XVI Insecticidal Activity of Some New Acridines Containing Fluorine

Forty-five new fluorinated acridines have been screened for their insecticidal activity against adult cockroaches (Periplanata americana), and six of them displayed significant activity.     

Synthesis of Some New Fluorine Containing 2-(N-Arylamino)/2-methyl-4-aryl Thiazoles and Their Bactericidal Activity

Sixteen fluorine containing 2-(N-arylamino)/2-methyl-4-aryl thiazoles have been synthesised and characterized by spectral (IR and NMR) studies. Some representative compounds have also been screened for their bactericidal activity.     

Synthesis and Antimicrobial Activity of Some 2-Pyridone Nucleosides Containing a Sulfonamide Moiety

Glycosylation of 2-pyridonesulfonamide 1a,b with glycosyl/galactosyl bromide gave the corresponding glycosides 2a,b, 3a,b, 6a,b, and 7a,b, respectively. Deacetylation of the resulting glycosides gave the corresponding glycosides 4a,b, 5a,b, 8a,b, and 9a,b, respectively, in good yields. Furthermore, reaction of 2-pyridonesulfonamide 1b with lactosyl bromide gave a mixture the corresponding N, O-lactosides 10 and 11, which were deacetylated to give the corresponding glycosides 12 and 13, respectively. The structures of the new synthesized compounds were characterized by using IR, ¹H, ¹³C NMR spectra, and microanalysis. Selected members of these compounds were screened for antimicrobial activity.     

Design,Synthesis, and Anti-Breast Cancer Activity of Some Hybrid Molecules Containing Coumarin Moiety

Russian Journal of Bioorganic Chemistry - (Benzimidazol-2-yl)-7-hydroxycoumarin and N-(2-hydroxyphenyl)-7-hydroxycoumarin-3-carboxamide have been synthesized by the condensation of ethyl...     

Synthesis and Biological Activity of Scyllatoxin-Based BH3 Domain Mimetics Containing Two Disulfide Linkages

The B cell lymphoma 2 (BCL2) proteins are a family of evolutionarily related proteins that act as positive or negative regulators of the intrinsic apoptosis pathway. Overexpression of anti-apoptotic BCL2 proteins in cells is associated with apoptotic resistance, which can result in cancerous phenotypes and pathogenic cell survival. Consequently, anti-apoptotic BCL2 proteins have attracted considerable interest as therapeutic targets. We recently reported the development of a novel class of synthetic protein based on scyllatoxin (ScTx) designed to mimic the helical BH3 interaction domain of the pro-apoptotic BCL2 protein Bax. These studies showed that the number and position of native disulfide linkages contained within the ScTx-Bax structure significantly influences the ability for these constructs to target anti-apoptotic BCL2 proteins in vitro. The goal of the present study is to investigate the contribution of two disulfide linkages in the folding and biological activity of ScTx-Bax proteins. Here, we report the full chemical synthesis of three ScTx-Bax sequence variants, each presenting two native disulfide linkages at different positions within the folded structure. It was observed that two disulfide linkages were sufficient to fold ScTx-Bax proteins into native-like architectures reminiscent of wild-type ScTx. Furthermore, we show that select (bis)disulfide ScTx-Bax variants can target Bcl-2 (proper) in vitro and that the position of the disulfide bonds significantly influences binding affinity. Despite exhibiting only modest binding to Bcl-2, the successful synthesis of ScTx-Bax proteins containing two disulfide linkages represents a viable route to ScTx-based BH3 domain mimetics that preserve native-like conformations. Finally, structural models of ScTx-Bax proteins in complex with Bcl-2 indicate that these helical mimetics bind in similar configurations as wild-type Bax BH3 domains. Taken together, these results suggest that ScTx-Bax proteins may serve as potent lead compounds that expand the repertoire of “druggable” protein–protein interactions.     

Synthesis and Biological Activity of Some Nucleoside Analogs of Hydroquinoline-3-Carbonitrile

Hydroquinoline acyclonucleosides 2, 4, 6a,b, 8a,b, 9a,b, and their corresponding N-alkyl derivatives (10–12) were obtained by the reaction of 1a,b with acetoxybutylbromide, (2-acetoxyethoxy)methyl bromide, 3-chloropropanol, 1,3-dichloro-2-propanol, epichlorohydrin, propargyl/allyl bromides in the presence of K₂CO₃ in dry dimethylformamide (DMF). In a similar manner, reaction of 1a,b with glycosyl/galactosyl and lactosyl bromide afforded the corresponding N-nucloside derivatives 13a,b, 15a,b, and 17, respectively. Deacetylation of the N-nucleosides derivatives in the presence of Et₃N/MeOH and few drops of water gave the deprotected derivatives 3, 5, 7a,b, 14a,b, 16a,b, and 18 in good yields, respectively. All the newly synthesized compounds are elucidated by infrared, ¹H, ¹³C NMR and elemental analyses. Some of these compounds were screened for antimicrobial activities.     

Synthesis and Antiviral Activity of Some 2-Substituted 3-Formyl-and 3-Cyano-5,6-Dichloroindole Nucleosides

A series of dichlorinated indole nucleosides has been synthesized and tested for activity against human cytomegalovirus (HCMV) and herpes simplex virus type-1 (HSV-1) and for cytotoxicity. The isopropylidene-protected analogs of the previously reported 3-formyl-2,5,6-trichloro-1-(β-D-ribofuranosyl)indole (FTCRI) and 3-cyano-2,5,6-trichloro-1-(β-D-ribofuranosyl)indole (CTCRI) were modified by nucleophilic displacement of the 2-chloro substituent using secondary amines. Deprotection of the intermediates provided 2-substituted analogs of FTCRI and CTCRI in good yield. There was a significant difference in reactivity between the isopropylidene-protected and the fully deprotected FTCRI and CTCRI with respect to nucleophilic displacement of the 2-chloro substituent using dialkylamines. This difference in reactivity was not observed with monoalkylamines or with alkoxides, and the corresponding 2-alkylamino- and 2-methoxy substituted analogs were synthesized from FTCRI and CTCRI directly. None of the synthesized analogs demonstrated potent antiviral activity without some corresponding cytotoxicity.     

Synthesis of Quinoxlines Containing 1,2,3-Triazoles and Their Anti-Bacterial and Anti-Cancer Activity

Russian Journal of Bioorganic Chemistry - A series of 1-((1aryl)-1H-1,2,3-triazol-4-yl)methyl)quinoxalin-2(1H)-ones have been synthesized in moderate to high yields and evaluated for their...     

Synthesis of Some Pyridine Ribosides and Their Biological Activity

Abstract

A synthesis of 1-(β-D-ribofuranosyl)-pyridin-2-thiones via reaction of 3-cyanopyridin-2(H)-thiones with 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide under basic conditions, followed by hydrolysis with methanolic ammonia is reported.     

Synthesis and Anticancer Activity Evaluation of Some Thienopyrimidine Derivatives

Russian Journal of Bioorganic Chemistry - The current study focused on effective and straightforward routes for preparing a new series of thieno[2,3-d]pyrimidine derivatives in addition to their...     

Synthesis and Antiproliferative Activity of Some Thiazolylbenzimidazole-4,7-diones

Some thiazolylbenzimidazole-4,7-diones were synthesized and tested in vitro on two tumor cell lines. Compounds 2d and 2e show a very good activity on K562 cells, whereas compounds 2a and 2b are active on SW620 cells. The importance of the methoxy group on the quinone moiety is confirmed and the function at 4-position of the thiazole ring plays a determining role for the activity.     

Synthesis and Antiviral Activity of Some N-Pentopyranosyl-2-Pyridinethiones

Abstract

A novel synthesis of 1-(β-D-pentopyranosyl)pyridinethione nucleosides utilizing pyridine-2(1H)-thiones and α-bromoxylose or β-bromoarabinose triacetate as starting components is described. The free nucleosides were tested for their potential activity against HIV and different types of tumor virus.     

Synthesis and Biological Activity of Some 2-Aminopurine Carbonucleosides

Abstract

A series of new o ne t wo subtituted c arbonucleoside analogues (OTC) of purine was synthesized and evaluated against cytomegalovims and varicella-zoster virus in human embryonic lung (HEL) cells.     

Synthesis and Antibacterial Activity Evaluation of Imidazole Derivatives Containing 6-Methylpyridine Moiety

A series of 2-cyclopropyl-5-(5-(6-methylpyridin-2-yl)-2-substituted-1H-imidazol-4-yl)-6-phenylimidazo[2,1-b][1,3,4]thiadiazoles ( 15a – t and 16a – f ) were synthesized and their antibacterial activities were evaluated. More than half of the compounds showed moderate or strong antibacterial activity. Among them, compounds 15t (MIC=1–2 μg/mL) and 16d (MIC=0.5 μg/mL) showed the strongest antibacterial activities. Notably, compound 16d did not exhibit cytotoxicity in HepG2 cells and did not show hemolysis like the positive control compound Gatifloxacin. The results suggest that compound 16d should be further investigated as a candidate antibacterial agent.     

The Synthesis and Antiherpetic Activity of DHBG and Some Analogs

Abstract

Several acyclic guanosine analogs have been synthesized and tested for antiviral activity.     

Synthesis and Antinematodal Activity of 3-n-Alkylphenols

Several 3-alkylphenols including 3-undecylphenol, which was isolated from a Sumatran rainforest plant, were synthesized to investigate their antinematodal activity against the phytopathogenic nematodes, Bursapherencus xylophilus. A three-step synthesis involving the treatment of 2-cyclohexen-1-one with the Grignard reagent, oxidation of the resulting 1-alkyl-2-cyclohexen-1-ol and subsequent aromatization of 3-alkyl-2-cyclohexen-1-one successfully afforded such phenols. Among the 3-alkylphenols, 3-nonylphenol showed the highest activity, while 3-decylphenol and 3-undecylphenol also showed high activity.     

Synthesis and Evaluation of Antimicrobial Activity of Some Pyrimidine Glycosides

Reaction of ethyl 4-thioxo-3,4-dihydropyrimidine-5-carboxylate derivatives 1a,b and ethyl 4-oxo-3,4-dihydropyrimidine-5-carboxylate 1c with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide in KOH or TEA afforded ethyl 2-aryl-4-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosylthio or/ oxy)-6-methylpyrimidine-5-carboxylate 6a-c. The glucosides 6a and 6b were obtained by the reaction of 1a and 1b with peracetylated glucose3 under MW irradiation. Mercuration of 1a followed by reaction with acetobromoglucose gave the same product 6a. The reaction of 1a-c with peracetylated ribose 4 under MW irradiation gave ethyl 2-aryl-4-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosylthio)-6-methylpyrimidine-5-carboxylate 8a–c. The deprotection of 6a–c and 8a–c in the presence of methanol and TEA/H₂O afforded the deprotected products 7a–c and 9a–c. The structure were confirmed by using ¹H and ¹³CNMR spectra. Selected members of these compounds were screened for antimicrobial activity.     

Adamantane Derivatives Containing Thiazole Moiety: Synthesis,Antiviral and Antibacterial Activity

International Journal of Peptide Research and Therapeutics - Herein, we report design and synthesis of series of adamantane derivatives containing modified peptides with thiazol moiety. New...     

Synthesis and Biological Activity of Some Unsaturated 6-Azauracil Acyclonucleosides

A useful route is described for obtaining Z and E unsaturated alkylating agents 3 and 4. Coupling 6-azauracils 5 and 6 with unsaturated alkylating agent followed by the deprotection with H⁺ resin gave acyclonucleosides 11–14 in good overall yields. Unsaturated acyclonucleosides phosphonates 19 and 20 were prepared using potassium carbonate as base and 4-bromobut-2-enyl diethyl phosphonate 16 as the alkylating agent. The introduction of a propargyl group at the N-3 position of acyclonucleosides 7, 8, 17, 18, 19, and 20 was achieved using potassium carbonate in DMF.