Studies toward the synthesis of anticancer bauhinoxepines C and D and one-pot synthesis of 3-cinnamoyl-3-hydroxyisobenzofuran-1(3H)-one derivatives

Name: Intouch Rakchaya

LCSH: Kasetsart University -- Theses. M.S. (Chemistry) 2023.

Classification :.LCCS: RC271.C5

LCSH: Kasetsart University. -- Department of Chemistry -- Theses.

LCSH: Antineoplastic agents.

LCSH: Bauhinia -- Therapeutic use.

Abstract: Bauhinoxepines C and D are natural products possessing dibenzo[b,f]oxepine as a core structure. These compounds were isolated from Bauhinia purpurea L. (family Leguminosae), and they have been found to possess several biological properties such as antimicrobial, antifungal and anticancer properties. Therefore, we have been interested in the synthesis of these natural products. The starting materials required for the construction of the sevenmembered ring was 2-methyl-3-nitrophenol (20) and substituted 2- fluorobenzaldehyde (21a or 21b), which was prepared from 2-methylresocinol in 6 steps. These two starting materials reacted under basic conditions via nucleophilic aromatic substitution (SNAr) and Knoevenagal condensation reactions to form dibenzo[b,f]oxepines 22a and 22b in 44% and 33% yields, respectively. Compound 22 was converted to bauhinoxepine C by hydrogenation followed diazotization in 30% overall yield (crude). Moreover, compound 22b was converted to intermediate 107 by hydrogenation in 91% yield. However, attempts to convert this intermediate to bauhinoxepine D have not been successful. Isobenzofuranone is a versatile compound that has been widely studied due to its various synthetic applications including medicine, natural products, perfume and food additives. This type of compounds possess various biological properties such as antimicrobial, anti-inflammatory, anticancer, antiviral, antioxidant, anti-HIV and blood pressure lowering properties. We have been interested in the synthesis of 3-cinnamoyl-3-hydroxyisobenzofuran-1(3H)-one (30) and its derivatives since these compounds contain isobenzofuranone as a core structure. In this work, these compounds were prepared from 2-hydroxy-3- methylnaphthalene-1,4-dione (31) and benzaldehydes 32a–32o in the presence of K3PO4 and AlCl3 in DMSO at 100 ºC. The desired products (E)-3-(3-(2- bromophenyl)acryloyl)-3-hydroxyisobenzofuran-1(3H)-one (33c) were obtained in up to 95% yield.

Kasetsart University. Office of the University Library

Address: Bangkok

Email: tdckulib@ku.ac.th

Name: Paiboon Ngernmeesri.

Role: Thesis Advisor

Name: Nutthawat Chuanopparat.

Role: Thesis Co-Advisor

Created: 2023

Modified: 2025-06-25

Issued: 2025-06-25

วิทยานิพนธ์/Thesis

วิทยานิพนธ์/Thesis

application/pdf

URL: http://www.lib.ku.ac.th/KUthesis/2566/intouch-rak-all.pdf

CallNumber: RC271.C5.I58

eng

DegreeName: Master of Science

Level: Master's Degree

Descipline: Chemistry

Grantor: Kasetsart University

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