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In this manuscript, a new series of 1,2,4-triazole-3-ones containing imin function was synthesized from 5-(4-bromobenzyl)-4-amino-2H-1,2,4-triazol-3(4H)-one and aromatic aldehyde by using microwave irradiation technique via schiff base reaction. Firstly, ethyl imido-p-bromophenylacetate hydrochloride (2) was synthesized according to the pinner method in the literature. Then, compound 2 was reacted with ethyl carbazate to synthesized ethyl p-bromophenylacetate etoxycarbonylhydrazone (3) compound. Then, 5-(4-bromobenzyl)-4- amino-2H-1,2,4-triazol-3(4H)-one (4) was synthesized from the reaction of ethyl p-bromophenylacetate etoxycarbonylhydrazone (3) with hydrazine monohydrate. Then, it was converted to their corresponding triazole containing Schiff bases (5a-e) with the reaction of corresponding aromatic aldehydes in ethanol by using the microwave irradiation method. This microwave technique has some advantages, including rapid and uniform heating, higher product yield and purity, mild reaction conditions, low energy requirement and shorter reaction time. The chemical structures of newly synthesized triazole containing schiff bases were identified using IR, 1HNMR, and mass spectroscopy data.

A series of new 2-(4/3-substitutedbenzyl)thieno[2,3-d]pyrimidin-4(3H)-ones (2a-f) and 2-(4/3-substituted benzyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one derivatives (3a-f) were synthesized for the first time by the reaction of corresponding 2-aminothiophene-3-carboxamide derivatives and appropriate iminoester hydrochlorides under suitable conditions. Using microdilution method, the antibacterial and antifungal activities of the synthesized compounds were tested against selected strains of Gram positive and Gram negative bacteria (Staphylococcus aureus, Enterecoccus faecalis, Escherichia coli and Pseudomonas aeruginosa) and yeast-like fungi (Candida albicans, C. krusei and C. parapsilosis). In these tests, compounds 3a-f showed higher antifungal activity than fluconazole against Candida fungus species. 2-Substituted thieno-[2,3-d]pyrimidin-4(3H)-ones (2a-f) showed better antibacterial activity than 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one derivatives (3a-f).

BACKGROUND The majority of prediabetic people are overweight and weight loss is still the most effective treatment strategy. The aim of this study was to evaluate the effects of short-term exercise and/or diet on weight loss and clinical parameters in subjects with insulin resistance (IR). METHODS A total of 60 subjects (BMI≥25.0 kg/m2) were included in the study. Subjects divided into two groups as follows: diet only (DI, N.=27) and diet and exercise (DEI, N.=27). DI group received an energy restricted diet program, while DEI group received a diet combined with an exercise program for four weeks. Anthropometric measurements and biochemical parameters were assessed at baseline and at the end. RESULTS Total body weight (BW) loss was 2.3 kg (2.5%) in DI group and 3.0 kg (3.2%) in DEI group at the end of four weeks. Fasting blood glucose (FBG) levels decreased significantly in DEI group (P=0.021). However, the reductions in FBG levels were mild and not statistically significant in DI group (P>0.05). Total cholesterol and LDL-c levels reduced in both groups, while triglyceride levels significantly decreased only in DI group (P

Aim The purpose of this study was to investigate the changes in serum irisin, fibroblast growth factor-21 (FGF21), visfatin, follistatin like protein-1 (FSTL1), and meteorin-like protein (Metrnl) levels in response to increased physical activity and/or diet interventions in overweight subjects with impaired glucose metabolism (IGM). Methods A total of 60 subjects (BMI > 25.0 kg/m2) with IGM were recruited in this single-centered interventional study. Twelve subjects dropped out during the study and the study was completed with 48 patients. Patients were divided into two groups as diet only (DI, n = 24) and diet and physical activity intervention (DPA, n = 24). Patients in DI group received a diet program while DPA group received a diet combined with a physical activity intervention for 12 weeks. Additional 24 healthy subjects were recruited to compare the baseline levels of proteins. Serum protein levels, anthropometric measurements, and biochemical parameters were assessed. Results Irisin, FGF21, visfatin, and FSTL1 levels significantly decreased in both groups after 12-week intervention (p 0.05). Likewise, the total change in weight was similar in both DI (−4.35 kg) and DPA (−4.85 kg) groups (p > 0.05). A 5% reduction in initial body weight with DPA therapy resulted in a stronger correlation between the changes in irisin, visfatin, and FSTL1 levels and fasting glucose and HbA1c levels. Conclusions These results demonstrate that serum irisin, FGF21, visfatin, and FSTL1 levels decreased in response to weight loss interventions. Weight loss induced by DI or DPA therapies had similar lowering effects on these proteins in subjects with IGM, and these myokines might be related to glucose metabolism biomarkers.

Today, the majority of the drugs used in the treatment of diseases are obtained by synthesis. A large proportion of the compounds have obtained heterocyclic structure. Therefore, synthesis of new heterocyclic compounds has always attracted and continues to attract scientist. It is known that compounds bearing triazole skeleton in the heterocyclic have an important place. The reactions of 4-amino-triazole compounds, especially with aromatic aldehydes, have been known for a long time and this reaction is carried out by conventional heating methods. However, the development of alternative heating methods to these conventional methods has also recently been studied. One of the most important of these is organic synthesis by microwave method and it is widely used. Another alternative method that has recently been used in organic synthesis is the realization of organic synthesis reactions with ultrasonic radiation. Ultrasound-assisted organic synthesis is an environmentally friendly, modern and economical method used to accelerate reactions. In this study, optimum conditions were determined for this reaction by using ultrasonic radiation method and the results were compared with the classical method. For this purpose, in the first step iminoester was synthesized by using Pinner method. The reaction of this iminoester with ethylcarbazate gave the corresponding hydrazone. Then the reaction of this obtained hydrazone derivative with hydrazine hydrate, the 4-amino-1,2,4-triazole derivative compound was synthesized. In the final reaction step, the interaction of this amino compound with 3-bromo-4-fluorobenzaldehyde was carried out by conventional and novel method (ultrasonic radiation) to obtain the targeted imine compound. The chemical structure of the new compound will be determined by spectroscopic methods such as 1H- and 13C-NMR and IR. The results compared in terms of reaction time, yield and purity between conventional and ultrasonic method. And we found that the ultrasonic radiation method is much more advantageous.

The synthesis, docking study, and investigation of the anticancer activities of some coumarin derivatives containing the triazole ring are reported in this study. The newly synthesized compounds were screened for their in vitro anticancer activity against the cell lines CRL5807 (human bronchioalveolar carcinoma), CRL5826 (human squamous cell carcinoma), MDA-MB231 (human breast cancer cells), HTB177 (human lung cancer), PC-3 (human prostate adenocarcinoma), PANC-1 (human pancreatic cancer cells), used as cancer cells, and CCD34Lu (normal human lung fibroblasts), used as a healthy cell line. Cytotoxicity effects of the samples were determined by the MTT (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) assay. In silico studies were also performed to explore the binding interactions of the molecules. © 2020 Deutsche Pharmazeutische Gesellschaft

A new series of 2-substituted quinazolin-4(3H)-one derivatives including coumarin nucleus has been synthesized and screened for their lipase and α-glucosidase inhibition properties. Among the synthesized compounds, N'-{2-[2-(3,4-dichlorobenzyl)-4-oxoquinazolin-3(4H)-yl]acetyl}-2-oxo-2H-chromene-3-carbohydrazide and N'-{2-[2-(4-bromobenzyl)-4-oxoquinazolin-3(4H)-yl]acetyl}-2-oxo-2H-chromene-3-carbohydrazide showed the best inhibitory effect against α-glucosidase with IC50 values of 6.11 ± 0.40 and 7.34 ± 0.37 μM,respectively. These compounds also showed strong anti-lipase activity (IC50 3.52 ± 0.49 and 2.85 ± 0.27 μM, respectively).

The synthesis of 2-substituted benzimidazoles from the reaction of o-phenylenediamine and an imino ester hydrochloride with ultrasound irradiation is reported. The procedure has an eco-friendly and simple workup with good yield in a short time.

Heterosiklikhalka sistemlerinde önemli bir rolü olan indol, önemli biyolojik etkilergöstermektedir. Isatin (1H-indol-2,3-dion),biyolojik özellikleri nedeniyle çok sayıda sentezde bir reaktif olarakkullanılmıştır. Ayrıca, isatin, indol ve kinolin türevlerinin eldesinde vereaksiyonlarında kullanılan, bir heterosiklik halka sistemidir. Bu çalışmada, iki yeni Schiff bazıbileşikleri, 2-aminoantrasen ile isatin/5-nitro-isatinin reaksiyonuylasentezlendi. Sentezlenen bileşiklerin yapısı, IR, 1H-NMR, 13C-NMRspektrumları ve Kütle analizi kullanılarak spektroskopik yöntemlerleaydınlatıldı., Indole,which has an important role in heterocyclic ring systems, exhibits significantbiological effects. Isatin (1H-indole-2,3-dione)has been used as a reagent in a large number of synthesis due to its biologicalproperties. In addition, it is a heterocyclic ring system used for obtaining andother reactions of indole and quinoline derivatives. In this study, two newSchiff base compounds were synthesized by the reaction of 2-aminoantracene withan isatin/5-nitro-isatin. The structure of the synthesized compounds, wereelucidated by spectroscopic methods using IR, 1H-NMR, 13C-NMRspectra and Mass analysis.

A series of new compounds containing both benzimidazole and 1,2,4-triazol-3-one rings was synthesized by microwave irradiation of mixtures containing 5-(alkyl/phenyl)-4-(4-carboxyphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-ones and 1,2-diaminobenzene derivatives. Also, benzimidazole derivatives were synthesized by the reaction of ethyl 2-(ethoxy(alkyl/phenyl)methylene)hydrazine-1-carboxylates with 2-aminobenzimidazole. A rapid and efficient combination of 1,2,4-triazol-3-one and benzimidazole ring systems was achieved for the first time in this study.

Novel 2-substitutedbenzyl-4(7)-phenyl-1H-benzo[d]imidazole compounds were synthesized and characterized. Although 2a and 2b were reported previously in the literature, 11 compounds were synthesized (nine of them were newly synthesized) and the tyrosinase inhibitory effects and antioxidant activities of these compounds were studied for the first time. All of the synthesized compounds displayed certain inhibitory effects on tyrosinase, with IC50 values ranging from 37.86 ± 0.24 to 75.81 ± 2.49 μM. Among the compounds, 2j exhibited similar tyrosinase inhibitory effect (IC50 = 37.86 ± 0.24 µM) to the positive control, kojic acid (IC50 = 21.93 ± 0.11 µM). Kinetic studies revealed it to act as non-competitive tyrosinase inhibitor with a Ki value of 50.2 µM. The antioxidant activities of the compounds were investigated by using in vitro antioxidant assays, including 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP). All of these results indicated that the compounds might have potential application as tyrosinase inhibitors.

I n this study, the reactions of the 1-adamantyl amine with 4 different ester ethoxycarbonyl hydrazone derivatives were studied. At first, iminoester hydrochloride derivatives were synthesized according to the Pinner method. Then they were reacted with ethyl carbazate to synthesize ester ethoxycarbonyl hydrazone derivative compounds. In the last step, 3-substituted-4-adamantyl-1,2,4-triazol-5-one derivatives were aimed to synthesize, the ester ethoxycarbonyl hydrazone compounds were heated in an oil bath dry to dry with 1-adamantyl amine. It has been observed, however, that the ring is not closed according to IR and ¹H-NMR analysis and the ethyl N-(adamantylcarbamoyl)alkylcarbohydrazonoate derivative compounds were synthesized as stabile and original compounds. The structures of the synthesized compounds were elucidated by spectroscopic methods using IR, ¹H-NMR, 13C-NMR spectra and LC/MS analysis.

This study describes the synthesis of a new series of benzimidazoles that contain a coumarin moiety. The high yielding synthetic reaction was between hydrazide derivatives of benzimidazoles and 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-one. The reaction was performed using a very small amount of the organic solvent and without the use of a catalyst.

A simple and practical method has been developed for the synthesis of bisbenzimidazoles. Iminoester hydrochlorides of phenylacetic acids were used as intermediates in this reaction with 3,3′-diaminobenzidine under microwave irradiation leading to the products with good yields and in short reaction times. This method can be a general technique for the synthesis of bisbenzimidazoles.

By using the microwave technology, a new protocol has been developed for the synthesis of new coumarin derivatives including 1,2,4-triazol-3-one skeleton. This protocol proves to be efficient and environmentally friendly in terms of easy work-up and good yields. All newly synthesized compounds were screened for their antimicrobial activity and lipase inhibition. Most of the compounds were found to be effective on Escherichia coli. N'-{[4-Amino-3-(2-bromobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}-6-bromo-2-oxo-2Hchromene-3-carbohydrazide and N'-{[4-amino-3-(3,4-dichlorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}-6-bromo-2-oxo-2H-chromene-3-carbohydrazide had a good effect on lipase inhibition.

A new series of 2-(4-bromobenzyl)- and 2-(4-fluorobenzyl)-1H-benzimidazole derivatives containing 1,2,4-triazole, 1,3,4-thiadiazole, 1,3,4-oxadiazole, and morpholine rings has been synthesized. The structures of the newly synthesized compounds were confirmed by 1H and 13C NMR and mass spectra, and all substances have been screened for their α-glucosidase inhibitory, antimicrobial and antioxidant activities. Hydrazide, oxadiazole, thiosemicarbazide, and 1,2,4-triazole-3-thiol derivatives showed very good ABTS scavenging activities (IC50 1.94-4.79 μM). Oxadiazole and thiosemicarbazide derivatives also revealed notable DPPH scavenging activity. 5-[(2-(4-Bromobenzyl)-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazole-2-thiol was found to be more potent than acarbose. 2-(4-Fluorobenzyl)-1H-benz- imidazole was effective against both Gram-positive and Gram-negative bacteria, especially, M. smegmatis.

In this study, a new series of benzimidazole and bisbenzimidazole derivatives were prepared via the reaction of iminoester hydrochlorides and o -phenylenediamines and then screened for their lipase inhibition properties. Among the synthesized molecules, compounds 7a , 8a and 8c showed the best inhibitory effect against lipase enzyme with IC 50 values of 1.72 ± 0.12 µM, 1.92 ± 0.28 and 0.98 ± 0.07 µM, respectively. Moreover, molecular modeling studies were performed in order to understand to the inhibitory activity of the molecules. Binding poses of the studied compounds were determined at the target sites using induced fit docking (IFD) algorithms.

Various triheterocyclic compounds containing benzimidazole, thiophene, and 1,2,4-triazole rings (3-6) were synthesized and screened for their antioxidant activities. The structures of the synthesized compounds (2-6) were judged by (1)H NMR, (13)C NMR, elemental analysis, and LC-MS spectral data. Antioxidant activities of the synthesized compounds (2-6) were determined with CUPric Reducing Antioxidant Capacity (CUPRAC), ABTS (2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)/persulfate, and DPPH (1,1-diphenyl-2-picrylhydrazyl) assays. Most of the compounds showed a significant antioxidant activity and especially, compound 5c showed very good SC50 value for DPPH method and compound 5h exhibited very high scavenging activity to ABTS method.

This study presents a synthesis of new series of some benzimidazole, bisbenzimidazole and perimidine derivatives via microwave technique, which, leads to the good product yields and short reaction times. The structure of newly synthesized compounds was confirmed by 1H-NMR and 13C-NMR spectra. These compounds were screened for their lipase inhibition activity. Then, all compounds were evaluated with regard to pancreatic lipase activity, and some of the 2-substituted perimidines, bisperimidine and bisbenzimidazole derivatives showed lipase inhibition at various concentrations.

In this study, a new series of fluorine containing benzimidazoles ( 4a–l ) and bisbenzimidazoles ( 6a–c , 8 ) were synthesized by the reaction of o -phenylenediamines with iminoester hydrochlorides ( 3a–l , 7 ) in methanol under microwave irradiation. The structures of these newly synthesized compounds were identified by IR, 1 H-NMR, 13 C-NMR, mass spectroscopy and elemental analysis data. The synthesized compounds were screened for their pancreatic lipase activities. Our results indicate that the compounds 6a , 6b and 6c can serve as an anti-lipase agent. The compounds 6b and 6c inhibited pancreatic lipase activity by 84.03% and 97.49% at a concentration of 3 µg/mL, respectively.

A series of new 1,2,4-triazole-3-one derivatives bearing the salicyl moiety were synthesized by using microwave irradiation, and their chemical structures were identified by IR, (1) H NMR, (13) C NMR, elemental analysis, and LC-MS. The anticonvulsant activities of the compounds 4a-c, 4e, and 5a-e were evaluated by the Anticonvulsant Screening Program of the National Institute of Health, USA. The compounds had moderate anticonvulsant activities in the maximum electroshock-induced seizure and minimal clonic seizure models in mice, without any neurotoxic effects.

The design, synthesis, and investigation of antitumor and anti-lipase activities of some coumarin-triazole hybrid molecules are reported. The synthesis of these hybrid molecules was performed under microwave irradiation and conventional heating procedures. The newly synthesized hybrid molecules were investigated as inhibitors against four tumor cell lines (BT20 human breast carcinoma, SK-Mel 128 melanoma, DU-145 prostate carcinoma, and A549 lung carcinoma) and porcine pancreatic lipase (PPL). Most of these compounds showed notable antitumor activities against the tested tumor cell lines, and compounds 8i and 8l showed the best anti-lipase activity of 99.30 ± 0.56% and 99.85 ± 1.21%, respectively, at a concentration of 10 μM.

4-Bromo-o-phenylenediamine and ethylimido-p-bromophenylacetate, 1, were subjected to microwave irradiation to synthesize benzimidazole derivative, compound 2. Ester derivative, 3, and hydrazide derivative, 4, of compound 2 were also synthesized, respectively. Finally, compound 4 was treated with 11 different aromatic aldehydes to obtain benzimidazole derivatives containing imine function. All reactions were carried out with microwave irradiation and conventional heating, and results were compared. Some of the newly synthesized compounds showed moderate antimicrobial activity against some tested organisms.

A new series of 2-aryl-5-fluoro-6-(4-phenylpiperazin-1-yl)-1H-benzimidazoles was synthesised from the reaction of 4-fluoro-5-(4-phenylpiperazin-1-yl)benzene-1,2-diamine and iminoester hydrochlorides. 4-Fluoro-5-(4-phenylpiperazin-1-yl)benzene-1,2-diamine was prepared from the reduction of 5-fluoro-2-nitro-4-(4-phenylpiperazin-1-yl)aniline by using Pd/C (10%) catalyst and hydrazine hydrate under microwave irradiation. The structures of newly synthesised compounds were identified by 1H NMR, 13C NMR, mass spectroscopy and elemental analysis data.

A simple and green protocol has been developed for the synthesis of benzimidazoles. In this protocol, 2-[(alkyl/aryl)(ethoxy)methylidene]hydrazinecarboxylates with 1,2-phenylenediamine derivatives under solvent- and catalyst-free conditions under microwave irradiation lead to products with good yields in short reaction times.

A new series of 2-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole derivatives containing a 1,2,4-triazole ring were synthesized via microwave technique. This efficient procedure provides pure products within a few minutes. The newly synthesized compounds were confirmed by (1) H NMR and (13) C NMR spectra and they were screened for their lipase inhibition and antioxidant activities. Compounds 4a, 4b, 5a, and 5b showed very good scavenging activity.

A number of triazole-3-one compounds have been synthesized, and reduction of the carbonyl group in the molecule has been carried out to give a corresponding hydroxyl group that possesses asymmetric carbon atom in good yields and short reaction times. It is ecofriendly because it is produced by straightforward microwave irradiation in the absence of solvent. All newly synthesized compounds were also screened for their antimicrobial activities. The antimicrobial activity study revealed that 2d, 2i, 3c, and 3g–j showed good activity against a variety of microorganisms. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

A growing body of literature has shown the effectiveness of using microwaves in chemical reactions. The aim of this study is to demonstrate a rapid and highly efficient synthesis of some new triazol-3-ones via microwave heating using a monomode microwave. Compared with the thermal process, the microwave heating induces a dramatic reduction of the reaction time and improvement of the yields. In this study, rapid N-benzylation and N-acetylation of triazol-3-ones were achieved by microwave irradiation method for the first time. The newly synthesized compounds showed moderate antimicrobial activity against the standard bacterial and fungal organisms tested.

Bu çalışmada,sekiz yeni bazı potansiyel biyolojik aktif 4-(arilidenamino)-2,4-dihidro-1H-1,2,4-triazol-3-on bileşikleri mikrodalga yöntemi kullanılarak sentezlendi. Bu bileşiklerin yapıları farklı spektroskopik yöntemle (IR, 1H NMR, 13C NMR and elemental analiz) kullanılarak karakterize edildi. Bu bileşiklerin asit ayrışma sabitleri teorik olarak 25oC’de yirmi beş farklı çözücü içerisinde SPARC bilgisayar programı vasıtasıyla belirlendi. Çözücülerin asit ayrışma sabitleri üzerindeki etkileri tartışıldı, In the present study, eight new 4-(arylideneamino)-2,4-dihydro-1H-1,2,4-triazol-3-ones that may show some potential biological properties were synthesized using microwave method. These compounds were characterized by different spectroscopic techniques (IR, 1H NMR, 13C NMR and elemental analysis). Acid dissociation constants (pKa) were determined theoretically with SPARC computer program in different twenty five solvents at 25oC. The effects of solvents composition on the acid dissociation constants are discussed.

A novel series of benzimidazole derivatives were prepared starting from o -phenylenediamine and 4-nitro- o -phenylenediamine with iminoester hydrochlorides. Acidic proton in benzimidazole was exchanged with ethyl bromoacetate, then ethyl ester group was transformed into hydrazide group. Cyclization using CS 2 /KOH leads to the corresponding 1,3,4-oxadiazole derivative, which was treated with phenyl isothiocyanate resulted in carbothioamide group, respectively. As the target compounds, triazole derivative was obtained under basic condition and thiadiazole derivative was obtained under acidic condition from cyclization of carbothioamide group. Most reactions were conducted using both the microwave and conventional methods to compare yields and reaction times. All compounds obtained in this study were investigated for α-glucosidase inhibitor activity. Compounds 6a , 8a , 4b , 5b , 6b and 7b were potent inhibitors with IC 50 values ranging from 10.49 to 158.2 μM. This has described a new class of α-glucosidase inhibitors. Molecular docking studies were done for all compounds to identify important binding modes responsible for inhibition activity of α-glucosidase.

Novel 2-substitutedbenzyl-4(7)-phenyl-1H-benzo[d]imidazole compounds were synthesized and characterized. Although 2a and 2b were reported previously in the literature, 11 compounds were synthesized (nine of them were newly synthesized) and the tyrosinase inhibitory effects and antioxidant activities of these compounds were studied for the first time. All of the synthesized compounds displayed certain inhibitory effects on tyrosinase, with IC

The high yielding reaction between benzimidazole hydrazides and (benzotriazolylcarbonyl)chromenone is performed in a very small amount of solvent without a catalyst.

An easy efficient method for the synthesis of N-(3,5-dichlorophenyl)-5-alkyl/aryl-3H-1,2,4-triazol-3-one derivatives under microwave irradiation has been developed using the reaction of 3,5-dichloroaniline and ethoxycarbonylhydrazones. This reaction occurs more efficiently and faster than the conventional heating method. We obtained 5-mercapto-1,3,4-oxadiazol derivatives by this method. The newly synthesised compounds have been tested for their antimicrobial activity against Enterobacter cloaceae, Escherichia coli, Klebsiella pneumonie, Pseudomonas aeruginosa, Proteus vulgaris, Salmonella typhimurium, Yersinia pseudotuberculosis, Bacillus subtilis and Staphylococcus aereus.

Microwave irradiation has been used to accelerate the conversion of isatin (1a) and 5-nitroisatin (1b) into their Schiff bases 3-[5 ’-aryl(alkyl)-2 ’,4 ’-dihydro-1 ’,2 ’,4 ’-triazol-3 ’-on-4 ’-yl]iminoisatin (3a–g) and 3-[5 ’-aryl(alkyl)-2 ’,4 ’-dihydro-1 ’,2 ’,4 ’-triazol-3 ’-on-4 ’-yl]imino-5-nitroisatin (4a–g), respectively. Reaction was achieved by microwave-induced technique, which reduced the reaction time drastically and improved the yield when compared to conventional heating. The newly synthesised bases showed moderate antimicrobial activity against the standard bacterial and fungal organisms tested

The novel 4-amino- or 4-aryl-substituted 2,4-dihydro-5-[(4-trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-ones 3a–3g were synthesized by reaction of N-(ethoxycarbonyl)-4-(trifluoromethyl)benzenehydrazonic acid ethyl ester (2) and primary amines or hydrazine by microwave irradiation. Compounds 3a–3g were potentiometrically titrated with tetrabutylammonium hydroxide (Bu4NOH) in four nonaqueous solvents, i.e., iPrOH, tBuOH, MeCN, and N,N-dimethylformamide (DMF). Also half-neutralization potential values and the corresponding pKa values were determined in all cases.

A series of 3-alkyl(aryl)-4-(p-hydroxy-phenyl)-4,5-dihydro-1H-1,2,4-triazol-5-ones 2 were obtained from the reaction of alkyl (aryl) ester ethoxycarbonyl hydrazones 1 with p-hydroxy aniline. The reaction of 1 with 1,4-diamino benzene (1:1) to afford 3-alkyl(aryl)-4-(p-aminophenyl)-4,5-dihydro-1H-1,2,4-triazol-5-ones 3. The reaction of 3 with benzaldehyde gave 3-alkyl(aryl)-4-(4′-benzilidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones 4. All of the above reactions occurred under microwave heating and conventional methods. Their structures were confirmed by 1H NMR, 13C NMR, IR, and elemental analyses. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:38–42, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20381

WOS: 000251996400018 Some new N-alkoxycarbonyl-N ''-benzoyl-benzamidrazones (p-toluamidrazones) 3a-3d, and 1,3,5-trisubstituted 1,2,4-triazole 4a-4h derivatives by starting from N-benzoylbenzimidates or N-benzoyl-p-toluimidates. The structures of compounds 3 and 4 were established on the basis of elemental analyses, IR, H-1 NMR, C-13 NMR and UV data. Antimicrobial experiments of the compounds performed by using agar-well diffusion and broth microdilution methods revealed that only compounds 3a-3d, 4a and 4b showed inhibitory effect only on Candida albicans ATCC 60193. However, compound 4b had also specific antibacterial activity against Staphylococcus aureus ATCC 25923. The other compounds showed neither antifungal nor antibacterial activities. Compounds 3a, 4a and 4b have been screened on three human tumor cell lines, breast cancer (MCF7), non small cell lung cancer (NCI-H460), and CNS cancer (SF-268) at the National Cancer Institute (NCI), USA, which were found to exhibit low antiproliferative activity.

Ozil, Musa/0000-0002-1980-1364 WOS: 000250741200005 New metal-free and metal (Zn, Ni, Cu and Co) phthalocyanines containing 4-(p-fluorophenyl)-3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one moiety have been prepared from 1-(3,4-dicyanophenyl)-4-(p-fluorophenyl)-3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one by both conventional and microwave-assisted methods. All of these compounds are soluble in CHCl3, DMF and DMSO. The new compounds have been characterized by elemental analysis, IR, NMR, UV-Vis spectroscopies. The crystal structures of compounds I and 11 were also determined by the single crystal diffraction technique. (C) 2007 Elsevier B.V. All rights reserved.

A series of fused and non-fused 1,2,4-triazole derivatives were prepared starting from ethyl 4-[1-(2-ethoxy-2-oxoethyl)-3-methyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]benzoate. Firstly, both ethyl ester groups were simultaneously transformed into hydrazide groups, then into 4-amino-5-mercapto-4H-1,2,4-triazol-3-yl groups using both microwave-assisted and conventional methods. The latter products interacted with 2 equiv of phenacyl bromides, chloroacetone, or chloroacetic acid to form ring assemblies containing two [1,2,4]triazolo-[3,4-b][1,3,4]thiadiazine fragments. Cyclization using 2 equiv of carboxylic acids, urea, or CS2 leads to the corresponding [1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole derivatives. The synthesized compounds were evaluated in regard to their antimicrobial, anti-lipase, and antiurease activities.