azole ring
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2022 ◽  
Vol 23 (2) ◽  
pp. 813
Author(s):  
István Kacsir ◽  
Adrienn Sipos ◽  
Attila Bényei ◽  
Eszter Janka ◽  
Péter Buglyó ◽  
...  

Platinum complexes are used in chemotherapy, primarily as antineoplastic agents. In this study, we assessed the cytotoxic and cytostatic properties of a set of osmium(II), ruthenium(II), iridium(III) and rhodium(III) half-sandwich-type complexes with bidentate monosaccharide ligands. We identified 5 compounds with moderate to negligible acute cytotoxicity but with potent long-term cytostatic activity. These structure-activity relationship studies revealed that: 1) osmium(II) p-cymene complexes were active in all models, while rhodium(III) and iridium(III) Cp* complexes proved largely inactive; 2) the biological effect was influenced by the nature of the central azole ring of the ligands—1,2,3-triazole was the most effective, followed by 1,3,4-oxadiazole, while the isomeric 1,2,4-oxadiazole abolished the cytostatic activity; 3) we found a correlation between the hydrophobic character of the complexes and their cytostatic activity: compounds with O-benzoyl protective groups on the carbohydrate moiety were active, compared to O-deprotected ones. The best compound, an osmium(II) complex, had an IC50 value of 0.70 µM. Furthermore, the steepness of the inhibitory curve of the active complexes suggested cooperative binding; cooperative molecules were better inhibitors than non-cooperative ones. The cytostatic activity of the active complexes was abolished by a lipid-soluble antioxidant, vitamin E, suggesting that oxidative stress plays a major role in the biological activity of the complexes. The complexes were active on ovarian cancer, pancreatic adenocarcinoma, osteosarcoma and Hodgkin’s lymphoma cells, but were inactive on primary, non-transformed human fibroblasts, indicating their applicability as potential anticancer agents.


Author(s):  
Zhibin Qi ◽  
Yong Lu ◽  
Rui-Jun Gou ◽  
Shu-Hai Zhang

In order to study the properties of new energetic compounds formed by introducing nitroazoles into 2,4,6-trinitrobezene, the density, heat of formation and detonation properties of 36 nitro-1-(2,4,6-trinitrobenzene)-1H-azoles energetic compounds are studied by density functional theory, and their stability and melting point are predicted. The results show that most of target compounds have good detonation properties and stability. And it is found that nitro-1-(2,4,6-Trinitrophenyl)-1H-pyrrole compounds and nitro-1-(2,4,6-trinitropenyl)-1H-Imidazole compounds have good thermal stability, and their weakest bond is C-NO2 bond, the bond dissociation energy of the weakest bond is 222 kJ mol-1-238 kJ mol-1 and close to TNT (235 kJ mol-1). The weakest bond of the other compounds may be the C-NO2 bond or the N-N bond, and the strength of the N-N bond is related to the nitro group on azole ring.


Heterocycles ◽  
2021 ◽  
Vol 102 (5) ◽  
pp. 900
Author(s):  
Naoyoshi Maezaki ◽  
Takuji Magata ◽  
Yoshimi Hirokawa ◽  
Yuki Rokuhara ◽  
Ryota Nakayama ◽  
...  

BMC Chemistry ◽  
2020 ◽  
Vol 14 (1) ◽  
Author(s):  
Ankit Siwach ◽  
Prabhakar Kumar Verma

AbstractAs we know that, Oxadiazole or furadi azole ring containing derivatives are an important class of heterocyclic compounds. A heterocyclic five-membered ring that possesses two carbons, one oxygen atom, two nitrogen atoms, and two double bonds is known as oxadiazole. They are derived from furan by the replacement of two methylene groups (= CH) with two nitrogen (-N =) atoms. The aromaticity was reduced with the replacement of these groups in the furan ring to such an extent that it shows conjugated diene character. Four different known isomers of oxadiazole were existed such as 1,2,4-oxadiazole, 1,2,3-oxadiazole, 1,2,5-oxadiazole & 1,3,4-oxadiazole. Among them, 1,3,4-oxadiazoles & 1,2,4-oxadiazoles are better known and more widely studied by the researchers due to their broad range of chemical and biological properties. 1,3,4-oxadiazoles have become important synthons in the development of new drugs. The derivatives of the oxadiazole nucleus (1,3,4-oxadiazoles) show various biological activities such as antibacterial, anti-mycobacterial, antitumor, anti-viral and antioxidant activity, etc. as reported in the literature. There are different examples of commercially available drugs which consist of 1,3,4-oxadiazole ring such as nitrofuran derivative (Furamizole) which has strong antibacterial activity, Raltegravir as an antiviral drug and Nesapidil drug is used in anti-arrhythmic therapy. This present review summarized some pharmacological activities and various kinds of synthetic routes for 2, 5-disubstituted 1,3,4-oxadiazole, and their derived products.


CORROSION ◽  
10.5006/3642 ◽  
2020 ◽  
Author(s):  
Hooman Rahmani ◽  
Efstathios Meletis

Adsorption and inhibition behavior of 1,2,3-benzotriazole (BTA) and 2,5-dimercapto-1,3,4-thiadiazole (DMTD) on brazing Cu-Ag alloy was studied in deionized water using potentiodynamic polarization measurement, adsorption isotherm investigation and X-ray photoelectron spectroscopy (XPS). Pure Ag and pure Cu were included to investigate the mere effect of each component on the alloy’s behavior. Results show better inhibition of DMTD for Ag and BTA for Cu, both by chemisorption. BTA was found to follow Langmuir isotherm while DMTD obeyed Temkin adsorption isotherm, despite both acting as a mixed type inhibitor. Combining the two inhibitors increased the inhibition efficiency over 80% for the Cu-Ag alloy. XPS spectra demonstrate the formation of DMTD protective film through DMTD’s functional groups of pyrrolic N from the azole ring and thiol S from the mercapto anchoring group on Ag and thiol S on Cu. Compared to BTA, the higher affinity of DMTD to Ag was attributed to the involvement of two heteroatoms with the Ag surface.


2020 ◽  
Vol 5 (443) ◽  
pp. 85-91
Author(s):  
Ibrayev M.K., ◽  
◽  
Takibayeva A.T., ◽  
Fazylov S.D., ◽  
Rakhimberlinova Zh.B., ◽  
...  

This article presents studies on the targeted search for new derivatives of azoles, such as benzthiazole, 3,5-dimethylpyrazole, 1,3,4-oxadiazole-2-thione, 1,3,4-thiadiazole. The possibility of combining in one molecule of the azole ring with other cyclic compounds: the alkaloid cytisine, morpholine, furan and some arenes has been studied. To obtain new compounds, the reactions of bromination, acylation, and interaction with isothiocyanates were studied. Optimal synthesis conditions were studied for all reactions. It was found that the reaction of 4-bromo-3,5-dimethylpyrazole with isothiocyanates, in contrast to the previously written derivatives of anilines, takes a longer time and requires heating the reaction mixture. The combination of a pirasol fragment with halide substituents often results in an enhanced therapeutic effect. The synthesized 2-bromine-N-(6-rodanbenzo[d]thiazole-2-yl)acetamide, due to the alkylbromide group, is an important synth in the synthesis of new benzthiazole derivatives. Its derivatives combine in one molecule the rest of rhodanbenzthiazole with alkaloid cytisine and biogenic amine morpholine and are potentially biologically active compounds, since the molecule structure contains several pharmacophoric fragments: benzthiazole and alkaloid (amine) heterocycles, rhodane and urea groups. The mechanism of formation of 1,3,4-oxadiazole-2-tyons from hydrazides under action on them by carbon disulfide was studied and assumed. It was shown that dithiocarbamates in acidic medium decompose with the release of hydrogen sulfide and the formation of highly reactive isothiocyanate group. Then, intra-molecular cyclization occurs, with the formation of end products - 1,3,4-oxadiazole-2-thions. The structures of the synthesized compounds were studied by 1H and 13C NMR spectroscopy. All synthesized substances are potentially biologically active compounds, since they contain several pharmacophore fragments in their structure.


2020 ◽  
Vol 27 ◽  
Author(s):  
Cindy Patinote ◽  
Natalina Cirnat ◽  
Pierre-Antoine Bonnet ◽  
Carine Deleuze-Masquéfa

: Heterocyclic compounds hold a huge and recognized place in the field of medicinal chemistry thanks to their multiple biological activities. Their synthetic pathways allow their easy and rapid access due to different bond forming methodologies and provide a huge amount of multi-functionalized compounds for drug delivery. The syntheses of heterocyclic compounds are today well known for the majority, described and reviewed in an extensive literature. In this review, we choose to gather and classify available information concerning the biological activities of quinoxaline-based compounds annulated at bond a containing one and more nitrogen atoms in the fused azole ring.


Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3944
Author(s):  
Wu ◽  
Wang ◽  
Zhang ◽  
Jin

The enantioselective transformations of indoles preferentially take place in the more-reactive azole ring. However, the methods for the enantioselective functionalization of the indole benzene ring are scarce. In this paper, a series of bifunctional (thio)urea derivatives were used to organocatalyze the enantioselective Friedel−Crafts hydroxyalkylation of indoles with isatins. The resulting products were obtained in good yields (65–90%) with up to 94% enantiomer excess (ee). The catalyst type and the substrate scope were broadened in this methodology.


2019 ◽  
Vol 17 (40) ◽  
pp. 9065-9069
Author(s):  
Dong Zhang ◽  
Di Gao ◽  
Jinlin Cai ◽  
Xiaoyu Wu ◽  
Hong Qin ◽  
...  
Keyword(s):  

The efficient and gentle ruthenium-catalyzed meta-selective CAr–H nitration of azole ring substituted arenes has been developed.


2017 ◽  
Vol 95 (12) ◽  
pp. 1285-1295 ◽  
Author(s):  
Nilanjan Adhikari ◽  
Sk. Abdul Amin ◽  
Tarun Jha ◽  
Shovanlal Gayen

Aromatase is a multienzyme complex responsible for the biosynthesis of estrogen and its level has been found higher in breast cancer. Although the designing strategy of aromatase inhibitors (AIs) has continued for more than four decades, it may still be in demand to design highly effective and less toxic AIs. In this study, several chemometric approaches have been used to explore the important structural features of a series of letrozole-based analogs for their promising aromatase inhibitory activity. All techniques are statistically validated individually and in turn, validated with each other along with the structure–activity relationship (SAR) observations. The imidazole ring has been found to interact with the heme iron, whereas the triazole ring system has not shown any interaction. Moreover, imidazole function is better than 1,2,3-triazole, whereas 1,2,3-triazole is better than the 1,2,5-triazole ring system. Additionally, a bulky aryl substitution in the azole ring along with the orientation of the azole nitrogens and the cyanophenyl function has an essential role in the inhibition of aromatase. Furthermore, a cyano group substituted at the phenyl moiety interacts with Arg115, Met374, and Ser478 at the enzyme active site to form hydrogen bonding interactions. These observations are useful for designing potential AIs in the future.


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