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1.
Hakan Bektaş Bahar B. Sökmen Sinem Aydın Emre Menteşe Adile Bektaş Gamze Dilekçi 《Journal of heterocyclic chemistry》2020,57(5):2234-2242
A new series of benzimidazole derivatives ( 1-15 ) containing 1,2,4-triazole, 1,3,4-thiadiazole, 1,3,4-oxadiazole, and thiazolidinon rings have been synthesized. All new synthesized benzimidazole compounds were confirmed by 1H NMR, 13C NMR spectra, and LC-MS, and they were examined for their antioxidant and antimicrobial activities. Compounds 7 and 1 showed the highest and the lowest antioxidant activities, respectively. The lowest minimum inhibition concentration value found in compound 5 against Enterobacter aerogenes. 相似文献
2.
Mustafa Er Hakan Tahtaci Tuncay Karakurt Abdurrahman Onaran 《Journal of heterocyclic chemistry》2019,56(9):2555-2570
In this study, a new series of substituted imidazo[2,1‐b][1,3,4]thiadiazole derivatives were synthesized. To this end, first 2‐amino‐1,3,4‐thiadiazole derivatives (compounds 2a and 2b ), the starting materials, were synthesized with high yields (82% and 79%, respectively). Then imidazo[2,1‐b][1,3,4]thiadiazole derivatives ( 4 – 16 ), the target compounds, were synthesized from reactions of 2‐amino‐1,3,4‐thiadiazole derivatives ( 2a and 2b ) with 2‐bromoacetophenone derivatives ( 3a – 3i ) (in yields of 52% to 71%). All of the synthesized compounds were characterized by 1H NMR, 13C NMR, Fourier transform infrared, elemental analysis, mass spectroscopy, and X‐ray diffraction analysis (compounds 4 – 12 , 14 , and 15 ) techniques. In vitro antifungal activity tests were performed for all of the synthesized compounds. Inhibition zones, percentage of inhibition, minimum fungicidal activity, minimum inhibitory concentration, and lethal dose values of the target compounds were determined against some plant pathogens. According to the results of the biological activity tests, all of the synthesized compounds showed moderate to high levels of antifungal activity. Theoretical calculations were performed to support the experimental results. The geometric parameters of selected compounds ( 5 , 6 , and 8 ) were optimized using the density functional theory B3LYP/6‐31G(d) method in the Gaussian 09W package program, and the frontier molecular orbitals (highest occupied molecular orbital–lowest unoccupied molecular orbital) were calculated theoretically. Finally, molecular docking studies were performed for antifungal activity studies of the selected compounds and to determine whether or not these compounds could be inhibitor agents for the 2RKV protein structure. 相似文献
3.
T. V. Melenchuk E. A. Danilova M. G. Stryapan M. K. Islyaikin 《Russian Journal of General Chemistry》2008,78(3):480-484
Refined synthetic procedure for preparation of 3,5-diamino-1,2,4-thiadiazole and 2,5-diamino-1,3,4-thiadiazole based on the reaction of dithiourea or amidinothiourea with hydrogen peroxide is developed. The optimal reagents ratio was found, and monitoring methods were developed. It resulted in the increase of the target product yield and in a shorter reaction time. On the basis of 2,5-diamino-1,3,4-thiadiazole the alkylsubstituted 1,3,4-diaminothiadiazolidines were synthesized. The compounds prepared were characterized by the elemental analysis data, the IR, 1H NMR, and electronic spectra, and also by mass spectrometry. 相似文献
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5.
Li-Hong Shen Hong-Yu Li Hui-Xia Shang Shu-Ting Tian Yi-Sheng Lai Li-Jie Liu 《中国化学快报》2013,24(4):299-302
In search of novel anticancer agents, a series of N-methyl colchiceinamide derivatives (7a-7i) containing 1,3,4-thiadiazole moieties were synthesized, and their structures were confirmed by spectral analysis. Cytotoxicity of these compounds was evaluated by MTT assay in vitro against four human tumor cell lines, i.e. A2780, A549, BEL7402, and MCF-7. The results indicated that most of the derivatives showed significant anticancer activities, particularly, compounds 7h and 7i showed more potent cytotoxic activities of all screened cancer cells than colchicine. 相似文献
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In the work discussed in this paper, a series of novel benzaldehyde derivatives containing 1,3,4-thiadiazole were prepared in high yield from 4-fluorobenzaldehyde and 2-amino-5-substituted-1,3,4-thiadiazole. The products were characterized by determination of melting point, elemental analysis, and UV–visible, IR, 1H NMR, and 13C NMR spectroscopy. The fluorescence properties of the compounds were also studied by recording their fluorescence emission spectra. 相似文献
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Synthesis and Antimicrobial Activity of Some Novel [4‐(1,2,3‐thiadiazol‐4‐yl)phenoxy]methylene anchored 1,3,4‐triazoles and 1,3,4‐thiadiazoles 下载免费PDF全文
A. G. Gadhave R. B. Gaikar S. R. Kuchekar B. K. Karale 《Journal of heterocyclic chemistry》2014,51(6):1849-1855
A series of novel [4‐(1,2,3‐thiadiazol‐4‐yl)phenoxy]methylene anchored 1,3,4‐triazoles ( 8a , 8b , 8c , 8d , 8e , 8f , 8g , 8h ) and 1,3,4‐thiadiazoles ( 9a , 9b , 9c , 9d , 9e , 9f , 9g , 9h , 9i ) were synthesized from thiosemicarbazide ( 7a , 7b , 7c , 7d , 7e , 7f , 7g , 7h , 7i , 7j ). The structures of these newly synthesized compounds were confirmed on the basis of IR, 1H‐NMR, mass spectral techniques, and elemental analysis. The in vitro antimicrobial screenings of the synthesized compounds were carried out against four bacterial pathogens, namely Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli, Pseudomonas aeruginosa and three fungal pathogens Candida albicans, Aspergillus niger and Aspergillus clavatus, using broth microdilution minimum inhibitory concentration method. The compounds 7d , 7j , 8a , 9a , 9b , and 9i exhibited promising antibacterial activity against the tested strains, whereas some compounds were found to be active against one of the tested bacterial strains. 相似文献
10.
Jie Han Feng-Yan Zhang Juan-Yu Wang Yan-Mei Wang Mei-Li Pang Ji-Ben Meng 《Liquid crystals》2013,40(8):825-833
A series of heterocyclic liquid crystalline compounds containing 1,3,4-oxadiazole/thiadiazole, furan and thiophene units were synthesised and characterised by means of electrospray ionisation-mass spectrometry (ESI-MS), high-resolution mass spectroscopy (HRMS), 1H nuclear magnetic resonance (NMR) and 13C NMR. The thermal behaviours were investigated by differential scanning calorimetry (DSC) and polarised optical microscopy (POM). The effect of the 1,3,4-oxadiazole, 1,3,4-thiadiazole, furan, thiophene and benzene rings on the liquid crystalline properties was discussed briefly in context with the geometrical and electronic factors. The results showed that the tendency to form mesophases follows the sequence: 1,4-disustituted benzene >2,5-disubstituted thiophene >2,5-disustituted furan and 1,3,4-thiadiazole >1,3,4-oxadiazole. 相似文献
11.
《Arabian Journal of Chemistry》2014,7(6):955-963
A series of 3-diphenylmethyl-6-substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives (4a–j and 5a–d) were synthesized by condensation of 4-amino-5-diphenylmethyl-4H-1,2,4-triazole-3-thiol with various substituted aromatic acids and aryl/alkyl-isothiocyanates. The structures of synthesized compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR and mass spectroscopic studies. These compounds were tested in vivo for their anti-inflammatory activity. The compounds which showed activity comparable to the standard drug ibuprofen were screened for their analgesic, ulcerogenic, lipid peroxidation and hepatotoxic effects. Compounds 6-(4-chlorophenyl)-3-diphenylmethyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (4a) and 6-(2,4-dichlorophenyl)-3-diphenylmethyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole(4c) emerged as the most active compounds of the series and were moderately more potent than the standard drug ibuprofen. 相似文献
12.
Sushmitha Bujji Praveen Kumar Edigi Naikal James Prameela Subhashini 《Journal of heterocyclic chemistry》2020,57(9):3318-3325
A series of novel 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole tethered chalcone derivatives were designed synthesized by using conventional as well as microwave assisted methods and characterized by 1H NMR, 13C NMR and mass spectral analysis. Microwave assisted synthesis caused an improvement in yield and significant reduction in the reaction time of all the derivatives. All the new synthesized derivatives were further evaluated for their anti-cancer activity against selected four human cancer cell lines; A549 (Lung), MCF-7 (Breast), Colo-205 (Colon) and A2780 (Ovarian). Among the synthesized compounds, 7b , 7c , 7d , 7e , 7g and 7h exhibited potent anticancer activity compared to control drug (etoposide). 相似文献
13.
《Journal of heterocyclic chemistry》2017,54(6):3241-3249
New derivatives of 2,5‐dimercapto‐1,3,4‐thiadiazole substituted both at one or two exocyclic sulfur atoms with a series of aroyl or ethoxycarbonyl groups were synthesized in reactions of 2,5‐dimercapto‐1,3,4‐thiadiazole salts with appropriate acid chlorides or ethyl chloroformate in mild conditions. The products were characterized by spectroscopy (1H NMR, 13C NMR, IR, and HRMS). Some from the synthesized compounds were screened in vitro and in vivo for antibacterial and antifungal activities against a panel of reference strains of microorganisms. The study revealed that ethyl S‐(5‐mercapto‐1,3,4‐thiadiazol‐2‐yl) carbonothioate seems to be the most active and versatile compound against Gram‐positive bacteria, Gram‐negative bacteria, and plant pathogenic fungi. 相似文献
14.
Man Ge Jie Feng Hailian Huang Xiaofeng Gou Chengwen Hua Bang Chen Junlong Zhao 《Journal of heterocyclic chemistry》2019,56(12):3297-3302
Six novel derivatives of 2‐ferrocenyl‐5‐aryl‐1,3,4‐oxadiazoles have been synthesized through catalytic oxidation of benzoylhydrazone with nitrophthalocyanine iron (II) as catalyst and tert‐butyl hydroperoxide as oxidant. All of the compounds have been characterized by high‐resolution mass spectrometry, 1H, 13C NMR, and infrared spectroscopy. Moreover, the antifungal activities of all new compounds have been evaluated and the results showed that the compounds exhibited excellent antifungal activities. In addition, the molecular structure of compound 1c could also be determined by X‐ray single‐crystal diffraction. 相似文献
15.
Zeba N. Siddiqui Farheen Farooq T.N. Mohammed Musthafa Anis Ahmad Asad U. Khan 《Journal of Saudi Chemical Society》2013,17(2):237-243
Two novel halopyrazole derivatives (3, 5) were synthesized from 5-chloro-3-methyl-1-phenylpyrazole-4-carboxaldehyde (1) using appropriate synthetic routes. Newly synthesized compounds were characterized using elemental analysis, spectral data (IR, 1H NMR, 13C NMR and mass spectrometry) and were evaluated for their in vitro antimicrobial activity. The minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC) and minimum fungicidal concentration (MFC) were determined for the test compounds as well as for reference standards. The investigation of antimicrobial screening revealed that compounds (3, 5) showed good antibacterial and antifungal activities, respectively. 相似文献
16.
In the present investigation, we describe some novel calixarene based heterocyclic compounds (5a-5i) in which 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives have been coupled with 5,11,17,23-tetra-tert-butyl-25,27-bis(chlorocarbonyl-methoxy)-26,28-dihydroxy calix[4]arene. All the newly synthesized calixarene based heterocyclic compounds have been characterized by elemental analysis and various spectroscopic methods like FTIR, (1)H NMR, (13)C NMR, and FAB-MS. All the final scaffolds have been subjected to antioxidant activity, in vitro antimicrobial screening against two gram (+ve) bacteria (S. aureus, S. pyogenes), two gram (-ve) bacteria (E. coli, P. aeruginosa) and two fungal strains (C. albicans, A. clavatus) and also have been screened for their antitubercular activity against Mycobacterium tuberculosis H(37)Rv. 相似文献
17.
《Journal of heterocyclic chemistry》2017,54(1):183-193
In this study, thiazole derivatives containing Schiff bases ( 7a , 7b , 7c , 7d , 7e , 7f , 8a , 8b , 8c , 8d , 8e , 8f , 9a , 9b , 9c , 9d , 9e , 9f ) were synthesized in moderate to high yields (49–94%) using the Hantzsch reaction with thiosemicarbazone derivatives ( 5a , 5b , 5c ) and 2‐bromo‐1‐phenylethanone derivatives ( 6a , 6b , 6c , 6d , 6e , 6f ). The structures of synthesized compounds were elucidated by IR, 1H NMR, 13C NMR, elemental analyses, mass spectroscopy and X‐ray diffraction analysis techniques. Moreover, the synthesized compounds were tested for their in vitro antifungal activity and most of them exhibited moderate to good activity against Fusariumoxysporumf.sp. lycopersici. 相似文献
18.
In the present work, we synthesized new sulfonamide derivatives with 1,3,4‐oxadiazole moiety and tetrazole ring. The synthesized derivatives of sulfonamides were characterized through Fourier transform infrared, 13C‐APT‐NMR, 1H‐NMR, and high‐resolution liquid chromatography–mass spectrometry. The biological activities of resulting compound were also investigated and observed that the compounds reveal strong antimicrobial activity over some important bacterial strains including Bacillus subtilis ATCC 6633, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 13883, and Staphylococcus aureus ATCC 29213. The in vitro antifungal properties of synthesized compounds were also a target using Candida albicans NRRL Y‐477 and Saccharomyces cerevisiae fungal strains. We have provided a useful guideline for future studies about the effect of the chemical structures of sulfonamide compounds on the biological activities. Among the target compounds, 7b , 7c , 7d , and 7e demonstrated surprisingly high antimicrobial activities than did others. 相似文献
19.
New interesting class of novel polyhydrazides containing 1,3,4-thiadiazole moieties in the main chain was synthesized. A solution polycondensation technique was used in the synthesis of these polymers. The new monomer namely: 2,5-bis(mercapto-acetichydrazide)-1,3,4-thiadiazole III was synthesized from the nucleophilic replacement of 2,5-dimercapto-1,3,5-thiadiazole I with ethylchloroacetate, followed by hydrazinolysis. The model compound VII was synthesized from the monomer 2,5-bis(mercapto-acetichydrazide)-1,3,4-thiadiazole III with benzoyl chloride and characterized by 1H- NMR, IR, and elemental analyses. The polyhydrazides were synthesized from the polymerization of monomer III with 4,4′-biphenic, 3,3′-azodibenzoyl, 4,4′-azodibenzoyl dichlorides. These polymers were characterized by elemental and spectral analyses, viscometry and solubility. The thermal properties of these polymers were determined by thermal gravimetric analyses, and differential thermal analysis, and correlated with their structure. The crystallinity of some polymers was tested by X-ray analyses. 相似文献
20.
Novel steroidal (6R)‐spiro‐1,3,4‐thiadiazoline derivatives were synthesized by the cyclization of steroidal thiosemicarbazones with acetic anhydride, screened in vitro against antibacterial activity using disc‐diffusion method and the minimum inhibitory concentration. The results showed that steroidal thiadiazoline derivatives exhibited better antibacterial activity than the steroidal thiosemicarbazone derivatives. Chloro and acetoxy substituents on the 3β‐position of the steroidal thiadiazoline ring increased the antibacterial activity. Among all the compounds, compound 7 and 8 were found better inhibitors of both types of bacteria (Gram‐positive and Gram‐negative) as compared to the respective drug amoxicillin. All the synthesized compounds were well characterized by spectroscopic methods such as IR, 1H‐NMR, 13C‐NMR mass, and elemental analysis and their stereochemistry was also discussed. 相似文献