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1.
Agnieszka Bogdanowicz Henryk Foks Katarzyna Gobis Ewa Augustynowicz‐Kopec 《Heteroatom Chemistry》2012,23(2):223-230
The synthesis of N′‐methyl‐4‐(pyrrolidin‐1‐yl)picolinohydrazide and N′‐methyl‐pyrimidine‐2‐carbohydrazide derivatives ( 5a and 5b ) was carried out. These compounds were used as starting materials to obtain methyl N′‐methylhydrazinecarbodithioates 6a and 6b , which, on reaction with either triethylamine or hydrazine, gave corresponding 1,3,4‐oxadiazioles 7a and 7b or 1,2,4‐triazoles 9a and 9b with the free NH2 group at the N‐4 position, respectively. Compounds 8a – e , particularly containing cyclic amines at N‐4 of the 1,2,4‐triazole ring, were also obtained. Synthesized compounds were tested in vitro for their activity against Mycobacterium tuberculosis. The structure–activity relationship analysis for obtained compounds was done. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:223–230, 2012; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.21008 相似文献
2.
Stefania‐Felicia Barbuceanu Gabriela Bancescu Gabriel Saramet Florica Barbuceanu Constantin Draghici Flavian Stefan Radulescu Aura Ionescu Simona Negres 《Heteroatom Chemistry》2013,24(4):309-321
In the present study, new 1,2,4‐triazoles, 1,3,4‐thiadiazoles, and acylthiosemicarbaz‐ides derived from 4‐(4‐chlorophenylsulfonyl)benzoic acid hydrazide were synthesized and screened for their antimicrobial and analgesic activities. Acylthiosemicarbazides 2–4 were synthesized by a reaction of 4‐(4‐chlorophenyl‐sulfonyl)benzoic acid hydrazide 1 with different arylisothiocyanates.4,5‐Disubstituted‐2,4‐dihydro‐3H‐1,2,4‐triazol‐3‐thiones 5–7 and 2,5‐disubstituted‐1,3,4‐thiadiazoles 8–10 were obtained by dehydrative cyclization of corresponding acylthiosemicarbazide derivatives 2–4 in basic media (8% aqueous sodium hydroxide) and in acidic media (sulfuric acid or phosphorous oxychloride), respectively. The structures of the newly synthesized compounds have been confirmed on the basis of elemental analysis and spectral studies (IR, 1H NMR, 13C NMR, MS). Their antimicrobial activities against some bacteria and yeasts were investigated. The analgesic activity of all compounds was performed with two pharmacological tests: the writhing test induced with acetic acid and hot‐plate test. The results showed that triazole 7 had the best antimicrobial activity against Bacillus cereus. In the chemical stimulus test, triazoles 6 and 7 were the most active compounds whereas in the hot‐plate test thiadiazoles 9 and 10 exhibited the highest analgesic activity. 相似文献
3.
3‐Methyl‐2‐benzofurancarboxylic acid hydrazide ( 2 ) reacts with carbon disulfide and pota‐ ssium hydroxide to give the corresponding potassium carbodithioate salt 3 . Treatment of the latter salt with hydrochloric acid, hydrazine hydrate, and with phen‐ acyl bromide afforded the corresponding 1,3,4‐oxadia‐ zole‐5‐thione 4 , 4‐amino‐1,2,4‐triazole‐5‐thione 5 , and thiazolidine‐2‐thione 9 derivatives, respectively. The reaction of either 1,3,4‐oxadiazole‐5‐thione 4 or 4‐amino‐1,2,4‐triazole‐5‐thione 5 with phenacyl bromide resulted in the formation of 1,2,4‐triazolo[3, 4‐b]‐1,3,4‐thiadiazine derivative 8 . Treatment of compounds 3 or 4 with hydrazonoyl halides 10a–d furn‐ ished the same 1,3,4‐thiadiazol‐2‐ylidene derivatives 11a–d . The 7‐arylhydrazono‐1,2,4‐triazolo[3,4‐ b ]‐1, 3,4‐thiadiazine derivatives 12a–d were obtained either by treatment of 4‐amino‐1,2,4‐triazole‐5‐thione 5 with hydrazonoyl halides 10a–d or by coupling of the 1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazine derivative 8 with diazonium salts. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:621–627, 2005; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20162 相似文献
4.
Abdelwareth A. O. Sarhan Hassa N. A. H. Elsherif Abdalla M. Mahmoud Osama M. A. Habib 《Journal of heterocyclic chemistry》2008,45(3):897-907
5.
Monika Wujec Agata Siwek Marta Swatko‐Ossor Liliana Mazur Zofia Rzaczynska 《Journal of heterocyclic chemistry》2008,45(6):1893-1896
6.
Latifeh Navidpour Mohsen Amini Abbas Shafiee 《Journal of heterocyclic chemistry》2007,44(6):1323-1331
7.
Synthesis,Characterization and Biological Evaluation of a Novel Series of 1,2,4‐Triazolo‐[3,4‐b]‐1,3,4‐thiadiazines Containing an Amide Linkage
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Pushpan Puthiyapurayil Boja Poojary Sunil Kumar Buridipad 《Journal of heterocyclic chemistry》2014,51(Z1):E55-E67
Two series of combinatorial library of 3,6‐disubstituted‐7H‐1,2,4‐triazolo‐[3,4‐b]‐1,3,4‐thiadiazines bearing an amide linkage were synthesized. All the newly synthesized compounds were characterized by spectral analyses. The newly synthesized compounds were screened for their cytotoxicity, anti‐inflammatory, and analgesic activities. Among the tested compounds, the compound 9g (Ar = 4‐(methoxybenzyl)piperazine) is the most promising molecule with half maximal inhibitory concentration (IC50) value of 14.24 μM in (MCF‐7) cells. Compounds 9f (Ar = 4‐(chlorobenzyl)piperazine), 9g , and 9k (Ar = 2‐(fluorophenyl)piperazine) exhibited excellent anti‐inflammatory activity at a dose level of 50 mg/kg, almost comparable with the standard drug. In case of analgesic activity among the tested compounds, the compounds 9f , 9g , and 9k showed more potent and consistent activity in both 100 and 200 mg/kg/po doses with less ulcerogenic risk. 相似文献
8.
Tomasz Plech Monika Wujec Barbara Kapro Urszula Kosikowska Anna Malm 《Heteroatom Chemistry》2011,22(6):737-743
In this investigation, several novel N2‐hydroxymethyl and N2‐aminomethyl derivatives of 5‐(3‐chlorophenyl)‐4‐(4‐methylphenyl)‐2,4‐dihydro‐ 3H‐1,2,4‐triazole‐3‐thione and 4‐(4‐bromophenyl)‐ 5‐(3‐chlorophenyl)‐2,4‐dihydro‐3H‐1,2,4‐triazole‐3‐ thione were prepared. All synthesized compounds were screened for their antibacterial activity against six Gram‐positive and four Gram‐negative bacterial strains. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:737–743, 2011; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.20737 相似文献
9.
Design,Synthesis, and Herbicidal Activities of 3‐Aryl‐4‐substituted‐5‐[3‐(trifluoromethyl)phenoxy]‐1,2,4‐triazoles
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In order to find novel bleaching herbicide lead compounds, a series of novel 3‐aryl‐4‐substituted‐5‐[3‐(trifluoromethyl)phenoxy]‐1,2,4‐triazoles were designed and synthesized by the multi‐step reactions. N‐(Arylformamido)phenylthioureas undergo ring closure in the presence of sodium hydroxide to generate 3‐aryl‐4‐substituted‐4H‐[1,2,4]triazol‐5‐thiols 1 , which reacted with methyl sulfate in the presence of K2CO3 to give 3‐aryl‐5‐methylsulfanyl‐4‐substituted‐4H‐[1,2,4]triazoles 2 . The target compounds 4 were synthesized by the oxidation of 2 in the presence of H2O2 and Na2WO4, followed by the substitution with 3‐(trifluoromethyl)phenol in moderate to good yields. Their structures were confirmed by IR, 1H NMR, EI–MS, and elemental analyses. The preliminary bioassay indicated that some of them displayed moderate to good selective herbicidal activity against Brassica campestris L at the concentration of 100 µg/mL. Compounds 4c and 4i possessed 75.0% and 82.6% inhibition against Brassica campestris L at the concentration of 100 µg/mL. However, the target compounds 4 showed weak herbicidal activity against Echinochloa crus‐galli at the concentration of 100 and 10 µg/mL. 相似文献
10.
Xin‐Ping Hui Heng‐Shan Dong Peng‐Fei Xu Zi‐Yi Zhang Qin Wang Yan‐Ni Gong 《中国化学会会志》2000,47(5):1115-1119
The condensation of 4‐amino‐5‐mercapto‐3‐(2‐phenylquinolin‐4‐yl)/3‐(1‐p‐chlorophenyl‐5‐methyl‐1,2,3‐triazol‐4‐yl)‐1,2,4‐triazoles 1a‐b with chloroacetaldehyde 2a‐b , ω‐bromo‐ω‐(1H‐1,2,4‐triazol‐1‐yl)acetophenone 3a‐b , chloranil 4a‐b , 2‐bromocyclohexanone 5a‐b , 2,4′‐dibromoacetophenone 6a‐b and 2‐bromo‐6′‐methoxy‐2′‐acetonaphthone 7a‐b are described. The structures of the compounds synthesized were confirmed by elemental analyses, IR, 1H NMR and mass spectra. The antibacterial activities were also evaluated. 相似文献
11.
Raid J. Abdel‐Jalil Raed A. Al‐Qawasmeh Wolfgang Voelter Peter Heeg Mustafa M. El‐Abadelah Salim S. Sabri 《Journal of heterocyclic chemistry》2000,37(5):1273-1275
The 2,3‐disubstituted 6‐fluoro‐7‐(4‐methyl‐1‐piperazinyl)‐quinoxalines ( 3–11 ) were synthesized for bioassay via reaction of 1.2‐diamino‐4‐fluoro‐5‐(4‐methyl‐1‐piperazinyl)benzene (2) with the appropriate 1,2‐dicarbonyl compounds. However, none of the tested compounds 3–11 showed significant in vitro activ ity against E. coli ATCC11229, S. aureus ATCC6538 and C.albicans SATCC10231. 相似文献
12.
Ahmed A. El‐Barbary Mahmoud A. El‐Badawi Yasser M. Loksha 《Journal of heterocyclic chemistry》2001,38(3):711-716
Some novel 3,7‐dimethyl‐6H‐pyrazolo[5,1‐c][1,2,4]triazin‐4‐ones were prepared (3a‐g) . Compounds 3a,b were treated with hydrazines to afford various products 7a,b, 8a,b, 9 and lla,b depending on the type of hydrazine derivative and reaction conditions. The benzoyloxyimino‐pyrazolo[5,1‐c][1,2,4]triazines (13a,b) were synthesized by refluxing of compounds 3a,b with hydroxylamine hydrochloride to afford the corresponding oxime derivatives followed by treatment with benzoyl chloride. 相似文献
13.
Victor M. Chernyshev Dmitry A. Khoroshkin Andrey N. Sokolov Vitaly A. Taranushich Eugene S. Gladkov Svetlana V. Shishkina Oleg V. Shishkin Sergey M. Desenko 《Journal of heterocyclic chemistry》2008,45(5):1419-1427
14.
Kiran S. Hon Hemantkumar N. Akolkar Bhausaheb K. Karale 《Journal of heterocyclic chemistry》2019,56(6):1780-1786
A series of novel 1‐methyl‐3‐(4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles was synthesized in three steps from 5‐(1‐methyl‐1H‐indazol‐3‐yl)‐4‐phenyl‐2H‐1,2,4‐triazole‐3(4H)‐thiones. 5‐(1‐Methyl‐1H‐indazol‐3‐yl)‐4‐phenyl‐2H‐1,2,4‐triazole‐3(4H)‐thiones were converted into 1‐methyl‐3‐(5‐(methylsulfonyl)‐4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles upon methylation followed by treatment with aq. KMnO4. The reaction of 1‐methyl‐3‐(5‐(methylsulfonyl)‐4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles with Raney nickel resulted in desulphonylation to afford corresponding 1‐methyl‐3‐(4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles. All the new synthesized compounds were characterized by spectral techniques. 相似文献
15.
A series of pyrazolo[4,3‐e]‐1,2,4‐triazolo‐[1,5‐c]pyrimidine derivatives, bearing phosphonylbenzyl chain in position 7, were conveniently synthesized in an attempt to obtain potent and selective antagonists for the A2A adenosine receptor or potent pesticide lead compounds. Diethyl[(5‐amino‐4‐cyano‐3‐methylsulfanyl‐pyrazol‐1‐yl)‐benzyl]phospho‐nate ( 3 ), which was prepared by the cyclization of diethyl 1‐hydrazinobenzylphosphonate ( 1 ) with 2‐[bis(methylthio)methylene]malononitrile ( 2 ), reacted with triethyl orthoformate to afford diethyl[(4‐cyano‐5‐ethoxymethyleneamino‐3‐methylsulfanyl‐pyrazol‐1‐yl)‐benzyl]phosphonate ( 4 ), which reacted with various acyl hydrazines in refluxing 2‐methoxyethanol to give the target compounds 5a–h in good yields. Their structures were confirmed by IR, 1H NMR, 13C NMR, MS, and elemental analysis. The crystal structure of 5e was determined by single crystal X‐ray diffraction © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:634–638, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20478 相似文献
16.
New 4‐aryl‐5‐(1‐phenyl‐5‐methyl‐1,2,3‐triazol‐4‐yl)‐1,2,4‐triazol‐3‐thiones 3 have been synthesized by the intramolecular cyclization of 4‐aryl‐1‐(1‐phenyl‐5‐methyl‐1,2,4‐triazol‐4‐formyl)thiosemicarbazides 2 with an 8% NaOH solution, and then 3 reacted with ω‐bromo‐ω‐(1H‐1,2,4‐triazol‐1‐yl)acetophenone to afford ω‐[4‐aryl‐5‐(1‐phenyl‐5‐methyl‐1,2,3‐triazol‐4‐yl)‐1,2,4‐triazol‐3‐thio]‐ω‐(1H‐1,2,4‐triazol‐1‐yl)‐acetophenones 4 . The preliminary biological test showed that the representative compounds possess some anti fungal activities. 相似文献
17.
Mehdi Kalhor Akbar Mobinikhaledi Akbar Dadras Maryam Tohidpour 《Journal of heterocyclic chemistry》2011,48(6):1366-1370
Several derivatives of substituted 1,2,4‐triazole bearing the pyrazole (or oxadiazole) ring were synthesized via the reaction of 2,4‐dihydro‐4‐benzyl‐5‐(isomeric pyridyl)‐3H‐1,2,4‐triazole‐3‐thione 1a , 1b , 1c with ethyl chloroacetate, hydrazine hydrate, and acetyl acetone (or CS2/KOH) in absolute ethanol. The intermediate then undergoes an intramolecular cyclization in acidic medium. The newly synthesized compounds 4a , 4b , 4c to 7a , 7b , 7c were characterized using IR, NMR, and MS Spectroscopy. Some of the synthesized compounds 4 , 5 , 7a , 7b , 7c were evaluated for their antibacterial and antifungal activities. Most of these compounds indicated activity comparable to Gentamycine. Also some of them are more active than Tolnaftate, a known antifungal drug. J. Heterocyclic Chem., (2011) 相似文献
18.
The reaction of 2H‐2‐oxobenzo[b]pyran‐3‐hydrazide ( 2 ) with carbon disulfide in basic DMF afforded potassium thiocarbamate 3 , which readily underwent heterocyclization upon its reaction with hydrazine and/or phenacyl bromide to yield 1,2,4‐tiazole ( 4 ) and thiazole 7 derivatives, respectively. Condensation of 4 with substituted phenacyl bromide and/or chloranil gave 1,2,4‐triazole[3,4‐b]thiadiazine ( 5a,b ) and 3,10‐bis‐[2H‐2‐oxobenzo[b]pyran‐3‐yl]‐6,13‐dichloro‐bis‐1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazino[5′,6′‐b:5′,6′‐e]cyclohexa‐1,4‐diene ( 6 ), respectively. Cyclization of thiosemicarbazide 10 by refluxing it in sodium hydroxide and/or phosphoryl chloride afforded triazole 13 and thiadiazole 15 derivatives, respectively. Also, 10 reacted with phenacyl bromide in the presence of anhydrous sodium acetate to give the oxothiazolidine derivative 17 . The structure of the synthesized compounds were confirmed by elemental analyses, IR, 1H NMR, and mass spectra. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:114–120, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10109 相似文献
19.
《Journal of heterocyclic chemistry》2017,54(5):2850-2858
Treatment of arylidene malononitriles 2A – C with 1‐cyanomethylisoquinoline 1 afforded 4‐amino‐2‐arylpyrido[2,1‐a ]isoquinoline‐1,3‐dicarbonitrile derivatives 5A – C , which converted to formimidates 6A – C via reaction with triethylorthoformate. Treatment of the latter compounds with hydrazine hydrate gave the corresponding amino–imino compounds 7A – C , which underwent Dimroth rearrangement to afford 13‐aryl‐1‐hydrazinylpyrimido[5′,4′:5,6]pyrido[2,1‐a ]isoquinoline‐12‐carbonitrile 8A – C . The latter reacted with aldehyde to give 9a – i . Oxidative cyclization of the latter compounds 9a – i gave [1,2,4]triazolo[4″,3″:1′,6′]‐pyrimido[5′,4′:5,6]pyrido[2,1‐a ]isoquinolines 10a , d , g . Such compounds isomerized to the thermodynamically more stable isomers [1,2,4]triazolo[1″,5″:1′,6′]pyrimido[5′,4′:5,6]‐pyrido[2,1‐a ]isoquinolines 11a , d , g . Antimicrobial activities for some compounds were studied. 相似文献
20.
The synthesis of some new S‐nucleosides of 5‐(4‐pyridyl)‐4‐aryl‐4H‐1,2,4‐triazole‐3‐thiols ( 4a‐n ) is described. Direct glycosylation of ( 4a‐n ) with tetra‐O‐acetyl‐α‐D‐glucopyranosyl bromide in the presence of potassium hydroxide followed by deacetylation using dry ammonia in methanol gave the corresponding 3‐S‐(ñ‐D‐glucopyranosyl)‐5‐(4‐pyridyl)‐4‐aryl‐4H‐1,2,4‐triazoles ( 6a‐n ) in good yields. All the compounds were fully characterized by means of 1HNMR, 13C NMR spectra and elemental analyses. To assist in the interpretation of the spectroscopic data, the crystal structure of 3‐S‐(2′,3′,4′,6′‐tetra‐O‐acetyl‐β‐D‐glucopyranosyl)‐5‐(4‐pyridyl)‐4‐phenyl‐4H‐1,2,4‐triazole ( 5a ) was determined by X‐ray diffraction. 相似文献