N-Substituted amides of endo-3-(3-methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid and 1-(5-methylthio-1,2,4-triazol-3-yl)cyclohexane-2-carboxylic acid were prepared by the condensation reaction of endo-S-methyl-N1-(bicyclo[2.2.1]hept-5-ene-2,3-dicarbonyl)isothiosemicarbazide and S-methyl-N1-(cyclohexane-2,3-dicarbonyl)isothiosemicarbazide with primary amines. The synthesized compounds were screened for their microbiological and pharmacological activities.

Download full-text PDF

Source

Publication Analysis

Top Keywords

n-substituted amides
12
amides endo-3-3-methylthio-124-triazol-5-ylbicyclo[221]hept-5-ene-2-carboxylic
8
endo-3-3-methylthio-124-triazol-5-ylbicyclo[221]hept-5-ene-2-carboxylic acid
8
biological activity
4
activity novel
4
novel n-substituted
4
acid n-substituted
4
amides 1-5-methylthio-124-triazol-3-ylcyclohexane-2-carboxylic
4
1-5-methylthio-124-triazol-3-ylcyclohexane-2-carboxylic acids
4
acids n-substituted
4

Similar Publications

Target cyclooxygenase 2 (COX-2) and 5-lipoxygenase (5-LOX) inhibitors; 5-([2,5-Dihydroxybenzyl]amino)salicylamides (Compounds 1-11) were examined for potential anticancer activity, with a trial to assess the underlying possible mechanisms. Compounds were assessed at a single dose against 60 cancer cell lines panel and those with the highest activity were tested in the five-dose assay. COMPARE analysis was conducted to explore potential mechanisms underlying their biological activity.

View Article and Find Full Text PDF

Secondary amines are vital functional groups in pharmaceuticals, agrochemicals, and natural products, necessitating efficient synthetic methods. Traditional approaches, including N-monoalkylation and reductive amination, suffer from limitations such as poor chemoselectivity and complexity. Herein, we present a streamlined deoxygenative photochemical alkylation of secondary amides, enabling the efficient synthesis of α-branched secondary amines.

View Article and Find Full Text PDF

Domino Knoevenagel-cyclization reactions of styrene substrates, containing an -(-formyl)aryl subunit, were carried out with -substituted 2-cyanoacetamides to prepare tetrahydro-4-pyrano[3,4-]quinolone and hexahydrobenzo[]phenanthridine derivatives by competing IMHDA and IMSDA cyclization, respectively. The diastereoselective IMHDA step with α,β-unsaturated amide, thioamide, ester and ketone subunits as a heterodiene produced condensed chiral tetrahydropyran or thiopyran derivatives, which in the case of Meldrum's acid were reacted further with amine nucleophiles in a multistep domino sequence. In order to simplify the benzene-condensed tricyclic core of the targets and get access to hexahydro-1-pyrano[3,4-]pyridine derivatives, a truncated substrate was reacted with cyclic and acyclic active methylene reagents in diastereoselective Knoevenagel-IMHDA reactions to prepare novel condensed heterocyclic scaffolds.

View Article and Find Full Text PDF

Synthetic Strategies for the Development of Ibuprofen Derivatives: A Classified Study.

Curr Top Med Chem

January 2025

Department of Pharmaceutical Chemistry, Gokaraju Rangaraju College of Pharmacy, Bachupally, Hyderabad 500090, Telangana.

Ibuprofen, a widely used NSAID from the aryl propionic acid class, effectively relieves pain, fever, and inflammation. On prolonged use, it leads to gastrointestinal, hepatic, and renal toxicities, particularly gastrointestinal ulcers. These side effects are largely attributed to the carboxylic acid functional group common to NSAIDs.

View Article and Find Full Text PDF

An unusual semiquinone-mediated self-catalysis redox mechanism for the reaction between halohydroquinones and N-substituted hydroxamic acids.

Free Radic Biol Med

January 2025

State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, The Chinese Academy of Sciences, Beijing, 100085, PR China; Sino-Danish College, University of Chinese Academy of Sciences, Beijing, 100049, PR China; College of Resources and Environment, University of Chinese Academy of Sciences, Beijing, 100049, PR China; Linus Pauling Institute, Oregon State University, Corvallis, OR, 97331, USA. Electronic address:

We found recently that a C-C bonding phenyl-quinone product was produced with high yield (96 %) from the reaction between 2,5-dichloro-1,4-benzoquinone (DCBQ) and N-phenylbenzohydroxamic acid (N-PhBHA) via an unusual Claisen rearrangement mechanism, accompanied with the concurrent formation of the minor byproducts amide (N-phenylbenzamide, N-PhBA; only 2 % yield) and hydroxychloroquinone (2 % yield). Surprisingly, when DCBQ was replaced with its reduced form 2,5-dichloro-1,4-hydroquinone (DCHQ), no C-C bonding product was detected, whereas N-PhBA (83 % yield) and hydroxychloroquinone (80 % yield) became the predominant products, indicating a dramatic mechanistic shift. The ascorbate reduction experiment suggested that it was not DCHQ itself, but its corresponding semiquinone radical, that directly reacts with N-PhBHA.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!