- 5-Nitroimidazole derivatives as possible antibacterial and antifungal agents
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Some novel 1-[2-[[5-(2-furanyl)-4-substituted 4H-1,2,4-triazol-3- yl]thio]ethyl]-2-methyl-5-nitro-1H-imidazoles (3), 1-[3-[[5-(2-furanyl/2- thienyl)-4-substituted 4H-1,2,4-triazol-3-yl]-thio]-2-hydroxypropyl]-2- methyl-5-nitro-1H-imidazoles (5) and 1-[3-[(N,N-disubstituted thiocarbamoyl)- thio]-2-hydroxypropyl]-2-methyl-5-nitro-1H-imidazoles (7) were synthesized and evaluated for in vitro antibacterial and antifungal activity. Some of 5 were found to be effective against bacteria and fungi (minimum inhibitory concentration (MIC) 7.3-125 μg/ml), whereas 7 were found to be effective against fungi (MIC 3-25 μg/ml).
- Guenay, Nur Sibel,Capan, Gueltaze,Ulusoy, Nuray,Ergenc, Nedime,Oetuek, Guelten,Kaya, Dilek
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- The syntheses and crystal structures of metronidazole-derived compounds
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Metronidazole (MET-OH), widely used as an antibacterial agent, is found to have some side effects on human bodies. Due to these disadvantages, people have been looking for its modification compounds for substituents. In this article, four MET-OH derivatives were designed, prepared, and structurally characterized by single crystal X-ray diffraction. These compounds are MET-OTs (1), MET-Br (2), MET-Cl (3), and MET-I (4). X-ray structure analyses revealed that, 1 crystallized in the monoclinic system with space group P2 1 /c, with a = 16.1178, b = 7.5473, c = 13.4161 A, V = 1520.3 A3, β = 111.3210o and Z = 4. 2 crystallized in the monoclinic system with space group P2 1 /c, with a = 12.079, b = 11.089, c = 6.380 A, V = 847.1 A3, β = 97.57o and Z = 4. 3 crystallized in the monoclinic system with space group P2 1 /c, with a = 12.098, b = 11.007, c = 6.295 A, V = 830.3 A3, β = 97.886o and Z = 4. 4 crystallized in the triclinic system with space group P1, with a = 6.192, b = 7.740, c = 10.001 A, V = 457.9 A3, α = 89.073, β = 86.903, γ = 73.097 o and Z = 2. In this article, metronidazole-derived compounds were prepared and structurally characterized by single crystal X-ray diffraction [Figure not available: see fulltext.]
- Li, Huan-Qiu,Xiao, Zhu-Ping,Fang, Rui-Qin,Zhu, Hai-Liang
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- Synthesis and leishmanicidal evaluation of sulfanyl- and sulfonyl-tethered functionalized benzoate derivatives featuring a nitroimidazole moiety
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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, LC50 = 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, LC50 = 4 and 1 μM) were the most active ones against the two Leishmania strains.
- Charris, Jaime,Deffieux, Denis,Domínguez, José,Fernández, Alexis,Gutiérrez, Joyce,Peixoto, Philippe A.,Pouységu, Laurent,Quideau, Stéphane,Rodríguez, Miguel,Rodríguez, Noris,Rojas, Luis
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- In vitro evaluation and in vivo efficacy of nitroimidazole-sulfanyl ethyl derivatives against Leishmania (V.) braziliensis and Leishmania (L.) mexicana
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The aim of this study was to synthesize several small molecules of the type 5-nitroimidazole-sulfanyl and evaluate biological properties against the main Leishmania species that cause cutaneous leishmaniasis in Venezuela. Final compounds 4–7 were generated through simple nucleophilic substitution of 1-(2-chloroethyl)-2-methyl-5-nitroimidazole 3 with 2-mercaptoethanol, 1-methyl-2-mercaptoethanol, and 2-thyolacetic acid derivative. Compound 8 was synthesized via a coupling reaction between 7 and (S)-Methyl 2-amino-4-methylpentanoate hydrochloride. The inhibitory concentrations of (3, 4, 7, 8) against Leishmania (L.) mexicana and (V.) braziliensis in promastigotes and experimentally infected macrophages were determined by in vitro activity assays. Compounds 7 and 8 shown high activity against both species of Leishmania and were selected for the in vivo evaluation. Animals were infected with promastigotes of the two species and divided into four groups of ten (10) animals and a control group. Intralesional injection way was used for the treatment. The parasitological diagnostic after treatment was obtained by PCR using species specific oligonucleotides. The two Leishmania species were susceptible to compounds 7 and 8 in vivo assays. The results indicated that both compounds reduce significantly (96%) the size of the lesion and cure 63% of the mice infected with L (L) mexicana or L (V) braziliensis as was determined by PCR. The results are indicating that both compounds may represent an alternative treatment for these two Leishmania species.
- Blanco, Zuleima,Mijares, Michael R.,Ramírez, Hegira,Fernandez-Moreira, Esteban,Oviedo, Henry J.,Rodríguez, Noris M.,Charris, Jaime E.
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p. 3307 - 3317
(2021/08/13)
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- A rifamycin - nitro imidazole coupled molecular preparation method of (by machine translation)
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The invention discloses a rifamycin - nitro imidazole coupling molecule of the preparation method. Preparation method of this invention to MTZ as raw materials, by changing the synthetic route, overcomes the reaction conditions must be controlled to the defect under the low temperature condition, and has improved the yield of target product. (by machine translation)
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Paragraph 0064-0066
(2017/09/12)
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- Synthesis and biological activity of new metronidazole derivatives
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The development of new antimicrobial and antiparasitic agents offers the possibility of generating structures of increased potency. To this end, three sulphonate ester derivatives of metronidazole were synthesized. Treatment of the tosylate analogue with NaSPh and NaN3 gave the thiophenolate and azide derivatives, respectively. Oxidation of phenylthio derivative with mCPBA afforded the sulfonyl analogue. Similarly, cycloaddition of azido-metronidazole with various symmetric acetylene compounds furnished the 1,2,3-triazole analogues. Treatment of dimethyl dicarboxylate metronidazole derivative with guanidine hydrochloride in the presence of base resulted in the formation of the ring-expanded (fat) derivative, triazolo-diazepam derivative of metronidazole. Treatment of chlorometronidazole with silylated quinolones gave the quinolone analogues of metronidazole. The antigardiasis and antifungal activities of the synthesized compounds were investigated. In addition, all synthesized compounds were evaluated for their in vitro anti-HIV activity in MT-4 cells as non-nucleoside reverse transcriptase inhibitors.
- Al-Masoudi, Najim A.,Abbas, Zina A. A.
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p. 383 - 390
(2016/02/16)
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- Design, synthesis and biological evaluation of 6-(nitroimidazole-1 H -alkyloxyl)-4-anilinoquinazolines as efficient EGFR inhibitors exerting cytotoxic effects both under normoxia and hypoxia
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A series of novel 6-(nitroimidazole-1H-alkyloxyl)-4-anilinoquinazoline derivatives (15a-15r) were designed, synthesized and evaluated as efficient EGFR inhibitors through introduction of hypoxia activated nitroimidazole moiety into the quinazoline scaffold of EGFR inhibitors. The majority of these newly synthesized compounds exhibited comparable EGFR inhibitory activities to gefitinib and moderate to excellent anti-proliferative activities against HT-29 cells under normoxia and hypoxia. The most promising compound 15c displayed the IC50 value of 0.47 nM against EGFR kinase and excellent cytotoxic effect against HT-29 cells under normoxia and hypoxia with the IC50 values of 2.21 μM and 1.62 μM, respectively. The mimic reductive activation study revealed that compound 15c exerted reductive activation properties under hypoxia, which were consistent with the in vitro metabolic study, wherein 15c was easily reductive activated under hypoxia and much more stable under normoxia. All these results suggested that 15c was a potential cancer therapeutic agent both under normoxia and hypoxia and was worth of further development.
- Cheng, Weiyan,Zhu, Shijun,Ma, Xiaodong,Qiu, Ni,Peng, Peng,Sheng, Rong,Hu, Yongzhou
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p. 826 - 834
(2015/01/08)
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- Direct cross-coupling access to diverse aromatic sulfide: Palladium-catalyzed double C-S bond construction using Na2S 2O3 as a sulfurating reagent
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The Pd-catalyzed cross-coupling of aryl halides, alkyl halides, and Na 2S2O3·5H2O to deliver aromatic thioethers is described. Pyridine, furan, thiophene, benzofuran, benzoxazole, benzothiophene, benzothiazole, and pyrazine are all amenable to this protocol. The odorless and stable solid Na2S2O 3·5H2O was used as a convenient and environmentally friendly source of sulfur. Pd-catalyzed cross-couplings without thiols or thiophenols to build C-S bonds have not previously been achieved, which renders our observation more striking.
- Qiao, Zongjun,Wei, Jianpeng,Jiang, Xuefeng
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p. 1212 - 1215
(2014/03/21)
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- Imidazole derivatives as possible microbicides with dual protection
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Twenty seven derivatives (2-28) of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol were synthesized and evaluated for anti-trichomonas, spermicidal and antifungal activities. Twenty six compounds were active against Trichomonas vaginalis at MIC ranging from 1-42 μM and seven compounds (9,18,19,22,24,26,28) immobilized 100% human spermatozoa at 1% concentration (w/v). Twenty three compounds (2,3,5,8-26,28) exhibited antifungal activity at 25-50 μg/mL concentration. Seven compounds (9,18,19,22,24,26,28) showed significant anti-trichomonas and spermicidal activities and also exhibited mild antifungal activity. All the compounds were highly safe towards human cervical cell line (HeLa) as shown by the cell-viability assay of HeLa cells at 200 μg/mL concentration, whereas nonoxynol-9 (N-9, the marketed spermicidal microbicide) was highly cytotoxic. Therefore, it may be concluded that introduction of the pharmacophore responsible for spermicidal activity into a proven anti-trichomonas structure may lead to a potent dual function microbicide better and safer than N-9.
- Kumar, Lalit,Sarswat, Amit,Lal, Nand,Sharma, Vishnu L.,Jain, Ashish,Kumar, Rajeev,Verma, Vikas,Maikhuri, Jagdamba P.,Kumar, Awanit,Shukla, Praveen K.,Gupta, Gopal
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experimental part
p. 817 - 824
(2010/04/06)
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- Substituted quinolines as antitumor agents
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The invention provides a compound of Formula (Ia), or a pharmaceutically acceptable salt. prodrug or solvate thereof. The invention also provides a process for the preparation of a compound of Formula (Ia), pharmaceutical compositions of a compound of Formula (Ia) and methods for the treatment or prevention of cancer comprising administering an effective amount of a compound of Formula (Ia).
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