Design, synthesis and biological evaluation of novel 6,7,8,9-tetrahydro-2-(2-aryloxypyrimidin-4-yl)-2H-[1,2,4]triazolo[4,3-a]azepin-3(5H)-ones

doi:10.1002/JHET.5570430520

Paper

Design, synthesis and biological evaluation of novel 6,7,8,9-tetrahydro-2-(2-aryloxypyrimidin-4-yl)-2H-[1,2,4]triazolo[4,3-a]azepin-3(5H)-ones

Published Sep 1, 2006 · Yi‐Feng Wang, Wei‐Min Liu, You-Quan Zhu

Journal of Heterocyclic Chemistry

Q3 SJR score

4

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

A series of novel 6,7,8,9-tetrahydro-2-(2-aryloxypyrimidin-4-yl)-2H-[1,2,4]triazolo[4,3-a]azepin-3(5H)-ones were designed and efficiently synthesized. Their structures were determined by IR, 13C and 1H NMR, mass spectroscopy, and elemental analysis. These compounds were screened for herbicidal activities against rape and barnyard grass. Compounds 5a-5f and 5m exhibited moderate herbicidal activity against rape. In addition, the synthesis of the intermediate 1-(azepan-2-ylidene)-2-(2-chloropyrimidin-4-yl)-hydrazine (3) was studied and the reason for the low yield in the initial procedure is discussed as well.

Study Snapshot

Novel 6,7,8,9-tetrahydro-2-(2-aryloxypyrimidin-4-yl)-2H-[1,2,4]triazolo[4,3-a]azepin-3(5H)-ones show moderate herbicidal activity against rape and barnyard

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Design, synthesis and biological evaluation of novel 6,7,8,9-tetrahydro-2-(2-aryloxypyrimidin-4-yl)-2H-[1,2,4]triazolo[4,3-a]azepin-3(5H)-ones

References

Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors.

3-arylpyrroles are a new class of light-activated, membrane-disrupting herbicides that effectively kill grass and broadleaf weeds at low rates, with potential for widespread adoption.

New 2,4-diamino-5-(2',5'-substituted benzyl)pyrimidines as potential drugs against opportunistic infections of AIDS and other immune disorders. Synthesis and species-dependent antifolate activity.

New 2,4-diamino-5-[2'-methoxy-5'-(substituted benzyl)]pyrimidines show potential as effective drugs against opportunistic infections in AIDS patients and those with immune disorders.

Natural products as sources of new drugs over the period 1981-2002.

Natural products remain a significant source of novel structures for new drugs, with 62% of small molecule cancer drugs being nonsynthetic, and their influence is notable in antihypertensive and antimigraine fields.

Discovery and development of a commercial synthesis of azafenidin

The new process enables efficient and economical production of azafenidin, a key herbicide for controlling weeds and pests.

Design, synthesis and structure–activity relationships of novel ALS inhibitors

The biophore model accurately predicts herbicidal activity of novel ALS inhibitors, with N,N'-[1-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-ylthio)butane-2,3-di

Structure–Activity Relationships of Herbicidal Aryltriazolinones†

Herbicidal aryltriazolinones show varying biological activity depending on the substituent at aromatic position 4, with the chloro group providing optimal biological activity.

Syntheses and 5-HT2 antagonist activity of bicyclic 1,2,4-triazol-3(2H)-one and 1,3,5-triazine-2,4(3H)-dione derivatives.

Bicyclic 1,2,4-triazol-3(2H)-one and 1,3,5-triazine-2,4(3H)-dione derivatives with a 4-(4-fluorobenzoyl)piperidine group show potent 5-HT2 antagonist activity, with potential as useful

Citations

Synthesis of Antimicrobial Benzo[1,2,4]triazoloazepinium Salts and Tetrahydronaphtho[1,2-e][1,2,4]triazines by Polar [3+ + 2] and [4 + 2]-Cycloaddition Reactions.

Antimicrobial benzo[1,2,4]triazoloazepinium salts and tetrahydronaphtho[1,2-e][1,2,4]triazines synthesized through polar [3+ + 2] and [4 + 2]-cycload

Aerobic copper-promoted oxidative dehydrosulfurative carbon–oxygen cross-coupling of 3,4-dihydropyrimidine-1H-2-thiones with alcohols

Copper-promoted oxidative dehydrosulfurative carbon-oxygen cross-coupling provides facile access to biologically valuable 2-alkoxypyrimidines with rapid diversification.

Synthesis of [1,2,4]-triazolo-annulated 3-aza-A-homocholestanes—A novel class of pentacyclic compounds

This study synthesized novel pentacyclic compounds, [1,2,4]-triazolo-annulated 3-aza-A-homocholestanes, using azocarbenium salts derived from 5-cholestan-3-one and inverse electron-demand reactions.

Design, Synthesis and Biological Evaluation of Novel 6,7,8,9-Tetrahydro-2-(2-aryloxypyrimidin-4-yl)-2H-[1,2,4]triazolo [4,3-a]azepin-3(5H)-ones.

Novel 6,7,8,9-tetrahydro-2-(2-aryloxypyrimidin-4-yl)-2H-[1,2,4]triazolo[4,3-a]azepin-3(5H)-ones show moderate herbicidal activity against rape and barnyard