- Synthesis and antifungal activities of 5-(o-hydroxy phenyl)-2-[4'aryl-3' chloro-2'azetidinon-1-yl]-1,3,4-thiadiazole
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New series of 5-(o-hydroxy phenyl)-2-[4'aryl-3'chloro-2'azetidinon- 1-yl]-1,3,4-thiadiazole have been synthesized and the structures of the new compounds were established on the basis of IR, 1H NMR spectral data. In vitro antifungal activity (MIC activity) was evaluated and compared with standard drugs of ketoconazole. Compounds 3c in the series has shown interesting antifungal activity against both C. albicans and A. niger fungus. In the gratifying result, most of the compounds were found to have moderate antifungal activity.
- Gupta, Shiv K.,Sharma,Bansal,Kumar
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- Synthesis, in vitro thymidine phosphorylase activity and molecular docking study of thiadiazole bearing isatin analogs
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A series of seventeen analogs (1─17) were synthesized and characterized through different spectroscopic techniques such as 1H, 13CNMR, HR-EI-MS and were evaluated for in vitro thymidine phosphorylase inhibition. All compounds showed excellent to good thymidine phosphorylase activity having IC50 value ranging between 4.10 ± 0.20 and 54.60 ± 1.40?μM when compared with standard drug 7-deazaxanthine (IC50 = 38.68 ± 1.12?μM). Among the series, compounds 1 (IC50 = 8.30 ± 0.30?μM), 6 (IC50 = 6.30 ± 0.10?μM), 11 (IC50 = 8.40 ± 0.30?μM) and 16 (IC50 = 4.10 ± 0.20?μM) were found more potent. Potent compounds were further subjected to molecular docking study to identify their interactions with the active site of amino acid. Structure activity relationship was done for all analogs mostly based on substitution pattern on phenyl and isatin rings. Graphic abstract: [Figure not available: see fulltext.]
- Ullah, Hayat,Liaqat, Anjum,Khan, Qudrat Ullah,Taha, Muhammad,Khan, Fahad,Rahim, Fazal,Uddin, Imad,Rehman, Zia Ur
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p. 213 - 224
(2021/09/09)
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- Synthesis, characterization and biological activity study of some new metal complexes with schiff's bases derived from [o-vanillin] with [2-amino-5-(2-hydroxy-phenyl)-1,3,4-thiadiazole]
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This study involves the preparation of a new series of dinuclear complexes Cr(III), Co(II), Ni(II), Cu(II) and Zn(II) complexes of the Schiff base (H2L) derived from Vanillin with 2amino-5-(2-hydroxy-phenyl)-1,3,4-thiadiazole has been synthesized tetradentate Schiff base ligands were used for complexation upon two metal ions of Cr(III),Co(II), Ni(II), Cu(II) and Zn(II) as dineucler formula M2L2.4H2O and M2L2. These ligands can be characterization IR ,UV-Vis , Mass, 1H-NMR and elemental microanalysis. The Synthesized complexes were characterized by IR, spectroscopy ,elemental microanalysis, electronic spectra, magnetic susceptibility conductive ,thermal Analysis (TGA) and atomic absorption on the basis of analytical data, the stoichiometry of metal to ligand in complexes and Schiff bases ligand. The Structures of complexes were proposed from the measurements. The bioactivity of the prepared complexes has been examined with antibacterial activity. Antimicrobial activities of the Schiff base ligand and their metal complexes reveal that the Schiff base transition metal complexes show significant activity against some fungi and bacteria.
- Shaalan, Naser,Mahdi, Shatha
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p. 4059 - 4067
(2021/07/31)
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- Further insight into the dual COX-2 and 15-LOX anti-inflammatory activity of 1,3,4-thiadiazole-thiazolidinone hybrids: The contribution of the substituents at 5th positions is size dependent
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Herin we report the design, synthesis, full characterization and biological investigation of new 15-LOX/COX dual inhibitors based on 1,3-thiazolidin-4-one (15-lipoxygenase pharmacophore) and 1,3,4-thiadiazole (COX pharmacophore) scaffolds. This series of molecular modifications is an extension of a previously reported series to further explore the structural activity relationship. Compounds 3a, 4e, 4n, 4q, 7 and 8 capable of inhibiting 15-LOX at (2.74, 4.2, 3.41, 10.21, 3.71 and 3.36 μM, respectively) and COX-2 at (0.32, 0.28, 0.28, 0.1, 0.28 and 0.27 μM, respectively). The results revealed that binding to 15-LOX and COX is sensitive to the bulkiness of the substituents at the 5 positions. 15-LOX bind better with small substituents, while COXs bind better with bulky substituents. Compounds 3a, 4r and 4q showed comparable in vivo anti-inflammatory activity to the reference drug (celecoxib). The ulcer liability test showed no sign of ulceration which ensures the safe gastric profile. Docking study was performed to explore the possible mode of interaction of the new compounds with the active site of human 15-LOX and COX-2. This study discloses some structural features for binding to 15-LOX and COX, thus pave the way to design anti-inflammatory agents with balanced dual inhibition of these enzymes.
- Abdel-Moty, Samia G.,Abdu-Allah, Hajjaj H. M.,Omar, Yasser M.
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- Synthesis, in vitro and in silico Anti-Proliferative Studies of Novel Piperiene-Oxadiazole and Thiadiazole Analogs
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Piperine is a component of pepper which has earlier been reported as anticancer active compound. This work is emphasized on the design and synthesis of new hybrid piperine analogs by coupling piperine with the amine group of oxadiazoles and thiadiazoles.
- Amperayani,Parimi
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p. 2301 - 2307
(2020/01/08)
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- Non-typical fluorescence effects and biological activity in selected 1,3,4-thiadiazole derivatives: Spectroscopic and theoretical studies on substituent, molecular aggregation, and pH effects
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The below article presents the results of spectroscopic research, theoretical (timedependent density functional theory (TD-DFT)), microbiological, and antioxidative calculations for three compounds from the group of 1,3,4-thiadiazoles: 2-amino-5-phenyl-1,
- Budziak, Iwona,Karc, Dariusz,Makowski, Marcin,Rachwa?, Kamila,Starzak, Karolina,Matwijczuk, Alicja,My?liwa-Kurdziel, Beata,Oniszczuk, Anna,Combrzyński, Maciej,Podle?na, Anna,Matwijczuk, Arkadiusz
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- Synthesis and Biological Evaluation of Some Heterocyclic Compounds from Salicylic Acid Hydrazide
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Different heterocyclic compounds were prepared starting from 2-hydroxy benzohydrazide; for example, cyclization of hydrazide hydrazone 3 derived from 2-hydroxybenzohydrazide 2 with acetic anhydride or concentrated sulfuric acid gave 1,3,4-oxadiazole derivatives 4–5. On the other hand, direct cyclization of 2-hydroxy benzohydrazide 2 with one carbon cyclizing agent gave a new derivative of 1,3,4-oxadiazole 7, 8, 9, 10, 11. Heating of hydrazide hydrazone 3 with thioglycolic acid in pyridine gave thiazolidinone 12. When 2-hydroxy benzohydrazide 2 reacted with aliphatic carboxylic acids such as formic acid or acetic acid, it gave the corresponding N-formyl or N-acetyl derivatives 6. Subsequent cyclization of 6 using phosphorous pentasulphide in pyridine gave 1,3,4-thiadiazoles 13. Cyclization of 2-hydroxy benzohydrazide with ethyl acetoacetate gives pyrazolone derivative 14. Finally, when an ethanolic solution of acid hydrazide 2 was treated with ammonium thiocyanate in 35% HCl, it gave the thiosemicarbazide 15. Subsequent treatment of 15 with concentrated sulfuric acid or 10% sodium hydroxide gave 5-amino-1,3,4-thiadiazole 16 and 1,2,4-triazole 17, respectively. The structures of all newly isolated compounds were confirmed using1H NMR, IR spectra, and elemental analyses. The antimicrobial activities for all isolated compounds were examined against different microorganisms.
- Sarshira,Hamada,Moghazi,Abdelrahman
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p. 1970 - 1982
(2016/11/23)
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- Alpha-amino phosphonate compound with 2-amino-1, 3, 4-thiadiazole structure and preparation method and application of alpha-amino phosphonate compound
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The invention discloses an alpha-amino phosphonate compound with a 2-amino-1, 3, 4-thiadiazole structure and a preparation method and application of alpha-amino phosphonate compound. The alpha-amino phosphonate compound has the sterilizing effect of alpha-amino phosphonate compounds and has a pesticide effect by introducing the 2-amino-1, 3, 4-thiadiazole group, and the alpha-amino phosphonate compound is wide in application range and good in sterilizing and pesticide effect by combining the alpha-amino phosphonate compound with the 2-amino-1, 3, 4-thiadiazole group. The preparation method is few in step, simple to operate, high in yield and productivity, capable of saving a large amount of time and cost in actual production and good in economic benefit. The 2-amino-1, 3, 4-thiadiazole has an inhibition effect on the growth and proliferation of alternaria solani and on the growth of mythimna separata and can be used as the pesticide intermediate to apply to the preparation of different agricultural fungicide.
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Paragraph 0060; 0061
(2016/12/26)
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- Thiadiazole phosphamide compound, preparation method thereof, and applications of thiadiazole phosphamide compound as pesticide
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The invention discloses a thiadiazole phosphamide compound, a preparation method thereof, and applications of the thiadiazole phosphamide compound as a pesticide. The thiadiazole phosphamide compound possesses high efficiency and low toxicity of O,O-diethyl phosphoramidothioate as an intermediate, high efficiency, broad spectrum, low residue, and low drug resistance of chlorpyrifos, short residual period, and excellent preventing and controlling effect on injurious insects of tea trees, mulberry, vegetables, and fruit trees, and soil insects and warehouse pest-insects. The preparation method comprises a few steps; operation is simple; yield and productivity are high; a large amount of time and cost are saved in practical production; and economic benefit is high. The thiadiazole phosphamide compound also possesses inhibition effects on growth of gloeosporium musarum, alternaria solani, fusarium oxysporum, and fusarium oxysporum f.sp.cubense, and can be used in preparation and applications of different agricultural fungicides as a pesticide intermediate.
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Paragraph 0062; 0063
(2017/04/03)
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- Molecular sieves promoted, ultrasound-mediated synthesis, biological evaluation and docking study of 3-(5-substituted-1,3,4-thiadiazol-2-ylimino)indolin-2-ones as a potential anticonvulsant agents
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In this work, the combined use of ultrasonic energy and molecular sieves was investigated for synthesis of 3-(5-substituted-1,3,4-thiadiazol-2-ylimino)indolin-2-one derivatives 5(a-j). The equimolar quantities of 5-substituted-1,3,4-thiadiazol-2-amine and
- Nikalje, Anna Pratima G.,Shaikh, Sameer I.,Kalam Khan, Firoz A.,Shaikh, Shoaib,Sangshetti, Jaiprakash N.
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p. 4058 - 4069
(2015/11/02)
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- Synthesis and pharmacological activity of certain thiadiazolo [2',3':2,3] imidazo [4,5-B] quinoxalines
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Derivatives of thiadiazolo [2',3':2,3] imidazo [4,5-b] quinoxalines were synthesized by the reaction of 5-substituted-1,3,4-thiadiazol-2-amine with 2,3-dichloro-6,7- dinitroquinoxalines. The synthesized compounds were characterized by using spectral data. They were then screened for analgesic, anti-inflammatory and ulcerogenic activity.
- Visagaperumal,Jayakumar,Anbalagan
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p. 311 - 314
(2019/01/21)
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- Thiadiazole derivatives as potential anticonvulsant agents
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A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR,1HNMR,13C NMR and mass spectral data confir
- Mullick, Pooja,Khan, Suroor A.,Verma, Surajpal,Alam, Ozair
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experimental part
p. 1011 - 1016
(2012/01/03)
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- Synthesis, characterization and antimicrobial activity of new thiadiazole derivatives
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A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR, 1H NMR, 13C NMR and mass spectral data confirmed the
- Mullick, Pooja,Khan, Suroor A.,Verma, Surajpal,Alam, Ozair
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experimental part
p. 2345 - 2350
(2010/11/16)
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- Thiadiazolyl quinazolones as potential antiviral and antihypertensive agents
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Phthalic anhydride on treatment with β-ethanol amine gives N-hydroxy ethyl phthalimide I which reacts with anthranilic acid in presence of ethanol containing concentrated hydrochloric acid affording 5-(N-ethylphthalimido)- anthranilic acid 2. This on treatment with benzoyl chloride in pyridine gives 6-(N-ethyl phthalimido)-2-phenyl-4-oxo-3, 4-dihydrobenzoxazine 3 which on reaction with 2-amino-5-aralkyl-1, 3, 4-thiadiazoles 4 in pyridine results in the formation of 6-(N-ethylphthalimido)-3-[2′-(5′-aralkyl-1′, 3′, 4′-thiadiazolyl)]-2-phenyl-4-oxo-(3H)-quinazolines 5. The antiviral and antihypertensive activities of 5 have been reported.
- Pandey,Tusi, Sarah,Tusi, Zehra,Raghubir,Dixit,Joshi,Bajpai
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p. 180 - 183
(2007/10/03)
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