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Journal articles on the topic '3-oxadiazol'

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Published: 4 June 2021
Last updated: 12 February 2022

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1

Stepanova, Elena V., and Andrei I. Stepanov. "UNUSUAL WAY OF REACTION OF 3-AMINO-4-(5-CHLOROMETHYL-1,2,4-OXADIAZOLE-3-YL)-FURAZAN WITH HYDRAZINE." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 60, no. 4 (May 12, 2017): 26. http://dx.doi.org/10.6060/tcct.2017604.5522.

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The results of our study of the pathways of selective reactivity of 3-amino-4-(5-chloromethyl-1,2,4-oxadiazole-3-yl)furazan versus 5-unsubstituted or 5-methyl and 5-trifluoromethyl substituted 4-(5R-1,2,4-oxadiazole-3-yl)furazans (R = H, Me, CF3) towards the action of hydrazine are discussed. If the reductive opening of 1,2,4-oxadiazole ring in unsubstituted at the С-5 atom (1,2,4-oxadiazol-3-yl)furazan derivatives under the treatment with hydrazine can be used as a method for the preparation of a range of amidrazones of 4-R-furazan-3-carboxylic acid. 3-amino-4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)furazan with hydrazine gives amidoxime of 4-aminofurazan-3-carboxylic acid. 3-amino-4-(5-methyl-1,2,4-oxadiazol-3-yl) furazan is inert to the action of hydrazine, on the contrary the reaction of 3-amino-4-(5-chloromethyl-1,2,4-oxadiazole-3-yl)furazan with hydrazine leads to oxidation of chloromethyl group of titled compound to the carbonyl one. In this case the product of reaction of 3-amino-4-(5-chloromethyl-1,2,4-oxadiazole-3-yl)furazan with hydrazine was isolated in a form of corresponding hydrazonomethyl derivative notably as 3-amino-4-(5-hydrazonomethyl-1,2,4-oxadiazole-3-yl)furazan. A possible reaction mechanism for the formation of hydrazonomethyl group by oxidation reaction of chloromethyl group by hydrazine is proposed. 3-Amino-4-(5-hydrazonomethyl-1,2,4-oxadiazol-3-yl)furazan undergoes a transhydrazination reaction with semicarbazide and thiosemicarbazide. But our attempts to its hydrolysis for the purpose to obtain free aldehyde were unsuccessful. Thus, hydrolysis of hydrazonomethyl derivative in acetic acid in the presence of catalytic amount of sulfuric acid results in azine – N,N'-bis(3-(4-aminofurazan-3-yl)-1,2,4-oxadiazol-5-ylmethylyden)hydrazine – precipitation, long-duration boiling in hydrochloric acid leads to Kishner-Wolff reduction of the carbonyl group to 3-amino-4-(5-methyl-1,2,4-oxadiazol-3-yl)furazan, and hydrolysis in alkaline medium leads to 1,2,4-oxadiazole ring opening to amidoxime of 4-aminofurazan-3-carboxylic acid. Synthesis of 3-amino-4-(5-chloromethyl-1,2,4-oxadiazole-3-yl)furazan (R = CH2Cl) was carried out by condensation of amidoxime of 4-aminofurazan-3-carboxylic acid with an excess of chloroacetyl chloride in toluene at elevated temperature. The reaction proceeds through formation of intermediate product – 3-chloromethylamino-4-(5-chloromethyl-1,2,4-oxadiazol-3-yl)furazan. Removing of N-chloroacetyl group in such obtained intermediate was performed by hydrolysis in acidic media. One-pot synthesis without the need for isolation and purification of intermediate is allowed. The structures of obtained compounds were proved by modern methods of physical-chemical analysis (1H, 13C NMR, IR and MS spectroscopy).Forcitation:Stepanova E.V., Stepanov A.I. Unusual way of reaction of 3-amino-4-(5-chloromethyl-1,2,4-oxadiazole-3-yl)furazan with hydrazine. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 4. P. 26-32.
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2

Tang, Yongxing, Chunlin He, Lauren A. Mitchell, Damon A. Parrish, and Jean'ne M. Shreeve. "Energetic compounds consisting of 1,2,5- and 1,3,4-oxadiazole rings." Journal of Materials Chemistry A 3, no. 46 (2015): 23143–48. http://dx.doi.org/10.1039/c5ta06898c.

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3-Nitroamino-4-(5-amino-1,3,4-oxadiazol-2-yl)furazan monohydrate (2·H2O), which is a combination of the nitroaminofurazan and 1,3,4-oxadiazole rings, was obtained by the nitration of 3-amino-4-(5-amino-1,3,4-oxadiazol-2-yl)furazan (1) with 100% nitric acid.
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3

Pagoria, Philip, Maoxi Zhang, Ana Racoveanu, Alan DeHope, Roman Tsyshevsky, and Maija Kuklja. "3-(4-Amino-1,2,5-oxadiazol-3-yl)-4-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole." Molbank 2014, no. 2 (May 22, 2014): M824. http://dx.doi.org/10.3390/m824.

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4

Saini, Sachin. "Synthesis and Anticonvulsant Studies of Thiazolidinone and Azetidinone Derivatives from Indole Moiety." Drug Research 69, no. 08 (December 20, 2018): 445–50. http://dx.doi.org/10.1055/a-0809-5098.

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Abstract2-Amino-5-(3’-indolomethylene)-1, 3 , 4 - oxadiazole (3) undergoes facile condensation with various aromatic aldehydes to gave 2-substitiuted arylidenylamino-5-(3’- indolomethylene) – 1, 3 , 4 – oxadiazole (4–8). Cyclocondensation of (4–8) with thioglycolic acid and triethylamine yielded 3-[5’-(3”- indolomethylene)- 1’, 3’, 4’- oxadiazol-2’-yl]- 2- (substituted aryl)-4- thiazolidinones (9–13) and 1-[5’-(3”- indolomethylene) -1’, 3’, 4’- oxadiazol - 2’- yl ] -4-(substituted aryl) -2- azetidinones (14–18). The structures of these compounds were established on the basis of analytical and spectral data. The newly synthesised compounds were evaluated for their anticonvulsant activity and acute toxicity.
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5

Maftei, Catalin V., Elena Fodor, Peter G. Jones, M. Heiko Franz, Gerhard Kelter, Heiner Fiebig, and Ion Neda. "Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties." Beilstein Journal of Organic Chemistry 9 (October 25, 2013): 2202–15. http://dx.doi.org/10.3762/bjoc.9.259.

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Taking into consideration the biological activity of the only natural products containing a 1,2,4-oxadiazole ring in their structure (quisqualic acid and phidianidines A and B), the natural product analogs 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4) and 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7) were synthesized starting from 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) in two steps by isolating the intermediates 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobutanoic acid (3) and (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic acid (6). The two natural product analogs 4 and 7 were then tested for antitumor activity toward a panel of 11 cell lines in vitro by using a monolayer cell-survival and proliferation assay. Compound 7 was the most potent and exhibited a mean IC50 value of approximately 9.4 µM. Aniline 1 was synthesized by two routes in one-pot reactions starting from tert-butylamidoxime and 4-aminobenzoic acid or 4-nitrobenzonitrile. The structures of compounds 1, 2, 4, 5 and 6 were confirmed by X-ray crystallography.
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6

Jia, Si-Yuan, Bo-Zhou Wang, Xue-Zhong Fan, Ping Li, and Seik Weng Ng. "4-[4-(4-Amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazol-3-yl]-1,2,5-oxadiazol-3-amine." Acta Crystallographica Section E Structure Reports Online 68, no. 5 (April 28, 2012): o1573. http://dx.doi.org/10.1107/s1600536812017825.

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7

Xiong, Hualin, Hongwei Yang, Caijin Lei, Pengjiu Yang, Wei Hu, and Guangbin Cheng. "Combinations of furoxan and 1,2,4-oxadiazole for the generation of high performance energetic materials." Dalton Transactions 48, no. 39 (2019): 14705–11. http://dx.doi.org/10.1039/c9dt02684c.

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Energetic materials, comprising furoxan and 1,2,4-oxadiazole backbones, were synthesized by nitrating 3,3′-bis(5-amino-1,2,4-oxadiazol-3-yl)-4,4′-azofuroxan, followed by cation metathesis, giving compounds with high density, high detonation performance and acceptable sensitivities.
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8

Tkachuk, V., T. Lyubchuk, T. Tkachuk, and O. Hordiyenko. "A DEVELOPMENT OF AN EFFECTIVE METHOD FOR THE SYNTHESIS OF 2-(5-OXO-4,5-DIHYDRO-1,2,4-OXADIAZOL-3-YL)BENZOIC ACID." Bulletin of Taras Shevchenko National University of Kyiv. Chemistry, no. 1 (57) (2020): 51–54. http://dx.doi.org/10.17721/1728-2209.2020.1(57).13.

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2-(5-Oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoic acid was synthesized using a new effective method – thermal heterocyclization of 3-(hydroxyimino)isoindolin-1-one, which occurs as a result of its interaction with 1,1'-carbonyldiimidazole (CDI) and subsequent base-promoted cycleopening of the obtained intermediate 3H,5H-[1,2,4]oxadiazolo[3,4-a]isoindole-3,5-dione. Direct cyclization of 3-(hydroxyimino)isoindolin-1-one by the reaction with diethyl carbonate in the presence of sodium ethylate in ethanol at room temperature and under heating was unsuccessful. The same result was observed when using triphosgene in the presence of triethylamine in dichloromethane. Treating 3-(hydroxyimino)isoindolin-1-one with methyl chloroformate gave 3-(((methoxycarbonyl)oxy)-imino)isoindolin-1-one which was thermally stable and was not cyclized into the desired acid by boiling in toluene and o-xylene for 24 hours. The reflux of the excess of CDI with 3-(hydroxyimino)isoindolin-1-one in anhydrous ethyl acetate and subsequent alkaline hydrolysis gave the desired 2-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoic acid in a total yield of 90%. An attempt to stop the process at the stage of formation of the intermediate 3H,5H-[1,2,4]oxadiazolo[3,4-a]isoindole-3,5-dione by carrying out the reaction in the absence of a base failed. Its partial hydrolysis took place during the reaction, and especially at the stage of isolation, and as a result a mixture of 3H,5H-[1,2,4]oxadiazolo[3,4-a]isoindole-3,5-dione and 2-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoic acid was formed in a ratio of about 2:3. The obtained substance after mixing with aqueousmethanolic NaOH solution and subsequent acidification with 1M HCl was quantitatively converted into the pure desired acid. The developed method allows the use of 3-(hydroxyimino)isoindolin-1-ones as convenient starting materials for the preparation of vic-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)aromatic acids and subsequently related compounds, in particular isomeric vic-carbamimidoyl(hetero)aromatic carboxylic acids, which cannot be obtained by other currently known methods. All the compounds obtained during the development of the method were studied by means of NMR spectroscopy.
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9

Wu, Xiang-Wen, Meng-Meng Xin, Jian-Ping Ma, Zhen-Hua Wu, and Yu-Bin Dong. "The coordination chemistry of two symmetric double-armed oxadiazole-bridged organic ligands with copper salts." Acta Crystallographica Section C Crystal Structure Communications 69, no. 6 (May 15, 2013): 601–5. http://dx.doi.org/10.1107/s0108270113010913.

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Two new symmetric double-armed oxadiazole-bridged ligands, 4-methyl-{5-[5-methyl-2-(pyridin-3-ylcarbonyloxy)phenyl]-1,3,4-oxadiazol-2-yl}phenyl pyridine-3-carboxylate (L1) and 4-methyl-{5-[5-methyl-2-(pyridin-4-ylcarbonyloxy)phenyl]-1,3,4-oxadiazol-2-yl}phenyl pyridine-4-carboxylate (L2), were prepared by the reaction of 2,5-bis(2-hydroxy-5-methylphenyl)-1,3,4-oxadiazole with nicotinoyl chloride and isonicotinoyl chloride, respectively. LigandL1 can be used as an organic clip to bind CuIIcations and generate a molecular complex, bis(4-methyl-{5-[5-methyl-2-(pyridin-3-ylcarbonyloxy)phenyl]-1,3,4-oxadiazol-2-yl}phenyl pyridine-3-carboxylate)bis(perchlorato)copper(II), [Cu(ClO4)2(C28H20N4O5)2], (I). In compound (I), the CuIIcation is located on an inversion centre and is hexacoordinated in a distorted octahedral geometry, with the pyridine N atoms of twoL1 ligands in the equatorial positions and two weakly coordinating perchlorate counter-ions in the axial positions. The two arms of theL1 ligands bend inward and converge at the CuIIcoordination point to give rise to a spirometallocycle. LigandL2 binds CuIcations to generate a supramolecule, diacetonitriledi-μ3-iodido-di-μ2-iodido-bis(4-methyl-{5-[5-methyl-2-(pyridin-4-ylcarbonyloxy)phenyl]-1,3,4-oxadiazol-2-yl}phenyl pyridine-4-carboxylate)tetracopper(I), [Cu4I4(CH3CN)2(C28H20N4O5)2], (II). The asymmetric unit of (II) indicates that it contains two CuIatoms, oneL2 ligand, one acetonitrile ligand and two iodide ligands. Both of the CuIatoms are four-coordinated in an approximately tetrahedral environment. The molecule is centrosymmetric and the four I atoms and four CuIatoms form a rope-ladder-type [Cu4I4] unit. Discrete units are linked into one-dimensional chains through π–π interactions.
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10

Jin, Guoxia, Yuqi Ji, Teng Wang, Yanyan Sun, Yulong Li, Guiying Zhu, and Jianping Ma. "Syntheses and characterization of dinuclear and tetranuclear AgI supramolecular complexes generated from symmetric and asymmetric molecular clips containing oxadiazole rings." Acta Crystallographica Section C Structural Chemistry 75, no. 10 (September 6, 2019): 1327–35. http://dx.doi.org/10.1107/s2053229619011744.

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A new asymmetric ligand, 5-{3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(pyridin-3-yl)-1,3,4-oxadiazole (L5), which contains two oxadiazole rings, was synthesized and characterized. The assembly of symmetric 2,5-bis(pyridin-3-yl)-1,3,4-oxadiazole (L1) and asymmetric L5 with AgCO2CF3 in solution yielded two novel AgI complexes, namely catena-poly[[di-μ-trifluoroacetato-disilver(I)]-bis[μ-2,5-bis(pyridin-3-yl)-1,3,4-oxadiazole]], [Ag2(C2F3O2)2(C12H8N4O)2] n or [Ag2(μ2-O2CCF3)2(L1)2] n (1), and bis(μ3-5-{3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(pyridin-3-yl)-1,3,4-oxadiazole)tetra-μ3-trifluoroacetato-tetrasilver(I) dichloromethane monosolvate, [Ag4(C2F3O2)4(C22H15N5O2)2]·CH2Cl2 or [Ag2(μ3-O2CCF3)2(L5)]2·CH2Cl2 (2). Complex 1 displays a one-dimensional ring–chain motif, where dinuclear Ag2(CF3CO2)2 units alternate with Ag2(L1)2 macrocycles. This structure is different from previously reported Ag–L1 complexes with different anions. Complex 2 features a tetranuclear supramolecular macrocycle, in which each ligand adopts a tridentate coordination mode with the oxadiazole ring next to the p-tolyl ring coordinated and that next to the pyridyl ring free. Two L5 ligands are bound to two Ag1 centres through two oxadiazole N and two pyridyl N atoms to form a macrocycle. The other two oxadiazole N atoms coordinate to the two Ag2 centres of the Ag2(O2CCF3)4 dimer. Each CF3CO2 − anion adopts a μ3-coordination mode, bridging the Ag1 and Ag2 centres to form a tetranuclear silver(I) complex. This study indicates that the donor ability of the bridging oxadiazole rings can be tuned by electron-withdrawing and -donating substituents. The emission properties of ligands L1 and L5 and complexes 1 and 2 were also investigated in the solid state.
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11

Mohammadi-Khanaposhtani, Maryam, Kiana Fahimi, Elahe Karimpour-Razkenari, Maliheh Safavi, Mohammad Mahdavi, Mina Saeedi, and Tahmineh Akbarzadeh. "Design, Synthesis and Cytotoxicity of Novel Coumarin-1,2,3-triazole-1,2,4- Oxadiazole Hybrids as Potent Anti-breast Cancer Agents." Letters in Drug Design & Discovery 16, no. 7 (June 27, 2019): 818–24. http://dx.doi.org/10.2174/1570180815666180627121006.

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Background: This work reports design, synthesis, and in vitro cytotoxicity of novel coumarin-1,2,3-triazole-1,2,4-oxadiazole hybrids against three breast cancer cell lines MCF-7, MDA-MB-231, and T-47D. Methods: Synthetic procedure for the preparation of desired compounds was started from the reaction of coumarins or with propargyl bromide to give O-propargylated coumarins or 5. Then, click reaction between the later compounds and 3-aryl-5-(chloromethyl)-1,2,4-oxadiazoles afforded the desired products in good yields. Results: Among the synthesized compounds, 4-((1-((3-(4-chlorophenyl)-1,2,4-oxadiazol-5- yl)methyl)-1H-1,2,3-triazol-4-yl)methoxy)-2H-chromen-2-one (9a) showed the best cytotoxicity against breast cancer cell lines. Conclusion: Compound 9a depicted the most activity toward MDA-MB-231 and T-47D cells while compounds 8a and 8c were the most potent compounds against MCF-7.
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12

Kaya, Betül, Weiam Hussin, Leyla Yurttaş, Gülhan Turan-Zitouni, Hülya Gençer, Merve Baysal, Abdullah Karaduman, and Zafer Kaplancıklı. "Design and Synthesis of New 1,3,4-Oxadiazole – Benzothiazole and Hydrazone Derivatives as Promising Chemotherapeutic Agents." Drug Research 67, no. 05 (February 21, 2017): 275–82. http://dx.doi.org/10.1055/s-0042-119070.

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AbstractLooking for new cytotoxic and antimicrobial agents with improved antitumor activity, a series of hydrazide and oxadiazole derivatives were designed and synthesized using 3-methoxyphenol as starting substance. Novel N’-(arylidene)-2-(3-methoxyphenoxy)acetohydrazide derivatives (4a–f)/1-(4-substitutedphenyl)-2-[(5-[(3-methoxyphenoxy)methyl]-1,3,4-oxadiazol-2-yl)thio]ethan-1-one derivatives (6a–f)/N-(6-substitutedbenzothiazol-2-yl)-2-[(5-[(3-methoxyphenoxy)methyl]-1,3,4-oxadiazol-2-yl)thio]acetamide derivatives (7a–e) were obtained and evaluated for their in vitro antimicrobial activity against various gram-positive, gram-negative bacteria and fungi. The antimicrobial activity potential of the compounds against gram-negative bacteria was found to have higher compared to the potential against gram-positive bacteria. Also, compounds were screened for their antiproliferative activity against 2 selected human tumor cell lines, A549 lung, MCF7 breast cancer cell line and mouse embryo fibroblast cell line, NIH/3T3 as healthy cell line. Among the compounds evaluated, compound 7c bearing 1,3,4-oxadiazole ring and 6-methoxy benzothiazole moiety exhibited the highest inhibitory activity against A549 and MCF-7 tumor cell lines in contrary to NIH/3T3 cell line, as desired.
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13

Salahuddin, Avijit Mazumder, and Mohammad Shaharyar. "Synthesis, Characterization, andIn VitroAnticancer Evaluation of Novel 2,5-Disubstituted 1,3,4-Oxadiazole Analogue." BioMed Research International 2014 (2014): 1–14. http://dx.doi.org/10.1155/2014/491492.

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In this series, we have synthesised a new 2,5-disubstituted 1,3,4-oxadiazole in search of potential therapeutics for cancer. The anticancer activities were evaluated on a panel of 60 cell lines by the National Cancer Institute according to its own screening protocol. Out of the 24 compounds, 11 were selected and evaluated via single high dose (10−5 M). In the next phase, two compounds have been selected for five-dose assay. The compounds 3-(5-benzyl-1,3,4-oxadiazol-2-yl)quinolin-2(1H)-one18(NSC-776965) and 3-[5-(2-phenoxymethyl-benzoimidazol-1-ylmethyl)-[1,3,4]oxadiazol-2-yl]-2-p-tolyloxy-quinoline27(NSC-776971) showed mean growth percentage of 66.23 and 46.61, respectively, in one-dose assay and their GI50values ranging between 1.41–15.8 μM and 0.40–14.9 μM, respectively, in 5-dose assay.
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14

Ribkovskaia, Zinaida, Serghei Pogrebnoi, Alic Barba, and Fliur Macaev. "Synthesis and Characterization of [(5-Mercapto-1,3,4-Oxadiazol-2-YL)Aryl]-3,5-Diaryl-4,5-Dihydro-1H-Pyrazole-1-Carbothioamides." Chemistry Journal of Moldova 6, no. 1 (June 2011): 90–100. http://dx.doi.org/10.19261/cjm.2011.06(1).04.

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The synthesis and characterization of [(5-mercapto-1,3,4-oxadiazol-2-yl)aryl]-3,5-diaryl-4,5-dihydro-1Hpyrazole-1-carbothioamides - derivatives of pyrazolines and 5-[4(3)-isothiocyanatophenyl]-2-thio-1,3,4-oxadiazoles were realized. The synthesized compounds, are crystalline substances, stable in storage and when exposed to air and light.
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Sattar, Almas, Aziz-ur-Rehman, Muhammad Athar Abbasi, Sabahat Zahra Siddiqui, Shahid Rasool, and Irshad Ahmad. "Synthesis of some novel enzyme inhibitors and antibacterial agents derived from 5-(1-(4-tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol." Brazilian Journal of Pharmaceutical Sciences 52, no. 1 (March 2016): 77–85. http://dx.doi.org/10.1590/s1984-82502016000100009.

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ABSTRACT Keeping in mind the pharmacological importance of the 1,3,4-oxadiazole moiety, a series of new S-substituted derivatives, 5a-h, of 5-(1-(4-tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol (3) were synthesized. The reaction of p-toluenesulfonyl chloride (a) and ethyl isonipecotate (b) produced ethyl 1-(4-tosyl)piperidin-4-carboxylate (1) which was further transformed into 1-(4-tosyl)piperidin-4-carbohydrazide (2) by hydrazine hydrate in methanol. Compound 2 was refluxed with CS2 in the presence of KOH to synthesize 5-(1-(4-tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol (3). The desired compounds, 5a-h, were synthesized by stirring 3 with aralkyl halides, 4a-h, in DMF using NaH as an activator. The structures of synthesized compounds were elucidated by 1H-NMR, IR and EI-MS spectral studies. These compounds were further evaluated for enzyme inhibitory activity against lipoxygenase and alpha-glucosidase, along with antibacterial activity against Gram-negative and Gram-positive bacteria.
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Sağırlı, Akın, and Yaşar Dürüst. "Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway." Beilstein Journal of Organic Chemistry 14 (December 10, 2018): 3011–17. http://dx.doi.org/10.3762/bjoc.14.280.

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The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted-1,2,4-oxadiazol-5-ylpropanes. To the best of our knowledge, the current synthetic route leading to decyanated products will be the first in terms of a decyanation process which allows the transformation of trisubstituted acetonitriles into alkanes by the incorporation of KCN with the association of in situ-formed HCN and most likely through the extrusion of cyanogen which could not be detected or isolated. In addition, the plausible mechanisms were proposed for both transformations. The structures of the title compounds were identified by means of IR, 1H NMR, 13C NMR, 2D NMR spectra, TOF–MS and X-ray measurements.
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17

Godovikova, T. I., S. K. Vorontsova, L. D. Konyushkin, S. I. Firgang, and O. A. Rakitin. "Synthesis of 5-(1,2,5-oxadiazol-3-yl)-1H-etrazoles from 3-cyano-1,2,5-oxadiazoles." Russian Chemical Bulletin 58, no. 2 (February 2009): 406–9. http://dx.doi.org/10.1007/s11172-010-0023-5.

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18

Variya, Hiren H., Vikram Panchal, Falguni G. Bhabhor, and G. R. Patel. "Synthesis and Characterization of Biologically Potent Chalcone Bearing 1,3,4-Oxadiazole Linkage." International Letters of Chemistry, Physics and Astronomy 61 (November 2015): 77–83. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.61.77.

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In this article, we have described to design and synthesized a series of substituted chalcone based 1,3,4-oxadiazole derivatives. Titled compounds (E)-S-(-5-phenyl-1,3,4-oxadiazol-2-yl) 2-(4-(3-(5-methyl-3oxo-2(p-tolyl)-2,3-dihydro-1H-pyrazol-4-yl)-3-oxoprop-1-en-1-yl) phenoxy) etanethioate (III1-6) were synthesized using of derivatives of S-(-5-phenyl-1,3,4 oxadiazole-2-yl)2-chloroethaethioate (I1-6) were reacted with (E)-4-(3-(4-hydroxyphenyl) acryloyl)-5-methyl-2(p-tolyl)-1H-pyrazol-3(2H)-one (II) in presence of K2CO3 in DMF as a solvent. The synthesized compounds were evaluated for their antimicrobial activity. The newly synthesized compounds were characterized by analytical and spectral (IR, 1H NMR, and LC-MS) Methods.
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Hatterman, Harlene M., Patrick J. Shea, and Ellen T. Paparozzi. "Weed Control in Annual Statice." Weed Science 35, no. 3 (May 1987): 373–76. http://dx.doi.org/10.1017/s0043174500053844.

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Experiments were conducted in 1982, 1983, and 1984 to determine whether herbicides can effectively control weeds in annual statice (Limonium sinuatum Mill.) without reducing the marketability of the crop. A greenhouse evaluation of chlorpropham (1-methylethyl 3-chlorophenylcarbamate), napropamide [N,N-diethyl-2-(1-naphthalenyloxy)propanamide], EPTC (S-ethyl dipropyl carbamothioate), oxadiazon {3-[2,4-dichloro-5-(1-methylethoxy)phenyl]-5-(1,1-dimethylethyi)-1,3,4-oxadiazol-2-(3H)-one}, and trifluralin [2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzenamine] indicated that preemergence applications of the latter three herbicides resulted in the most effective weed control and least statice injury. Oxadiazon was the most effective for broadleaf and grass ed control in field-grown statice. Yield and quality were greatest in oxadiazon-treated plots and exceeded those of the handweeded controls. Annual statice was most sensitive to trifluralin.
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Panchal, Ishan I., Roshani Rajput, and Ashish D. Patel. "Design, Synthesis and Pharmacological Evalution of 1,3,4-Oxadiazole Derivatives as Collapsin Response Mediator Protein 1 (CRMP 1) Inhibitors." Current Drug Discovery Technologies 17, no. 1 (April 17, 2020): 57–67. http://dx.doi.org/10.2174/1570163815666181106090708.

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Objective: The series of 2-(4-Phenylamino)-N-(5-((4-nitrophenoxy)methyl) -1,3,4-oxadiazol- 2-yl)aceta-mide (5a-5e) and substituted N-(5-(Phenoxymethyl)-1,3,4-oxadiazol-2-yl)-2- (phenylamino)acetamide (5f-5i) was designed, synthesized and investigated for Collapsin Response Mediator Protein 1 (CRMP 1) inhibitors as small lung cancer. Design: Design of compounds was determined by literature review and molecular docking studies in iGEMDOCK 2.0. Materials and Methods: Novel 1, 3, 4 Oxadiazole derivatives were synthesized and characterized by melting point, TLC, IR Spectroscopy, Mass spectroscopy and 1H NMR. In vitro biological evaluation was performed on NCI-H2066 cell line for different concentrations 10-1000μM by telomeric repeat amplification protocol assay. The assay of telomerase in cellular extracts was modified from the PCR-based Telomeric-Repeat Amplification Protocol (TRAP), using the oligonucleotides TS and CX. Results: Novel substituted 2-(4-Phenylamino)-N-(5-((4-nitrophenoxy)methyl)-1,3,4-oxadiazol-2- yl) acetamide (5a-5e) and substituted N-(5-(Phenoxymethyl)-1,3,4-oxadiazol-2-yl)-2-(phenylamino) acetamide (5f-5i) were synthesized, and characterized using spectral and analytical data. All compounds have shown considerable % inhibition of Cell Growth with respect to Bevacizumab, but compound 5a and 5f were equipotent with respect to activity as compared to standard Bevacizumab. Conclusion: Amongst the hybrids, p-nitro substituted derivative (5a) and p-chloro substituted (5f) showed the highest activity against human lung cancer cell line NCI-H2066 by TRAP assay.
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J Khairnar, Bhikan, Rahul S. Salunke, Premchand B. Patil, Sanjay A. Patil, Rajeshwar J. Kapade, Pravin S. Girase, and Bhata R. Chaudhari. "Synthesis and Antimicrobial Activity of Some New 1, 4-Benzothiazine Containing Thiosemicarbazides and 1, 3, 4-Oxadiazole Derivatives." E-Journal of Chemistry 9, no. 1 (2012): 318–22. http://dx.doi.org/10.1155/2012/902784.

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A series of novel 3- methyl-7-substituted-4H,4-benzothiazine-2-carbohydrazide (3a-e) and corresponding thiosemicarbazides (4-a-q); 2-[3-methyl-7-substituted- 4H-1, 4-benzothiazine-2-yl]-N-(aryl) hydrazine carbothiamide have been synthesized. The thiosemicarbazide when cyclized with iodine via intramolecular cyclisation gave benzothiazonyl oxadiazoles (5-a-q); 5-(3-methyl -7-substitued-4H- 1,4-benzothiazin-2-yl)-N—aryl- 1,3,4- oxadiazol -2-amine and the compounds were tested for antibacterial and antifungal activities against different microorganisms.
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22

Ding, Bin, Jie Wu, Xiang Xia Wu, Jian Zhong Huo, Zhao Zhou Zhu, Yuan Yuan Liu, and Fang Xue Shi. "Syntheses, structural diversities and characterization of a series of coordination polymers with two isomeric oxadiazol-pyridine ligands." RSC Advances 7, no. 16 (2017): 9704–18. http://dx.doi.org/10.1039/c6ra28153b.

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In this work two positional-isomeric oxadiazol-pyridine ligands 3-(5-methyl-1,3,4-oxadiazol-2-yl)pyridine (L1) and 4-(5-methyl-1,3,4-oxadiazol-2-yl)pyridine (L2) have been designed and synthesized.
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23

Wehtje, Glenn R., Charles H. Gilliam, and Ben F. Hajek. "Adsorption, Desorption, and Leaching of Oxadiazon in Container Media and Soil." HortScience 28, no. 2 (February 1993): 126–28. http://dx.doi.org/10.21273/hortsci.28.2.126.

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Adsorption of 14C-labeled oxadiazon was evaluated in three soilless media and a mineral soil at concentrations between 0.1 and 100 mg·kg-1. Adsorption, which was at least 96%, was not influenced by absorbent type (medium vs. soil) or by oxadiazon concentration. However, desorption was greater in the media than in the soil. After five water extractions, 5.4% of the applied oxadiazon was recovered from media, but only 0.4% was recovered from the soil. In the soil and in two of the media, leaching with water failed to displace oxadiazon 2 cm below the surface to which it had been applied. No oxadiazon was detected below 4 cm in the third medium. Oxadiazon is sufficiently adsorbed to resist leaching-based displacement. Oxadiazon is not likely to enter the environment by escaping from treated containers. Chemical name used: 3-[2,4-dichloro-5-(1-methylethoxy)phenyl]-5-(1,1-di-methylethyl)-1,3,4-oxadiazol-2-(3H)-one (oxadiazon).
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24

Nguyen Tien, Cong, Duc Tran Thi Cam, Ha Bui Manh, and Dat Nguyen Dang. "Synthesis and Antibacterial Activity of Some Derivatives of 2-Methylbenzimidazole Containing 1,3,4-Oxadiazole or 1,2,4-Triazole Heterocycle." Journal of Chemistry 2016 (2016): 1–6. http://dx.doi.org/10.1155/2016/1507049.

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5-[(2-Methyl-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazole-2-thiol or 5-[(2-methyl-1H-benzimidazol-1-yl)methyl]-4-(4-methylphenyl)-1,2,4-triazol-3-thiol which were prepared starting from 2-methylbenzimidazole in the reaction with appropriateN-aryl-2-chloroacetamides afforded two series ofN-aryl-2-{5-[(2-methyl-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-yl}sulfanylacetamides andN-aryl-2-{5-[(2-methyl-1H-benzimidazol-1-yl)methyl]-4-(4-methylphenyl)-4H-1,2,4-triazol-3-ylthio}acetamides, respectively. The structures of the compounds were elucidated on the basis of IR, MS,1H-NMR, and13C-NMR spectral data. The compounds containing 1,3,4-oxadiazole or 1,2,4-triazole heterocycle also were tested for their antimicrobial activity against bacteria, mold, and yeast.
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Ahsan, Mohamed Jawed, Lakshya Bhandari, Shally Makkar, Rajan Singh, Mohd Zaheen Hassan, Mohammed H. Geesi, Mohamed Afroz Bakht, et al. "Synthesis, Antiproliferative, and Antioxidant Activities of Substituted N-[(1,3,4-Oxadiazol-2-yl) Methyl] Benzamines." Letters in Drug Design & Discovery 17, no. 2 (February 13, 2020): 145–54. http://dx.doi.org/10.2174/1570180816666181113110033.

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Background: Oxadiazole emerged as an important class of heterocyclic compound with diverse biological activities like anticancer, antitubercular, anticonvulsant, anti-tubulin, antimicrobial, anti-inflammatory, antioxidant etc. Objective: The objective of this study is to synthesis series of twelve substituted N-[(1,3,4-oxadiazol-2- yl)methyl]benzamines (6a-l) and their evaluation as antiproliferative and antioxidant agents. Methods: The substituted N-[(1,3,4-oxadiazol-2-yl)methyl]benzamines (6a-l) analogues were synthesized as per the reported procedure. The antiproliferative activity was tested against nine different panels cancer cell lines (leukemia, colon, renal, non-small cell lung, breast, CNS, melanoma, prostate, and ovarian cancer) at 10 µM drug concentrations as per the NCI US Protocol. Results: 2-(5-((3-Chloro-4-fluorophenylamino)methyl)-1,3,4-oxadiazol-2-yl)phenol (6e) revealed the significant antiproliferative activity among the series of title compounds (6a-l). The compound, 6e showed maximum sensitivity towards CCRF-CEM, MCF-7, MOLT-4, T-47D, and SR cell lines with percent growth inhibitions (%GIs) of 79.92, 56.67, 39.62, 34.71 and 33.35, respectively. Furthermore, the compounds, 6e and 6c showed promising antioxidant activity with an IC50 value of 15.09 and 19.02 µM, respectively in DPPH free radicals (FR) scavenging activity.R Conclusion: The present study may support a significant value in cancer drug discovery programme.
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26

Hoque, M. E., R. M. Wilkins, A. Kennedy, and J. A. Garratt. "Sorption behaviour of oxadiazon in tropical rice soils." Water Science and Technology 56, no. 1 (July 1, 2007): 115–21. http://dx.doi.org/10.2166/wst.2007.442.

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The soprtion behaviour of a pre-emergent herbicide, oxadiazon (5-tert-butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazol-2 (3H)-one) was investigated in tropical rice soils using a batch equilibrium method. There is no information available on the fate of oxadiazon in Bangladeshi soils; Bangladesh rice soil is a unique environment. The experiment was performed using radiolabelled (14C) oxadiazon. The sorption and desorption isotherm of oxadiazon was described using the Freundlich equation. L-type sorption isotherms were observed. The correlation coefficient (r2) was 0.995 to 0.997 and the linearity of the slope was in the range 0.96–1.07. Sorption of oxadiazon was related to organic carbon. Sorption of oxadiazon by soil was a rapid process; sorption kinetics indicated that most of the sorption occurred within two hours. Changes in sorption of oxadiazon by soils was investigated by repeated application. Sorption after the first cycle was in the range 81–92% whereas sorption capacity decreased in the following cycles.
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27

Santos, Suseanne K. M., Ricardo A. W. Neves Filho, Adailton J. Bortoluzzi, and Rajendra M. Srivastava. "3-[3-(3-Fluorophenyl)-1,2,4-oxadiazol-5-yl]propionic acid." Acta Crystallographica Section E Structure Reports Online 65, no. 1 (December 17, 2008): o146. http://dx.doi.org/10.1107/s1600536808042001.

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28

Srivastava, Rejendra M., Marilu L. de Oliveira, and Julianna F. C. de Alburquerque. "Methyl 3-[3-(Aryl)-1,2,4-Oxadiazol-5-Yl]Propionates." Journal Of The Brazilian Chemical Society 3, no. 3 (1992): 117–19. http://dx.doi.org/10.5935/0103-5053.19920025.

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29

Szafrański, Krzysztof, Jarosław Sławiński, Łukasz Tomorowicz, and Anna Kawiak. "Synthesis, Anticancer Evaluation and Structure-Activity Analysis of Novel (E)- 5-(2-Arylvinyl)-1,3,4-oxadiazol-2-yl)benzenesulfonamides." International Journal of Molecular Sciences 21, no. 6 (March 23, 2020): 2235. http://dx.doi.org/10.3390/ijms21062235.

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To learn more about the structure–activity relationships of (E)-3-(5-styryl-1,3,4-oxadiazol-2-yl)benzenesulfonamide derivatives, which in our previous research displayed promising in vitro anticancer activity, we have synthesized a group of novel (E)-5-[(5-(2-arylvinyl)-1,3,4-oxadiazol-2-yl)]-4-chloro-2-R1-benzenesulfonamides 7–36 as well as (E)-4-[5-styryl1,3,4-oxadiazol-2-yl]benzenesulfonamides 47–50 and (E)-2-(2,4-dichlorophenyl)-5-(2-arylvinyl)-1,3,4-oxadiazols 51–55. All target derivatives were evaluated for their anticancer activity on HeLa, HCT-116, and MCF-7 human tumor cell lines. The obtained results were analyzed in order to explain the influence of a structure of the 2-aryl-vinyl substituent and benzenesulfonamide scaffold on the anti-tumor activity. Compound 31, bearing 5-nitrothiophene moiety, exhibited the most potent anticancer activity against the HCT-116, MCF-7, and HeLa cell lines, with IC50 values of 0.5, 4, and 4.5 µM, respectively. Analysis of structure-activity relationship showed significant differences in activity depending on the substituent in position 3 of the benzenesulfonamide ring and indicated as the optimal meta position of the sulfonamide moiety relative to the oxadizole ring. In the next stage, chemometric analysis was performed basing on a set of computed molecular descriptors. Hierarchical cluster analysis was used to examine the internal structure of the obtained data and the quantitative structure–activity relationship (QSAR) analysis with multiple linear regression (MLR) method allowed for finding statistically significant models for predicting activity towards all three cancer cell lines.
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30

Godovikova, T. I., S. K. Vorontsova, L. D. Konyushkin, S. I. Firgang, and O. A. Rakitin. "ChemInform Abstract: Synthesis of 5-(1,2,5-Oxadiazol-3-yl)-1H-tetrazoles from 3-Cyano-1,2,5-oxadiazoles." ChemInform 41, no. 34 (July 29, 2010): no. http://dx.doi.org/10.1002/chin.201034148.

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31

Johnson, B. J. "Differential Large Crabgrass Control with Herbicides in Tall Fescue and Common Bermudagrass." HortScience 28, no. 10 (October 1993): 1015–16. http://dx.doi.org/10.21273/hortsci.28.10.1015.

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Pendimethalin and oxadiazon are used commonly to control crabgrasses (Digitaria spp.) in tall fescue (Festuca arundinacea Schreb.) and common bermudagrass [Cynodon dactylon (L.) Pers.]. A field experiment was conducted for 2 years to determine if reduced pendimethalin and oxadiazon application rates would control large crabgrass [D. sanguinalis (L.) Sco.] effectively in tall fescue and common bermudagrass. Oxadiazon applied at 1.1 kg a.i./ha in each of two applications at a 60-day interval (less than recommended rate) effectively controlled large crabgrass (≥93%), regardless of turfgrass species. Pendimethalin applied at 1.1 kg a.i./ha in each of two applications controlled large crabgrass in common bermudagrass effectively (≥90%) but not large crabgrass in tall fescue (47%). The difference in pendimethalin performance between the two species was attributed to the ability of common bermudagrass to compete more successfully than tall fescue with large crabgrass during late summer. Chemical names used: 3-[2,4-dichloro-5-(1-methylethoxy)phenyl]-5-(1,1-dimethylethy1)-l,3,4-oxadiazol-2-(3 H)-one (oxadiazon); N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine (pendimethalin).
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32

Sravya, Gundala, Ummadi Nagarjuna, Venkatapuram Padmavathi, Galla Rajitha, Sakuri Chandi priya, and Adivireddy Padmaja. "Synthesis, Antioxidant and Anti-inflammatory Activities of 5-((styrylsulfonyl) methyl)-1,3,4-Oxadiazol / Thiadiazol-2-amine Derivatives." Letters in Drug Design & Discovery 16, no. 11 (October 23, 2019): 1233–47. http://dx.doi.org/10.2174/1570180816666181102114529.

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Background: A new class of 5-(styrylsulfonylmethyl)-1,3,4-oxadiazol-2-amine and 5- (styrylsulfonylmethyl)-1,3,4-thiadiazol-2-amine derivatives were prepared by derivatization of amino function. Methods: All the synthesized compounds were tested for antioxidant and anti-inflammatory activities. Results: The 2-amino-3-chloro-N-(5-(4-methylstyrylsulfonylmethyl)-1,3,4-oxadiazol-2-yl)-propanamide (12b) and 3-chloro-N-(5-(4-methylstyrylsulfonylmethyl)-1,3,4-oxadiazol-2-yl)-butanamide (14b) displayed significant antioxidant activity, greater than the standard Ascorbic acid. Conclusion: Moreover, 12b and 14b also exhibited promising anti-inflammatory activity
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33

Anokhina, P. V., T. V. Romanova, S. F. Mel’nikova, and I. V. Tselinskii. "Reduction of 3,4-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole 2-oxide." Russian Journal of Organic Chemistry 47, no. 10 (October 2011): 1606–7. http://dx.doi.org/10.1134/s1070428011100319.

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34

Nguyen Tien, Cong, Thin Nguyen Van, Giang Le Duc, Manh Vu Quoc, Trung Vu Quoc, Thang Pham Chien, Hung Nguyen Huy, Anh Dang Thi Tuyet, Tuyen Nguyen Van, and Luc Van Meervelt. "Synthesis, structure and in vitro cytotoxicity testing of some 1,3,4-oxadiazoline derivatives from 2-hydroxy-5-iodobenzoic acid." Acta Crystallographica Section C Structural Chemistry 74, no. 7 (June 18, 2018): 839–46. http://dx.doi.org/10.1107/s2053229618008719.

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The syntheses of nine new 5-iodosalicylic acid-based 1,3,4-oxadiazoline derivatives starting from methyl salicylate are described. These compounds are 2-[4-acetyl-5-methyl-5-(3-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6a), 2-[4-acetyl-5-methyl-5-(4-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6b), 2-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-4-iodophenyl acetate, C19H17IN2O4 (6c), 2-[4-acetyl-5-(4-fluorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C19H16FIN2O4 (6d), 2-[4-acetyl-5-(4-chlorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C19H16ClIN2O4 (6e), 2-[4-acetyl-5-(3-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6f), 2-[4-acetyl-5-(4-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6g), 2-[4-acetyl-5-methyl-5-(4-methylphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6h) and 2-[5-(4-acetamidophenyl)-4-acetyl-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6i). The compounds were characterized by mass, 1H NMR and 13C NMR spectroscopies. Single-crystal X-ray diffraction studies were also carried out for 6c, 6d and 6e. Compounds 6c and 6d are isomorphous, with the 1,3,4-oxadiazoline ring having an envelope conformation, where the disubstituted C atom is the flap. The packing is determined by C—H...O, C—H...π and I...π interactions. For 6e, the 1,3,4-oxadiazoline ring is almost planar. In the packing, Cl...π interactions are observed, while the I atom is not involved in short interactions. Compounds 6d, 6e, 6f and 6h show good inhibiting abilities on the human cancer cell lines KB and Hep-G2, with IC50 values of 0.9–4.5 µM.
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35

Zelenin, Alexander K., Edwin D. Stevens, and Mark L. Trudell. "Synthesis and structure of 4-[(4-Nitro-1,2,5-oxadiazol-3-yl)-NNO-azoxyl]-1, 2,5-oxadiazol-3-amine." Structural Chemistry 8, no. 5 (October 1997): 373–77. http://dx.doi.org/10.1007/bf02281251.

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36

Zhang, Fang, Fei Liu, Qifan Chen, and Mingdong Dong. "3-[3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl]propanoic acid." Acta Crystallographica Section E Structure Reports Online 67, no. 1 (December 18, 2010): o193. http://dx.doi.org/10.1107/s1600536810051639.

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37

Wang, Bohan, Hualin Xiong, Guangbin Cheng, Zaichao Zhang, and Hongwei Yang. "An unexpected method to synthesise 1,2,4-oxadiazolone derivatives: a class of insensitive energetic materials." New Journal of Chemistry 42, no. 24 (2018): 19671–77. http://dx.doi.org/10.1039/c8nj04428g.

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A new and effective method for the preparation of 3-(4-amino-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5(4H)-one is presented. Explosophore groups such as NO2NH–, NO2–, C(NO2)3CH2NH– and –NN– were incorporated by a variety of functionalization strategies.
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38

Zhang, Ming-Zhi, Nick Mulholland, David Beattie, Dianne Irwin, Yu-Cheng Gu, Qiong Chen, Guang-Fu Yang, and John Clough. "Synthesis and antifungal activity of 3-(1,3,4-oxadiazol-5-yl)-indoles and 3-(1,3,4-oxadiazol-5-yl)methyl-indoles." European Journal of Medicinal Chemistry 63 (May 2013): 22–32. http://dx.doi.org/10.1016/j.ejmech.2013.01.038.

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39

Yang, Rui, Yifei Liu, Zhen Dong, Haiyan Li, and Zhiwen Ye. "3-R-4-(5-Methyleneazide-1,2,4-oxadiazol-3-yl)furazan and its ionic salts as low-sensitivity and high-detonation energetic materials." New Journal of Chemistry 45, no. 25 (2021): 11380–89. http://dx.doi.org/10.1039/d1nj01099a.

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40

Wang, Hai-Bo, Zhi-Qian Liu, and Xiao-Chen Yan. "Methyl 2-{[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]methoxy}phenylacetate." Acta Crystallographica Section E Structure Reports Online 62, no. 5 (April 13, 2006): o1839—o1840. http://dx.doi.org/10.1107/s1600536806010014.

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The title compound, C19H18N2O5, was synthesized by the reaction of methyl (2-hydroxyphenyl)acetate and 5-chloromethyl-3-(3-methoxyphenyl)-1,2,4-oxadiazole. The plane of the oxadiazole ring forms a small dihedral angle of 15.2 (2)° with the plane of the benzene ring directly bonded to it, whereas the second benzene ring is approximately orthogonal to the oxadiazole plane, the dihedral angle being 79.1 (2)°.
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41

Glidewell, Christopher, John N. Low, Janet M. S. Skakle, and James L. Wardell. "3-Phenyl-4H,6H-1,2,4-oxadiazol-5-one." Acta Crystallographica Section C Crystal Structure Communications 60, no. 11 (October 22, 2004): o818—o820. http://dx.doi.org/10.1107/s0108270104023406.

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42

Kang, Si-shun, Hai-Lin Li, Hai-su Zeng, Hai-bo Wang, and Pin-liang Wang. "4-[3-(Chloromethyl)-1,2,4-oxadiazol-5-yl]pyridine." Acta Crystallographica Section E Structure Reports Online 63, no. 12 (November 14, 2007): o4654. http://dx.doi.org/10.1107/s1600536807055559.

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43

Yan, Xiao-Chen, Hai-Bo Wang, and Zhi-Qian Liu. "[3-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]methanol." Acta Crystallographica Section E Structure Reports Online 62, no. 10 (September 6, 2006): o4226—o4227. http://dx.doi.org/10.1107/s1600536806024433.

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44

Yan, Xiao-Chen, Hai-Bo Wang, and Zhi-Qian Liu. "[3-(2-Methylphenyl)-1,2,4-oxadiazol-5-yl]methanol." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (March 10, 2006): o1302—o1303. http://dx.doi.org/10.1107/s1600536806008142.

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Yan, Xiao-Chen, Hai-Bo Wang, and Zhi-Qian Liu. "[3-(2-Chlorophenyl)-1,2,4-oxadiazol-5-yl]methanol." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 28, 2006): o3007—o3008. http://dx.doi.org/10.1107/s1600536806018952.

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46

Yamuna, Thammarse S., Jerry P. Jasinski, Brian J. Anderson, H. S. Yathirajan, and Manpreet Kaur. "Raltegravir monohydrate." Acta Crystallographica Section E Structure Reports Online 69, no. 12 (November 6, 2013): o1743—o1744. http://dx.doi.org/10.1107/s1600536813029747.

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The hydrated title compound [systematic name:N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-{1-methyl-1-[(5-methyl-1,3,4-oxadiazol-2-ylcarbonyl)amino]ethyl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide monohydrate], C20H21FN6O5·H2O, is recognised as the first HIV integrase inhibitor. In the molecule, the dihedral angles between the mean planes of the pyrimidine ring and the phenyl and oxadiazole rings are 72.0 (1) and 61.8 (3)°, respectively. The mean plane of the oxadiazole ring is twisted by 15.6 (3)° from that of the benzene ring, while the mean plane of amide group bound to the oxadiaole ring is twisted by 18.8 (3)° from its mean plane. Intramolecular O—H...O and C—H...N hydrogen bonds are observed in the molecule. The crystal packing features O—H...O hydrogen bonds, which include bifurcated O—H...(O,O) hydrogen bonds from one H atom of the water molecule. In addition, N—H...O hydrogen bonds are observed involving the two amide groups. These interactions link the molecules into chains along [010].
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47

Srivastava, Rajendra M., Aníbal J. C. N. da Silva, and Marilu L. de Oliveira. "Synthesis of 5,5'-(1,2-Ethanediyl)-bis[3-(Aryl)-1,2,4-Oxadiazoles] and 3-[3-(Aryl)-1,2,4-Oxadiazol-5-yl] Propionic Acids." Journal Of The Brazilian Chemical Society 4, no. 2 (1993): 84–87. http://dx.doi.org/10.5935/0103-5053.19930019.

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48

Han, Lu-Na, Ran-Zhe Lu, Min Zhang, and Hai-bo Wang. "2-{3,4-Dibutoxy-5-[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]thiophen-2-yl}-5-(3-methylphenyl)-1,3,4-oxadiazole." Acta Crystallographica Section E Structure Reports Online 65, no. 3 (February 28, 2009): o622. http://dx.doi.org/10.1107/s1600536809006539.

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49

Shen, Hong, Shu-Yuan Bai, Xin-Yi Han, Xiang-Zhi Li, and Hai-Bo Wang. "8-{[3-(3-Methoxyphenyl)-1,2,4-oxadiazol-5-yl]methoxy}quinoline monohydrate." Acta Crystallographica Section E Structure Reports Online 69, no. 5 (April 20, 2013): o760. http://dx.doi.org/10.1107/s1600536813010271.

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50

Maddi, N. V. D. Harikiran, Srinivas Garaga, Ambati V. Raghava Reddy, Paul Douglas Sanasi, and Raghubabu Korupolu. "Synthesis and characterization of related substances of Azilsartan Kamedoxomil." Current Issues in Pharmacy and Medical Sciences 30, no. 1 (March 28, 2017): 31–35. http://dx.doi.org/10.1515/cipms-2017-0007.

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Abstract Azilsartan Kamedoxomil is an AT1-subtype angiotensin II receptor blocker (ARB). During the laboratory synthesis of Azilsartan Kamedoxomil, four related substances of Azilsartan Kamedoxomil were observed and identified. These were 2-Ethoxy-3-[[4-[2- [4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-5-oxo-1,2,4-oxadiazol-3-yl]phenyl]phenyl] methyl] benzimidazole-4-carboxylic acid (azilsartan N-medoxomil, 9), (5-methyl-2-oxo- 1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-[4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-5- oxo-1,2,4-oxadiazol-3-yl]phenyl]phenyl] methyl] benzimidazole-4-carboxylate (azilsartan dimedoxomil, 10), (5-methyl-2-oxo-1,3-dioxo-4-yl)methyl 1-[2’-(4,5-dihydro-5-oxo-4H- 1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]-2-methoxy-1H-benzimidazole-7-carboxylate (methoxy analogue of azilsartan medoxomil, 11), Methyl 1-((2’-amidobiphenyl-4-yl) methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (amide methyl ester, 12). The present work describes the origin, synthesis and characterization of these related substances.
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