Imidazole derivatives as possible microbicides with dual protection

Kumar, Lalit; Sarswat, Amit; Lal, Nand; Sharma, Vishnu L.; Jain, Ashish; Kumar, Rajeev; Verma, Vikas; Maikhuri, Jagdamba P.; Kumar, Ashish; Shukla, Praveen Kumar; Gupta, Gopal

doi:10.1016/j.ejmech.2009.10.021

Cited by 38 publications

(17 citation statements)

References 23 publications

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“…Many fungicides that target different pathogens and diseases have been reported2345, but because of problems relating to toxic residues, disease resurgence and pathogen resistance678910, the use of many fungicides is restricted. Therefore, researchers have been searching for fungicides with low toxicity, high selectivity, and high activity against fungal strains that are resistant to other fungicides.…”

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Activity of the novel fungicide SYP-Z048 against plant pathogens

Chen

Han

Liu

et al. 2014

Sci Rep

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In in vitro tests with 18 plant pathogens, the fungicide 3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl] pyridine (SYP-Z048) was highly effective on inhibiting mycelial growth of various ascomycota and basidiomycota, with EC50 values ranging from 0.008 to 1.140 μg/ml. SYP-Z048 had much weaker activity against growth of oomycota with EC50 values > 100 μg/ml. In a second in vitro test with Monilinia fructicola isolates, SYP-Z048 inhibited mycelial growth (EC50 = 0.013 μg/ml), germ tube elongation (EC50 = 0.007 μg/ml), and sporulation but did not affect spore germination. In a detached pear fruit assay inoculated with M. fructicola isolates, SYP-Z048 showed protective and curative activity. Field tests indicated that SYP-Z048 was an efficacious fungicide for control of brown rot disease in two peach orchards. When applied to a single spot on a tomato leaflet in a compound leaf, SYP-Z048 suppressed the growth of Botrytis cinerea isolates on the rest 4 leaflets, indicating that the fungicide has systemic movement in plant tissues. These results indicate that SYP-Z048 has potential for management of brown rot causing by M. fructicola and other diseases caused by ascomycota and basidiomycota.

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confidence: 99%

Activity of the novel fungicide SYP-Z048 against plant pathogens

Chen

Han

Liu

et al. 2014

Sci Rep

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“…Our synthesis work began from metronidazole® 1 , whose primary alcohol was substituted by either a chlorine atom or a mesyl group. Following known procedures, [ 27,28 ] upon reaction with thionyl chloride, 1 was converted into the corresponding hydrochloride salt, which was then treated with water and Et 3 N until pH 11, to obtain 1‐(2‐chloroethyl)‐2‐methyl‐5‐nitroimidazole ( 2 ) with a yield of 96% (Scheme 1). Alternatively, treatment of 1 with mesyl chloride and Et 3 N in dichloromethane (CH 2 Cl 2 ), at room temperature, afforded O ‐mesylated metronidazole ( 3 ) in a very good yield of 96%.…”

Section: Resultsmentioning

confidence: 99%

“…Subsequent nucleophilic substitution of 3 , using sodium iodide in refluxing acetone, gave the iodinated compound 4 in 96% yield. [ 27,28 ] The nucleophilic substitution of 2 and 4 with 2‐mercaptoethanol furnished the thioether‐linked metronidazole analog 5 . This compound was obtained in a good yield (61%) when the reaction was carried out with 2 as the starting material, but the modified experimental protocol using 4 turned out to be more efficient and allowed us to prepare 5 in an even better yield (77%).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and leishmanicidal evaluation of sulfanyl‐ and sulfonyl‐tethered functionalized benzoate derivatives featuring a nitroimidazole moiety

Rodríguez

Gutiérrez

Domínguez

et al. 2020

Archiv der Pharmazie

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A series of new nitroimidazole-containing derivatives was synthesized by coupling of 2-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylthio]ethanol with diversely substituted benzoic acids. Upon treatment with m-CPBA, 12 of these sulfanyl compounds were further oxidized to their sulfonyl analogs. All the 26 synthetic compounds were examined for in vitro activity against Leishmania (V.) braziliensis and Leishmania (L.) mexicana, and some of them displayed an efficient antileishmanial activity. Among the compounds tested, the catecholic derivative 2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]sulfanyl}ethyl 3,4-dihydroxybenzoate (9a, LC 50 = 13 and 11 µM) and the pyrogallolic derivative 2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]sulfanyl}ethyl 3,4,5-trihydroxybenzoate (9b, LC 50 = 4 and 1 µM) were the most active ones against the two Leishmania strains. K E Y W O R D S antiproliferative agents, nitroimidazole, synthesis 1 | INTRODUCTION Leishmaniasis is an infectious disease caused by protozoa of the genus Leishmania. A recent review has shown that over 98 countries and territories are endemic for leishmaniasis transmission, with an overall prevalence of 12 million cases. Over 20 Leishmania species known to be infective to humans are transmitted by the bite of infected female phlebotomine sandflies, thus causing three main types of leishmaniasis: visceral (VL), cutaneous (CL), and mucocutaneous (MCL). It is estimated that approximately 0.2-0.4 million of new VL cases and 0.7-1.2 million of new CL cases occur each year. These diseases are responsible annually for approximately S C H E M E 1 Synthesis of the 2-{[2-(1H-imidazol-1-yl)ethyl]sulfanyl}ethyl benzoate derivatives 7a-l and 9a,b 2 of 10 | RODRÍGUEZ ET AL.

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“…[ 1 ] Alongside dithiocarbamate nucleus is a well established pharmacophore possessing anti- Trichomonas activity. [ 2 ] In our ongoing efforts a series of benzenepropanamine-dithiocarbamate hybrids ( 14-28 ) as N-alkyl/aralkyl-4-(3-substituted-3-phenylpropyl)piperazine-1-carbodithioates have been designed, synthesized and evaluated for their anti- Trichomonas activity profile to be useful as vaginal microbicide. All compounds were tested for safety through cytotoxic assay against human cervical cell line ( Hela ) and compatibility with vaginal flora, Lactobacillus .…”

Section: Methodsmentioning

confidence: 99%