Synthesis and Spectral Characterization of Some Novel Thiazolyl-Pyrazoline Derivatives Containing 1,2,3-Triazole Moiety

Abstract

A series of novel 3-aryl-5-(2-aryl-1,2,3-triazol-4-yl)-1-(4-aryl-2-thiazoyl)-pyrazolines 6a–6r were synthesized using 2-aryl-4-formyl-1,2,3-triazoles 1a,b as the starting materials. Thus, reacting 1a,b with 1-arylethanones 2a–2c gave 1-aryl-3-(2-aryl-1,2,3-triazol-4-yl)-2-propen-1-ones 3a–3f. The reaction of the latter with thiosemicarbazide afforded 3-aryl-5-(2-aryl-1,2,3-triazol-4-yl)-1-thiocarbamoyl-pyrazolines 4a–4f, which condensed with 2-bromo-1-arylethanones 5a–5c to afford the target compounds 6a–6r. The chemical structures of the compounds were verified by means of their IR, ¹H NMR, ESI-MS spectroscopic data, and elemental analysis.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

GRAPHICAL ABSTRACT     

新型含三唑及噻唑环的腙类化合物的合成及生物活性研究

为寻找具有医用或农用生物活性的新颖化合物,以对氯苯胺为起始原料,经由四步反应,制得1-对氯苯基-5-甲基-1,2,3-三唑-4-乙酮缩氨基硫脲(3),随后中间体3与ω-溴代芳基乙酮在无水乙醇中回流或在超声波辐射下反应,得到了一系列新型N-(1-对氯苯基-5-甲基-1,2,3-三唑-4-乙酰基)-N'-(4-芳基-噻唑-2-基)腙类化合物.用1H NMR MS谱和元素分析对所有化合物进行了结构表征.初步生物活性测试表明,化合物4d和4e表现出一定的生物活性.     

Synthesis, Characterization, and Evaluation of Antimicrobial Activity of Some 1,2,4-Triazole Derivatives Bearing an Antipyryl Moiety

Summary.  Some novel 4-[[2-[[5-(2-furanyl)-4-alkyl/aryl-4H-1,2,4-triazol-3-yl]thio]-acetyl/propionyl]-amino]-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazoles were synthesized and evaluated for in vitro antibacterial activity against Staphylococcus aureus ATCC 29213, Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 25922, and Enterococcus faecalis ATCC 29212 and antifungal activity against Candida albicans ATCC 10231, Candida parapsilosis ATCC 22019, Candida krusei ATCC 6258, Candida parapsilosis, Trichophyton mentagrophytes var. erinacei NCPF 375, Microsporum gypseum NCPF 580, and Trichophyton rubrum using the microbroth dilution method. All of the compounds were found to be ineffective against the above bacteria within the applied MIC ranges. On the other hand, they were effective against fungi to different degrees. Three compounds showed high activity against C. parapsilosis and T. mentagrophytes var. erinacei NCPF 375 (MIC = 8 μg cm⁻³). The in vitro antimycobacterial activity of the new compounds was also investigated against Mycobacterium tuberculosis H₃₇RV (ATCC 27294) in BACTEC 12B medium using a broth microdilution assay, the Microplate Alamar Blue Assay (MABA). Compounds exhibiting fluorescence were tested in the BACTEC 460 radiometric system. The most active compound was found with 66% inhibition at >6.25 μg cm⁻³. Corresponding author. E-mail: nurayulusoy@yahoo.com Received July 24, 2002; accepted August 26, 2002     

含三唑基及噻唑基的杂环醛腙类化合物的合成

以2-苯基-1,2,3-三唑-4-甲醛(1)为原料,与氨基硫脲缩合,生成醛缩氨基硫脲(2),分别与5种α-溴代芳基乙酮、5种α-溴代-α-(1H-1,2,4-三唑-1-基)芳基乙酮在无水乙醇中回流10～30 min反应,合成了10种新型的含三唑及噻唑基的杂环基醛腙类化合物(3a～3e,4a～4e)。所得化合物的结构经1R、1H NMR和MS及元素分析测试技术确证。     

Synthesis, Crystal Structure and Biological Activity of a New 1,2,4-Triazole Derivative

A new 1,2,4-triazole containing cyclopropane moiety was synthesized and characte- rized by 1H NMR, MS and elemental analyses. The crystal structure of the title compound (C13H14FN3S, Mr = 263.33) has been determined by single-crystal X-ray diffraction. The crystal is of monoclinic, space group P21/c with a = 12.614(3), b = 7.0202(14), c = 15.556(3), β = 110.92(3)°, V = 1286.7(4)3 , Z = 4, F(000) = 552, Dc = 1.359 g/cm 3 , μ = 0.25 mm-1 , the final R = 0.0336 and wR = 0.0898 for 2568 observed reflections with Ⅰ > 2σ(Ⅰ). A total of 10093 reflections were collected, of which 3045 were independent (Rint = 0.0268). The herbicidal activity of the title compound was determined, and this compound displays excellent herbicidal activity against Brassica campestris.     

Synthesis,Antiviral, and Antimicrobial Activity of 1,2,4-Triazole Thioglycoside Derivatives

Abstract

The reaction of 5-(2-methylthio)phenyl-1,2,4-triazole-3-thiol with glucosyl, galactosyl, lactosyl bromide, and peracetylated ribose under the conventional and microwave irradiation methods afforded the corresponding S-glycosides. Deacetylation of S-glycosides gave the corresponding deacetylated derivatives. Reaction of 5-(2-methylthio)phenyl-1,2,4-triazole-3-thiol with 4-acetoxybutyl bromide, 2-acetoxyethoxymethyl bromide, 3-chloropropanol, 1,3-dichloroopropan-2-ol, epichlorohydrin, allyl bromide, and propargayl bromide gave the corresponding S-acyclonucleosides, which were deacetylated to give the corresponding deacetylated compounds. All the newly synthesized compounds were characterized by the IR, ¹H, ¹³C NMR, and elemental analyses. Some of these compounds were screened for their antiviral and antimicrobial activity.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the related elements to view the free supplemental file.     

Versatile Synthesis of Fused Tricyclic 1,2,4-Triazole Derivatives

ABSTRACT

A rapid and general method for the synthesis of symmetrical disulfides involves reaction of sulfur with sodium hydroxide under PTC-microwave irradiation condition to give sodium disulfide, which reacts with alkyl halides to afford the disulfides in good to excellent isolated yields.     

Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties

A series of new symmetrical s-tetrazine derivatives, coupled via a 1,4-phenylene linkage with a 4H-1,2,4-triazole ring, were obtained. The combination of these two rings in an extensively coupled system has significant potential applications, mainly in optoelectronics. The methodology used turned out to be useful regardless of the type of five-membered ring or the nature of the individual substituents. All the products were identified by spectroscopic methods, and the target compounds were tested for luminescent properties. This study showed that all the synthesized highly-conjugated triazoles exhibited luminescence; in particular, one derivative, 3,6-bis(4-(5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazol-3-yl)phenyl)-1,2,4,5-tetrazine (13b), showed strong fluorescence emission and ahigh quantum yield close to 1.     

Synthesis and Biological Activities of Novel 1,2,4-Triazole Derivatives Containing 1,2,3-Thiadiazole Ring

A series of novel 1,2,4-triazole derivatives containing 1,2,3-thiadiazole ring was designed and synthesized. Their structures were confirmed by IR, 1^H NMR, high resolution mass spectrometer（HRMS） and electrospray ionization-mass spectromcter（ESI-MS） combined with melting points and elemental analysis. Preliminary bioassays indi- cate that these compounds exhibit good insecticidal activity against Aphis laburni at 100 μg/mL, especially compound 6b shows mortality of no less than 95%. Most of the compounds show good activities against tobacco mosaic virus（TMV） with different modes in vivo at 100 μg/mL. Compound 6d standed out, showing a good insecticidal activity and very high induction effects against TMV in vivo. Collectively, our data demonstrate a new strategy for insect and virus control.     

Synthesis and Antioxidant Evaluation of Some Novel Thiophene,Pyrazole, Chromene,Pyrazolotriazine Derivatives Bearing Sulfonamide Moiety

As a part of ongoing studies in developing new potent antioxidant agents, N‐[4‐(aminosulfonyl)phenyl]‐2‐cyanoacetamide ( 3 ) was utilized as key intermediate for the synthesis of some new thiophene, chromene, and pyrazolotriazine pyridine derivatives. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, ¹H‐NMR, and mass spectral data. Representative compounds of the synthesized products were tested and evaluated as antioxidant. Compounds 7 and 30 are promising compounds.     

Synthesis and Biological Evaluation of Novel Saccharin Derivatives Containing 1,2,3-Triazole Moiety

A series of novel saccharin derivatives containing 1,2,3-triazole moiety was synthesized in satisfactory yields. The structures of all the compounds were elucidated and confirmed by Fourier transform infrared(FTIR) spectroscopy, ¹H and ¹³C nuclear magnetic resonance(¹H NMR, ¹³C NMR) spectroscopy, and high resolution mass spectrometry(HRMS). The bioassays indicated that most of the title compounds displayed some extent herbicidal activities at 100 μg/mL.     

Synthesis and Antibacterial Activity of Substituted Thiosemicarbazides and of 1,3,4-Thiadiazole or 1,2,4-Triazole Derivatives

The synthesized series of new thiosemicarbazide derivatives ( 1 , 6–10 ) in reactions with carbon disulphide produced, according to the reaction conditions, the dithioacids ( 4 , 30 ) or the 5-substituted 1,3,4-thiadiazolo-2-thiol derivatives ( 2 , 27 ). The dithioacids were cyclized, in the reaction with hydrazine, into the 4-ami-no-1,2,4-triazolo-2-thiol derivatives ( 5 , 31 ). One of these compounds ( 31 ) was transformed into the 1,2,4-triazolo-1,3,4-thiadiazine derivative ( 33 ). The compo-unds 6–9 were also exposed to the condensation with aldehydes. 4-phenylpipera-zinocarbothiohydrazide ( 6 ) was exposed to the action of isothiocyanates, which gave the compounds 16–20 , and these cyclized to the 1,3,4-thiadiazoloamino derivatives ( 21–23 ).

The susceptibility of aerobic and anaerobic bacteria to some of the new derivatives were tested. The anaerobes were the most susceptible at concentrations in ranges less than 6.2 to 100 μg/mL to derivative: 9 (64% were susceptible), 1 , 13 (for 60%), and 7 (for 56%).     

Synthesis and Antimicrobial Properties of New Thiosemicarbazide, 1,2,4-Triazole,and 1,3,4-Thiadiazole Derivatives of Sulfanylacetic Acid

Abstract

1,2,4-triazole and 1,3,4-thiadiazole derivatives are still considered a viable lead structure for the synthesis of more efficient antimicrobial agents having a broad spectrum of activity. This study presents the synthesis and antimicrobial evaluation of a new series of substituted 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Reaction of 4-phenyl-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thione with ethyl bromoacetate yields the corresponding ethyl acetate (1). In the subsequent reaction with 100% hydrazine hydrate, the hydrazide (2) was obtained, which was converted with isothiocyanates to new acyl derivatives of thiosemicarbazide (3a–l). The cyclization of these compounds in alkaline media resulted in the formation of new derivatives of 1,2,4-triazole (4a–i), whereas in acidic media new derivatives of 1,3,4-thiadiazole (5a,b,g) were obtained. All synthesized compounds were screened for their in vitro antimicrobial activities.     

含噻唑、硫醚结构的1,2,4-三唑类化合物的合成及生物活性

以三氟乙酰乙酸乙酯、磺酰氯、水合肼、异硫氰酸苯酯、碘代芳烃、氯乙酸等为原料,设计、合成了7种新型的含噻唑环、硫醚和三氟甲基的1,2,4-三氮唑类化合物,通过¹H NMR、¹³C NMR、¹⁹F NMR和MS等技术手段对新化合物进行了结构表征。 杀菌活性测试表明,化合物6b、6d和6g在浓度为100 mg/L时对纹枯病菌(Rhizoctoniasolani)的抑制率分别为91%、92%和93%。     

Synthesis of Novel Ferrocenyl-containing Thiazole Derivatives

Ferrocenes and their derivatives have been used in material chemistry, electrochemistry and in nonlinear optics. Recently, increasing interests have been focused on their biological activity1. Ferrocifen is a ferrocene derivative of tamoxifen, will be sub…     

Synthesis and Antibacterial Activity of Some New Derivatives of Thiosemicarbazide and 1,2,4-Triazole

Abstract

In a reaction of hydrazides of cyclohexylacetic acid 1 and phenylacetic acid 2 with isothiocyanates, respective thiosemicarbazide derivatives 3–18 were obtained. Further cyclization with 2% NaOH led to the formation of 5-(cyclohexylmethyl/benzyl)-4-substituted-2,4-dihydro-3H-1,2,4-triazole-3-thiones 19–34. Structures of all new products were confirmed by analytical and spectroscopic methods. All compounds were screened for their in vitro activity against some species of bacteria and fungi.

[Supplementary materials are available for this article. Go to the publisher's online edition ofPhosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional figures and tables.]     

Reactions of 3-Nitro-1,2,4-Triazole Derivatives with Alkylating Agents. 2. Alkylation of a Neutral Heterocycle by Dimethyl Sulfate

The reaction of 3-nitro-1,2,4-triazole and 5-methyl-3-nitro-1,2,4-triazole with dimethyl sulfate leads to mixtures of N-mono- and N,N-dimethylnitrotriazolium compounds and products of the subsequent conversion of the latter, namely, N,N-dimethyl-1,2,4-triazol-5-ones. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1168–1173, August, 2005.     

Novel Etodolac-Based 1,2,4-Triazole Derivatives as Antimicrobial Agents: Synthesis,Biological Evaluation,and Molecular Docking Study

Russian Journal of Organic Chemistry - A series of novel 1,2,4-triazole nonsteroidal anti-inflammatory drugs (NSAIDs) derived from etodolac were designed and synthesized. The synthesized compounds...     

Synthesis,Structure, and In Vitro Anti-HIV Activity of New Pyrazole, 1,2,4-Thiadiazole,and 1,2,4-Triazole Derivatives

α,α′-Dichloroazo compounds 6 react with Lewis acid to furnish 1-(chloroalkyl)-1-aza-2-azoniaallene salts 4. The cations 4 react with acetylenes, isothiocyanates, isocyanates, and carbodiimides under [3+2]-cycloaddition. The cycloadducts undergo consecutive reactions, e.g., [1,2]-shifts of alkyl groups. The newly synthesized products were evaluated for their anti-HIV-1 and anti-HIV-2 activity in MT-4 cells.     

Design,Synthesis, and Biological Activity of Novel Triazole Sulfonamide Derivatives Containing a Benzylamine Moiety

The triazole sulfonamide played a very important role in the field of research of new agrochemical compounds as a novel heterocyclic compound with lack of reported resistance. For the research on the innovative triazole sulfonamide fungicide effective against cucumber downy mildew (CDM), the present article designed an array of 1,2,4‐triazole‐1,3‐disulfonamide derivatives. The derivatives were synthesized via coupling multiple benzylamine with triazole sulfonamide groups. ¹H‐NMR, ¹³C‐NMR, and LC–MS spectrometry were used to characterize these synthesized compounds. Most of these derivatives exhibited better fungicidal activities than that of the commercial cyanosole using bioassays. In particular, compounds 6g and 6h showed the best fungicidal activity against CDM (EC₅₀ = 6.91 and 10.62 mg/L). Comparative experiments demonstrated that the fungicidal activity of 6g and 6h was better than the commercial pesticides amisulbrom and cyanosole. According to the study, the compound 6g had a giant application potential on fungicide against CDM.