Synthesis and anticancer activity evaluation of benzo[6,7]oxepino[3,2-b] pyridine derivatives

Phanida Thongaram; Suparerk Borwornpinyo; Phongthon Kanjanasirirat; Kedchin Jearawuttanakul; Mesayamas Kongsema; Nutthawat Chuanopparat; Paiboon Ngernmeesri

doi:10.1016/j.tet.2020.131473

Synthesis and anticancer activity evaluation of benzo[6,7]oxepino[3,2-b] pyridine derivatives

Phanida Thongaram
, Suparerk Borwornpinyo
, Phongthon Kanjanasirirat
, Kedchin Jearawuttanakul
, Mesayamas Kongsema
, Nutthawat Chuanopparat
, Paiboon Ngernmeesri

Kasetsart University
Mahidol University

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

A cascade reaction of 3-hydroxy-2-methylpyridine 1-oxide and substituted 2-fluorobenzal-dehydes involving nucleophilic aromatic substitution (S_NAr) and Knoevenagel condensation has been developed. This reaction provided easy access to benzo[6,7]oxepino[3,2-b]pyridine 1-oxide derivatives in moderate to good yields. Subsequent reduction of these compounds provided their deoxygenated forms in good to excellent yields. Moreover, some of the synthesized compounds were found to be active against human colorectal cancer cells (HCT-116 cell lines) with IC₅₀ values in the range of 24.95–45.80 μM.

Original language	English
Article number	131473
Journal	Tetrahedron
Volume	76
Issue number	39
DOIs	https://doi.org/10.1016/j.tet.2020.131473
Publication status	Published - 25 Sept 2020
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Anticancer
Benzo[6,7]oxepino[3,2-b]pyridine
Knoevenagel condensation
Nucleophilic aromatic substitution

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10.1016/j.tet.2020.131473

Cite this

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title = "Synthesis and anticancer activity evaluation of benzo[6,7]oxepino[3,2-b] pyridine derivatives",

abstract = "A cascade reaction of 3-hydroxy-2-methylpyridine 1-oxide and substituted 2-fluorobenzal-dehydes involving nucleophilic aromatic substitution (SNAr) and Knoevenagel condensation has been developed. This reaction provided easy access to benzo[6,7]oxepino[3,2-b]pyridine 1-oxide derivatives in moderate to good yields. Subsequent reduction of these compounds provided their deoxygenated forms in good to excellent yields. Moreover, some of the synthesized compounds were found to be active against human colorectal cancer cells (HCT-116 cell lines) with IC50 values in the range of 24.95{\textendash}45.80 μM.",

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author = "Phanida Thongaram and Suparerk Borwornpinyo and Phongthon Kanjanasirirat and Kedchin Jearawuttanakul and Mesayamas Kongsema and Nutthawat Chuanopparat and Paiboon Ngernmeesri",

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year = "2020",

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doi = "10.1016/j.tet.2020.131473",

language = "English",

volume = "76",

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TY - JOUR

T1 - Synthesis and anticancer activity evaluation of benzo[6,7]oxepino[3,2-b] pyridine derivatives

AU - Thongaram, Phanida

AU - Borwornpinyo, Suparerk

AU - Kanjanasirirat, Phongthon

AU - Jearawuttanakul, Kedchin

AU - Kongsema, Mesayamas

AU - Chuanopparat, Nutthawat

AU - Ngernmeesri, Paiboon

PY - 2020/9/25

Y1 - 2020/9/25

N2 - A cascade reaction of 3-hydroxy-2-methylpyridine 1-oxide and substituted 2-fluorobenzal-dehydes involving nucleophilic aromatic substitution (SNAr) and Knoevenagel condensation has been developed. This reaction provided easy access to benzo[6,7]oxepino[3,2-b]pyridine 1-oxide derivatives in moderate to good yields. Subsequent reduction of these compounds provided their deoxygenated forms in good to excellent yields. Moreover, some of the synthesized compounds were found to be active against human colorectal cancer cells (HCT-116 cell lines) with IC50 values in the range of 24.95–45.80 μM.

AB - A cascade reaction of 3-hydroxy-2-methylpyridine 1-oxide and substituted 2-fluorobenzal-dehydes involving nucleophilic aromatic substitution (SNAr) and Knoevenagel condensation has been developed. This reaction provided easy access to benzo[6,7]oxepino[3,2-b]pyridine 1-oxide derivatives in moderate to good yields. Subsequent reduction of these compounds provided their deoxygenated forms in good to excellent yields. Moreover, some of the synthesized compounds were found to be active against human colorectal cancer cells (HCT-116 cell lines) with IC50 values in the range of 24.95–45.80 μM.

KW - Anticancer

KW - Benzo[6,7]oxepino[3,2-b]pyridine

KW - Knoevenagel condensation

KW - Nucleophilic aromatic substitution

UR - https://www.scopus.com/pages/publications/85089752759

U2 - 10.1016/j.tet.2020.131473

DO - 10.1016/j.tet.2020.131473

M3 - Article

AN - SCOPUS:85089752759

SN - 0040-4020

VL - 76

JO - Tetrahedron

JF - Tetrahedron

IS - 39

M1 - 131473

ER -

Synthesis and anticancer activity evaluation of benzo[6,7]oxepino[3,2-b] pyridine derivatives

Abstract

UN SDGs

Keywords

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