2028-79-7Relevant articles and documents
Design and synthesis of novel 1,3,4-oxadiazole derivatives bearing azo moiety as biologically significant scaffolds
Khan, Bilal Ahmad,Zafar, Safeena,Mughal, Ehsan Ullah,Ahmed, Muhammad Naeem,Hamdani, Syeda Shamila,Akhtar, Tashfeen,Ihsan-ul-Haq,Sadiq, Amina,Khan, Khalid Mohammed
, p. 1346 - 1355 (2018/11/01)
Introduction: Oxadiazoles having azo-functionality represent a new and an exciting class of physiologically active heterocyclic compounds. A number of molecules with these moieties have significant role in medicinal chemistry due to their diverse biological activities. Methodology: A series of 1,3,4-oxadiazole-2-thiol derivatives bearing azo-moiety have been designed and synthesized by multistep reaction sequences staring from p-aminobenzoic acid by employing literature know procedures. These compounds were investigated for their antimicrobial, cytotoxic, α-amylase and protein kinase inhibitory and antileishmanial potential. Results and Discussion: The newly synthesized compounds were characterized by spectroscopic techniques (IR, UV-Vis, NMR and MS). Antibacterial activity was investigated against four bacterial strains i.e. E. coli, P. aeruginosa, S. aureusand B. subtilis and good level of microbial inhibition was exhibited by most of the compounds with MIC 6.25 μg/mL. Brine Shrimp lethality assay revealed that the compound 31 is an excellent cytotoxic agent. (E)-5-(4-((4-Butoxyphenyl) diazenyl)phenyl)-1, 3,4-oxadiazole-2-thiol (21) showed good α-amylase inhibition (46.3± 0.45%) and (E)-2-(Decyloxythio)-5-(4-((propoxyphenyl)diazenyl)phenyl)-1,3,4-oxadiazole (30) exhibited excellent antileishmanial activity (88.4± 0.34%) at 10 μg/mL concentration. In case of protein kinase inhibition, remarkably, the oxadiazole-2-thiols (20-25) were found more active than the standard surfactinat tested concentration (25 μg/disc). Conclusion: We have designed, synthesized and characterized an interesting series of biologically active oxadiazole bearing diazene moiety derivatives. Noteworthy, the presence of diazene functionality, polar heterocyclic moiety as well as hydrophobic alkyl chain is special feature of these compounds. These studies provide a basic idea to further explore these types of scaffolds as biologically potent molecules in drug design and development.
Synthesis and biological evaluation of new N-substituted-N′-(3,5-di/ 1,3,5-trimethylpyrazole-4-yl)thiourea/urea derivatives
Kaymakcioglu, Bedia Kocyigit,Rollas, Sevim,Koercegez, Eylem,Aricioglu, Feyza
, p. 97 - 103 (2007/10/03)
Several thiourea and urea derivatives were prepared by the reaction of 4-aminopyrazoles with substituted isothiocyanates or isocyanates. The novel compounds were tested anticonvulsant activity using by pentylenetetrazole- induced seizure (PTZ) and maximal electroshock seizure (MES) tests. Among the tested compounds, thiourea derivatives of 4b were afforded 90 and 100% protection in PTZ and MES tests at 50 mg/kg, respectively. Urea derivatives of 5a and 5b were afforded 82 and 100% protection both at 25 and 50 mg/kg. Also synthesized compounds were screened for antituberculosis activity against Mycobacterium tuberculosis H37Rv at 6.25 μg/mL concentration but they were not found active at these concentration. In addition, some selected compounds were evaluated for in vitro anti-HIV activity and they were all negative.
Synthesis and Stereochemistry of Optically Active Selenonium Imides
Kamigata, Nobumasa,Taka, Hideo,Matsuhisa, Ayumi,Matsuyama, Haruo,Shimizu, Toshio
, p. 2257 - 2264 (2007/10/02)
Diastereomeric mixtures of 4-phenyl(methyl)selenonium-N-toluene-4'-sulfonimides (dia.-1) amd 4-phenyl(2',4',6'-triisopropylphenyl)selenonium-N-toluene-4''-sulfonimides (dia.-7) were synthesized.Optical resolution by the fractional recrystallization of dia.-7 from methanol gave the optically pure (-)-selenonium imide as stable crystals.The absolute configuration around the selenium atom was determined to be S based on the CD spectra.The kinetics for the epimerization by pyramidal inversion of the optically active selenonium imide were studied.
Open-chain nitrogen compounds. Part IV. Synthesis of 5-hydroxy-1,2,3-triazoles from 1-aryl-3-(ethoxycarbonylmethyl)triazenes: a new route to α-diazo-N-arylacetamides
Baines, Kim M.,Vaughan, Keith,Hooper, Donald R.,Leveck, Lorne F.
, p. 1549 - 1556 (2007/10/02)
A series of triazenes of type ArN=N-NH-CH2CO2Et, N-arylazoglycine ethyl esters, have been prepared by coupling the arene diazonium salt, ArN2+*X-, with ethyl glycinate, NH2CH2CO2Et; an electron-withdrawing substituent, e.g.NO2, CN, CO2R, and Cl, in the ortho or para position of the aryl group is essential for efficient coupling.The p-substituted arylazoglycine ethyl esters cyclize when treated with alcoholic potassium hydroxide to afford the potassium salts of the 1-aryl-5-hydroxy-1,2,3-triazoles, which can be obtained free by acidification of the potassium salt solution with acetic acid.Reaction of the potassium salts with acetic anhydride yields the 1-aryl-5-acetoxy-1,2,3-triazoles.The 5-hydroxytriazoles, when heated in ethanol, rearrange to α-diazoacetanilides, ArNH*COCHN2.The diazoamides can be obtained in low yield directly from the triazenes by prolonged refluxing in ethanol. o-Substituted aryltriazenes do not cyclize under the same conditions but fragment to the arylamine.
1,2,3-Triazabutadienes. XIV. Investigations into the Acidic Cleavage of the Z-E-Isomeric 1-Aryl-3-- and 1-Aryl-3--triazenes
Fanghaenel, E.,Hohlfeld, J.
, p. 253 - 261 (2007/10/02)
The rate of the acid cleavage of the Z-E-isomeric 1-aryl-3-- and 1-aryl-3--triazenes 1 - 5 is investigated in dependence on the substituents in the aryl and benzo residue.The Z-isomer
Antigens and immunoassays for morphine and related 3-oxybenzomorphan compounds
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, (2008/06/13)
Antigens capable of generating antibodies specific to morphine and other 3-oxybenzomorphan compounds are prepared by conjugating 3-oxybenzomorphan derivatives with immunogenic carriers employing a linking site on an aryl group of the 3-oxybenzomorphan oth
