 4,000 V, the spray gas flow at 5 L/min, heating gas temperature at 325 °C and the fragmentor potential at 215 V. All chemical reagents were obtained from the Aldrich Chemical Company.
1,3,4-Thiadiazole synthesis - Organic Chemistry Portal
2-(substituted phenyl)-5-(2-phenylhydrazinyl)-1,3,4-thiadiazole: a mixture of N’’-phenylthiocarbonohydrazide (0.10 mol), an aromatic acid and phosphorous oxychloride (25 ml) was refluxed for 18-22 hr. after cooling to RT the reaction mixture was poured into the crushed ice and kept overnight. The solid thus separated was filtered, washed with water, dried and purified by recrystallization from methanol.
Novel thiophene, pyrimidine, 1,3-thiazole, 1,3,4-thiadiazole,thieno[2,3-]pyrimidine, and thiazolo[3,2-]pyrimidine derivatives bearing pyridine moiety were synthesized starting from the readily accessible 3-oxo--(pyridin-2-yl)butanamide.
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ChemInform Abstract: 1,3,4-Thiadiazole
A series of 1, 3, 4-thiadiazole derivatives were synthesized. The structures of these compounds were established by means of IR, 1H-NMR and mass spectrum analysis. All the compounds were evaluated for antibacterial and antifungal activities. Most of the compounds have shown significant antibacterial and antifungal activity when compared with the standard drugs
1,3,4-Thiadiazole-2,5-dithiol 98% | Sigma-Aldrich
A series of 5-substituted-2-phenyl-1, 3, 4-thiadiazole were prepared by the reaction of different substituted benzoylisothiocyanate with 5-amino -2-phenyl -1, 3, 4-thiadiazole. The target molecules were characterized by CHNS analysis, IR, NMR and mass spectra. All these new compounds were screened for antibacterial and antifungal activity. Some of those compounds had promising antimicrobial activity.
New 1,3,4-Thiadiazole derivatives were synthesized
N2 - A series of 5-substituted-2-phenyl-1, 3, 4-thiadiazole were prepared by the reaction of different substituted benzoylisothiocyanate with 5-amino -2-phenyl -1, 3, 4-thiadiazole. The target molecules were characterized by CHNS analysis, IR, NMR and mass spectra. All these new compounds were screened for antibacterial and antifungal activity. Some of those compounds had promising antimicrobial activity.
Find 2-Amino-1,3,4-thiadiazole available at Sigma-Aldrich.
In view of the emergence and frequency of multidrug-resistant and extensively drug-resistant tuberculosis and consequences of acquired resistance to clinically used drugs, we undertook the design and synthesis of novel prototypes that possess the advantage of the two pharmacophores of thiourea and 1,3,4-thiadiazole in a single molecular backbone. Three compounds from our series were distinguished from the others by their promising activity profiles against strain H37Rv. Compounds 11 and 19 were the most active representatives with minimum inhibitory concentration (MIC) values of 10.96 and 11.48 µM, respectively. Compound 15 was shown to inhibit strain H37Rv with an MIC value of 17.81 µM. Cytotoxicity results in the Vero cell line showed that these three derivatives had selectivity indices between 1.8 and 8.7. In order to rationalize the biological results of our compounds, molecular docking studies with the enoyl acyl carrier protein reductase (InhA) of were performed and compounds 11, 15, and 19 were found to have good docking scores in the range of −7.12 to −7.83 kcal/mol.
Synthesis of imidazo[2,1-b][1,3,4]thiadiazole–chalcones …
Compounds with thiourea, acylthiourea and thioamide moiety have been synthesized as a result of drawing inspiration from second line antituberculosis pro-drugs; ethionamide (ETH), prothionamide, thiacetazone and isoxyl (thiocarlide).–) It was already known that, ETH inhibits cell wall biosynthesis of . Baulard reported the identification of ETH-activator; Rv3854c which was then termed EthA.) Another noteworthy work, revealed the mechanism of activation of ETH due to corresponding -oxide by monooxygenase Rv3854c.) It was noted that isoxyl activation also requires EthA-mediated oxidation.) Isoxyl has been reported to be non-toxic in isoxyl-treated individulas at therapeutic doses but its poor solubility in water decreases its bioavalibility henceforth a new administration route-direct pulmonary delivery has been suggested due to refurbishment of old agents for emerging clinical needs.) All of these phenomenon maintain undivided interest in thiourea synthesis. As well as thiourea based compounds, new candidates bearing both heterocycles and thiourea moieties have been shown as promising antituberculosis agents.,,,) It is known that heterocyclic scaffolds possess a leading role in designing novel class of chemotypes as drug candidates. Among them, 1,3,4-thiadiazoles have been reported to possess a wide range of biological activities including antiproliferative, antibacterial, antifungal, and antimycobacterial functions.–) Based on reported antitumor and uricogenic activity of 2-amino-1,3,4-thiadiazole (ATDA, NSC4728); Abdel Rahman and Mohamed) synthesized 1,3-disubstituted thioureas 5-(4-bromophenyl)-1,3,4-thiadiazol-2-amine. Some analogues from this series, that unite 1,3,4-thiadiazol ring with thiourea moiety, were reported to demonstrate promising IC50 values (2.58–6.47 µm) against A549 (Non-small Cell Lung Cancer) cell line.) Another work on very similar chemotypes with our compounds has reported the synthesis of triazolothiadiazolethiones and thiadiazolothiadiazolimines that were gained by heterocyclization of -(4-chlorophenyl)/phenyl-′-[5-(4-methoxyphenyl)/(2-chlorophenyl)/phenyl-1,3,4-thiadiazol-2-yl]thioureas and -phenyl/(2-chlorophenyl)-′-(5-phenyl-1,3,4-thiadiazol-2-yl)thioureas as well as their antifungal activity against and .)
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