Regioselective lithiation of chiral 3-acylamino-2-alkylquinazolin-4(3H)ones: application in synthesis

Reaction of 3-amino-2-alkylquinazolin-4(3H)-ones with several chiral acid chlorides was found to be dependent on the molar proportions. When a 1:1 molar mixture was heated under reflux, the corresponding 3-(diacylamino)- derivatives were obtained in poor yields. However, when a 2:1 molar mixture was reacted in refluxing toluene, the 3-acylamino- derivatives were obtained in good yields based on the acid chloride. Lithiation of the 3-acylamino-2-alkyl­quinazolin-4(3H)-ones was achieved by the use of lithium diisopropylamide (LDA) in anhydrous THF at -78 °C and the reaction was regioselective at the carbon α to position 2 of the quinazolin-4(3H)-one moiety. The dilithio reagents thus obtained reacted with electrophiles to give the corresponding 2-substituted derivatives in very good yields. The NMR spectra of the products show the expected diastereotopism for all the CH2 groups and provide evidence for long-range asymmetric induction

CYTOTOXICITY OF IMIDACLOPRID AND MYCLOBUTANIL PESTICIDES ON THREE CANCER CELL LINES

Three cancer cell lines, i.e. HEpG-2 (human liver carcinoma), MCF-7 (human breast adeno-carcinoma), and PC3 (Prostatic Small Cell Carcinoma) were used to determine the cytotoxic effects of the neonicotinoid insecticide (imidacloprid) and conazole fungicide (myclobutanil). Cytotoxicity was measured by neutral red incorporation (NRI) assay. The lowest concentration of the tested pesticides (0.5 μg/ml) was toxic. With the increase of the concentration up to 80 μg/ml, the Department of plant protection, Faculty of Agric., Ain Shams University, shoubra  Elkheima, Cairo, Egypt Department of Genetics, Faculty of Agric., Ain Shams University, Cairo, Egypt damage degree of the cellular form and size was more serious. The midpoint cytotoxicity value, (NRI50) for imidacloprid and myclobutanil for HEpG-2, MCF-7, and PC3 cancer cell lines were 110.5, 67.7 and 67.6 μg/ml and 38.12, 41 and 27.5 μg/ml, respectively. In general, myclobutanil was very toxic in the three cancer cell lines compared with imidacloprid

Genotoxicity assessment of amino zinc nanoparticles in wheat (Triticum aestivum L.) as cytogenetical perspective

This is the final version. Available on open access from Elsevier via the DOI in this record. Nanoparticles have a positive impact in several subjects especially in agriculture, while their safety is still being debated. Numerous commercial nano pesticide, insecticides, and fertilizers products are found in the local markets without any intensely studies on the side effect of these products on plant, human as well as environmental effects. The present study aimed to evaluate the genotoxicity of commercial amino zinc nanoparticles (AZ NPs) on Triticum aestivum L. during seeds germination and root elongation using concentration ranges (50, 100, and 150 ppm) at different exposure times (8, 16 and 24 hrs). Long term exposure to AZ NPs, exhibited only slight variation in germination rates and the elongation of roots was affected by AZ NPs treatment ranged from 97.66 to 100%. Significant reduction in the mitotic index was 35.33% after 24 hrs and 150 ppm of AZ NPs, was also observed comparing with control which was 88.0%. Genotoxicity was evaluated at a cytological level in root meristems that revealed sever variations in mitotic activity, chromosomal aberrations, and micronuclei release. Results exhibited that nano amino zinc could enter effortlessly into the cells and inhibit the normal cellular function. The decrease in the emergence of chromosomal aberrations resulting from AZ NPs exposure in a dose-dependent manner was clearly indicated that AZ NPs has induced genotoxic effect on wheat root tips.King Saud University, Riyadh, Saudi Arabi

Medical prospects of cryptosporidiosis in vivo control using biofabricated nanoparticles loaded with Cinnamomum camphora extracts by Ulva fasciata

Background and Aim: Global efforts are continuing to develop preparations against cryptosporidiosis. This study aimed to investigate the efficacy of biosynthesized Ulva fasciata loading Cinnamomum camphora oil extract on new zinc oxide nanoparticles (ZnONPs shorten to ZnNPs) and silver nanoparticles (AgNPs) as alternative treatments for Cryptosporidium parvum experimental infection in rats. Materials and Methods: Oil extract was characterized by gas chromatography-mass spectrometry, loaded by U. fasciata on ionic-based ZnO and NPs, and then characterized by transmission electron microscopy, scanning electron microscopy, and X-ray diffraction. Biosafety and toxicity were investigated by skin tests. A total of 105 C. parvum oocysts/rat were used (n = 81, 2–3 W, 80–120 g, 9 male rats/group). Oocysts shedding was counted for 21 d. Doses of each preparation in addition to reference drug were administered daily for 7 d, starting on post-infection (PI) day (3). Nitazoxanide (100 mg) was used as the reference drug. After 3 weeks, the rats were sacrificed for postmortem examination and histopathological examination. Two blood samples/rat/group were collected on the 21st day. Ethylenediaminetetraacetic acid blood samples were also used for analysis of biochemistry, hematology, immunology, micronucleus prevalence, and chromosomal abnormalities. Results: C. camphora leaves yielded 28.5 ± 0.3 g/kg oil and 20 phycocompounds were identified. Spherical and rod-shaped particles were detected at 10.47–30.98 nm and 18.83–38.39 nm, respectively. ZnNPs showed the earliest anti-cryptosporidiosis effect during 7–17 d PI. Other hematological, biochemical, immunological, histological, and genotoxicity parameters were significantly fruitful; hence, normalized pathological changes induced by infestation were observed in the NPs treatments groups against the infestation-free and Nitazoxanide treated group. Conclusion: C. camphora, U. fasciata, ZnNPs, and AgNPs have refluxed the pathological effects of infection as well as positively improved host physiological condition by its anticryptosporidial immunostimulant regenerative effects with sufficient ecofriendly properties to be proposed as an alternative to traditional drugs, especially in individuals with medical reactions against chemical commercial drugs

The Action of Methylmagnesioum Iodide on 6-Bromo-2-Phenyl-4H-3,l-Benzoxazinone and its 4(3H)-Quinazolinones

6-Bromo-2-phenyl-4H-3,l-benzoxazinone (7) reacted with methylmagnesium iodide to give 2-benzoylamino-5- bromophenyldimethylcarbinol (8) in 54% purified yield. Similarly, 3-anilino-6-bromo-2-phenyl-4(3H)-quinazolinone (9) afforded the corresponding dimethylcarbinol 10 in 65% yield after crystallization on its reaction with methylmagnesium iodide. However, reaction of methylmagnesium iodide with 6-bromo-3-(4-chloro-phenylidene)-2-phenyl- 4(3H)-quinazolinone (11) gave 6-bromo-3-[l-(4-chlorophenyl) ethylamino]-4(3H)-quinazolinone (12) in 48% yield after purification

Synthesis of glycosides containing quinazolin-4(3H)-one ring System

Reactions of various aminoquinazolin-4(3H)-ones with monosaccharides in the presence of a catalytic amount of glacial acetic acid afforded the corresponding N-glycosylamines as a mixture of b- and a-anomers. Acetylation of this mixture gave the corresponding b-glycoside acetates. However, b-glycoside acetates could be obtained directly from reactions of per-O-acetyl-b-D-glucosyl bromides with quinazolin-4(3H)-one derivatives which deacetyalted to the corresponding b-glycosides. A series of S-glycosides have been synthesised from reaction of per-O-acetyl-b-D-glucosyl bromides with quinazolinethiones

Synthesis of Glycosides Containing Quinazolin-4(3H)-one Ring System

Reactions of various aminoquinazolin-4(3H)-ones with monosaccharides in the presence of a catalytic amount of glacial acetic acid afforded the corresponding N-glycosylamines as a mixture of b- and a-anomers. Acetylation of this mixture gave the corresponding b-glycoside acetates. However, b-glycoside acetates could be obtained directly from reactions of per-O-acetyl-b-D-glucosyl bromides with quinazolin-4(3H)-one derivatives which deacetyalted to the corresponding b-glycosides. A series of S-glycosides have been synthesised from reaction of per-O-acetyl-b-D-glucosyl bromides with quinazolinethiones