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Journal articles on the topic 'Oxirane derivative'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

Khalili, Gholamhossein, Patrick McCosker, Timothy Clark, and Paul Keller. "Synthesis and Density Functional Theory Studies of Azirinyl and Oxiranyl Functionalized Isoindigo and (3Z,3’Z)-3,3’-(ethane-1,2-diylidene)bis(indolin-2-one) Derivatives." Molecules 24, no. 20 (2019): 3649. http://dx.doi.org/10.3390/molecules24203649.

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The design and synthesis of functionalized isoindigo compounds by reaction of isoindigo with (S)-glycidyl tosylate, epibromohydrin, 2-(bromomethyl)-1-(arylsulfonyl)aziridine, and 2-(bromomethyl)-1-(alkylsulfonyl)aziridine in the presence of MeONa proceed under mild conditions in moderate yields. (3Z,3’Z)-3,3’-(Ethane-1,2-diylidene)bis(1-(oxiran-2-ylmethyl)indolin-2-one), with an extended central olefin π-conjugated moiety was also reacted with methyl-oxiranes to give the corresponding N,N’-disubstituted derivative. Calculations with DFT and TD-DFT of hypothetical isoindigo-thiophene DA molecul

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2

Barmaki, Mohammad, Gulgaz Valiyeva, Abel A. Maharramovm, and Mirze M. Allaverdiyev. "Synthesis of 2,3-Dihydro-6-methyl-2-thiopyrimidin-4(1H)-one (6-Methylthiouracil) Derivatives and Their Reactions." Journal of Chemistry 2013 (2013): 1–6. http://dx.doi.org/10.1155/2013/176213.

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The synthesis and characterization of 2,3-dihydro-6-methyl-2-thioxopyrimidin-(1H)-one (I) and some of its derivatives has been performed in our lab. Ring-closing cyclization, as a result of the condensation of ethyl-3-oxobutanoate with thiourea in KOH in an ethanol medium produced 2,3-dihydro-6-methy -2-thioxopyrimidin-(1H)-one (I). The reaction of compound (I) with 2- chloroacetic acid in an alkaline KOH solution produced the carboxylate derivative, 2-(2,6-dihydro-4-methyl-6-oxopyrimidin-2-yl-thio)ethanoic acid (II). The reaction of the resulted derivative of carboxylate (II) with the salt of

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3

Janeba, Zlatko, Antonín Holý, and Milena Masojídková. "Transformation of 8-[(2-Hydroxyalkyl)sulfanyl]adenines to 6-Amino-7H-purin-8(9H)-one Derivatives." Collection of Czechoslovak Chemical Communications 66, no. 9 (2001): 1393–406. http://dx.doi.org/10.1135/cccc20011393.

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Alkylation of 6-amino-7H-purin-8(9H)-thione (8-sulfanyladenine, 1) with one equivalent of (R)-[(trityloxy)methyl]oxirane gave its S-alkyl derivative 2, which was converted to the 6-amino-7H-purin-8(9H)-one (3), while alkylation of 1 with two equivalents of (S)-[(trityloxy)methyl]oxirane afforded a mixture of N3,S-dialkylated product 4a, N9-monoalkyl and N7,N9-dialkyl derivatives of 6-amino-7H-purin-8(9H)-one, 5a and 6a, respectively. This approach can be used for rapid and easy transformation of 8-[(2-hydroxyalkyl)sulfanyl]adenines to the derivatives of 6-amino-7H-purin-8(9H)-one (8-hydroxyade

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4

Okopi, S. O., and L. M. Affiku. "Synthesis and Olfactory Characteristics of Hydroxyether Derivatives of Methyl Eugenol." Journal of Applied Sciences and Environmental Management 24, no. 9 (2020): 1503–7. http://dx.doi.org/10.4314/jasem.v24i9.3.

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Methyl eugenol is a naturally occurring substance found in the essential oils of several plant species. It is a cheap and abundant material with a rather limited interest as perfuming ingredient. This research investigated the structure-odour relationship of methyl eugenol and its derivatives, focusing on the chemical transformation of the double bond to hydroxyether derivatives in a controlled manner. Two derivatives 2-(4-ethyl- 3-methoxybenzyl)oxirane (68.8% yield) and 1-(3,4-dimethoxyphenyl)-3-ethoxypropan-2-ol (63.58% yield), were synthesized from methyl eugenol. This research found that t

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5

Salanti, Anika, Luca Zoia, and Marco Orlandi. "Chemical modifications of lignin for the preparation of macromers containing cyclic carbonates." Green Chemistry 18, no. 14 (2016): 4063–72. http://dx.doi.org/10.1039/c6gc01028h.

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An epoxidized lignin derivative was prepared directly inserting epichlorohydrin on the phenolic functionalities and then the oxirane rings were converted to cyclic carbonate through the coupling reaction with CO<sub>2</sub>.

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6

Eshtukova-Shcheglova, E. A., K. A. Perevoshchikova, A. V. Eshtukov-Shcheglov, D. A. Cheshkov, and M. A. Maslov. "Amination of epoxides as a convenient approach for lipophilic polyamines synthesis." Fine Chemical Technologies 17, no. 4 (2022): 323–34. http://dx.doi.org/10.32362/2410-6593-2022-17-4-323-334.

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Objectives. Alkylated derivatives of polyamines are able to block the growth of cancer cells due to their embedding into the polyamine biosynthesis mechanisms. The study aimed to synthesize lipophilic derivatives of norspermine or triethylenetetramine based on the formation of a C–N bond during the opening of the oxirane ring by primary amines to expand a number of synthetic polyamine derivatives with antitumor activity.Methods. The starting compounds—glycidol alcoholate or epichlorohydrin—were reacted with hexadecyl bromide or sodium hexadecanolate to give glycidyl hexadecyl ether. The key re

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7

Mali, Suraj N., Sudhir Sawant, Hemchandra K. Chaudhari, and Mustapha C. Mandewale. "In Silico Appraisal, Synthesis, Antibacterial Screening and DNA Cleavage for 1,2,5-thiadiazole Derivative." Current Computer-Aided Drug Design 15, no. 5 (2019): 445–55. http://dx.doi.org/10.2174/1573409915666190206142756.

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Background: : Thiadiazole not only acts as “hydrogen binding domain” and “two-electron donor system” but also as constrained pharmacophore. Methods:: The maleate salt of 2-((2-hydroxy-3-((4-morpholino-1, 2,5-thiadiazol-3-yl) oxy) propyl) amino)- 2-methylpropan-1-ol (TML-Hydroxy)(4) has been synthesized. This methodology involves preparation of 4-morpholino-1, 2,5-thiadiazol-3-ol by hydroxylation of 4-(4-chloro-1, 2,5-thiadiazol-3-yl) morpholine followed by condensation with 2-(chloromethyl) oxirane to afford 4-(4-(oxiran-2-ylmethoxy)-1,2,5-thiadiazol- 3-yl) morpholine. Oxirane ring of this com

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8

Chalupová, Šárka, Antonín Holý, and Milena Masojídková. "Synthesis of Some N4-Substituted Derivatives of 1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine (HPMPC, Cidofovir)." Collection of Czechoslovak Chemical Communications 70, no. 12 (2005): 2053–65. http://dx.doi.org/10.1135/cccc20052053.

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N4-Substituted derivatives of HPMPC were synthesized in four-step synthesis which included treatment of 4-methoxypyrimidin-2(1H)-one (1) with (S)-[(trityloxy)methyl]oxirane in DMF. Condensation of intermediary 1-[2-hydroxy-3-(trityloxy)propyl]-4-methoxypyrimidin-2(1H)-one (2) with (diisopropoxyphosphoryl)methyl tosylate in the presence of sodium hydride resulted in fully protected 4-methoxypyrimidin-2(1H)-one derivative 3 which gave on reaction with an appropriate primary amine in dioxane N4-substituted products 4a-4i. The reaction with bromotrimethylsilane simultaneously cleaved the trityl gr

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9

Keglevich, András, Szabolcs Mayer, Réka Pápai, et al. "Attempted Synthesis of Vinca Alkaloids Condensed with Three-Membered Rings." Molecules 23, no. 10 (2018): 2574. http://dx.doi.org/10.3390/molecules23102574.

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Our successful work for the synthesis of cyclopropanated vinblastine and its derivatives by the Simmons–Smith reaction was followed to build up further three-membered rings into the 14,15-position of the vindoline part of the dimer alkaloid. Halogenated 14,15-cyclopropanovindoline was prepared by reactions with iodoform and bromoform, respectively, in the presence of diethylzinc. Reactions of dichlorocarbene with vindoline resulted in the 10-formyl derivative. Unexpectedly, in the case of the dimer alkaloids vinblastine and vincristine, the rearranged products containing an oxirane ring in the

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10

S., A. EL-ABBADY, and M. AGAMAI S. "Synthesis and Selected Reactions of 9-(2-Cyanoethyl)-1-oxa-9-azatricyclo[ 4.2.1.0 2,8]nonan-3-one-6-carbonitrile." Journal of Indian Chemical Society Vol. 73, Dec 1996 (1996): 663–65. https://doi.org/10.5281/zenodo.5918343.

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Department of Chemistry, University College for Girls, Am Shams University, Heliopolis, Cairo, Egypt <em>Manuscript received 27 January 1994, revised 16 March 1995, accepted 31 May 1995 </em> Oxirination of the activated 3,4-olefinic double bond of 8-(2-cyanoethyl)-8-azabicyclo[3.2.1]oct-3-en-2-one-6-carbonitrile (1) with basic hydrogen peroxide afforded 9-(2-cyanoethyl)-1-oxa-9-azatricyclo[4.2.1.0<sup>2,8</sup>]nonan-3-one-6-carbonitrile (2). Ring opening of the oxirane ring in 2 has been investigated using 10% sodium hydroxide, acetic acid and phenylhydrazine to give 4, 7 and 8 respecti

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11

Šála, Michal, Hubert Hřebabecký, Milena Masojídková, and Antonín Holý. "Synthesis of Racemic 2-Hydroxy-4- and 2-Hydroxy-5-(hydroxymethyl)cyclohexane Pyrimidine C-Nucleoside Analogues." Collection of Czechoslovak Chemical Communications 69, no. 4 (2004): 918–32. http://dx.doi.org/10.1135/cccc20040918.

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The oxirane ring opening of 3-[(benzyloxy)methyl]-7-oxabicyclo[4.1.0]heptane with sodium salt of diethyl malonate followed by treatment with TsOH gave (3aR*,6R*,7aS*)-6-[(benzyloxy)methyl]hexahydro-1-benzofuran-2(3H)-one (3a) and (3aR*,5R*,7aS*)-5-[(benzyloxy)methyl]hexahydro-1-benzofuran-2(3H)-one (3b). Lactones 3a and 3b were formylated and then treated with thiourea or guanidine to give, after deprotection, racemic 5-[2-hydroxy-4- and 2-hydroxy-5-(hydroxymethyl)cyclohexyl]-2-thiouracil (5a and 5b) or -isocytosine (12a and 12b). Simple transformations of the 2-thiouracil derivative led to ur

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12

Bravo, Pierfrancesco, Massimo Frigerio, Giovanni Fronza, et al. "Stereoselective oxirane formation by reaction of diazomethane on 1-fluoro-3-[(4-methylphenyl)sulfinyl]-3-phenylpropan-2-one." Canadian Journal of Chemistry 72, no. 8 (1994): 1769–79. http://dx.doi.org/10.1139/v94-224.

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(2S, 2′R,RS)-2-(Fluoromethyl)-2-{[(4-methylphenyl)sulfinyl][phenyl]methyl}oxirane (4) was obtained in high chemical yield and with high diastereoselectivity by reacting diazomethane with pure (3R, RS)-1-fluoro-3-[(4-methylphenyl)sulfinyl]-3-phenylpropan-2-one (3), but also with its (3S, RS)-3-diastereoisomer, in the latter case through inversion of the configuration at carbon 3. The corresponding methyl enol ethers 6 were isolated as by-products. NMR experiments and molecular modelling calculations were performed in order to clarify the equilibria in solution and the preferred conformations of

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13

Čapek, Karel, Tomáš Vydra, Mojmír Ranný, and Petr Sedmera. "Structures of hexa-O-acetylsucroses formed by deacetylation of sucrose octa-O-acetate." Collection of Czechoslovak Chemical Communications 50, no. 10 (1985): 2191–200. http://dx.doi.org/10.1135/cccc19852191.

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A fraction corresponding to hexa-O-acetylsucrose was isolated in 34% yield from the reaction mixture after deacetylation of sucrose octa-acetate by aluminium oxide impregnated by potassium carbonate. Its subsequent reaction with p-toluenesulfonyl chloride in pyridine provided crystalline 1',2,3,4,6,6'-hexa-O-acetyl-3',4'-di-O-p-toluenesulfonylsucrose (III). With triphenylphosphine-diethyl azodicarboxylate reagent, 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-β-D-lyxo-hexulofuranoside (VI) was obtained. Treatment of ditosyl derivative III with sodium methoxide followed

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14

Banwell, Martin G., Shen Tan, Zhongnan Xu, Xin-Ting Liang, Jian-Guo Song, and Lorenzo V. White. "Total Synthesis of the Prenylated Indole Alkaloid (±)-Notoamide N via an Electrochemically Mediated Vilsmeier–Haack Formylation of a Chlorinated Indole." SynOpen 09, no. 01 (2025): 1–9. https://doi.org/10.1055/s-0043-1773504.

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AbstractA total synthesis of the racemic modification of the prenylated indole alkaloid notoamide N has been realised. A crucial step involved the electrochemically mediated Vilsmeier–Haack formylation of a chlorinated 1,7-dihydropyrano[2,3-g]indole. The product aldehyde was engaged in biomimetic and tandem aldol condensation/intramolecular Diels–Alder reactions with a diketopiperazine derivative to give a diazabicyclo[2.2.2]octane-containing adduct. Epoxidation of this adduct led, via an in situ semi-pinacolic rearrangement of the initially formed oxirane, to the targeted spiro-oxindole notoa

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15

Djurendić, Evgenija A., Marina P. Zaviš, Marija N. Sakač, Vesna V. Kojić, Gordana M. Bogdanović, and Katarina M. Penov Gaši. "Synthesis and Biological Evaluation of Some A,D-Ring Modified 16,17-Secoandrostane Derivatives." Collection of Czechoslovak Chemical Communications 73, no. 5 (2008): 627–36. http://dx.doi.org/10.1135/cccc20080627.

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Starting from 3β-hydroxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), the new 16,17-secoandrostane derivatives 2-11 were synthesized. Protection of the 17-oxo function of compound 1 with ethylene glycol yielded compounds 2 and 3. The Oppenauer oxidation of 2 or oxidation with H2O2 in alkaline conditions gave the respective compounds 4 and 10. Epoxidation of compound 4 yielded a mixture of 4α,5α- and 4β,5β-epoxides 5 and 6 and a mixture of 4α,5α- and 4β,5β-epoxy-carboxamides 7 and 8. Opening of the oxirane ring of a mixture of compounds 5 and 6 with formic acid afforded the 4-hydroxy derivati

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16

Vaze, S., and D. A. Tirrell. "Preparation of Poly[(3-bromopropyl)oxirane]: A Reactive Derivative of Poly(ethylene Oxide)." Journal of Bioactive and Compatible Polymers 1, no. 1 (1986): 79–83. http://dx.doi.org/10.1177/088391158600100108.

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17

Brenna, Elisabetta, Danilo Colombo, Giuseppe Di Lecce, et al. "Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route." Molecules 25, no. 8 (2020): 1882. http://dx.doi.org/10.3390/molecules25081882.

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A chemo-enzymatic approach for the conversion of oleic acid into azelaic and pelargonic acid is herein described. It represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. Azelaic acid is produced in high chemical purity in 44% isolation yield after three steps, avoiding column chromatography purifications. In the first step, the lipase-mediated generation of peroleic acid in the presence of 35% H2O2 is employed for the self-epoxidation of the unsaturated acid to the corresponding oxirane derivative. This intermediate is submitte

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18

Yamashita, Yu, Yoichi Hirano, Akiomi Takada, Hiroshi Takikawa, and Keisuke Suzuki. "Total Synthesis of Bis-anthraquinone Antibiotic BE-43472B." Synthesis 50, no. 13 (2018): 2490–515. http://dx.doi.org/10.1055/s-0037-1610136.

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This is a full account of our synthetic endeavor on the total synthesis of bis-anthraquinone antibiotic BE-43472B, an unusual octacyclic aromatic polyketide with a bis-anthraquinone scaffold. Three key steps enabled a facile access to the anthraquinone unit corresponding to the ABCF rings; (1) cyclo-condensation or -addition of benzonitrile oxides with cyclic enone derivatives, (2) benzoin cyclization for the stereoselective ring fusion with an angular hydroxy group, and (3) pinacol rearrangement for stereoselective installation of the angular aryl group. Other keys for the success include, (4

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19

Petrosyan, Artyom V., Astghik A. Shahkhatuni, Andranik M. Davinyan, et al. "Thiol-Epoxy Click Chemistry: The Synthesis of Vicinal Amino Alcohols Containing a 1,2,4-Triazole Ring." Chemistry 7, no. 2 (2025): 53. https://doi.org/10.3390/chemistry7020053.

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As examples of “Click Chemistry”, the reaction of 1-(oxiran-2-ylmethyl)piperidine with several 1,2,4-triazoles derivatives was studied. As a result, the reaction shows that the oxirane ring opens regiospecifically, according to Krasusky’s rule, without using a catalyst. The basic nitrogen present in 1-(oxiran-2-ylmethyl)piperidine has a catalytic (anchimer) effect.

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20

Trtek, Tomáš, Miloslav Černý, Tomáš Trnka, Miloš Buděšínský та Ivana Císařová. "Synthesis of Tricycles Based on 1,6-Anhydro-β-D-hexopyranoses Fused with Morpholine. 3,10,12-Trioxa-6-azatricyclo[7.2.1.02,7]dodecanes". Collection of Czechoslovak Chemical Communications 68, № 7 (2003): 1295–308. http://dx.doi.org/10.1135/cccc20031295.

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The key step of the synthetic route was opening of the oxirane ring in 1,6:3,4-dianhydro-2-O-tosyl-β-D-galactopyranose (1) with 2-chloroethanol to give 1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose (2), which was converted in four steps into 4-O-(2-aminoethyl)-1,6:2,3-dianhydro-β-D-mannopyranose (6). The latter compound underwent intramolecular cyclisation to afford the fused morpholine derivative 3-amino-1,6-anhydro-3-deoxy-3-N,4-O-ethylene-β-D-altropyranose (7) which gave the corresponding quaternary ammonium salt 11 by N-methylation. Acid cleavage of the 1,6-anhydro bond in 7

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21

Trtek, Tomáš, Miloslav Černý, Tomáš Trnka, Miloš Buděšínský та Ivana Císařová. "Synthesis of Some 1,4-Oxazepanes Fused with 1,6-Anhydro-β-D-hexopyranoses. 3,11,13-Trioxa-7-azatricyclo[8.2.1.02,8]tridecane Derivatives". Collection of Czechoslovak Chemical Communications 69, № 9 (2004): 1818–28. http://dx.doi.org/10.1135/cccc20041818.

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Some 1,4-oxazepanes based on 1,6-anhydro-β-D-hexopyranoses were prepared from 1,6:3,4-dianhydro-2-O-tosyl-β-D-galactopyranose (1). Cleavage of its oxirane ring with 3-chloropropanol gave 1,6-anhydro-4-O-(3-chloropropyl)-2-O-tosyl-β-D-glucopyranose (2), which was converted in three steps into 4-O-(3-aminopropyl)-1,6:2,3-dianhydro-β-D-mannopyranose (5). The latter compound underwent intramolecular cyclization to afford 3-amino-1,6-anhydro-3-deoxy-3-N,4-O-(propane-1,3-diyl)-β-D-altropyranose (6) that gave the corresponding quaternary ammonium salt 10 by N-methylation. Acid cleavage of the 1,6-anh

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22

Saleh, Mohamed B., Ahmed A. Abdel Gaber, Moustafa M. R. Khalaf, and Ahmed M. Tawfeek. "Novel Sm(III) Ion‐Selective Polymeric Membrane Sensor Based on Spiro[Oxirane‐Pyrazolidinedione] Derivative Ionophore." Analytical Letters 39, no. 1 (2006): 17–31. http://dx.doi.org/10.1080/00032710500423351.

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23

Holý, Antonín, Ivan Votruba, Eva Tloušťová, and Milena Masojídková. "Synthesis and Cytostatic Activity of N-[2-(Phosphonomethoxy)alkyl] Derivatives of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds." Collection of Czechoslovak Chemical Communications 66, no. 10 (2001): 1545–92. http://dx.doi.org/10.1135/cccc20011545.

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N6-Substituted adenine and 2,6-diaminopurine derivatives of 9-[2-(phosphonomethoxy)- ethyl] (PME), 9-[(R)-2-(phosphonomethoxy)propyl] [(R)-PMP] and enantiomeric (S)-PMP series were synthesized by reactions of primary or secondary amines with 6-chloro-9-{[2-(diisopropoxyphosphoryl)methoxy]alkyl}purines (26-28) or 2-amino-6-chloro-9-{[2-(diisopropoxy- phosphoryl)methoxy]alkyl}purines (29-31) followed by treatment of the diester intermediates32with bromo(trimethyl)silane and hydrolysis. Diesters32were also obtained by reaction ofN6-substituted purines with synthons23-25bearing diisopropoxyphospho

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24

Nshimiyimana, Robert, Charles N. Serhan, and Nicos A. Petasis. "On the Total Synthesis of 7,8(S,S)-Epoxy-17(S)-hydroxy-4(Z),9(E),11(E),13(Z),15(E),19(Z)-docosahexaenoic Acid Derivative." Molecules 30, no. 8 (2025): 1858. https://doi.org/10.3390/molecules30081858.

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The stereoselective total synthesis of an allylic epoxide-containing polyunsaturated fatty acid, in its triethylsilyl (TES) ether and methyl ester form, is described. Key features include a Sharpless enantioselective epoxidation to install the oxirane unit and Wittig coupling reactions to forge critical alkenyl configuration and secure the core carbon skeleton. The deprotected epoxy acid was recently demonstrated to play a central role as the precursor to biologically active resolvins D1, D2, and the cysteinyl conjugate in tissue regeneration (RCTR1) by human leukocytes. These natural products

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25

Raji, Mounir, Tam Minh Le, Ferenc Fülöp, and Zsolt Szakonyi. "Synthesis and Investigation of Pinane-Based Chiral Tridentate Ligands in the Asymmetric Addition of Diethylzinc to Aldehydes." Catalysts 10, no. 5 (2020): 474. http://dx.doi.org/10.3390/catal10050474.

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A library of pinane-based chiral aminodiols, derived from natural (−)-β-pinene, were prepared and applied as chiral catalysts in the addition of diethylzinc to aldehydes. (−)-β-Pinene was reacted to provide 3-methylenenopinone, followed by a reduction of the carbonyl function to give a key allylic alcohol intermediate. Stereoselective epoxidation of the latter and subsequent ring opening of the resulting oxirane with primary and secondary amines afforded aminodiols. The regioselectivity of the ring closure of the N-substituted secondary aminodiols with formaldehyde was examined and exclusive f

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26

Fernandes, Maria José G., David M. Pereira, Renato B. Pereira, A. Gil Fortes, Elisabete M. S. Castanheira, and M. Sameiro T. Gonçalves. "Synthesis and Insecticidal Activity of O-alkylated Oxirane Eugenol Derivatives." Chemistry Proceedings 3, no. 1 (2020): 36. http://dx.doi.org/10.3390/ecsoc-24-08335.

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The synthesis of three O-alkylated eugenol derivatives, bearing a hydroxypropyl chain and propyl esters, were synthesized and further converted into the corresponding oxiranes. Oxirane derivatives were then evaluated against their effect upon the viability of the insect cell line Sf9 (Spodoptera frugiperda), in comparison with the starting O-alkylates. The results pointing to their potential as bioinsecticides, with structural changes eliciting significant effects in terms of potency.

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Sedenkova, Kseniya N., Olga V. Ryzhikova, Svetlana A. Stepanova, et al. "Bis(oxiranes) Containing Cyclooctane Core: Synthesis and Reactivity towards NaN3." Molecules 27, no. 20 (2022): 6889. http://dx.doi.org/10.3390/molecules27206889.

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Reactions of oxirane ring opening provide a powerful tool for regio- and stereoselective synthesis of polyfunctional and heterocyclic compounds, widely used in organic chemistry and drug design. Cyclooctane, alongside other medium-sized rings, is of interest as a novel molecular platform for the construction of target-oriented leads. Additionally, cyclooctane derivatives are well known to be prone to transannular reactions, which makes them a promising object in the search for novel approaches to polycyclic structures. In the present work, a series of cyclooctanediones was studied in Corey-Cha

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28

Hertz, R., and J. Bar–Tana. "Prevention of peroxisomal proliferation by carnitine palmitoyltransferase inhibitors in cultured rat hepatocytes and in vivo." Biochemical Journal 245, no. 2 (1987): 387–92. http://dx.doi.org/10.1042/bj2450387.

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1. The induction of peroxisomal beta-oxidation activities by bezafibrate in cultured rat hepatocytes and in the rat in vivo was prevented by inhibitors of carnitine acyltransferase, e.g. 2-bromopalmitate, 2-[5-(4-chlorophenyl)pentyl]oxirane-2-carboxylate or 2-tetradecylglycidic acid. 2. The prevention of peroxisomal proliferation by carnitine palmitoyltransferase inhibitors could not be accounted for by inhibition of mitochondrial beta-oxidation, since 2-bromo-octanoate, acting as an inhibitor of beta-oxidation, did not prevent the induction of peroxisomal activities in cultured rat hepatocyte

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29

Tedesco, Daniele, Edoardo Fabini, Vakhtang Barbakadze, et al. "Stopped-flow enantioselective HPLC-CD analysis and TD-DFT stereochemical characterization of methyl trans-3-(3,4-dimethoxyphenyl)glycidate." Chirality 27 (October 8, 2015): 914–18. https://doi.org/10.1002/chir.22539.

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This is the peer reviewed version of the article which has been published in final form on Chirality 27:914–918 (2015), available at https://doi.org/10.1002/chir.22539. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s ver

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Čapek, Karel, Tomáš Vydra, and Petr Sedmera. "Structure of penta-O-acetylsucroses formed by deacetylation of octa-O-acetylsucrose. Reaction of 2,3,4,6,6'-penta-O-acetylsucrose." Collection of Czechoslovak Chemical Communications 53, no. 6 (1988): 1317–31. http://dx.doi.org/10.1135/cccc19881317.

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Chromatographic separation of penta-O-acetylsucrose fraction from deacetylation of octa-O-acetylsucrose by treatment with aluminium oxide impregnated by potassium carbonate gave 1',3,4,6,6'-penta-O-acetylsucrose (XII), 1,2,3,4,6-penta-O-acetylsucrose (XIII), and the prevailing 2,3,4,6,6'-penta-O-acetylsucrose (XIV). Reaction of compound XIV with two equivalents of p-toluenesulfonyl chloride in pyridine produced besides the 1'-O-p-toluenesulfonyl derivative XXI and 1',3',4'-tri-O-tosyl derivative XXII also 1',3'-di-O-tosyl derivative XXIII and 1',4'-di-O-tosyl derivative XX. 1',2-anhydro-(3,4,6

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Kuş, Melih, Cenk Omur, Sıla Karaca, and Levent Artok. "Iron-Promoted 1,5-Substitution Reaction of Endocyclic Enyne Oxiranes with MeMgBr: A Stereoselective Method for the Synthesis of Exocyclic 2,4,5-Trienol Derivatives." Chemistry 5, no. 4 (2023): 2682–99. http://dx.doi.org/10.3390/chemistry5040173.

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The iron-promoted 1,5-substitution reaction of endocyclic oxiranes with MeMgBr yields exocyclic 2,4,5-trienols with high diastereomeric ratios of up to 100:0. However, for the method’s success, the oxirane ring must have a trans-configuration. The reactions exhibit strong stereoselectivity concerning the methylation mode and the configuration of the resulting exocyclic double bond. Enantiomerically pure enyne oxiranes can be synthesized through Sharpless asymmetric dihydroxylation and subsequent manipulations. With these reagents, it has been possible to produce exocyclic 2,4,5-trienols in ena

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Startseva, V. A., L. E. Nikitina, and V. V. Plemenkov. "ChemInform Abstract: trans-Diepoxy Derivative of Limonene. Synthesis, Structure, and Products of Oxirane Ring Opening with Sulfur-Containing Reagents." ChemInform 32, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.200139194.

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Askerov, O. V., A. F. Mamedova, and D. R. Nurullayeva. "SYNTHESIS AND PROPERTIES OF ORGANOSILICON EPISULFIDES." Azerbaijan Chemical Journal, no. 4 (December 8, 2021): 43–48. http://dx.doi.org/10.32737/0005-2531-2021-4-43-48.

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A study was made of the interaction of thiourea with saturated and unsaturated organosilicon oxiranes in absolute methyl alcohol in a medium of potassium hydroxide, and methods were developed for the synthesis of unsaturated and unsaturated organosilicon silicides with a yield of 65–75%.The studies carried out revealed that the synthesized organosilicon episulfides are very reactive compounds and can react with nucleophilic and electrophilic reagents, while forming the corresponding silicon derivatives. The IR- spectra of the products were studied. It should be noted that, when comparing the I

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Mali, Nand, Rajeev Mehta, Preeti Mehta, and Pankaj Sen. "Synthesis and Characterization of Ether-Dimer Impurity of Drug - Ranolazine Using 2, 2’- (oxybis (methylene)) Bis (Oxirane)." American Journal of Applied Scientific Research 11, no. 2 (2025): 120–26. https://doi.org/10.11648/j.ajasr.20251102.12.

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Ranolazine became the first approved member of a new family of antianginal medications in nearly 25 years when it was licensed in 2006 for the treatment of chronic angina pectoris. The exact mechanism of action of Ranolazine is unclear. Ranolazine was originally believed to work by partially inhibiting the oxidation of fatty acids. Ranolazine may lessen calcium excess in ischemic myocytes by inhibiting the late sodium current, according to more recent data. Headache, nausea, constipation, and dizziness are the most commonly reported side effects. Ranolazine is listed among the top 200 drugs by

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Archana, Singh, Prasad Virendra, Rajkhowa Sanchayita, D. Tripathi Vishwa, and K. Tiwari Vinod. "Synthesis of glycosylated aminothiol from D-glucose as promising anti-tubercular agent." Journal of Indian Chemical Society Vol. 97, Feb 2020 (2020): 213–25. https://doi.org/10.5281/zenodo.5651696.

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Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi-221 005, Uttar Pradesh, India <em>E-mail</em>: tiwari_chem@yahoo.co.in, vinod.tiwari@bhu.ac.in Department of Chemistry, Gauhati University, Guwahati-781 014, Assam, India Department of Chemistry, M. K. College, L. N.Mithila University, Darbhanga-846 004, Bihar, India <em>Manuscript received online 29 September 2019, revised and accepted 18 January 2020</em> A facile method for a series of novel glycosylated β-aminothiols by employing TBAB/NEt<sub>3</sub> -catalyzed ring opening of thiirane ring of D-glucose-

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Mammadov, El Sh. "SELENOLANES, SELENATRANS AND ESTERS OF SELENIC ACID." Azerbaijan Chemical Journal, no. 4 (December 8, 2022): 95–101. http://dx.doi.org/10.32737/0005-2531-2022-4-95-101.

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It is known that selenic acid and selenium dioxide act as oxidizing agents in reactions with α-oxides when heated. The proposed paper presents data on the synthesis of organoselenium compounds based on reactions of α-oxides with selenic acid and its anhydride, where the latter act as selenation agents. It was found that in the presence of catalytic amounts of boron trifluoride esterate in the reactions of oxiranes with acid the oxirane ring opens both according to the rule and against the Krasussky rule with the formation of a mixture of α- and β- isomers of selenic acid esters. In contrast to

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K., H. Popat, H. Purohit D., T. Chovatia P., and S. Joshi H. "Synthesis of some thiosemicarbazone and oxirane derivatives as potent antitubercular agents." Journal of Indian Chemical Society Vol. 82, Oct 2005 (2005): 940–41. https://doi.org/10.5281/zenodo.5827255.

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Department of Chemistry, Saurashtra University, Rajkot-360 005, India <em>E-mail</em> : drhsjoshi@yahoo.com                            <em>Fax</em>: 91-281-2578512 <em>Manuscript received 13 August 2004, revised 7 July 2005, accepted 14 July 2005</em> Condensation of thiosemicarbazide with 1-aryl-3-(3'-chlorophenyl)-2-propene-1-ones (la-j) afforded corresponding 4-α( 3'-chlorostyryl)-benzylidene-thiosemicarbazones (2a-j) and the compounds (1a-j) on reaction with alkaline H<sub>2</sub>O<sub>2</sub> gave 3-(3&#39

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Dzedulionytė, Karolina, Melita Veikšaitė, Vít Morávek, et al. "Convenient Synthesis of N-Heterocycle-Fused Tetrahydro-1,4-Diazepinones." Molecules 27, no. 24 (2022): 8666. http://dx.doi.org/10.3390/molecules27248666.

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A general approach towards the synthesis of tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one, tetrahydro[1,4]diazepino[1,2-a]indol-1-one and tetrahydro-1H-benzo[4,5]imidazo[1,2-a][1,4]diazepin-1-one derivatives was introduced. A regioselective strategy was developed for synthesizing ethyl 1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylates from easily accessible 3(5)-aryl- or methyl-1H-pyrazole-5(3)-carboxylates. Obtained intermediates were further treated with amines resulting in oxirane ring-opening and direct cyclisation—yielding target pyrazolo[1,5-a][1,4]diazepin-4-ones. A straightforward tw

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Shen, Chuang, Xiang Guo, Jun Yu, et al. "Synthesis of 2-(phenoxymethyl)oxirane derivatives through unexpected rearrangement of oxiran-2-ylmethyl benzenesulfonates." Synthetic Communications 47, no. 4 (2017): 273–78. http://dx.doi.org/10.1080/00397911.2016.1258579.

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Solomek, Tomas, Peter Stacko, Aneesh Tazhe Veetil, Tomas Pospisil, and Petr Klan. "Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives." Journal of Organic Chemistry 75, no. 21 (2010): 7300–7309. http://dx.doi.org/10.1021/jo101515a.

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Jaseja, Mahesh, Rabindra N. Rej, François Sauriol, and Arthur S. Perlin. "Novel regio- and stereoselective modifications of heparin in alkaline solution. Nuclear magnetic resonance spectroscopic evidence." Canadian Journal of Chemistry 67, no. 9 (1989): 1449–56. http://dx.doi.org/10.1139/v89-221.

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Nuclear magnetic resonance spectroscopic evidence is presented in characterizing three new structurally modified forms of heparin. One of these, polymer M-I, represents a conversion of about two-thirds of the α-L-iduronic acid 2-sulfate residues (1) into residues of a 2,3-anhydro derivative (3), through the action of sodium hydroxide. The formation of 3 is attributed to a base-catalysed displacement of the sulfate group of 1 by an intramolecular attack of O-3 on C-2. In more concentrated sodium hydroxide solution, heparin is transformed almost quantitatively into polymer M-II, which differs fr

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Salomatina, Oksana V., Aleksandra V. Sen’kova, Arseny D. Moralev, et al. "Novel Epoxides of Soloxolone Methyl: An Effect of the Formation of Oxirane Ring and Stereoisomerism on Cytotoxic Profile, Anti-Metastatic and Anti-Inflammatory Activities In Vitro and In Vivo." International Journal of Molecular Sciences 23, no. 11 (2022): 6214. http://dx.doi.org/10.3390/ijms23116214.

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It is known that epoxide-bearing compounds display pronounced pharmacological activities, and the epoxidation of natural metabolites can be a promising strategy to improve their bioactivity. Here, we report the design, synthesis and evaluation of biological properties of αO-SM and βO-SM, novel epoxides of soloxolone methyl (SM), a cyanoenone-bearing derivative of 18βH-glycyrrhetinic acid. We demonstrated that the replacement of a double-bound within the cyanoenone pharmacophore group of SM with α- and β-epoxide moieties did not abrogate the high antitumor and anti-inflammatory potentials of th

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Skachko, Stanislav, Orest Hevus, and Larysa Dolynska. "Novel Functional Derivatives of Methyl-cis-9,10-Epoxy-Octadecanoate." Chemistry & Chemical Technology 4, no. 3 (2010): 167–70. http://dx.doi.org/10.23939/chcht04.03.167.

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The synthesis of functional derivatives of epoxystearic acid methyl ester by oxirane ring opening and transesterification of ester group has been described. Some novel surface-active and peroxide-containing compounds have been obtained. Major features of the process have been investigated and main characteristics have been determined.

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Elling, L., and MR Kula. "Immunoaffinity partitioning: synthesis and use of polyethylene glycol‐oxirane for coupling to bovine serum albumin and monoclonal antibodies." Biotechnology and Applied Biochemistry 13, no. 3 (1991): 354–62. http://dx.doi.org/10.1111/j.1470-8744.1991.tb00158.x.

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Polyethylene glycol (PEG)‐oxirane was synthesized by reacting aminated monomethoxy‐PEG 5000 (NH2‐MPEG 5000) with butanediol diglycidyl ether and used to derivatize bovine serum albumin (BSA) and monoclonal antibodies (mAb) against horseradish peroxidase (HRP) and porcine lactate dehydrogenase isoenzyme 5, respectively. Determination of oxirane end groups revealed a very high number, which arise from the chain breaks of the polymer. Covalent coupling of PEG‐oxirane to BSA resulted in 30–50 times higher partition coefficients under optimized conditions. The mAb investigated could be modified wit

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El-Sayed, Amira A., Maher A, El Hashash, and Sameh A. Rizk. "Ultrasonic and solvent free Synthesis of Regioselective Diastereomeric Adducts and Heterocyclic Products as antibacterial agent." JOURNAL OF ADVANCES IN CHEMISTRY 13, no. 2 (2017): 5977–88. http://dx.doi.org/10.24297/jac.v13i12.6152.

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Oxirane ring containing the carboxylic group in the Î±,Î²-position are useful intermediates in the synthesis of biologically active compounds. Epoxidation of 4-(4-acetylamino and/or bromophenyl)-4-oxo-but-2-enoic acids via ultrasound condition afforded Î±-oxirane carboxylic acid followed by regioselective diastereomeric adducts of camphor. The steric factor plays an important role in regioselectivity. Formation of oxirane and furan derivatives via ultrasonic condition was considered as key steps for synthesis of some important heterocyclic compounds. The structure of new synthesized compounds

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Dvořáková, Hana, Antonín Holý, and Ivan Rosenberg. "Synthesis of Some 2'-C-Alkyl Derivatives of 9-(2-Phosphonomethoxyethyl)adenine and Related Compounds." Collection of Czechoslovak Chemical Communications 59, no. 9 (1994): 2069–94. http://dx.doi.org/10.1135/cccc19942069.

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To study the effect of β-substitution in 2'-alkyl derivatives of 9-(2-phosphonomethoxyethyl)adenine (Ia) on the antiviral activity or group specificity, these derivatives were synthesized. 9-(2-Hydroxyalkyl)adenines VIII were prepared by alkylation of adenine with suitably substituted oxiranes XIII or 2-hydroxyalkyl p-toluenesulfonates IV and VI. After protection of the adenine amino group by benzoylation (compounds IX) or amidine formation (compounds X), the intermediates were alkylated with diisopropyl p-toluenesulfonyloxymethanephosphonate (XI) in the presence of sodium hydride. After depro

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Tian, Ziqi, Yuanjing Xiao, Xiangai Yuan, Zuliang Chen, Junliang Zhang, and Jing Ma. "Control of Chemoselectivity by Coordinated Water and Relative Size of Ligands to Metal Cations of Lewis Acid Catalysts for Cycloaddition of an Oxirane Derivative to an Aldehyde: Theoretical and Experimental Study." Organometallics 33, no. 7 (2014): 1715–25. http://dx.doi.org/10.1021/om500068m.

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Krečmerová, Marcela, Antonín Holý, and Milena Masojídková. "Pyrimidine Acyclic Nucleotide Analogues with Aromatic Substituents in C-5 Position." Collection of Czechoslovak Chemical Communications 72, no. 7 (2007): 927–51. http://dx.doi.org/10.1135/cccc20070927.

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NH2-protected 5-phenylcytosine and its derivatives 2a-2d were treated with (2S)-2-[(trityloxy)methyl]oxirane (3) followed by etherification with diisopropyl [(tosyloxy)methyl]phosphonate (5) in the presence of sodium hydride. The intermediary phosphonate esters 6 were debenzoylated and subsequently transformed to free phosphonic acids, i.e. (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-phenylcytosine (5-phenyl-HPMPC) derivatives (8a-8d) by the action of bromotrimethylsilane and subsequent hydrolysis. Deamination of these compounds with 3-methylbutyl nitrite afforded corresponding (S)-1-[3-hyd

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Saputri, Dita Ayu, Dedy Suhendra, Erin Ryantin Gunawan, and Murniati Murniati. "Effect of Acid Catalyst on Epoxydation Reaction of Nyamplung Seed Oil." Jurnal Pijar Mipa 20, no. 1 (2025): 135–40. https://doi.org/10.29303/jpm.v20i1.6338.

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Epoxy is a cyclic ether compound that contains an oxirane group and has been widely applied as a stabilizer, plasticizer in polyvinyl chloride (PVC), surfactant, pesticide raw material, and as a polymer resin coating. The raw materials in epoxy synthesis come from petroleum derivatives, which are non-renewable natural resources. Therefore, there is a need for alternative raw materials that can be renewed, such as vegetable oil. In this study, nyamplung seed oil was used. Epoxy synthesis is usually carried out using carboxylic acid epoxidation with the help of an acid catalyst. This research ai

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Julianto, T. S., F. J. Rachmawaty, H. A. Tamhid, and B. S. Putri. "THE POTENTIAL ANTIMALARIAL DRUG OF ARYL AMINO ALCOHOL DERIVATIVES FROM EUGENOL: SYNTHESIS, in-vitro AND in-silico ANALYSIS OF BIOACTIVITY." RASAYAN Journal of Chemistry 16, no. 03 (2023): 1425–34. http://dx.doi.org/10.31788/rjc.2023.1636940.

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Malaria is a significant cause of death in numerous countries, and the discovery of effective drugs is crucial. In this research, a new method was employed to synthesize a derivative of aryl amino alcohol using eugenol. Initially, an epoxide compound called 2-methoxy-4-(oxiran-2-ylmethyl) phenol was synthesized from eugenol by reacting it with peroxyacetic acid in dichloromethane. Subsequently, the epoxide compound was subjected to a reaction with various amine compounds, including aniline, naphthylamine, and diphenylamine for 10 minutes under 100 W microwave conditions, resulting in the produ

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