Structural modification of piperine from piper nigruml

Name: Suwichada Jaipea

LCSH: Burapha University -- Chemistry Faculty Of Science

Classification :.DDC: 572

LCSH: Acetylcholinesterase

LCSH: Butyrylcholinesterase

LCSH: Herbs

LCSH: Peppers -- Derivatives

LCSH: Extraction (Chemistry)

Abstract: Piperine is a major alkaloid from seeds of black pepper (Piper nigrum L.), possess diverse biological properties such as anti-inflammatory,anti-oxidant, antimicrobial, and neuroprotective activities. This natural compound has gained the wide attention in the medical community. This work was aimed to modify the piperine structure to improve the efficacy for the treatment of Alzheimer's disease. The thesis was divided into two parts, the first part, a novel series of piperine amide analogues were designed and synthesized from piperine via aminolysis reaction to obtain the new 29 analogues in moderate to excellent yields. In the second part, novel 1,2,3- triazole piperine analogues were designed and synthesized by performing a key step click reaction through one-pot two-step to obtain new 25 analogues in low to excellent yields. All synthetic compounds were investigated for their antioxidant, acetylcholinesterase (AChE), and butyrylcholinesterase (BuChE) activities. Among the design compounds having a hydroxy group at the piperazine showed the most potent antioxidant activity (IC50 of 0.04 ± 0.00 μM). Its activity was also superior to that of standard ascorbic acid. Compound 7a had good anti-AChE activity with an IC50 of 37.37 ± 0.04 µM. Furthermore, compound 3z was found to be the most potent anti-BuChE derivative with an IC50 value of 4.60 ± 0.01µM and higher than galantamine as a standard drug up to 8-fold. Molecular modeling and kinetic studies showed that compounds 7a and 3z bound simultaneously to the peripheral anionic site (PAS) and catalytic sites (CAS) of the AChE and BChE. Thus, compounds 7a and 3z would be promising candidates as lead for further development as an anti-AChE and anti-BuChE agent for the treatment of Alzheimer's disease.

Burapha University. Library

Address: CHONBURI

Email: buulibrary@buu.ac.th

Name: Rungnapha Saeeng

Role: Principal advisor

Created: 2022

Modified: 2023-02-22

Issued: 2023-02-22

วิทยานิพนธ์/Thesis

application/pdf

CallNumber: Th 572 Su968S

eng

DegreeName: Master of Science

Level: Master's Degree

Descipline: Chemistry

Grantor: Burapha University

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