Abstract Reaction of the quaternary ammonium salts 2a – i with electrophilic alkenes 3 , active alkylating agents 7 or aromatic aldehydes 11 carried out in basic two‐phase systems A–D, afforded cyclopropanes 4 cyanoalkenes 8 cyanooxiranes 12 respectively, via corresponding ylides 2 + . The method is very simple, and gives high yield. Under similar conditions, 1‐cyanodienes 8aa ba were cyclopropanated at γ,δ‐double bond formation vinylcyclopropanes 9a b stereochemistry prepared was elucidated...

Enzymes involved in thymidylate biosynthesis, synthase (TS), and dihydrofolate reductase (DHFR) are well-known targets cancer chemotherapy. In this study, we demonstrated for the first time, that human TS DHFR form a strong complex vitro co-localize normal colon cell cytoplasm nucleus. Treatment of cells with methotrexate or 5-fluorouracil did not affect distribution either enzyme within cells. However, 5-FU, but MTX, lowered presence DHFR-TS nucleus by 2.5-fold. The results may suggest...

A newly synthetized series of N-phenacyl derivatives 2-mercaptobenzoxazole, including analogues 5-bromo- and 5,7-dibromobenzoxazole, were screened against Candida strains the action mechanism was evaluated. 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(4-bromophenyl)ethanone (5d), 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(2,3,4-trichloro-phenyl)ethanone (5i), 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(2,4,6-trichlorophenyl)ethanone (5k) 2-[(5-bromo-1,3-benzoxazol-2-yl)sulfanyl]-1-phenylethanone (6a) showed anti-C....

Ammonium ylides generated from ammonium salt 1a-e with a base react derivatives of 3-nitropyridine 2a-c and 2-nitrothiophene (3) to form products vicarious nucleophilic substitution (VNS) 7, 8, or 9 respectively. The VNS 10, 11, 12 are also produced the corresponding salts, 4-chloro-nitrobenzene (4), nitrobenzene (5), 1-nitronaphthalene (6), In few products, an exchange alkoxy group 7c chlorine by alkoxyl 8a,b occured.

Abstract N-Cyanomethyl-N,N-dimethyl-N-(α-methoxycarbonyl)benzylammonium salts 5 were synthesized and treated with different base/solvent systems, giving the products of sigmatropic rearrangements [2,3] 7 [1,2] 8. In reactions carried out in liquid ammonia, rearrangement definitively prevailed. Pure 7(or mixture 8) deprotected to afford methyl 2-formylphenyl acetate (9) good yield.

Abstract Novel benzoxazole derivatives were synthesized, and their antitubercular activity against sensitive drug‐resistant Mycobacterium tuberculosis strains ( M. H 37 Rv, sp. 210, 192, scrofulaceum , intracellulare fortuitum avium kansasii ) was evaluated. The chemical step included preparation of ketones, alcohols, esters bearing moiety. All racemic mixtures alcohols separated in Novozyme SP 435‐catalyzed transesterification hydrolysis, respectively. reactions carried out various organic...

A novel domino reaction featuring a Michael addition/[1,2]-Stevens rearrangement of pyrrolidinium ylides with electrophilic alkenes is described. Ylides generated under mild conditions from 2-aryl-N-cyanomethyl-N-methylpyrrolidinium salts entered the addition, followed by [1,3]-hydrogen shift and finally [1,2]-Stevens to give 3-aryl-2-cyano-2-(2-EWG-ethyl)-1-methylpiperidines.

Darzen's condensation of tert-butyl-chloroacetate with aromatic, α,β-unsaturated, and aliphatic aldehydes in the presence sodium hydroxide, afforded tert-butyl-glycidates, trans/cis ratios 2.38−7.75. When TBAB was added as catalyst, ratio reversed to cis/trans 1.67−4.52. Rate constants halohydrin anion formations, their cyclization, hydrolysis diastereoisomers glycidates well structure corresponding conformers anions are considered explain these results.

Our study aimed to characterise the action mode of N-phenacyldibromobenzimidazoles against C. albicans and neoformans. Firstly, we selected non-cytotoxic most active benzimidazoles based on structure–activity relationships showing that group 5,6-dibromobenzimidazole derivatives are less vs. 4,6-dibromobenzimidazole analogues (5e–f 5h). The substitution chlorine atoms benzene ring N-phenacyl substituent extended anti-C. (5e with 2,4-Cl2 or 5f 3,4-Cl2). excellent results for...

An efficient method for the synthesis of new 4,5,6,7-tetrabromo-1H-benzimidazole derivatives has been developed. New ketones were obtained by N-alkylation TBBi or 2-Me-TBBi with various phenacyl halides and then reduced to corresponding alcohols. All compounds satisfactory yields in range 40-91 %. The synthesized appeared a weak CK2 PIM-1 inhibitors but exhibit an interesting cytotoxic activity against cancer cell lines, i.e. MCF-7, PC-3, CCRF-CEM, K-562....

Abstract N ‐(EWG‐CH 2 )‐ ‐methyl‐2‐phenylpyrrolidinium (EWG ‐ electron‐withdrawing group) salts were obtained in two different ways. )‐2‐phenylpyrrolidines quaternized with iodomethane, dimethylsulfate or methyl trifluoromethanesulfonate forming pyrrolidinium iodides, methylsulfates and triflates. The counterion exchange the was carried out yielding respective tetrafluoroborates. second method based on quaternization of ‐methyl‐2‐phenylpyrrolidine α‐halogenoacetate phenacyl bromide. All...

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Antifungal N-phenacyl derivatives of 4,6- and 5,6-dibromobenzimidazoles are interesting substrates in the synthesis new antimycotics. Unfortunately, their application is limited by low yields time-consuming separation procedure. In this paper, we present optimization conditions purification methods N-phenacyldibromobenzimidazoles. The reactions were carried out various base solvent-systems including K2CO3, NaH, KOH, t-BuOK, MeONa, NaHCO3, Et3N, Cs2CO3, DBU, DIPEA, or DABCO as a base, MeCN,...

Abstract On treatment with a base, pyrrolidinium salts like (I) undergo ring expansion towards piperidines.