Synthesis,Characterization, Antibacterial,and Antifungal Activity of Novel 2‐(2‐hydroxy‐5‐((aryl)‐diazenyl)phenyl)‐3‐(4‐hydroxyphenyl)‐thiazolidin‐4‐one

A series of novel thiazolidinones, that is, 2‐(2‐hydroxy‐5‐((aryl)‐diazenyl)phenyl)‐3‐(4‐hydroxyphenyl)‐thiazolidin‐4‐one, have been synthesized by reaction of various Schiff bases 2‐(4‐hydroxyphenylimino)methyl)‐4‐(aryl)diazenyl)phenol with ethanolic thioglycolic acid. Schiff bases were obtained by the reactions of 4‐amino phenol with 2‐hydroxy‐5‐((aryl)diazenyl)benzaldehyde. The structures of the newly synthesized compounds were confirmed by IR, ¹H NMR, mass spectra, and C, H, N elemental analysis. The thiazolidinone derivatives were evaluated for their antibacterial and antifungal activity.     

New synthesized ligands for detection of heavy metal ions

Some new chemo-sensors (4,4'-((1E,1′E)-(2,2′-dichloro-[1,1′-biphenyl]-4,4′-diyl)bis(diazene-2,1-diyl))bis(3,5-dihydroxybenzoic acid), 4-((E)-(4-(N-(4-((E)-(4-carboxy-2,6-dihydroxyphenyl)diazenyl)phenyl)sulfamoyl)phenyl)diazenyl)-3,5-dihydroxybenzoic acid, 4-((E)-(4-((4-((E)-(4-carboxy-2,6-dihydroxyphenyl)diazenyl)-2-sulfophenyl)amino)phenyl)diazenyl)-3,5-dihydroxybenzoic acid) were synthesized. These synthesized sensors were then characterized by FTIR, TLC, UV–Visible spectrophotometry, and NMR techniques. The sensors showed the best results for detection of all type of heavy metal ions simply by changing the colour of metal ion solution and by shifting in the λ_max values of sensors due to interactions.     

New benzimidazole derivatives: Design,synthesis, docking,and biological evaluation

The aim of this study was to synthesize novel enaminonitrile derivatives starting from 2-aminobenzimidazole and utilize this derivative for the preparation of novel heterocyclic compounds and assess their function for biological activity screening. The key precursor N-(1H-benzo[d]imidazol-2-yl)carbonohydrazonoyl dicyanide (2) was prepared in pyridine by coupling of diazotized 2-aminobenzimidazole (1) with malononitrile. Compound 2 was subjected to react with various secondary amines such as piperidine, morpholine, piperazine, diphenylamine, N-methylglucamine, and diethanolamine in boiling ethanol to give the acrylonitriles (2Z)-2-((1H-benzo[d]imidazol-2-yl)diazenyl)-3-amino-3-(piperidin-1-yl)acrylonitrile (3), (2Z)-2-((1H-benzo[d]imidazol-2-yl)diazenyl)-3-amino-3-morpholinoacrylonitrile (4), (2Z)-2-((1H-benzo[d]imidazol-2-yl)diazenyl)-3-amino-3-(piperazin-1-yl)acrylonitrile (5), (2Z)-2-((1H-benzo[d]imidazol-2-yl)diazenyl)-3-amino-3-(diphenylamino)acrylonitrile (6), (2Z)-2-((1H-benzo[d]imidazol-2-yl)diazenyl)-3-amino-3-(methyl((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)amino)acrylonitrile (7), and (2Z)-2-((1H-benzo[d]imidazol-2-yl)diazenyl)-3-amino-3-(bis(2-hydroxyethyl)amino)acrylonitrile (8), respectively. It has been found that the behaviour of nitrile derivative 2 towards hydrazine hydrate to the creation of 4-((1H-benzo[d]imidazol-2-yl)diazenyl)-1H-pyrazole-3,5-diamine (9). The reaction of malononitrile with compound 2 in an ethanolic solution catalyzed with sodium ethoxide afforded 4-amino-1-(1H-benzo[d]imidazol-2-yl)-6-imino-1,6-dihydropyridazine-3,5-dicarbonitrile (11). Moreover, malononitrile reacted with 7 in a boiling ethanolic sodium ethoxide solution to give 2-(5-((1H-benzo[d]imidazol-2-yl)diazenyl)-4-amino-6-(methyl((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)amino)pyrimidin-2-yl)acetonitrile (14). Heating 7 in boiling acetic anhydride and pyridine afforded (2R,3R,4R,5S)-6-(((1E)-2-((1-acetyl-1H-benzo[d]imidazol-2-yl)diazenyl)-1-(N-acetylacetamido)-2-cyanovinyl)(methyl)amino)hexane-1,2,3,4,5-pentayl pentaacetate (15). When compound 15 is heated for a long time in refluxing DMF including a catalytic of TEA, cyclization occurs to give the corresponding (2R,3R,4R,5S)-6-((1-acetyl-3-((1-acetyl-1H-benzo[d]imidazol-2-yl)diazenyl)-4-amino-6-oxo-1,6-dihydropyridin-2-yl)(methyl)amino)hexane-1,2,3,4,5-pentayl pentaacetate (16). In addition, triethyl orthoformate was reacted with compound 7 in the presence of acetic anhydride to afford the corresponding ethoxymethyleneamino derivative (2R,3R,4R,5S)-6-(((1E)-2-((1-acetyl-1H-benzo[d]imidazol-2-yl)diazenyl)-2-cyano-1-(((E) ethoxymethylene)amino)vinyl)(methyl)amino)hexane-1,2,3,4,5-pentayl pentaacetate (17). Also, it has been found that heating a mixture of 7 with DMF/DMA in anhydrous xylene yielded compound (1E)-N'-((1E)-2-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-cyano-1-(methyl((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)amino)vinyl)-N,N-dimethylformimidamide (18). In addition, compound 7, when reacted with several acid anhydrides, allowed the matching phthalimide derivatives 19–26. The results showed that compound 14 has significantly higher ABTS and antitumor activities than the other compounds. Molecular modelling was also studied for compounds 22 and 24. The viability of four many cell lines—the African green monkey kidney epithelial cells (VERO), human breast adenocarcinoma cell line (MCF-7), human lung fibroblast cell line (WI-38), and human hepatocellular liver carcinoma cell line (HepG2) was examined to determine the antitumor activities of the newly synthesized compounds. Also, it was found that compounds 9, 11, 15, 16, 22, 23, 24 and 25 are strong against HepG2 cell lines, while 16, 22, and 25 are strong against WI-38 cell lines. Moreover, it was also found that compounds 16 and 22 are strong against VERO cell lines. On the other hand, compounds 7, 14, 15, 16, and 22 are strong while the rest of the other compounds are moderate against the MCF-7 cell line. The result of docking showed that compound 24 got stabilized inside the pocket with a very promising binding score of ? 8.12 through hydrogen bonds with Arg184 and Lys179, respectively.     

Utilization of DmbNHNH2 in the synthesis of amino-substituted 4-((3,5-diamino-1H-pyrazol-4-yl)diazenyl)phenols

(2,4-Dimethoxybenzyl)hydrazine (DmbNHNH₂) was utilized in the synthesis of Dmb-protected 4-((3,5-diamino-1H-pyrazol-4-yl)diazenyl)phenols. This unambiguous protection of the pyrazole endocyclic nitrogen atom enabled the preparation of amino-substituted 4-((3,5-diamino-1H-pyrazol-4yl)diazenyl)phenols that were inaccessible through direct substitution. The Boc group could be selectively cleaved in the presence of the Dmb group.     

Synthesis of some novel 3,4,5-trisubstituted triazole derivatives bearing quinoline ring and evaluation of their antimicrobial activity

Abstract

Some 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.     

One-pot multi-component synthesis of novel ethyl-2-(3-((2-(4-(4-aryl)thiazol-2-yl)hydrazono)methyl)-4-hydroxy/isobutoxyphenyl)-4-methylthiazole-5-carboxylate derivatives and evaluation of their in vitro antimicrobial activity

A novel series of ethyl-2-(3-((2-(4-(4-aryl)thiazol-2-yl)hydrazono)methyl)-4-hydroxy/isobutoxyphenyl)-4-methylthiazole-5-carboxylate derivatives ( 4a-f and 5a-f ) were synthesized by employing one-pot multi-component approach involving ethyl 2-(3-formyl-4-oxy/isobutoxyphenyl)-4-methylthiazole-5-carboxylate, thiosemicarbazide and various phenacyl bromides/3-(2-bromoacetyl)-2H-chromen-2-one/2-(2-bromoacetyl)-3H-benzo[f]chromen-3-onein ethanol in the presence of catalytic amount of acetic acid. The structures of all the synthesized compounds were confirmed with spectral analysis, ie, IR, 1H NMR, 13C NMR and mass spectrometry, and all the compounds were screened for their in vitro antimicrobial activity.     

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita

Abstract

A 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.     

A new fluorescent-colorimetric chemosensor for fluoride anion based on benzimidazolium salt

Two new benzimidazolium salts with the same cationic moiety and different anions 3-(2′-((8″-hydroxy-9″,10″-dioxo-9″,10″-dihydroanthracen-1″-yl)oxy)ethyl)-1-(pyridin-2?-ylmethyl)-1H-benzo[d]imidazol-3-ium bromide and 3-(2′-((8″-hydroxy-9″,10″-dioxo-9″,10″-dihydroanthracen-1″-yl)oxy)ethyl)-1-(pyridin-2?-ylmethyl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate were prepared and characterized. The single crystal structure of 3-(2′-((8″-hydroxy-9″,10″-dioxo-9″,10″-dihydroanthracen-1″-yl)oxy)ethyl)-1-(pyridin-2?-ylmethyl)-1H-benzo[d]imidazol-3-ium bromide was determined by X-ray single crystal diffraction. Particularly, anion recognition using 3-(2′-((8″-hydroxy-9″,10″-dioxo-9″,10″-dihydroanthracen-1″-yl)oxy)ethyl)-1-(pyridin-2?-ylmethyl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate as a chemosensor was carried out via fluorescence and ultraviolet spectroscopy, ¹H NMR titrations, HRMS and IR spectra. The response of this chemosensor to fluoride anion can be observed through both remarkable fluorescence quenching and color change under visible light (from orange to purple). The results indicated that this chemosensor can distinguish fluoride anion from other anions via the instrument and naked eyes, and this is greatly convenient in practical operation.     

Synthesis and characterization of novel triazenes from the reaction of the cyclic aminal 1,3,6,8-tetraazatricyclo[4.3.1.1]undecane (TATU) with diazonium ions

The reaction of the cyclic aminal 1,3,6,8-tetraazatricyclo[4.3.1.1^3,8]undecane (TATU, 4) with diazonium salts resulted in the formation of a new series of bis-triazenes, namely 3,8-bis[(4-methoxyphenyl)diazenyl]-1,3,6,8-tetraazabicyclo[4.3.1]decane 6a, 3,8-bis[(2-methoxyphenyl)diazenyl]-1,3,6,8-tetraazabicyclo[4.3.1]decane 6b, 3,8-bis(p-tolyldiazenyl)-1,3,6,8-tetraazabicyclo[4.3.1]decane 6c. When aniline derived diazonium salt 5d was coupled with TATU, 3,8-bis(phenyldiazenyl)-1,3,6,8-tetraazabicyclo[4.3.1]decane 6d and bis[1,5-bis-((E)-phenyldiazenyl)-1,3,5-triazepan-3-yl]methane 7 were obtained. These compounds were characterized by HR-MS, ¹H and ¹³C NMR and 2D-NMR. Additionally, the structure of compound 7 was confirmed by X-ray crystallography.     

Substituted 1-(isoxazol-3-yl)methyl-1H-1,2,3-triazoles: Synthesis,palladium(II) complexes,and high-turnover catalysis in aqueous media

New substituted 3-((1H-1,2,3-triazol-1-yl)methyl)-5-arylisoxazoles (aryl?=?Ph, p-Tol) and 2-(5-phenylisoxazol-3-yl)-5-(2-(1-((5-(p-tolyl)isoxazol-3-yl)methyl)-1H-1,2,3-triazol-4-yl)ethyl)-1,3,4-oxadiazole were synthesized by means of click-chemistry procedures. The obtained compounds were used as ligands in preparation of palladium(II) complexes, and the latter proved to be high-turnover-number catalysts for CC cross-coupling reactions under Green Chemistry conditions. One of the ligands was structurally characterized by single crystal X-ray diffraction, and the structure of complexes was determined by ¹H, ¹³C, ¹⁵N NMR spectroscopy and quantum-chemical modeling.     

Biological evaluation of copper(II) complexes on N(4)−substituted thiosemicarbazide derivatives and diimine co-ligands using DNA interaction,antibacterial and in vitro cytotoxicity

Abstract

A number of alternatives were made to overcome numerous life-threatening infectious diseases by metal-based anticancer compounds. At present, thiosemicarbazones and their metal complexes have received significant consideration as a result of their metal DNA-interaction, structural diversity and availability of bonding modes. In this study, the coordination characteristics of nine diimine copper(II) complexes with sulfur containing ligands, [Cu(L)₂] (1–3), [Cu(L)(bpy)]Cl (4–6) and [Cu(L)(phen)]Cl (7–9) (L?=?H(L1)–H(L3), phen = 1,10-phenanthroline, bpy = 2,2′-bipyridyl, H(L1) = (Z)-2-((4-methoxynaphthalen-1-yl)methylene)-N-methylhydrazinecarbothioamide, H(L2) = (Z)-N-ethyl-2-((4-methoxynaphthalen-1-yl)methylene)hydrazinecarbothioamide and H(L3) = (Z)-2-((4-methoxynaphthalen-1-yl)methylene)-N-phenylhydrazinecarbothioamide] have been synthesized from 4-methoxy-1-naphthaldehyde along with N(4)-substituted thiosemicarbazide derivatives. The synthesized ligands and their Cu(II) complexes were characterized through different spectroscopic techniques and square-planar coordination was proposed. Biological evaluation such as DNA-cleavage, antibacterial and in vitro cytotoxicity of thiosemicarbazone ligands and their resultant Cu(II) complexes were analyzed. Interestingly, Cu(II) complex containing heteroaromatic moiety 9 had potential cytotoxic activity with strong DNA-interaction. In the future, these may be helpful to design more effective novel chemotherapeutic drugs.     

Diazenyl schiff bases: Synthesis,spectral analysis,antimicrobial studies and cytotoxic activity on human colorectal carcinoma cell line (HCT-116)

A series of diazenyl schiff bases have been synthesized by reaction of salicylaldehyde containing azo dyes with various substituted aniline derivatives in the presence of acetic acid as catalyst. The structures of diazenyl derivatives were determined by FTIR, UV–vis, ¹H NMR, ¹³C NMR, CHN analysis, fluorimetric and mass spectroscopic studies. The synthesized derivatives were screened for their in vitro antimicrobial activity against various Gram-positive (S. aureus, B. subtilis, B. cereus), Gram-negative (S. typhi, S. enterica, E. coli, P. aeruginosa) bacterial and fungal (C. albicans, A. niger and A. fumigatus) strains, using cefadroxil (antibacterial) and fluconazole (antifungal) as standard drugs. The diazenyl schiff bases were also screened for their cytotoxicity against human colorectal carcinoma cell line (HCT-116) using 5-fluorouracil as standard drug by Sulforhodamine-B Stain (SRB) assay. The schiff bases exhibited significant activity toward both Gram-positive, Gram-negative bacterial and fungal strains. Most of the synthesized derivatives showed high activity against S. enterica. 4-((2,5-Dichlorophenyl)diazenyl)-2-((3-bromophenylimino)methyl)phenol (SBN-40) was found to be very active against S. aureus, B. cereus and E. coli, with MIC = 0.69 (µM/ml × 10²). The compound 4-((2-bromophenyl)diazenyl)-2-((4-nitrophenylimino)methyl)phenol (SBN-13) possessed comparable activity (IC₅₀ = 7.5 µg/ml) to the standard drug 5-fluorouracil (IC₅₀ = 3.0 µg/ml) against human colorectal carcinoma cell line (HCT-116).     

Synthesis,characterization, and antimicrobial and catalytic activity of a new Schiff base and its metal(II) complexes

We presented the synthesis of a new Schiff base and its complexes properties with some transition metal ions in this study. (1-amino-2-thioxo-4-p-tolyl-1,2-dihydropyrimidin-5-yl)(p-tolyl)methanone was synthesized as the starting material, and (1-((2-hydroxynaphthalen-1-yl)methyleneamino)-2-thioxo-4-p-tolyl-1,2-dihydropyrimidin-5-yl)(p-tolyl)methanone (Hnafmmp) (1) and its Ni(II) (2), Pd(II) (3), Pt(II) (4), Cu(II) (5), Co(II) (6) complexes were prepared using above-mentioned starting material. The structures of these new compounds (ligand and its complexes) were characterized with UV–Vis, FTIR, LC–MS, ¹H NMR, ¹³C NMR, magnetic susceptibility, conductivity measurement, X-ray powder diffraction method, and thermal analyses techniques. The ¹H NMR chemical shifts of all complexes were calculated by using the gauge-invariant atomic orbital HF (3.21G) method in DMSO phases. All measured results were compared with the experimental data. The ligand and its complexes were also evaluated as antimicrobial agents against representative strains bacteria. Furthermore, we studied the catalytic activity of these compounds in Suzuki–Miyaura cross-coupling reaction in aqueous media.     

Novel synthesis of isoxazoline indolizine amides for potential application to tropical diseases

Synthetically challenging isoxazoline indolizine amide compounds were designed and prepared for potential application to tropical diseases. Indolizine core structures were synthesized strategically as common intermediates for efficient derivatization. The chemistry for the syntheses of 8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)indolizine-5-carboxamide (3) and 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)-indolizine-8-carboxamide (4) is described in this Letter.     

Synthesis and Antimicrobial Activity 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

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.]     

Synthesis and thermal behavior of Janus dendrimers,part 1

Eight Janus-type dendrimers up to the second generation were synthesized, and their thermal properties were evaluated. Compounds consist of the dendritic bisMPA based polyester moieties, and either 3,4-dihexyloxybenzoic acid or 3,4-dihexadecyloxybenzoic acid moieties, attached to opposite sides of the pentaerythritol core. The structures of the molecules were verified with ¹H NMR, ¹³C NMR, ESI TOF mass spectrometry and elemental analysis. The thermal stability was evaluated by thermogravimetric analysis, displaying onset decomposition temperatures (T_d) ranging from 241 to 308 °C. Phase transitions were studied by differential scanning calorimetry. Based on the performed studies it was confirmed that OH terminated dendrimers 2, 4, 6 and 8 exhibited liquid crystalline phases. Also, the X-ray powder diffraction measurements were accomplished for the dendrimers having terminal hydroxyl groups.     

Synthesis,antioxidant activity,and α-glucosidase enzyme inhibition of α-aminophosphonate derivatives bearing piperazine-1,2,3-triazole moiety

A novel series of piperazine-1,2,3-triazole bearing dimethyl(((2-(4-((1H-1,2,3-triazole-4-yl)methyl)piperazin-1-yl)ethylamino)(2-hydroxyaryl)methyl)phosphonate derivatives have been prepared via copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) (Click Reaction) and Schiff base reactions. The synthesized compounds were confirmed by spectral characterization (¹H, ¹³C and ³¹P NMR, and mass). The title compounds were evaluated for in vitro alpha glucosidase enzyme inhibition and in vitro antioxidant activity using DPPH and H₂O₂ methods.     

Novel Synthesis of Isoquinoline Derivatives Derived from (Z)-4-(1,3-Diphenylpyrazol-4-yl)isochromene-1,3-dione

A series of isoquinoline derivatives were synthesized via the reaction of the (Z)-4-(1,3-diphenylpyrazol-4-yl)isochromene-1,3-dione with different hydrazides, primary amines, diamines, 2-aminothiophenol, 2-aminobenzoic acid, p-aminoacetophenone, and ethyl 2-amino-4,5,6,7-tetrahydrobenzo-[b]thiophene-3-carboxylate. All the synthesized compounds were characterized by infrared, ¹H NMR, and mass spectra besides the analytical data.     

Synthesis of novel pyrimidine derivatives with (pyridin-3-ylmethyl)thio and phenylamino moieties and evaluation of their antifungal activity

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.