Synthesis of anticancer compounds,III (Bioorg Med Chem Lett 17, 6091, 2007), carbinol derivatives of azanaphthoquinone annelated pyrroles

Abstract  A series of carbinols has been synthesized by attachment of different piperidinyl side chains to the quinone structure of azanaphthoquinone annelated pyrroles. The synthesized compounds were screened for their cytotoxic activities. Compared to previously published results, they exhibited only moderate activities, thus showing that the existence of the quinone moiety seems to be essential for anticancer activities of this group. Graphical abstract        

Design,Synthesis, and Evaluation of the Anticancer Properties of Novel Quinone Bearing Carbamyl β‐Lactam Hybrids

This paper describes a simple and practical protocol for the direct synthesis of a series of new hybrid molecules of carbamyl β‐lactam derivatives bearing quinone moiety via [2 + 2] cycloaddition of Staudinger reaction. The β‐lactam ring is tolerating carbamylation and further leads to a variety of quinone hybrid derivatives. The structures of the compounds were characterized by IR, MS, nuclear magnetic resonance, and high‐resolution mass spectra analysis. All the new synthesized compounds were screened for their in vitro antiproliferative activity using an MTT assay analysis. Out of 14 derivatives synthesized in the current study, compounds 9h , 9k , 9i , and 9b exhibited the very good anticancer activities in B16F10 cell line.     

Synthesis, structural and biological characterization of 5-phenylhydantoin derivatives as potential anticonvulsant agents

Abstract  

Considering the importance of hydantoin derivatives in treatment of status epilepticus, four 5-phenylhydantoins, whose lipophilicities were estimated to be similar to that of phenytoin, were synthesized. Evaluation of their anticonvulsant activities was performed on rats by subcutaneous pentylenetetrazol seizure test and intravenous pentylenetetrazol threshold test, and spontaneous locomotor activity test was used to assess possible sedative effects. X-ray analysis of three compounds suggested that certain analogies might be drawn between interactions in crystal packing and biological interactions responsible for their anticonvulsant activity. It was found that 5-ethyl-5-phenyl-3-propylhydantoin exhibits the most favorable pharmacological properties among the synthesized compounds, i.e., anticonvulsant activity comparable to phenytoin with lower liability for induction of sedation in rats.     

Synthesis and biological activities of novel ethers of quinolinone linked with coumarins

Abstract  

A series of new ethers of quinolinone linked with different substituted coumarins and benzofurans were synthesized from 4-(bromomethyl)quinolinones. All newly synthesized compounds were screened for their in vitro antibacterial and antifungal activities. Most of the compounds with chloro substitution at the C-6 or C-7 position in quinolinone showed potent antibacterial and antifungal activities. In pharmacological evaluations, some of these chloroquinolinones also showed 70–77% inhibition of inflammation after 8 h, whereas the other compounds showed 51–55% inhibition. Most of the compounds showed potent analgesic activity compared to the standard and control. The structures of all newly synthesized compounds were characterized by elemental analysis, IR, ¹H NMR, ¹³C NMR, and EI-MS.     

Synthetic utility of bifunctional thiophene derivatives and antimicrobial evaluation of the newly synthesized agents

Abstract  

The key intermediate ethyl 2-amino-5-benzoyl-4-methylthiophene-3-carboxylate was prepared by a Gewald reaction starting from benzoylacetone, sulfur, and ethyl cyanoacetate in the presence of diethylamine. This intermediate reacted with various reagents to afford different fused and polyfunctional substituted thiophenes. Antimicrobial screening of the synthesized compounds exhibited promising antimicrobial activities.     

Bicyclic amido compounds with antiprotozoal activity

Abstract  

Aroyl derivatives of 2-aminobicyclo-octanes and 2-azabicyclo-nonanes have been synthesized and tested for their activities against the causative organisms of East African trypanosomiasis and malaria tropica. The acylation induced in general loss of antiprotozoal activity, but a single compound showed good antiplasmodial activity against a multiresistant strain of Plasmodium falciparum.     

Synthesis and biological evaluation of novel piperidin-4-ol derivatives

Abstract  

A series of novel piperidin-4-ol derivatives were designed, synthesized, and evaluated for potential treatment of HIV. The compounds were obtained via an efficient synthetic route in excellent yields and have been characterized by ¹H NMR, ¹³C NMR, MS, and elemental analysis. The CCR5 antagonistic activities of the compounds have also been evaluated.     

Synthesis and biological studies of some new acrylic acid ethyl esters of quinolinone

Abstract  

A series of new acrylic acid ethyl esters of quinolinones were synthesized from 4-(bromomethyl)quinolinones and screened for in vitro antimicrobial and in vivo analgesic and anti-inflammatory activities. Most of the compounds with chloro substitution at the C-6 or C-7 position in the quinolinone moiety and a methoxy group in the aryloxy moiety showed potent antibacterial and antifungal activities when compared with non-halogenated quinolinones and the quinolinones bearing a CH₃ at the C-8 position. In a pharmacological evaluation, the halogen substitution at the C-6 or C-7 position in quinolinones was found to enhance both analgesic and anti-inflammatory activities of the molecule when compared with a simple unsubstituted (non-halogenated) quinolinone. The structures of all newly synthesized compounds were characterized by elemental analysis, IR, ¹H NMR, ¹³C NMR, and FAB-MS.     

One-step synthesis of a novel carbon-based strong acid catalyst through hydrothermal carbonization

Abstract  

A novel carbon-based strong acid catalyst was synthesized through the one-step hydrothermal carbonization of furaldehyde and p-toluenesulfonic acid (PTSA) in aqueous solution at 180 °C for only 4 h. The novel carbon-based solid acid possessed high acidity, and the catalytic activities were investigated by esterification and oxathioketalization. The results showed that the novel catalyst demonstrated much greater activity than the traditional solid acids and was comparable to sulfuric acid. The one-step method provides an efficient procedure for the synthesis of various functionalized carbons by one-step hydrothermal carbonization.     

Synthesis and antiviral evaluation of new 2,5-disubstituted 1,3,4-oxadiazole derivatives and their acyclic nucleoside analogues

Abstract  

A number of new 5-[(naphthalen-1-yloxy)-methyl]-1,3,4-oxadiazole derivatives were synthesized. Sugar 2-[5-[(naphthalen-1-yloxy)methyl]-1,3,4-oxadiazol-2-ylthio]acetohydrazones were prepared by condensation of the hydrazide with the corresponding monosaccharides. Cyclization of the sugar hydrazones with acetic anhydride afforded the substituted oxadiazoline derivatives. The synthesized compounds displayed different degrees of antiviral activities or inhibitory actions against HCV and HIV viruses.     

Synthesis and antimicrobial activity of tetrazolo[1,5-a]quinoline-4-carbonitrile derivatives

Abstract  

A series of new tetrazolo[1,5-a]quinoline-4-carbonitrile derivatives were synthesized for the first time via tetrazolo[1,5-a]quinoline derivatives. Elemental analysis, IR, ¹H NMR, ¹³C NMR, and mass spectral data were used to elucidate the structures of all newly synthesized compounds. In vitro antimicrobial activities of synthesized compounds were investigated against Gram-positive Bacillus subtilis, Gram-negative Escherichia coli, and two fungi, Candida albicans and Aspergillus niger, in comparison with standard drugs. Some of the tested compounds showed significant antimicrobial activity.     

Novel pyrrolidinone and pyrazolo[1,5-a][1,3,5]triazine derivatives bearing a biologically active sulfamoyl moiety as a new class of antitumor agents

Abstract  

Sulfonamides possess many types of biological activities and have recently been reported to show substantial antitumor activity in vitro and/or in vivo. There are a variety of mechanisms for the anticancer activity. The present work reports the synthesis of some novel pyrrole, oxopyrrole, and related pyrroloacetamide derivatives, hydrazones, aminopyrazolinone, thiocarbamoyl, and pyrazolo[1,5-a][1,3,5]triazine derivatives bearing a substituted sulfonamide moiety. All newly synthesized compounds were evaluated for their in vitro anticancer activity against the breast cancer cell line MCF7. Most of the screened compounds showed interesting cytotoxic activities compared with doxorubicin as a reference drug.     

Characterization of yeast histone H3-specific type B histone acetyltransferases identifies an <Emphasis Type="Italic">ADA2</Emphasis>-independent Gcn5p activity

Background  

The acetylation of the core histone NH₂-terminal tails is catalyzed by histone acetyltransferases. Histone acetyltransferases can be classified into two distinct groups (type A and B) on the basis of cellular localization and substrate specificity. Type B histone acetyltransferases, originally defined as cytoplasmic enzymes that acetylate free histones, have been proposed to play a role in the assembly of chromatin through the acetylation of newly synthesized histones H3 and H4. To date, the only type B histone acetyltransferase activities identified are specific for histone H4.     

Synthesis of some pyridine, thiopyrimidine, and isoxazoline derivatives based on the pyrrole moiety

Abstract  

Condensation of 2-acetylpyrrole with 5-methylfuran-2-carboxyaldehyde and 4-chlorobenzaldehyde in 20% NaOH give the corresponding 2-chalconylpyrroles. Some new 2-alkoxy-3-cyano-4,6-diarylpyridines were synthesized by condensation of chalcones with malononitrile, followed by cyclization in sodium alkoxide. The reactivity of chalcones towards nitrogen nucleophiles such as thiourea and hydroxylamine hydrochloride to provide thiopyrimidines and isoxazolines was investigated.     

Synthesis of imidazo[4,5-a]acridones and imidazo[4,5-a]acridines as potential antibacterial agents

Abstract  

New imidazo[4,5-a]acridone derivatives were synthesized from the rearrangement of 3H-imidazo[4′,5′:3,4]benzo[c]isoxazoles. New imidazo[4,5-a]acridines were obtained from the reaction of imidazo[4,5-a]acridones in boiling POCl₃. All of these compounds exhibited antimicrobial activities comparable to streptomycin as reference drug.     

Synthesis, characterization, and polymerization of vinylmelamines

Abstract  

Vinyl functionalized melamine derivatives for cross-linking based on polymerization were synthesized as potential substitutes for harmful formaldehyde in melamine resins. Methylmelamines undergo direct vinylation with acetylene to the corresponding vinylmelamines in more than 95% conversion. Their chemical structures were fully characterized by mass spectrometry, Fourier transform infrared (FTIR) spectroscopy, elementary analysis, ¹H, ¹³C, and 2D correlation nuclear magnetic resonance (NMR) experiments. Linear and cross-linked polymers were prepared by free radical polymerization neat and in solution and characterized by size exclusion chromatography (SEC) and matrix-assisted laser desorption ionization time-of-flight (MALDI-ToF) mass spectrometry.     

Ghrelin-like peptide with fatty acid modification and O-glycosylation in the red stingray, Dasyatis akajei

Background  

Ghrelin (GRLN) is now known to be an appetite-stimulating and growth hormone (GH)-releasing peptide that is predominantly synthesized and secreted from the stomachs of various vertebrate species from fish to mammals. Here, we report a GRLN-like peptide (GRLN-LP) in a cartilaginous fish, the red stingray, Dasyatis akajei.     

Synthesis, complete NMR spectral assignments, and antifungal screening of new 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one oxime derivatives

Abstract  

A series of differently substituted 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one oximes have been synthesized and their ¹H and ¹³C NMR chemical shifts have been unambiguously assigned using H,H-COSY, NOESY, HSQC, and HMBC spectral data. On the basis of the NMR studies, irrespective of the nature and position of the substituents, all reported compounds exist in twin-chair conformation with equatorial disposition of the phenyl groups at C-2 and C-4 of the 3-azabicyclononane moiety. Among the synthesized oxime derivatives, compounds with halo-substituents at ortho/para positions of the phenyl showed good antifungal profile against all tested organisms.     

Synthesis and antiproliferative activity of multisubstituted N-fused heterocycles against the Hep-G2 cancer cell line

Abstract  

Pyrrolo[1,2-a]imidazole and pyrrolo[2,1-b]thiazole derivatives were synthesized in a one-pot procedure by [3 + 2] cycloaddition reactions of the corresponding imidazolium ylides and thiazolium ylides with an alkene followed by oxidative aromatization of the primary cycloadducts under the action of the mild oxidant tetrakispyridinecobalt(II) dichromate. Antiproliferative activity of 14 new bicyclic N-fused heterocycles against the human hepatocellular liver carcinoma (Hep-G2) cell line were examined by the MTT method. Some of the compounds showed favorable antiproliferative activity, especially compound 3i displayed potent antiproliferative activities with an IC₅₀ value of 0.36 μg/cm³.     

Design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides

Abstract  

A series of cyanonitrovinyl neonicotinoids were designed and synthesized via five steps in about 35% overall yields. All compounds were structurally characterized by ¹H nuclear magnetic resonance (NMR), ¹³C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction analysis of 2-[1-[(6-chloropyridin-3-yl)methyl]-2-imidazolidinylidene]-2-nitroacetonitrile revealed that the double bond is (E)-configured. The preliminary agriculture bioassay indicated that one compound exhibited moderate insecticidal activity against pea aphid.