ChemInform Abstract: SUBSTITUENT INTERACTIONS IN DI- AND TRI-ACYL DERIVATIVES OF CIS- AND TRANS-2-HYDRAZINOCYCLOPENTANOL

1973 ◽  
Vol 4 (33) ◽  
pp. no-no
Author(s):  
J. A. CAMPBELL ◽  
DONALD MACKAY
Keyword(s):  
Cis And Trans ◽  
Derivatives Of ◽  
Acyl Derivatives

Substituent Interactions in Di- and Tri-acyl Derivatives of cis- and trans- 2-Hydrazinocyclopentanol

1973 ◽  
Vol 51 (10) ◽  
pp. 1587-1597 ◽  
Author(s):  
J. A. Campbell ◽  
Donald Mackay
Keyword(s):  
Acetyl Derivative ◽  
Ester Group ◽  
Major Product ◽  
Amide Group ◽  
Acid Mixture ◽  
Tosyl Chloride ◽  
Cis And Trans ◽  
Work Up ◽  
Derivatives Of ◽  
Acyl Derivatives

The action of thionyl chloride followed by an alkaline work-up quantitatively isomerizes trans-1,2-dibenzoyl-1-(2-hydroxylcyclopentyl)hydrazine(5) to cis-2-benzoyl-1-(2-benzoyloxycyclopentyl)hydrazine (3). One equivalent of tosyl chloride in pyridine converts 5 to an intermediate which can be hydrolyzed to a mixture of 3 and 5 or can be transformed to the N-tosyl derivative 13 by tosylation and then hydrolysis. Oxazolidine structures are suggested as intermediates for these reactions.The alcohol 2 can also be isomerized to 3, using 0.8 N aqueous ethanolic hydrochloric acid, to which 5 is inert. The ester 3 is again the major product in the hydrolysis by this acid mixture of the cis-tribenzoyl derivative 17, the cis-N1-p-anisoyl derivative 21a and the cis-N1-acetyl derivative 21b, the amide group being cleaved much more rapidly than the ester, especially in the case of 21b. A mechanism involving ester participation by way of an oxazolidinium cation is proposed for these amide hydrolyses, and this is supported by tracer studies.The trans-esters 24a and b hydrolyze mainly at the ester group with retention of configuration.Polymorphism is a common phenomenon among the title compounds.

scholarly journals Synthesis, Antiproliferative Activity and Radical Scavenging Ability of 5-O-Acyl Derivatives of Quercetin

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1608
Author(s):  
Stephen Lo ◽  
Euphemia Leung ◽  
Bruno Fedrizzi ◽  
David Barker
Keyword(s):  
Antiproliferative Activity ◽  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Breast Cancer Cell Lines ◽  
Scavenging Activity ◽  
Plant Materials ◽  
Wide Range ◽  
Derivatives Of ◽  
Acyl Derivatives

Quercetin is a flavonoid that is found in many plant materials, including commonly eaten fruits and vegetables. The compound is well known for its wide range of biological activities. In this study, 5-O-acyl derivatives of quercetin were synthesised and assessed for their antiproliferative activity against the HCT116 colon cancer and MDA-MB-231 breast cancer cell lines; and their radical scavenging activity against the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical species. Four derivatives were found to have improved the antiproliferative activity compared to quercetin whilst retaining radical scavenging activity.

ChemInform Abstract: O-ACYL DERIVATIVES OF 2-PYRIDINALDOXIME

1978 ◽  
Vol 9 (52) ◽  
Author(s):  
P. YA. ROMANOVSKII ◽  
A. YU. KRIKIS ◽  
G. I. CHIPENS
Keyword(s):  
Derivatives Of ◽  
Acyl Derivatives
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