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Journal articles on the topic '4-oxadiazoly'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 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 (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-oxadiaz

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2

Ahsan, Mohamed Jawed, Arun Choupra, Rakesh Kumar Sharma, et al. "Rationale Design, Synthesis, Cytotoxicity Evaluation, and Molecular Docking Studies of 1,3,4-oxadiazole Analogues." Anti-Cancer Agents in Medicinal Chemistry 18, no. 1 (2018): 121–38. http://dx.doi.org/10.2174/1871520617666170419124702.

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Background: 1,3,4-Oxadiazole heterocycles possess a broad spectrum of biological activities. They were reported as potent cytotoxic agents and tubulin inhibitors; hence it is of great interest to explore new oxadiazoles as cytotoxic agents targeting tubulin polymerization. Objective: Two new series of oxadiazoles (5a-h and 12a-h) were synthesized, structurally related to the heterocyclic linked aryl core of IMC-038525, NSC 776715, and NSC 776716, with further modification by incorporating methylene linker. Method: The 2,5-disubstituted-1,3,4-oxadiazoles (5a-h and 12a-h) were synthesized by ref

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3

Mohammadi-Khanaposhtani, Maryam, Kiana Fahimi, Elahe Karimpour-Razkenari, et al. "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 (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-oxa

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4

Saini, Sachin. "Synthesis and Anticonvulsant Studies of Thiazolidinone and Azetidinone Derivatives from Indole Moiety." Drug Research 69, no. 08 (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

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5

Godovikova, T. I., S. K. Vorontsova, L. D. Konyushkin, S. I. Firgang, and O. A. Rakitin. "4-Methyl-1,2,5-oxadiazole-3-carbonitrile in the synthesis of 1,2,5-oxadiazolyl-1,2,4-oxadiazoles." Russian Chemical Bulletin 57, no. 11 (2008): 2440–42. http://dx.doi.org/10.1007/s11172-008-0349-4.

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6

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·H<sub>2</sub>O), 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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7

Ahsan, Mohamed Jawed, Mohd Zaheen Hassan, Surender Singh Jadav, et al. "Synthesis and Biological Potentials of 5-aryl-N-[4-(trifluoromethyl) phenyl]-1,3,4-oxadiazol-2-amines." Letters in Organic Chemistry 17, no. 2 (2020): 133–40. http://dx.doi.org/10.2174/1570178616666190401193928.

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Oxadiazoles are an important class of heterocyclic compounds, having broad-spectrum activity. They were also reported as anticancer, and antioxidant agents, hence it is of significant importance to explore new oxadiazoles. A series of eleven (5-aryl-N-[4-(trifluoromethyl)phenyl]-1,3,4- oxadiazol-2-amines (6a-k) was synthesized based on the structures of reported compounds, SU-101, IMC38525, and FTAB. All these oxadiazoles were synthesized, characterized by spectral data, and further tested against melanoma, leukemia, colon, lung, CNS, ovarian, renal, breast and prostate cancer cell lines’ pane

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8

Yadav, Mange, Shrikant Shirude, Devendra Puntambekar, et al. "Studies in 3,4-diaryl-1,2,5-oxadiazoles and their N-oxides: Search for better COX-2 inhibitors." Acta Pharmaceutica 57, no. 1 (2007): 13–30. http://dx.doi.org/10.2478/v10007-007-0002-z.

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Studies in 3,4-diaryl-1,2,5-oxadiazoles and theirN-oxides: Search for better COX-2 inhibitorsA series of 3,4-diaryl-1,2,5-oxadiazoles and 3,4-diaryl-1,2,5-oxadiazoleN-oxides were prepared and evaluated for COX-2 and COX-1 binding affinityin vitroand for anti-inflammatory activity by the rat paw edema method.p-Methoxy (p-OMe) substituted compounds 9, 21, 34, 41, 42 showed COX-2 enzyme inhibition higher than that showed by compounds with other substituents. 3,4-Di(4-methoxyphenyl)-1,2,5-oxadiazoleN-oxide (42) showed COX-2 enzyme inhibition of 54% at 22 μmol L-1and COX-1 enzyme inhibition of 44%

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9

Jin, Guoxia, Yuqi Ji, Teng Wang, et al. "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 (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

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10

Yurttaş, Leyla, Betül K. Çavuşoğlu, Gülşen A. Çiftçi, and Halide E. Temel. "Synthesis and Biological Evaluation of New 1,3,4-Oxadiazoles as Potential Anticancer Agents and Enzyme Inhibitors." Anti-Cancer Agents in Medicinal Chemistry 18, no. 6 (2018): 914–21. http://dx.doi.org/10.2174/1871520618666180322123327.

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Background: 1,3,4-Oxadiazoles have been known with a wide variety of pharmacological activities including anticancer activity. Objective: In this study, novel 2,5-disubstituted 1,3,4-oxadiazole derivatives were synthesized and evaluated for determining their anticancer, anticholinesterase and lipoxygenase (LOX) inhibitory activity. Methods: All compounds were tested against C6 rat glioma, A549 human lung carcinoma and NIH/3T3 mouse embryo fibroblast cell lines to define cytotoxic concentrations and apoptosis induction levels which they cause. Results: Many of the compounds exhibited remarkable

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11

Maftei, Catalin V., Elena Fodor, Peter G. Jones, et al. "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

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12

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 (2014): M824. http://dx.doi.org/10.3390/m824.

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13

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 (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,

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14

Kysil, Andrii, Angelina Biitseva, Oleksandra Bugera, Tetyana Yegorova, and Zoia Voitenko. "Synthesis of 2-(1,2,4-oxadiazol-5-yl)-2,3-dihydro-4H-chromen-4-ones." French-Ukrainian Journal of Chemistry 8, no. 2 (2020): 176–82. http://dx.doi.org/10.17721/fujcv8i2p176-182.

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Simple and efficient synthesis of 2-(1,2,4-oxadiazol-5-yl)-2,3-dihydro-4H-chromen-4-ones is elaborated. The method relies on CDI-mediated cyclocondensation of substituted 4-oxochromane-2-carboxylic acids and amidoximes. The protocol allows the preparation of 2-oxadiazolylchromanones decorated with two pharmacophores (2,3-dihydro-4H-chromen-4-one and 1,2,4-oxadiazole) that are in high demand in drug discovery.

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15

Wołek, Barbara, Mateusz Werłos, Magdalena Komander, and Agnieszka Kudelko. "Efficient Synthesis of Novel 1,3,4-Oxadiazoles Bearing a 4-N,N-Dimethylaminoquinazoline Scaffold via Palladium-Catalyzed Suzuki Cross-Coupling Reactions." Molecules 25, no. 21 (2020): 5150. http://dx.doi.org/10.3390/molecules25215150.

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Two series of novel (symmetrical and unsymmetrical) quinazolinylphenyl-1,3,4-oxadiazole derivatives were synthesized using palladium-catalyzed Suzuki cross-coupling reactions. The presented synthetic methodology is based on the use of bromine-substituted 2-phenyl-4-N,N-dimethylaminoquinazolines and either a boronic acid pinacol ester or a diboronic acid bis(pinacol) ester of 2,5-diphenyl-1,3,4-oxadiazole. The reactions are conducted in a two-phase solvent system in the presence of catalytic amounts of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), sodium carbonate, and tetrabuty

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16

Mercer, F. W. "Aromatic Poly(ether imide oxadiazole)s." High Performance Polymers 4, no. 2 (1992): 73–80. http://dx.doi.org/10.1088/0954-0083/4/2/002.

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Two oxadiazole containing aromatic diamines were synthesized. The diamines were prepared by reaction of aminophenols with 2,5-bis(4-fluorophenyl)-4l3,4-oxadiazole in a polar aprotic solvent in the presence of potassium carbonate. Reaction of the resulting 2,5-bis(4-(aminophenoxy)phenyl)-1,3,4-oxadiazoles with dianhydrides gave a series of polymeric amic acids. Thermal treatment yielded poly(imide ether oxadazole) films which displayed good thermal stability, flexibility, and glass transition temperatures ranging from 241 to 344C. The dielectric constants of the films were characterized as a fu

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17

Hamciuc, Corneliu, Elena Hamciuc, and Maria Bruma. "Poly(1, 3, 4-Oxadiazole-Amide)s Containing Pendent Phenoxy Groups." High Performance Polymers 8, no. 4 (1996): 507–14. http://dx.doi.org/10.1088/0954-0083/8/4/003.

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A series of new poly(1, 3, 4-oxadiazole-amide)s have been synthesized by solution polycondensation of aromatic diamines containing preformed 1, 3, 4-oxadiazole rings with phenoxyterephthalic diacid chloride or by the reaction of the same diacid chloride with p-aminobenzhydrazide resulting in a polyhydrazide-amide which was cyclodehydrated to the corresponding oxadiazolic structure. The new polymers were soluble or partially soluble in polar amidic solvents, were stable up to 375–400 °C in air and had a glass transition temperature in the range of 225–272 °C.

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18

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 spe

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19

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 a

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20

Barbuceanu, Stefania-Felicia, Gabriela Laura Almajan, Ioana Saramet, Constantin Draghici, and Cristian Enache. "The Behaviour of Some Acylthiosemicarbazides in the Reaction with a-Halogenated Esters." Revista de Chimie 59, no. 3 (2008): 304–8. http://dx.doi.org/10.37358/rc.08.3.1753.

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New six unexpected 1,3,4-oxadiazoles were obtained starting from acylthiosemicarbazides. N1-[4-(4-X-phenylsulfonyl)benzoyl]-N4-(2/3-methoxyphenyl)-thiosemicarbazides 2,3a-c were treated with ethyl chloro- or bromoacetate in presence of anhydrous sodium acetate in order to obtain new thiazolidin-4-ones compounds. However, formation of desired thiazolidin-4-ones from these acylthiosemicarbazides failed and instead 1,3,4-oxadiazoles were obtained. For confirmation presence of these compounds, 5-[4-(phenylsulfonyl)phenyl]-2-(3-methoxyphenylamino)-1,3,4-oxadiazole 5a was synthetized by cyclodesulfu

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21

Tauchman, Jiří, Jakub Trnka, Ivana Císařová, and Petr Štěpnička. "Synthesis, crystal structures and electrochemistry of ferrocenyl-substituted 1,3,4-oxadiazoles." Collection of Czechoslovak Chemical Communications 75, no. 10 (2010): 1023–40. http://dx.doi.org/10.1135/cccc2010064.

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Two ferrocenyl-substituted 1,3,4-oxadiazoles, 2-ferrocenyl-1,3,4-oxadiazole (1) and 2,5-diferrocenyl-1,3,4-oxadiazole (2), have been prepared from the corresponding hydrazides, (ferrocenecarbonyl)hydrazine (3) and 1,2-bis(ferrocenecarbonyl)hydrazine (4), and characterized by conventional spectroscopic methods (IR, NMR, MS) and elemental analyses. The solid-state structures of 1, 2 and 4 have been determined by single-crystal X-ray diffraction analysis. The redox behavior of 1 and 2 was studied by electrochemical methods. Compound 1 underwent a reversible one-electron oxidation attributed to th

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22

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 (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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23

Meng, Xingang, Niao Wang, Xiaofang Long, Lingzhu Chen, and Deyu Hu. "Qualitative and Quantitative Analysis of the New Sulfone Bactericide 2-(4-Fluorophenyl)-5-(Methylsulfonyl)-1,3,4-Oxadiazole and Identification of Its Degradation Pathways in Paddy Water." Journal of Chromatographic Science 58, no. 9 (2020): 859–67. http://dx.doi.org/10.1093/chromsci/bmaa055.

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Abstract Rapid and simple methods for the determination of Jiahuangxianjunzuo (JHXJZ) in paddy water, brown rice, soil and rice straw was developed and validated. This method involved the use of ultrahigh-performance liquid chromatography equipped with photodiode array detector. The most important factor was chromatographic conditions, as identified through an orthogonal experimental design. This method showed good recoveries and precisions, thereby indicating its suitability for monitoring of JHXJZ residues in paddy water, brown rice, soil and rice straw. Furthermore, hydrolysis experiment wa

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24

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 (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 com

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25

Ahsan, Mohamed Jawed, Jyotika Sharma, Monika Singh, Surender Singh Jadav, and Sabina Yasmin. "Synthesis and Anticancer Activity ofN-Aryl-5-substituted-1,3,4-oxadiazol-2-amine Analogues." BioMed Research International 2014 (2014): 1–9. http://dx.doi.org/10.1155/2014/814984.

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In continuance of our search for anticancer agents, we report herein the synthesis and anticancer activity of some novel oxadiazole analogues. The compounds were screened for anticancer activity as per National Cancer Institute (NCI US) protocol on leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers cell lines.N-(2,4-Dimethylphenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-amine (4s) showed maximum activity with mean growth percent (GP) of 62.61 and was found to be the most sensitive on MDA-MB-435 (melanoma), K-562 (leukemia), T-47D (breast cancer), and HCT-15 (colo

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26

Kaya, Betül, Weiam Hussin, Leyla Yurttaş, et al. "Design and Synthesis of New 1,3,4-Oxadiazole – Benzothiazole and Hydrazone Derivatives as Promising Chemotherapeutic Agents." Drug Research 67, no. 05 (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 a

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27

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 (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 a

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Patel, Navin, Sabir Pathan, and Hetal I. Soni. "3,4-Dihydropyrimidin-2(1H)-One Analogues: Microwave irradiated Synthesis with Antimicrobial and Antituberculosis Study." Current Microwave Chemistry 6, no. 1 (2019): 61–70. http://dx.doi.org/10.2174/2213335606666190724093305.

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Background: For rapid and sustainable synthesis, microwave irradiation method is serviceable. This present study deals with the preparation of oxadiazole and pyridine bearing 1,2,3,4- tetrahydro pyrimidine derivatives by microwave irradiation. Objective: The present study aims to carry out rapid synthesis of chloro-acetamides of oxadiazoles of Biginelli product and amino cyano derivative of pyridine by microwave-assisted heating. Our efforts are focused on the introduction of chemical diversity in the molecular framework in order to synthesize pharmacologically interesting compounds. Methods::

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29

J Khairnar, Bhikan, Rahul S. Salunke, Premchand B. Patil, et al. "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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30

Das, Rina, and Dinesh Kumar Mehta. "Evaluation and Docking Study of Pyrazine Containing 1, 3, 4-Oxadiazoles Clubbed with Substituted Azetidin-2-one: A New Class of Potential Antimicrobial and Antitubercular." Drug Research 71, no. 01 (2020): 26–35. http://dx.doi.org/10.1055/a-1252-2378.

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Abstract Background Tuberculosis (TB) caused by Mycobacterium tuberculosis is one of the main killers of people all over the world. The major hurdles with existing therapy are the lengthy regimen and appearance of multi drug resistant (MDR) and extensively drug resistant (XDR) strains of M.tuberculosis. Aims The present work was aimed to synthesize and determine antitubercular and antimicrobial potential of some novel 3-chloro-4-aryl-1-[4-(5-pyrazin-2-yl[1,3,4]oxadiazole-2-ylmethoxy)-phenyl]-azetidin-2-one derivatives 7(a-h) from pyrazinoic acid as precursor, which is a well-established antitu

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31

El-Sayed, Wael A., Farag A. El-Essawy, Omar M. Ali, Barsis S. Nasr, Mohamed M. Abdalla, and Adel A. H. Abdel-Rahman. "Anti-HIV Activity of New Substituted 1,3,4-Oxadiazole Derivatives and their Acyclic Nucleoside Analogues." Zeitschrift für Naturforschung C 64, no. 11-12 (2009): 773–78. http://dx.doi.org/10.1515/znc-2009-11-1203.

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A number of new 5-[(naphthalen-5-yloxy)methyl]-1,3,4-oxadiazole derivatives, 2 - 5 and 8 - 11, were synthesized. The 2-{5-[(naphthalen-5-yloxy)methyl]-1,3,4-oxadiazol-2-ylthio}acetohydrazones 6a and 6b were synthesized by the reaction of the hydrazide 4 with the corresponding monosaccharides. Cyclization of the sugar hydrazones 6a and 6b with acetic anhydride afforded the substituted oxadiazoline derivatives 7a and 7b. The synthesized compounds were evaluated for their antiviral activity against, the human immunodefi ciency virus (HIV-1) and some of these compounds showed moderate to high anti

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32

Xiao, Qiaobin, Sergei Vakulenko, Mayland Chang, and Shahriar Mobashery. "Mutations inmmpLand in the Cell Wall Stress Stimulon Contribute to Resistance to Oxadiazole Antibiotics in Methicillin-Resistant Staphylococcus aureus." Antimicrobial Agents and Chemotherapy 58, no. 10 (2014): 5841–47. http://dx.doi.org/10.1128/aac.03501-14.

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ABSTRACTStaphylococcus aureusis a leading cause of hospital- and community-acquired infections, which exhibit broad resistance to various antibiotics. We recently disclosed the discovery of the oxadiazole class of antibiotics, which hasin vitroandin vivoactivities against methicillin-resistantS. aureus(MRSA). We report herein that MmpL, a putative member of the resistance, nodulation, and cell division (RND) family of proteins, contributes to oxadiazole resistance in theS. aureusstrain COL. Through serial passages, we generated twoS. aureusCOL variants that showed diminished susceptibilities t

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33

Ahsan, Mohamed Jawed, Lakshya Bhandari, Shally Makkar, 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 (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 test

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34

S. Ahmed, Wurood, Ammar A. Razzak Mahmood, and Redha I. Al-Bayati. "Synthesis and Evaluation of Antimicrobial Activity of New Imides and Schiff Bases Derived from Ethyl -4-Amino Benzoate." Oriental Journal of Chemistry 34, no. 5 (2018): 2477–86. http://dx.doi.org/10.13005/ojc/340533.

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A series of disubstituted 1,3,4-oxadiazole derivatives, including imides and Schiff bases, was achieved from the starting material, ethyl-4-aminobenzoate, which was converted to the corresponding 4-aminobenzohydrazide (1), by its reaction with hydrazine hydrate in absolute ethanol. Two oxadiazole parent nuclei had been synthesized from (1), the first nucleus 5-(4-aminophenyl)-1,3,4-oxadiazol-2-amine(2), and the second is 5-(4-aminophenyl)-1,3,4-oxadiazole-2-thione (3). Compound (2) Obtained from stirring methanolic solution of (1) with cyanogen bromide (CNBr) and sodium bicarbonate (NaHCO3) at

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35

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 (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 twi

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36

Wang, Lei, Yu-Ran Wu, Shu-Ting Ren, et al. "Synthesis and bioactivity of novel C2-glycosyl oxadiazole derivatives as acetylcholinesterase inhibitors." Heterocyclic Communications 24, no. 6 (2018): 333–38. http://dx.doi.org/10.1515/hc-2018-0166.

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Abstract A series of glycosyl-substituted 1,3,4-oxadiazoles were synthesized by cyclization of glycosyl-acylthiosemicarbazides via a base-catalyzed reaction. The starting glycosyl-acylthiosemicarbazide derivatives were obtained by the reaction of glycosyl isothiocyanate with various hydrazides. The acetylcholinesterase (AChE) inhibitory activities of the products were tested by Ellman’s method. The most active compounds were subsequently evaluated for the 50% inhibitory concentration (IC50) values. N-(1,3,4,6-tetra-O-benzyl-2-deoxy-β-D-glucopyranosyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole-2-amin

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37

Sindhu, Jayant, Harjinder Singh, Jitender Mohan Khurana, Chetan Sharma, and Kamal Rai Aneja. "Multicomponent Synthesis of Novel 2-Aryl-5-((1-aryl-1H-1,2,3-triazol-4-yl)methylthio)-1,3,4-oxadiazoles using CuI as Catalyst and their Antimicrobial Evaluation." Australian Journal of Chemistry 66, no. 6 (2013): 710. http://dx.doi.org/10.1071/ch13082.

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A series of novel 2-aryl-5-((1-aryl-1H-1,2,3-triazol-4-yl)methylthio)-1,3,4-oxadiazoles have been synthesised by C–S bond formation and azide–alkyne cyclocondensation between [5-(aryl)-[1,3,4]oxadiazol-2-yl]methanethiol, propargyl bromide, and substituted aryl azides in one pot with an aim to explore their effect on the in vitro growth of microorganisms causing microbial infection. In vitro antibacterial activity was determined against four strains, namely Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa and antifungal activity against two fungal strains,

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38

Gaonkar, Santosh L., Izuru Nagashima, and Hiroki Shimizu. "Microwave-Assisted Solution Phase Synthesis of Novel 2-{4-[2-(N-Methyl-2-pyridylamino)ethoxy]phenyl}-5-Substituted 1,3,4-Oxadiazole Library." Organic Chemistry International 2011 (January 3, 2011): 1–5. http://dx.doi.org/10.1155/2011/751894.

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A new series of 2-{4-[2-(N-methyl-2-pyridylamino)ethoxy]phenyl}-5-substituted 1,3,4-oxadiazoles were synthesized by the oxidative cyclization of hydrazones derived from 4-[2-(methylpyridin-2-ylamino)ethoxy]benzaldehyde and aryl hydrazines using chloramine-T as an efficient catalyst. All steps were assisted by microwave irradiation. Microwave enables all these reactions to be simple, rapid, high yielding, and avoid chromatograph purification and led environmentally benign total synthesis of focused oxadiazole library. All the synthesized compounds were isolated in good yield and characterized b

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39

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 (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

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40

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 (2011): 1606–7. http://dx.doi.org/10.1134/s1070428011100319.

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41

Fallon, Gary D., Craig L. Francis, Katarina Johansson, Andris J. Liepa, and Ruth C. J. Woodgate. "N,N-Dialkyl-N´-Chlorosulfonylchloroformamidines in Heterocyclic Synthesis. II. Thiazolo-, Thiadiazolo-, and Oxadiazolo-Fused [1,2,4,6]Thiatriazine Dioxides." Australian Journal of Chemistry 58, no. 12 (2005): 891. http://dx.doi.org/10.1071/ch05070.

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N,N-dialkyl-N′-chlorosulfonylchloroformamidines 1 were treated with 2-aminothiazoline, 2-aminothiazoles, 2-aminobenzothiazoles, 2-amino-1,3,4-thiadiazoles, and 2-amino-1,3,4-oxadiazoles to give a 6,7-dihydrothiazolo[3,2-b][1,2,4,6]thiatriazine dioxide 3, a 6,7-dihydrothiazolo[2,3-c][1,2,4,6]thiatriazine dioxide 4, thiazolo[3,2-b][1,2,4,6]thiatriazine dioxides 5, [1,2,4,6]thiatriazino[3,2-b]benzothiazole dioxides 7, a [1,2,4,6]thiatriazino[3,4-b]benzothiazole dioxide 8, [1,3,4]thiadiazolo[2,3-c][1,2,4,6]thiatriazine dioxides 10, [1,3,4]thiadiazolo[3,2-b][1,2,4,6]thiatriazine dioxides 11, [1,3,4

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42

Epishina, M. A., A. S. Kulikov, and N. N. Makhova. "Synthesis of macrocyclic systems from 4,4′-diamino-3,3′-bi-1,2,5-oxadiazole and 3(4)-amino-4(3)-(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole 2-oxides." Russian Chemical Bulletin 57, no. 3 (2008): 644–51. http://dx.doi.org/10.1007/s11172-008-0101-0.

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43

Almalki, Abdulraheem S. A., Syed Nazreen, Azizah M. Malebari, et al. "Synthesis and Biological Evaluation of 1,2,3-Triazole Tethered Thymol-1,3,4-Oxadiazole Derivatives as Anticancer and Antimicrobial Agents." Pharmaceuticals 14, no. 9 (2021): 866. http://dx.doi.org/10.3390/ph14090866.

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A library of 1,2,3-triazole-incorporated thymol-1,3,4-oxadiazole derivatives (6–18) hasbeen synthesized and tested for anticancer and antimicrobial activities. Compounds 7, 8, 9, 10, and 11 exhibited significant antiproliferative activity. Among these active derivatives, compound 2-(4-((5-((2-isopropyl-5-methylphenoxy)methyl)-1,3,4-oxadiazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)phenol (9) was the best compound against all three tested cell lines, MCF-7 (IC50 1.1 μM), HCT-116 (IC50 2.6 μM), and HepG2 (IC50 1.4 μM). Compound 9 was found to be better than the standard drugs, doxorubicin and 5-f

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44

Kottakki, Naveen Kumar, Soujanya Kumari P V D, Gopi G, Amperayani Karteek Rao, and Devi Parimiuma. "SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF PIPERAZINE ANALOGUES CONTAINING [1, 3, 4]-OXADIAZOLE RING." INDIAN DRUGS 57, no. 01 (2020): 19–26. http://dx.doi.org/10.53879/id.57.01.12165.

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A new series of piperazine-1, 3, 4-oxadiazole deviatives were synthesized by the condensation of 1, 3, 4-thidaizole with substituted piperazine, in the presence of N, N-diisopropylethylamine. The structures were confirmed by IR, 1H NMR, 13C NMR and Mass spectroscopy. All the precursors were screened for anti-bacterial activity and the results indicate that phenyl substituted chloro (PO2) and hydroxy (PO6) functional derivatives possess better anti-bacterial activity towards to Gram-positive bacteria and gram-negative bacteria, Maximum zone of inhibition was observed in (PO2) against Bacillus s

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45

Manojkumar, Parameswaran, Thengungal Ravi, and Gopalakrishnan Subbuchettiar. "Synthesis of coumarin heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells." Acta Pharmaceutica 59, no. 2 (2009): 159–70. http://dx.doi.org/10.2478/v10007-009-0018-7.

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Synthesis of coumarin heterocyclic derivatives with antioxidant activity andin vitrocytotoxic activity against tumour cellsThe aim of the present work was to synthesise coumarinyl heterocycles and to elucidate the potential role of these compounds as antioxidants and cytotoxic agents against Dalton's lymphoma ascites tumour cells (DLA) and Ehrlich ascites carcinoma cells (EAC). The synthesis of coumarin derivatives containing pyrazole, pyrazolone, thiazolidin-4-one, 5-carboxymethyl-4-thiazolidinone and 3-acetyl-1,3,4-oxadiazole ring is reported. 4-Methylcoumarinyl-7-oxyacetic acid hydrazide (1

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46

Et al., Khammas. "Synthesis, Cytotoxicity, Xanthine Oxidase Inhibition, Antioxidant of New Pyrazolo{3,4 d}Pyrimidine Derivatives." Baghdad Science Journal 16, no. 4(Suppl.) (2019): 1003. http://dx.doi.org/10.21123/bsj.2019.16.4(suppl.).1003.

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Allopurinol derivative were prepared by reacting the (1-chloroacetyl)-2-Hydropyrazolo{3,4-d}pyrimidine-4-oneiwith 5- methoxy- 2-aminoibenzothiazoleiunder certain conditions to obtain new compound ( N- (2-aminoacetyl (5-methoxy) benzothiazole -2yl) (A4), Reaction of 5-(P-dimethyl amine benzene)-2-amino-1,3,4- oxadiazole in the presence of potassium carbonate anhydrous to yield new compound (N-(2- aminoacetyl-5-(P-dimethyl amine benzene )-1,3,4-oxadiazoles-2-yl)(A30) and Azo compound (N-(5-(Azo-2-hydroxy-5-amino benzene)-1,3-Diazol-2yl)Allopurinol(A46). The structure of prepared compounds were c

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47

Annam, Sri Charitha, K. V. Padmavathi, N. Murali Krishna, and Mannam Subbarao. "Computational Designing of Low Energy Band Gap of New Donor-Acceptor (D-A) Copolymer Monomers for Organic Solar Cells: DFT and TD-DFT Study." Science & Technology Journal 8, no. 2 (2020): 44–54. http://dx.doi.org/10.22232/stj.2020.08.02.08.

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Via this look at efforts have been made to increase a chain of latest donor-acceptor (D-A) systems through the usage of 4-methoxy-2,7,nine-trimethyl-9H-carbazole (2,7-MMCB) as a electron donor and benzo[c][1,2,5] oxadiazole (BCO); benzo[c] [1,2,5] thiadiazole (BCT); benzo[c][1,2,5]selenadiazole (BCS); [1,2,5]oxadiazolo[3,4-c]pyridine (OCP); [1,2,5] thiadiazolo [3,4-c]pyridine (TCP); [1,2,5] selenadiazolo [3,4-c]pyridine (SCP); [1,2,5] oxadiazolo[3,4-d]pyridazine (ODP); [1,2,5] thiadiazolo[3,4-d]pyridazine (TDP) as electron acceptors. In this work, we executed calculations of DFT and TD-DFT/B3L

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48

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 (2012): o1573. http://dx.doi.org/10.1107/s1600536812017825.

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49

Li, Hai-Lin, Hong-Wei Wang, Ran-Zhe Lu, and Hai-Bo Wang. "2-(4-Chlorophenyl)-5-{3,4-dibutoxy-5-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]thiophen-2-yl}-1,3,4-oxadiazole." Acta Crystallographica Section E Structure Reports Online 64, no. 12 (2008): o2298. http://dx.doi.org/10.1107/s1600536808035848.

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50

Rasool, Shahid, Aziz-ur-Rehman, Muhammad Athar Abbasi, et al. "Synthesis, Structural Elucidation, and Antibacterial Evaluation of Some New Molecules Derived from Coumarin, 1,3,4-Oxadiazole, and Acetamide." Organic Chemistry International 2016 (September 7, 2016): 1–10. http://dx.doi.org/10.1155/2016/8696817.

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Because of the reported biological activities of coumarin, 1,3,4-oxadiazole, and acetamides, some new compounds incorporating these moieties were synthesized and evaluated for their biological potential against Gram-positive and Gram-negative bacteria. In the present work, 4-chlororesorcinol (1) and ethyl acetoacetate (2) were mixed in a strong acidic medium to synthesize 6-chloro-7-hydroxy-4-methyl-2-oxo-2H-chromene (3) which was subjected to the intermolecular cyclization after consecutive three steps to synthesize 5-[(6-chloro-4-methyl-2-oxo-2H-chromen-7-yl)oxy]methyl-1,3,4-oxadiazol-2-thio

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