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1.
Design and synthesis of novel triazole antifungal derivatives based on the active site of fungal lanosterol 14a-demethylase (CYP51) 总被引:3,自引:2,他引:1
Zhi Gang Dan Jun Zhang Shi Chong Yu Hong Gang Hu Xiao Yun Chai Qing Yan Sun Qiu Ye Wu 《中国化学快报》2009,20(8):935-938
A series of 1-(1H-1,2,4-triazole-1-y1)-2-(2,4-difluorophenyl)-3-(N-isoproyl-N-substituted-amino)-2-propanols have been designed and synthesized on the basis of the active site of lanosterol 14a-demethylase(CYP51).Their structures were confirmed by MS and ~1H NMR.In vitro antifungal activities of these synthesized compounds were evaluated against eight human pathogenic fungi.The results showed that all title compounds exhibited activity against fungi tested to some extent.Compounds 3c,3d,7a,7b and 7c exhi... 相似文献
2.
Hui Tang Can-Hui Zheng Xiao-Hui Ren Jia Liu Na Liu Jia-Guo Lv Ju Zhu You-Jun Zhou 《中国化学快报》2013,24(3):219-222
A series of 1-(benzylamino)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-l-yl)propan-2-ols compounds were synthesized and evaluated for their antifungal activities in vitro.The results showed that compounds 6A and 6B exhibited good antifungal activity.Compound 6A8 showed the strongest antifungal activity,which was significantly higher than that of the lead compounds and positive-control drugs Fluconazole and Itraconazole.In particular,the antifungal activity of compound 6A8 against Candida albicans and Candida krusei(MIC80 both at 0.00097μg/mL) was 515 and 64 times that of Fluconazole,respectively.The structure-activity relationships of the synthesized compounds were discussed,and the docking model of the target compounds with fungal lanosterol 14α-demethylase (CYP51) was analyzed. 相似文献
3.
Jaiprakash N. Sangshetti ;Firoz A. Kalam Khan ;Rashmi S. Chouthe ;Manoj G. Damale ;Devanand B. Shinde 《中国化学快报》2014,25(7):1033-1038
A novel series of 5-((5-substituted-1H-1,2,4-triazol-3-yl)methyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridines 5(a–i) has been synthesized from thienopyridine hydrazide, substituted aromatic nitriles using 4-dimethylaminopyridine(DMAP) as a catalyst under microwave irradiation and evaluated for their in vitro antifungal activity. Compound 5g is found to be more potent against Candida albicans when compared with miconazole. Docking study of the newly synthesized compounds was performed, and results showed good binding mode in the active site of fungal enzyme P450 cytochrome lanosterol 14 ademethylase. ADMET properties of synthesized compounds were also analyzed and showed good drug like properties. The results of in vitro antifungal activity, docking study and ADMET prediction revealed that the synthesized compounds have potential antifungal activity and can be further optimized and developed as a lead compound. 相似文献
4.
Ghouse Khan Swamy Sreenivasa Shivaraja Govindaiah Vivek Chandramohan Raghurama Shetty P 《Journal of heterocyclic chemistry》2020,57(4):2010-2023
A series of novel 1,2,4 triazole derivatives were synthesized by treating 4-bromo-2-(4H-1,2,4-triazole-3-yl)aniline (4) with different substituted benzene sulfonyl chlorides 5(a-f) and benzyl bromides 7(a-e) . IR, 1H-NMR, 13C-NMR, and mass analysis confirmed the structures of the newly synthesized compounds. All derivatives were screened for their in vitro antibacterial activity against two bacterial strains viz Escherichia coli and Staphylococcus aureus, antifungal activity against Aspergillus flavus and Candida albicans, anthelmintic activity against Pheretima posthuma and also cytotoxicity activity against MDA-MB 231 and A375 cancer cell lines. It was found that some of the derivatives showed significant antibacterial, antifungal, anthelmintic, and cytotoxic activities when compared to respective standard drugs. Molecular docking studies have assisted the theoretical binding mode of the target molecules. Compounds were also explored for fingerprint application. 相似文献
5.
Bao Gang Wang Shi Chong Yu Xiao Yun Chai Yong Zheng Yan Hong Gang Hu Qiu Ye Wu 《中国化学快报》2011,22(5):519-522
Based on the active site of lanosterol 14α-demethylase of azole antifungal agents,sixteen 1-(1H-1,2,4-triazole-1-yl)- 2-(2,4- difluorophenyl)-3-(N-n-butyl-N-1-substitutedbenzyl-4-methylene-1H-1,2,3-triazole)-2-propanols have been designed,synthesized and evaluated as antifungal agents.Results of preliminary antifungal tests against eight human pathogenic fungi in vitro showed that some of the compounds exhibited excellent activities with broad spectrum. 相似文献
6.
Nath M Sulaxna Song X Eng G Kumar A 《Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy》2008,70(4):766-774
Some di- and triorganotin(IV) triazolates of general formula, R(4-n)SnLn (where n=2; R=Me, n-Bu and Ph; n=1; R=Me, n-Pr, n-Bu and Ph and HL=4-amino-3-methyl-1,2,4-triazole-5-thiol (HL-1); and 4-amino-3-ethyl-1,2,4-triazole-5-thiol (HL-2)) were synthesized by the reaction of R(4-n)SnCln with sodium salt of HL-1 and HL-2. The bonding and coordination behavior in these derivatives have been discussed on the basis of IR and 119Sn M?ssbauer spectroscopic studies in the solid state. Their coordination behavior in solution is discussed by multinuclear (1H, 13C and 119Sn) NMR spectral studies. The IR and 119Sn M?ssbauer spectroscopic studies indicate that the ligands, HL-1 and HL-2 act as a monoanionic bidentate ligand, coordinating through Sexo- and Nring. The distorted skew trapezoidal-bipyramidal and distorted trigonal bipyramidal geometries have been proposed for R2SnL2 and R3SnL, respectively, in the solid state. In vitro antimicrobial screening of some of the newly synthesized derivatives and of some di- and triorganotin(IV) derivatives of 3-amino-1,2,4-triazole-5-thiol (HL-3) and 5-amino-3H-1,3,4-thiadiazole-2-thiol (HL-4) along with two standard drugs such as fluconazole and ciprofloxacin have been carried out against the bacteria, viz. Staphylococcus aureus and Escherichia coli, and against some fungi, viz. Aspergillus fumigatus, Candida albicans, Candida albicans (ATCC 10231), Candida krusei (GO3) and Candida glabrata (HO5) by the filter paper disc method. The studied organotin(IV) compounds show mild antifungal activity as compared to that of fluconazole, however, they show almost insignificant activity against the studied Gram-positive (Staphylococcus aureas) and Gram-negative (Escherichia coli) bacteria as compared to that of standard drug, ciprofloxacin. 相似文献
7.
《Journal of Saudi Chemical Society》2020,24(12):1051-1059
Four novel heterocyclic1,3,4-oxadiazole, 1,2,4-triazole derivatives, namely: 5-[1-amino-3-(methylsulfanyl)propyl]-1,3,4-oxadiazole-2(3H)-thione (4), 4-amino-5-[1-amino-3-(methylsulfanyl)propyl]-4H-1,2,4-triazole-3-thiol (5), 1-amino-3-[1-amino-3-(methylsulfanyl)propyl]-1H-1,2,4-triazole-5-thiol (7), and 5-[1-amino-3-(methylsulfanyl)propyl]-1H-1,2,4-triazole-3-thiol (9) have been synthesized from l-methionine and characterized by different spectroscopic techniques (FT-IR, UV–Vis, 1H NMR, 13C NMR and MS). Complex formation with Hg++ and Fe+++ ions were formed from the four heterocyclic 4, 5, 7 and 9. The antimicrobial activities for synthetic intermediates and final four products were assisted using paper disk diffusion method against Gram-negative bacteria: Escherichia coli, Pseudomonas aeroginosae and Gram-positive bacteria: Staphylococus aureus 25923, Staphylococus aureus 43300 and showed variant activity against some of the microorganisms tested. 相似文献
8.
《Arabian Journal of Chemistry》2014,7(6):955-963
A series of 3-diphenylmethyl-6-substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives (4a–j and 5a–d) were synthesized by condensation of 4-amino-5-diphenylmethyl-4H-1,2,4-triazole-3-thiol with various substituted aromatic acids and aryl/alkyl-isothiocyanates. The structures of synthesized compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR and mass spectroscopic studies. These compounds were tested in vivo for their anti-inflammatory activity. The compounds which showed activity comparable to the standard drug ibuprofen were screened for their analgesic, ulcerogenic, lipid peroxidation and hepatotoxic effects. Compounds 6-(4-chlorophenyl)-3-diphenylmethyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (4a) and 6-(2,4-dichlorophenyl)-3-diphenylmethyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole(4c) emerged as the most active compounds of the series and were moderately more potent than the standard drug ibuprofen. 相似文献
9.
A series of N-(1,2,4-triazole-4-yl)-N′-(fluorine-containing-phenyl)carbamimidothioates 5a-i were synthesized by reacting 4-amine-1,2,4-trizaole with corresponding aryl isothiocyanates in ethanol at room temperature and, in a subsequent step, with methyl iodide. The antifungal activities of the title compounds against the fungi Rhizoctonia solan and Pyricularia orizae were screened. 相似文献
10.
Mamdouh A. M. Taha 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):2525-2533
4-Amino-4H-3-methylthio{7H-1,2,4-triazolo[1,5-d]tetrazol-6-yl}-1,2,4-triazole-5thi-ol (1) was condensed with various substituted aromatic aldehydes or acid chlorides to yield a series of arylideneamines 2 or aroylamines 3. These were easily cyclized to the corresponding 6-aryl-3-methylthio7H-1,2,4-triazolo[1,5-d]tetrazol-6-yl-1,2,4-triazolo [3,4-b]-1,3,4-thiadiazoles (4) on treatment with palladium-on-charcoal or phosphorus oxychloride. Compounds 4 were also prepared directly via the reaction of 1 with aromatic carboxylic acids in the presence of phosphorus oxychloride. Cyclocondensation of 1 with a variety of two-carbon cyclizing reagents, namely chloroacetone, pyruvic acid, benzoylformic acid, and benzoin led to the formation of 3-methylthio{7H-1,2,4-triazolo[1,5-d]tetrazol-6-yl}-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (5?8). Some of the newly synthesized compounds were tested for their antibacterial and antifungal activity against a variety of microorganisms. 相似文献
11.
Anna Pachuta-Stec Barbara Rajtar Anna Biernasiuk Zbigniew Karczmarzyk Łukasz Świątek Anna Malm Waldemar Wysocki Katarzyna Stepaniuk Małgorzata Polz-Dacewicz Monika Pitucha 《Journal of the Iranian Chemical Society》2018,15(4):839-853
In this study, we described the synthesis of the derivatives of thiosemicarbazide, dicarboximide, 1,2,4-triazole-5-thione and 4-oxo-1,3-thiazolidine. Two different dicarboxylic acid anhydrides reacted with 4-substituted-3-thiosemicarbazide, and derivatives of thiosemicarbazide and dicarboximide were obtained. Next, cyclization reaction of dicarboximide derivatives in alkaline media was used to prepare 1,2,4-triazole-5-thione. The 4-oxo-1,3-thiazolidine was synthesized by the reaction of dicarboximide with ethyl bromoacetate. All obtained derivatives were analysed by 1H and 13C NMR spectra, and for one compound, the X-ray crystallography was done. Antimicrobial, antiviral and in vitro evaluations of cytotoxicity were examined. According to the preliminary antiviral screening, compounds 3 and 4 presented the antiviral activity against HSV-1 and CVB3. Additionally, compound 3 shows selective in vitro toxic effect against human epithelial cells FaDu, without affecting normal animal cell line (Vero). The same derivatives 3 and 4 also displayed a wide spectrum of antimicrobial activity against reference microorganisms and indicated both antibacterial and antifungal potential activities. 相似文献
12.
Qing Jie Zhao Yan Song Hong Gang Hu Shi Chong Yu Qiu Ye Wu School of Pharmary Second Military Medical University Shanghai China 《中国化学快报》2007,18(6):670-672
Twenty-three 1 -(1H-1,2,4-triazole-1 -y1)-2-(2,4-difluorophenyl)-3-(iV-cycloproyl-N-substituted-amino)-2-propanols were designed and synthesized on the basis of the active site of lanosterol 14α-demethylase. In vitro antifungal activities showed that some of the title compounds had higher antifungal activity and broader antifungal spectrum than fluconazole. 相似文献
13.
Moustafa T. Gabr Nadia S. El-Gohary Eman R. El-Bendary Mohamed M. El-Kerdawy Nanting Ni Mona I. Shaaban 《中国化学快报》2015,26(12):1522-1528
New series of benzothiazole derivatives were designed and synthesized. The newly synthesized compounds were screened for their antibacterial activity against Escherichia coli, Staphylococcus aureus and Bacillus cereus. Compounds 6j and 6o showed the highest activity against E. coli and S. aureus. The antifungal activity of these compounds was also tested against Candida albicans and Aspergillus fumigatus293. Compounds 4c, 4g and 6j exhibited the highest activity against C. albicans. In addition, compounds4 a and 6j displayed promising activity against A. fumigatus 293. The same compounds were examined for their antiquorum-sensing activity against Chromobacterium violaceum ATCC 12472, whereas compounds4 a, 6j and 6p showed moderate activity. The in vitro cytotoxicity testing of the synthesized compounds was performed against cervical cancer(Hela) and kidney fibroblast cancer(COS-7) cell lines. Results indicated that all tested compounds have IC50 values 50 mmol/L against both cell lines. Molecular properties, toxicities, drug-likeness, and drug score profiles of compounds 4a–c, 5a, 6g,h, 6j, 6l, 6o and7 c,d were also assessed. 相似文献
14.
《中国化学会会志》2017,64(1):36-42
Substituted‐1,2,4‐triazines were conveniently synthesized in one pot by the cyclization of arylnitroformaldehyde hydrazone derivatives 1 and 5 with different primary amines in ~37% formaldehyde solution. The synthesized compounds were arranged into novel mono‐, bis‐, and tris‐nitro‐1,2,4‐triazine derivatives 2 , 3 , 4 , 6 , and 7 . The antibacterial and antifungal activity of the synthesized compounds were screened against bacterial strains Escherichia coli (as Gram − ve) and Staphylococcus aureus (as Gram + ve), and fungal strains Aspergillus flavus and Candida albicans . All the synthesized compounds exhibit various patterns of inhibitory activity on the two pathogenic bacterial strains. However, the same compounds showed no activity against the tested fungal strains. 相似文献
15.
The synthesis and antimicrobial activity of 2,4-thiazolidinedione derivatives 5a–g and 6a–g are described. The structures of the newly synthesized compounds were confirmed by IR, NMR, mass and elemental analyses. All compounds were evaluated for their preliminary in vitro antibacterial and antifungal activity. The results revealed that most of the compounds showed high or moderate biological activity against tested microorganisms. 相似文献
16.
A series of 5-substituted-4-amino-1,2,4-triazole-3-thioesters was synthesized by converting variously substituted organic acids successively into the corresponding esters, hydrazides, 5-substituted-1,3,4-oxadiazole-2-thiols, 5-substituted-1,2,4-triazole-2-thiols and 5-substituted-1,3,4-oxadiazole-2-thioesters. Finally the target compounds were obtained by refluxing 5-substituted-1,3,4-oxadiazole-2-thioesters in the presence of hydrazine hydrate and absolute alcohol. The structures of the synthesized compounds were established by physicochemical and spectroscopic methods. The synthesized compounds were evaluated for their in vitro antifungal activity. Some of the evaluated compounds possessed significant antifungal activity as compared to a terbinafine standard. 相似文献
17.
A series of 2,4-dichloro-5-fluorophenyl substituted arylidenetriazolothiazolidinones were obtained by one-pot reaction of
3-(2,4-dichloro-5-fluorophenyl)-4H-1,2,4-triazole-5-thiol with substituted benzaldehydes and monochloroacetic acid in the presence of acetic anhydride, acetic
acid, and sodium acetate. The structures of the newly synthesized compounds were characterized and confirmed by IR, 1H NMR, mass spectra, and elemental analysis. Compounds bearing the 4-methylthiophenyl, 3,4-methylenedioxyphenyl, and 2,3,5-trichlorophenyl
moiety showed excellent antiinflammatory activity. The antimicrobial screening studies revealed that compounds with 4-anisyl,
4-methylthiophenyl, 3,4-methylenedioxyphenyl, and 2,3,5-trichlorophenyl at position 5 of the arylidenetriazolothiazolidinone
moiety showed excellent activity against all tested strains at 6.25 μg cm−3 concentrations.
Correspondence: Mari Sithambaram Karthikeyan, Department of Chemistry, Mangalore University, Mangalagangothri 574199, Karnataka,
India. 相似文献
18.
19.
Yusuf Ozdemir Olcay Bekircan Nimet Baltaş Emre Menteşe 《Journal of heterocyclic chemistry》2020,57(12):4239-4253
In this study, starting from 4-amino-5-(4-chlorobenzyl)-2,4-dihydro-3H-1,2,4-triazole-3-one ( 1 ), the 4-Amino-5-(4-chlorobenzyl)-2-undecyl-2,4-dihydro-3H-1,2,4-triazol-3-one ( 2 ) was first synthesized and this compound was converted to Schiff base derivatives ( 3a-e ). In the second step of the study, the 2-[3-(4-chlorobenzyl)-5-oxo-1-undecyl-1,5-dihydro-4H-1,2,4-triazole-4-yl]-acetohydrazide ( 6 ), which was used as a key product in the synthesis of many heterocyclic compounds was synthesized in four steps, and then this compound was converted into methylidene acetohydrazide ( 7a-e ), thiosemicarbazide ( 8a-e ), and 1,2,4-triazole-5-thione ( 9a-e ) derivatives. Also, in the last part of the study, 1,2,4-triazole-5-thione derivatives were changed into Mannich bases ( 10a-b ) bearing a 4-phenylpiperazine ring. These new compounds were tested with regard to pancreatic lipase (PL) inhibition activity, and compound 3b , 3d , 7d , 8d , and 9d showed a considerable anti-lipase activity at various concentrations. The activity of compounds 7b (IC50 = 1.45 ± 0.12 μM) was the highest in terms of IC50, comparable to that of orlistat, a well-known PL inhibitor used as an antiobesity drug. 相似文献
20.
Eto H Kaneko Y Takeda S Tokizawa M Sato S Yoshida K Namiki S Ogawa M Maebashi K Ishida K Matsumoto M Asaoka T 《Chemical & pharmaceutical bulletin》2001,49(2):173-182
New 1,2,4-triazoles (2) having a difluoro(substituted sulfonyl)methyl moiety were designed and synthesized via alpha,alpha-difluoro-alpha-(substituted thio)acetophenones (3). Compounds (2) showed potent antifungal activities against C. albicans, C. krusei, A. flavus and A. fumigatus in vitro and against C. albicans in vivo for oral and i.v. administrations. Especially, (-)-2a, (-)-2b and (-)-2d showed potent antifungal activities. 相似文献