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1.
Junhu Qin Mei Zhu Hongmei Zhu Liqiong Zhang Yihong Fu Jiamin Liu 《Phosphorus, sulfur, and silicon and the related elements》2020,195(7):592-599
AbstractA series of novel pyridazinone derivatives containing the 1,3,4-thiadiazole moiety were synthesized and characterized by 1H NMR, 13C NMR, spectroscopies HRMS and IR. Among them, the structure of compound 5c (2-(Tert-butyl)?4-chloro-5-((5-((2-ethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was unambiguously confirmed via single crystal X-ray diffraction analysis. The inhibitory activity of all the target compounds against MGC-803 and Bcap-37 was determined by MTT assay, with doxorubicin (the inhibition rates were 95.5?±?0.4% and 95.7?±?1.0% respectively) as a control. The preliminary results showed that the inhibitory activity of compound 5n (2-(Tert-butyl)?4-chloro-5-((5-((3-fluorophenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was superior to the others. The inhibition rates of MGC-803 and Bcap-37 cells were 86.3?±?2.2% and 92.3?±?0.6% at a concentration of 10?μmol/L, respectively. The preliminary structure-activity relationship showed that when the 2-position of the benzene ring was substituted by a methyl group, such as compound 5j (2-(Tert-butyl)?4-chloro-5-((5-((2,3-dimethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), it exhibited good anticancer activity on MGC-803 cells. Besides, introducing fluorine, chlorine, or trifluoromethyl group onto the benzene ring, such as compound 5?m (2-(Tert-butyl)?4-chloro-5-((5-((4-(trifluoromethoxy)phenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), displayed good anticancer activity on MGC-803 and Bcap-37 cells. 相似文献
2.
In this study, we synthesized a new series of substituted aliphatic 1,3,4-thiadiazol-2(3H)-one derivatives (6-24) in yields ranging from 42 to 70% with an interesting mechanism that involves internal nucleophilic substitution followed by an SN2-type nucleophilic substitution. First, 1-(4-chlorophenyl)-2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethanone (3) was synthesized from the reaction of 5-methyl-1,3,4-thiadiazole-2-thiol (1) with 2-bromo-1-(4-chlorophenyl)ethanone (2) in the presence of potassium hydroxide. Then, 1-(4-chlorophenyl)-2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethanol (4) was synthesized by a reduction reaction of this compound using NaBH4. Finally, 5-methyl-3-alkyl-1,3,4-thiadiazol-2(3H)-one derivatives (6-24), which are the target compounds, were synthesized from the reaction of this compound (4), which is a secondary alcohol with various alkyl halides (5a-n) in the presence of sodium hydride (NaH). This study presents an interesting reaction mechanism related to the synthesis of aliphatic 1,3,4-thiadiazol-2(3H)-one derivatives that is not recorded in the literature. 相似文献
3.
以氨基硫脲和二硫化碳为起始原料,合成了15个新型的1,3,4-噻二唑衍生物(6a~6o),其结构经1H NMR,13C NMR,IR,ESI-MS和元素分析表征。生物活性测试结果表明:大部分化合物对水稻白叶枯细菌有良好的抑制活性,其中,N-[5-(2,4-二氯苄基)硫醚]-1,3,4-噻二唑-2-(2-N-甲基哌嗪)-乙酰胺(6b)和N-[5-(4-三氟甲氧基苄基)硫醚]-1,3,4-噻二唑-2-(2-N-甲基哌嗪)-乙酰胺(6e)的EC50分别为17.5 μg·mL-1和19.8 μg·mL-1; N-[5-(3-甲基苄基)硫醚)-1,3,4-噻二唑-2-(2-哌嗪)-乙酰胺(6k)在浓度为500 μg·mL-1时,对烟草花叶病毒有一定的抑制活性。 相似文献
4.
Reaction of 5-pentadecyl-1,3,4-thiadiazol-2-amine 2 with ethyl cyanoacetate gave 2-cyano-N-(5-pentadecyl-1,3,4-thiadiazol-2-yl)acetamide 3, which was used to synthesize different heterocyclic derivatives with coumarin, pyrazole, thiazole, pyridine, pyrimidine, and thiophene rings. Propoxylation of these compounds by using 5 mol of propylene oxide produced nonionic surface active agents. Antimicrobial and surface activities were evaluated. 相似文献
5.
Vikunjana K. Akbari Piyush P. Savaliya 《Phosphorus, sulfur, and silicon and the related elements》2013,188(5):711-719
Abstract A new series of 2-substituted-3-((3-(6-nitrobenzo[d]thiazol-2-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)methyl)-1,3,4-thiadiazol-3-ium-5-thiolate 6(a–j) was synthesized starting from anthranilic acid 1. The structures of the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, mass spectra, and elemental analysis. The final compounds were tested for their antimicrobial activity against several microbes. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional text and tables.] 相似文献
6.
Asaf E. Evren Leyla Yurttas Büşra Ekselli Gülşen Akalin-Ciftci 《Phosphorus, sulfur, and silicon and the related elements》2013,188(8):820-828
AbstractNew N-(5-methyl-4-phenylthiazol-2-yl)-2-(substituted thio)acetamides were synthesized and studied for their anticancer activity. The title compounds were procured by reacting 2-chloro-N-(5-methyl-4-phenylthiazol-2-yl)acetamide with some mercapto derivatives. The structural elucidation of the compounds was performed by 1H-NMR, 13C-NMR and LC-MS/MS spectral data and elemental analyses. The synthesized compounds were investigated for their antitumor activities against A549 human lung adenocarcinoma cells and NIH/3T3 mouse embryoblast cell line for determining their selective cytotoxicity. 2-[(1-methyl-1H-tetrazol-5-yl)thio]-N-(5-methyl-4-phenylthiazol-2-yl)acetamide (4c) showed high selectivity, and whose IC50 value was determined as 23.30?±?0.35?µM and >1000?µM against A549 human lung adenocarcinoma cells and NIH/3T3 mouse embryoblast cell lines, respectively. 2-[(1-Methyl-1H-imidazol-2-yl)thio]-N-(5-methyl-4-phenyl thiazol-2-yl)acetamide (4a) and 2-[(1-Methyl-1H-tetrazol-5-yl)thio]-N-(5-methyl-4-phenyl thiazol-2-yl)acetamide (4c) exhibited the highest apoptosis percentage among those tested, but not as high as the standard, cisplatin. 相似文献
7.
Xiulei Chen Zhen Zhou Zhong Li 《Phosphorus, sulfur, and silicon and the related elements》2020,195(3):194-200
AbstractA series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The bioassay results showed that compounds 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-7-methoxybenzo[d][1–3]triazin-4(3H)-one, 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-6-nitrobenzo[d][1–3]triazin-4(3H)-one, 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0?mg L?1 in vivo. Compound 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0?mg L?1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further. 相似文献
8.
9.
Wael A. El-Sayed Mohamed I. Hegab Hala E. M. Tolan Adel A.-H. Abdel-Rahman 《Monatshefte für Chemie / Chemical Monthly》2008,139(9):1055-1060
A series of new N- and S-substituted 1,3,4-oxadiazole derivatives were synthesized. 5-Pyridin-3-yl-3-[2-(5-thioxo-4,5-dihydro-l,3,4-thiadiazol-2-yl)ethyl]-1,3,4-oxadiazole-2(3H)-thione and 5-[(5-(pyridin-3-yl)-1,3,4-oxadiazol-2-ylthio)methyl]-N-phenyl-1,3,4-thiadiazol-2-amine were formed by cyclization of 3-(5-pyridin-3-yl-2-thioxo-1,3,4-oxadiazol-3(2H)-ylpropanimidohydrazide and 2-[(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)thio]thiosemicarbazide with CS2 and H2SO4. On the other hand, a number of new bicyclic 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives were synthesized. 6-Pyridin-3-ylbis[1,2,4]‐triazolo[3,4-b:4′,3′-d][1,3,4]thiadiazole-3(2H)-thione was synthesized by reaction of 6-(hydrazino)-3-pyridine-3-yl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole with CS2/KOH/EtOH. The structures of the newly synthesized compounds were elucidated by the spectral and analytical data IR, Mass, and 1H NMR spectra.
Correspondence: Adel A.-H. Abdel-Rahman, Department of Chemistry, Faculty of Science, Menoufia University, Shebin El-Koam,
Egypt; Wael A. El-Sayed, National Research Centre, Department of Photochemistry, Cairo, Egypt. 相似文献
10.
AbstractA series of novel pyrethrin derivatives containing hydrazone and 1,3,4-oxadiazole thioether moieties were designed, synthesized, and evaluated for their insecticidal activity. Bioassays indicated that some of the target compounds exhibited good insecticidal activities against Plutella xylostella (P. xylostella), Vegetable aphids (V. aphids), and Empoasca vitis (E. vitis). In particular, compound (E)-2-((5-(2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropyl)-1,3,4-oxadiazol-2-yl)thio)-N'-(4-(trifluoromethyl)benzylidene)acetohydrazide (6s) revealed excellent insecticidal activities against P. xylostella, V. aphids, and E. vitis with the 50% lethal concentration (LC50) values of 5.23, 7.07, and 1.61?mg/L, respectively, which were similar to or even better than those of chlorpyrifos, beta cypermethrin, spinosad, and azadirachtin. These results indicated that novel pyrethrin derivatives containing hydrazone and 1,3,4-oxadiazole thioether moieties could be developed as novel and promising insecticides. 相似文献
11.
Hui Li Aoyun Lu Yanqiu Zhang Yanqing Peng 《Phosphorus, sulfur, and silicon and the related elements》2020,195(5):371-375
AbstractTo explore a new skeleton with nematicidal activity, a series of novel azabicyclo derivatives containing a thiazole moiety were designed, synthesized and evaluated for their nematicidal activities. The bioassay results against pine-wood nematodes (Bursaphelenchus xylophilus) showed that most of the title compounds displayed nematicidal activity at a concentration of 40?mg/L. Especially, the title compounds2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)oxy)-4-(4-chlorophenyl)thiazole (7e), 2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)thio)-4-phenylthiazole (10a) and 2-((8-methyl-8-azabicyclo [3.2.1]octan-3-yl)thio)-4-(4-chlorophenyl)thiazole (10e) exhibited more than 90% mortality against Bursaphelenchus xylophilus. 相似文献
12.
Leyla Yurttaş Aslıhan Kubilay Asaf Evrim Evren İpek Kısacık Hülya Karaca Gençer 《Phosphorus, sulfur, and silicon and the related elements》2020,195(9):767-773
AbstractSome new 3,4,5-trisubstituted 1,2,4-triazole derivatives were synthesized and studied for their antimicrobial activity. The lead compounds were obtained starting from 8-hydroxyquinoline and ethyl 2-chloroacetate. The obtained ester compound (1) first reacted with hydrazine hydrate (2) then with phenyl isothiocyanate (3). Ring closure by KOH led to 3-mercapto-1,2,4-triazole derivative (4). Lastly, it reacted with 2-chloro-N-(substituted (benzo)/thiazole)acetamide derivatives to obtain the final compounds (5a–j). The structural elucidation of the compounds was performed by 1H NMR and 13C NMR spectroscopy and high resolution mass spectrometry techniques and elemental analysis. The synthesized compounds were investigated for their antimicrobial activities against seven bacteria and four fungi. As a result of the activity studies, it was observed that compounds N-(6-nitrobenzothiazol-2-yl)-2-[[4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-yl]thio]acetamide (5a) and N-(6-fluorobenzothiazol-2-yl)-2-[[4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-yl]thio]acetamide (5d) were the most active molecules. Also, the antifungal activity of the compounds was found to be higher than their antibacterial activity although lower than the standard drug’s potential. Additionally, the physicochemical properties of the compounds were calculated which were evaluated to be at a suitable range for oral administration. 相似文献
13.
14.
Gülhan Turan Begüm Nurpelin Sağlik Ulviye Acar Çevik Serkan Levent Betül Kaya Çavuşoğlu 《Phosphorus, sulfur, and silicon and the related elements》2020,195(6):491-497
AbstractIn this study, a novel series of benzothiazole-thiazolylhydrazine (3a–3i) was synthesized and their structures were characterized by 1H-NMR, 13C-NMR spectrometry, and mass spectroscopy. These compounds were evaluated as inhibitors of type A and type B monoamine oxidase (MAO) enzymes. The most active compound 3b (2-((2-(2-(4-(4-Nitrophenyl)thiazol-2-yl)hydrazineylidene)-2-phenylethyl)thio)benzothiazole) showed strong inhibitory activity at hMAO-A (IC50 of 0.095?±?0.004?µM). Furthermore, compound 3i (2-((2-(2-(4-(2,4-dichlorophenyl)thiazol-2-yl)hydrazineylidene)-2-phenylethyl)thio)benzothiazole) showed significant inhibition profile on hMAO-A with the IC50 values 0.141?±?0.006?µM. 相似文献
15.
Novel 2-(5-R-1,3,4-thiadiazol-2-yl)aminothiazolin-4-ones 6a—h and 2-imino-3-(5-R-1,3,4-thiadiazol-2-yl)thiazolidin-4-ones 7a—h were prepared by treating N-(5-R-1,3,4-thiadiazol-2-yl)thioureas 4a—h with chloroacetic acid on various solid supports under microwave irradiation. Tautomeric mixtures of compounds 6a—h and 7a—h were obtained in all cases. In alkaline and neutral media, compounds 6a—h were the major products, while in acid media, 7a—h were the major products. 相似文献
16.
The following compounds have been synthesized: 2-Amino-5-trifluoromethyl-1,3,4-thiadiazole; N-(5-trifluoromethyl - 1,3,4-thiadizol-2-yl)benzenesulfonamide; N1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)sulfanilamide, its N4-acetyl, N4-succinyl, and N4-pathalyl derivatives; o - m - and p-trifluoromethylbenzoylthiosemicarbazide, their corresponding 2-amino-1,3,4-thiadiazoles, their corresponding sulfanilamides, their N4-acetyl, N4-succinyl and N4-phthalyl derivatives; 3-o-trifluoromethylphenyl-4H-1,2,4-triazole-5-thiol. Preliminary in-vitro assays show that synthesized sulfanilamide derivatives have antibacterial activity against Staphylococcus aureus. 相似文献
17.
Sreelakshmi Poola Mohan Gundluru Maheshwara Reddy Nadiveedhi Madhu Sudhana Saddala Prasada Rao P. T. S. R. K. 《Phosphorus, sulfur, and silicon and the related elements》2020,195(5):409-420
AbstractA new series of α-thiazolyl aminomethylene bisphosphonates were synthesized by a three component reaction of 4-aryl substituted thiazol-2-amine with different dialkyl/aryl phosphites and triethyl orthoformate in the presence of Ag NPs (nano particles) as a catalyst under solvent free conditions. All the synthesized target compounds were characterized by 1H, 13C, 31P, mass and elemental analysis. The target compounds were screened for their in vitro antioxidant, antibacterial and antifungal activity. Molecular docking studies were also performed. The results revealed that among the synthesized compounds tetramethyl(((4-(4-methoxyphenyl)thiazol-2-yl)amino) methylene)bis(phosphonate) (5d), tetramethyl(((4-(4-fluorophenyl)thiazol-2-yl)amino) methylene) bis(phosphonate) (5h), and tetramethyl(((4-(4-bromophenyl)thiazol-2-yl)amino)methylene) bis (phosphonate) (5j) showed remarkably higher antioxidant activity by DPPH and H2O2 than the standard ascorbic acid. Compounds tetramethyl(((4-phenyl thiazol-2-yl)amino) methylene) bis(phosphonate) (5a), 5d, 5h and tetraethyl(((4-(4-bromophenyl)thiazol-2-yl) amino)methylene)bis (phosphonate) (5k) showed good antibacterial activity. 5a, 5d, and 5h also showed rather higher antifungal activity than the standard flucanozole. Computational docking methods have been used to predict how several aminomethylene bisphosphonate derivatives compete against the inhibitor BPH-1330 at the crystal enzyme structure of the 4H3A protein active site and how R and R1 influence their binding ability. 相似文献
18.
Shi-Chun Wang Ji-Gang Gao Shuai Zhang Si Liu 《Phosphorus, sulfur, and silicon and the related elements》2018,193(4):245-248
A series of novel pyrimidine derivatives with (pyridin-3-ylmethyl)thio and phenylamino moieties were synthesized from ethyl acetoacetate, thiourea, 3-pyridinylmethyl chloride hydrochloride, and substituted anilines by multi-step reactions. The structures of the target compounds were characterized by IR, 1H NMR, 13C NMR and elemental analysis. The in vitro antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum were evaluated. The result showed that N-phenyl-6-methyl-2- ((pyridin-3-ylmethyl)thio) pyrimidin-4-amine (4a) displayed high inhibition activity against Botrytis cinerea with 87.5%inhibition at 100 µg/mL; 4a, and N-(4-isopropylphenyl)-6-methyl-2-((pyridin-3-ylmethyl)thio)pyrimidin-4-amine (4c), N-(4-methoxyphenyl)-6-methyl-2-((pyridin-3-ylmethyl)thio)pyrimidin-4-amine (4d) and N-(2-hydroxy-5-chloro)-6-methyl-2-((pyridin-3-ylmethyl)thio)pyrimidin- 4-amine (4h) exhibited sufficient activities against Sclerotinia sclerotiorum with 86.6% –93.7% inhibitions at the same concentration. 相似文献
19.
P. Koparir M. Karaarslan C. Orek M. Koparir 《Phosphorus, sulfur, and silicon and the related elements》2013,188(7):864-870
Abstract (1R,2R)-1,2-bis[5-(arylideneamino)-1,3,4-thiadiazol-2-yl]ethane-1,2-diol (2a–d) were synthesized by using appropriate aldehydes and (1R,2R)-1,2-bis(5-amino-1,3,4-thiadiazol-2-yl)ethane-1,2-diol (1) as a starting compound. Then, the phosphinic acid component (3a–d) were obtained from (2a–d) and hypophosporus acid. In addition, the structures of the novel chiral compounds (2a–d) and (3a–d) were confirmed by elemental analyses, IR, 1H-NMR, 13C-NMR, and 31P-NMR spectra. 1H NMR and 13C NMR spectra for 1, 2a, and 3a (Figures S1–S6) are available online in the Supplemental Materials. 相似文献
20.
Łukasz Popiołek Urszula Kosikowska Maria Dobosz Anna Malm 《Phosphorus, sulfur, and silicon and the related elements》2013,188(4):468-481
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. 相似文献