Synthesis of alkyl derivatives of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane and evaluation of their biological activity

Today 3,7,10-trioxo-2,4,6,8,9,11-hexaaaza[3.3.3]propellane (THAP) has not yet received widespread re-search attention due to the complexity of the synthesis. This work is devoted to the development of a method for the THAP derivatives synthesis, as well as to the study of their biological activity in comparison with al-kyl-substituted glycolurils (subject of comparison). ТНАРwas N-alkylated to furnish novel hexaalkyl deriva-tives of ТНАРwith methyl, ethyl and propyl substituents. The conditionsfor obtaining the maximum yield of the target productwere optimizedon the base of methyl derivative. The reaction proceeded in DMSO/КОНat 75–80ºC for 13hours in a moderate yield of 56%. The ethyl and propyl derivatives of ТНАРwere synthe-sized under the same conditions. The biological activity of the obtained ТНАРalkyl derivatives and glycoluril alkyl derivatives was evaluated against Sporosarcina ureae, Bacillus pumilus, Salmonella typhimurium and Staphylococcus aureus bacteria and influenza A virus. All the samples were found to exhib-it antibacterial activity against Staphylococcus aureus.It was shown that 2,4,6,8,9,11-hexapropyl-ТНАР, di-tert-butyl-diphenyl-, di-tert-butyl-dibenzyl-, di-tert-butyl-dimethyl-and di-isopropyl-dibenzylglycoluril, have exhibited also toxicity to living cells besides antiviral activity

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The synthesis and prediction of biological activity in silico for new alkyl derivatives of 4-r-3-(morfolinometylen)-4H-1,2,4-triazole-5-thioles

Ukraïns’kij bìofarmacevtičnij žurnal ◽

10.24959/ubphj.16.36 ◽

2016 ◽

Vol 0 (3(44)) ◽

pp. 34-38

Author(s):

R. O. Shcherbyna

Keyword(s):

Biological Activity ◽

In Silico ◽

Alkyl Derivatives ◽

Derivatives Of

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Synthesis , Characterization and Study of Biological Activity of Some New Schiff Bases ,1,3-Oxazepine and Tetrazole Derived from 2,2 di thiophenyl Acetic Acid

Ibn AL- Haitham Journal For Pure and Applied Science ◽

10.30526/31.1.1866 ◽

2018 ◽

Vol 31 (1) ◽

pp. 189 ◽

Cited By ~ 1

Author(s):

Eman M. Hussain ◽

Hussam Z. Naji

Keyword(s):

Mass Spectrometry ◽

Staphylococcus Aureus ◽

Acetic Acid ◽

Biological Activity ◽

Hydrazine Hydrate ◽

Schiff Bases ◽

Sodium Azide ◽

Derivatives Of ◽

Tetrazole Derivatives ◽

And Staphylococcus Aureus

In this study new derivatives of Schiff bases 5-8 , 1,3- oxazepine 9-16 and tetrazoles 17-19 have been synthesized from the new starting material 1 which has synthesized the reaction of one mole of dichloro acetic acid and two moles of thiophenol , the esters 2-3 were synthesized from the reaction of compound 1 with methanol or ethanol respectively in the presence of H2SO4 as catalyst then 2,2-dithiophenylaceto Hydrazide 4 were synthesized from the reaction of 2 or 3 with hydrazine hydrate 80 % , Schiff bases 5-8 were synthesized from the reaction of 4 with appropriate aldehyde or ketone .Treatment of Schiff bases with maleic and phathalic anhydride in dry benzene to give 1,3-oxazepen derivatives 9-16 and with sodium azide in tetrahydrofuran (THF) afforded tetrazole derivatives 17-19. All these compounds have been characterized from their melting pointes, FTIR , 1HNMR and compounds 1,5 and 18 by mass spectrometry . Derivatives 6,7,11,16,17 and 18 were tested against inhibition of E.coli and. Staphylococcus- aureus and were all funds to be active. Scheme (1).

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Synthesis and Biological Activity of 1H-benzotriazole and 1H-benzimidazole Analogues — Inhibitors of the NTPase/Helicase of HCV and of Some Related Flaviviridae

Antiviral Chemistry and Chemotherapy ◽

10.1177/095632020501600504 ◽

2005 ◽

Vol 16 (5) ◽

pp. 315-326 ◽

Cited By ~ 25

Author(s):

Maria Bretner ◽

Andrea Baier ◽

Katarzyna Kopańska ◽

Andżelika Najda ◽

Anna Schoof ◽

...

Keyword(s):

Biological Activity ◽

Hepatitis C Virus ◽

Hepatitis C ◽

Inhibitory Activity ◽

Alkylating Agents ◽

Alkyl Halides ◽

Helicase Activity ◽

Alkyl Derivatives ◽

Flash Column Chromatography ◽

Derivatives Of

To improve anti-helical activity of analogues of 1 H-benzotriazole and 1 H-benzimidazole their N-alkyl derivatives were synthesized and tested for anti-helicase activity against enzymes of selected Flaviviridae including hepatitis C virus (HCV), West Nile virus (WNV), Dengue virus (DENV) and Japanese encephalitis virus (JEV). 1- and 2-alkyl derivatives of 4,5,6,7-tetrabromo-1 H-benzotriazole were obtained by direct alkylation of 4,5,6,7-tetrabromo-1 H-benzotriazole with the use of respective alkyl halides in the presence of KOH in methanol, to give a mixture of 1- and 2- isomers, which was separated by flash column chromatography in good yield. The proportion of isomers strongly depended on the reaction time and temperature. 1- and 2-hydroxyethyl and 1- and 2-chloroethyl derivatives of the tetrabromobenzo-triazole were synthesized with the use of 2-bromoethanol and 1-bromo-2-chloroethane respectively as alkylating agents. N-alkylation of this benzotriazole compound enhanced inhibitory activity and selectivity towards the helicase activity of HCV NTPase/helicase. The most active were the 2-methyl, 2-ethyl and 2-propyl derivatives (IC50∼6.5 μM in the presence of DNA as a substrate). Derivatives of the benzotriazole in which hydroxyethyl or chloroethyl replaced the alkyl substituents lost their inhibitory activity. Brominated or methylated benzotriazole N(1) ribosides also did not exert helicase inhibitory activity. Although a number of N(1) and N(2) alkyl derivatives exerted good HCV and WNV helicase inhibitory activity when DNA was used as substrate, the activity was strongly decreased or even disappeared when RNA was used as substrate. The cytotoxicity tests in Vero and HeLa Tat cells showed a substantial decrease of cytotoxicity of N-alkyl derivatives as compared to the parent benzotriazole.

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Synthesis and Biological Activity of Novel O-Alkyl Derivatives of Naringenin and Their Oximes

Molecules ◽

10.3390/molecules22091485 ◽

2017 ◽

Vol 22 (9) ◽

pp. 1485 ◽

Cited By ~ 14

Author(s):

Joanna Kozłowska ◽

Bartłomiej Potaniec ◽

Barbara Żarowska ◽

Mirosław Anioł

Keyword(s):

Biological Activity ◽

Alkyl Derivatives ◽

Derivatives Of

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Synthesis and biological activity of the N-alkyl derivatives of ibotenic acid

Pharmaceutical Chemistry Journal ◽

10.1007/bf02508408 ◽

1999 ◽

Vol 33 (1) ◽

pp. 12-16

Author(s):

M. A. Dumpis ◽

H. Brauner-Osborn ◽

U. Madsen ◽

L. B. Piotrovskii

Keyword(s):

Biological Activity ◽

Ibotenic Acid ◽

Alkyl Derivatives ◽

Derivatives Of

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Synthesis, characterization and antimicrobial activity of copper(II) complexes with some S-alkyl derivatives of thiosalicylic acid. Crystal structure of the binuclear copper(II) complex with S-methyl derivative of thiosalicylic acid

Polyhedron ◽

10.1016/j.poly.2014.04.053 ◽

2014 ◽

Vol 79 ◽

pp. 80-87 ◽

Cited By ~ 9

Author(s):

Miloš V. Nikolić ◽

Marina Ž. Mijajlović ◽

Verica V. Jevtić ◽

Zoran R. Ratković ◽

Ivana D. Radojević ◽

...

Keyword(s):

Crystal Structure ◽

Antimicrobial Activity ◽

Binuclear Copper ◽

Methyl Derivative ◽

Acid Crystal ◽

Thiosalicylic Acid ◽

Alkyl Derivatives ◽

Derivatives Of

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ChemInform Abstract: Synthesis and Biological Activity of N-Alkyl Derivatives of Ibotenic Acid.

ChemInform ◽

10.1002/chin.199923151 ◽

2010 ◽

Vol 30 (23) ◽

pp. no-no

Author(s):

M. A. Dumpis ◽

Kh. Brauner-Osborn ◽

U. Madsen ◽

L. B. Piotrovskii

Keyword(s):

Biological Activity ◽

Ibotenic Acid ◽

Alkyl Derivatives ◽

Derivatives Of

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Synthesis of Some New Derivatives of Pyrrolidine-2-one and Studying Their Antibacterial Potentials

Engineering and Technology Journal ◽

10.30684/etj.v38i3b.706 ◽

2020 ◽

Vol 38 (3B) ◽

pp. 128-141

Author(s):

Nadia A. Betti ◽

Redha Ib. Hussain ◽

Sahar Ab. Kadhem

Keyword(s):

Escherichia Coli ◽

Staphylococcus Aureus ◽

Biological Activity ◽

Hydrazine Hydrate ◽

1H Nmr ◽

Mass Spectra ◽

Biological Activities ◽

Ft Ir ◽

Derivatives Of ◽

And Staphylococcus Aureus

New derivatives of pyrrolidine-2-one have been synthesized through lactamization of γ –butyrolactone (GBL) by hydrazine hydrate (80%), ethylene diamine and ethanol amine to afford compounds (1-aminopyrrolidin-2-one), (1-(2-aminoethyl)pyrrolidine-2-one) and (1-(2-hydroxyethyl)pyrrolidine-2-one), respectively. Compound (1-aminopyrrolidin-2-one) underwent several reactions to synthesize the rest of these derivatives. All synthesized compounds were approved by their FT-IR, 1H-NMR and some by Mass spectra. The biological activities of these derivatives were evaluated against Escherichia coli and Staphylococcus aureus. Many of these derivatives showed moderate biological activity against one or both kind of bacteria in comparison to amoxicillin and some showed no biological activity at all.

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