Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents

Prasanta Das; Ann O. Omollo; Lungile J. Sitole; Eric McClendon; Edward J. Valente; Drazen Raucher; Leslie R. Walker; Ashton T. Hamme

doi:10.1016/j.tetlet.2015.02.059

Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents

Prasanta Das
, Ann O. Omollo
, Lungile J. Sitole
, Eric McClendon
, Edward J. Valente
, Drazen Raucher
, Leslie R. Walker
, Ashton T. Hamme

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

38 Citations (Scopus)

Abstract

A series of structurally diverse 4-bromo spiro-isoxazolines possessing a variety of aromatic and aliphatic substituents at the 3 position, were synthesized through a 1,3-dipolar cycloaddition followed by intramolecular cyclization of a pendant hydroxyl or carboxylic acid group. The biochemical antiproliferative activity was evaluated in vitro by using two breast cancer cell lines (MCF-7 and MDA-MB-231) and two prostate cancer cell lines (PC-3 and DU-145) using the MTT viability assay, and the IC₅₀ values were obtained. Spiro-isoxazoline derivatives bearing a p-chloro or an o-dichloro aromatic substituent at the 3-position of the isoxazoline showed considerable antitumor activities in all four cell lines with IC₅₀ values ranging from 43 μM to 56 μM.

Original language	English
Pages (from-to)	1794-1797
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	14
DOIs	https://doi.org/10.1016/j.tetlet.2015.02.059
Publication status	Published - 1 Apr 2015
Externally published	Yes

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

1,3-Dipolar cycloaddition
Bioevaluation
Regioselectivity
Spiro-isoxazolines
Stereoselective intramolecular cyclization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.02.059

Cite this

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title = "Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents",

abstract = "A series of structurally diverse 4-bromo spiro-isoxazolines possessing a variety of aromatic and aliphatic substituents at the 3 position, were synthesized through a 1,3-dipolar cycloaddition followed by intramolecular cyclization of a pendant hydroxyl or carboxylic acid group. The biochemical antiproliferative activity was evaluated in vitro by using two breast cancer cell lines (MCF-7 and MDA-MB-231) and two prostate cancer cell lines (PC-3 and DU-145) using the MTT viability assay, and the IC50 values were obtained. Spiro-isoxazoline derivatives bearing a p-chloro or an o-dichloro aromatic substituent at the 3-position of the isoxazoline showed considerable antitumor activities in all four cell lines with IC50 values ranging from 43 μM to 56 μM.",

keywords = "1,3-Dipolar cycloaddition, Bioevaluation, Regioselectivity, Spiro-isoxazolines, Stereoselective intramolecular cyclization",

author = "Prasanta Das and Omollo, \{Ann O.\} and Sitole, \{Lungile J.\} and Eric McClendon and Valente, \{Edward J.\} and Drazen Raucher and Walker, \{Leslie R.\} and Hamme, \{Ashton T.\}",

year = "2015",

month = apr,

day = "1",

doi = "10.1016/j.tetlet.2015.02.059",

language = "English",

volume = "56",

pages = "1794--1797",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents

AU - Das, Prasanta

AU - Omollo, Ann O.

AU - Sitole, Lungile J.

AU - McClendon, Eric

AU - Valente, Edward J.

AU - Raucher, Drazen

AU - Walker, Leslie R.

AU - Hamme, Ashton T.

PY - 2015/4/1

Y1 - 2015/4/1

N2 - A series of structurally diverse 4-bromo spiro-isoxazolines possessing a variety of aromatic and aliphatic substituents at the 3 position, were synthesized through a 1,3-dipolar cycloaddition followed by intramolecular cyclization of a pendant hydroxyl or carboxylic acid group. The biochemical antiproliferative activity was evaluated in vitro by using two breast cancer cell lines (MCF-7 and MDA-MB-231) and two prostate cancer cell lines (PC-3 and DU-145) using the MTT viability assay, and the IC50 values were obtained. Spiro-isoxazoline derivatives bearing a p-chloro or an o-dichloro aromatic substituent at the 3-position of the isoxazoline showed considerable antitumor activities in all four cell lines with IC50 values ranging from 43 μM to 56 μM.

AB - A series of structurally diverse 4-bromo spiro-isoxazolines possessing a variety of aromatic and aliphatic substituents at the 3 position, were synthesized through a 1,3-dipolar cycloaddition followed by intramolecular cyclization of a pendant hydroxyl or carboxylic acid group. The biochemical antiproliferative activity was evaluated in vitro by using two breast cancer cell lines (MCF-7 and MDA-MB-231) and two prostate cancer cell lines (PC-3 and DU-145) using the MTT viability assay, and the IC50 values were obtained. Spiro-isoxazoline derivatives bearing a p-chloro or an o-dichloro aromatic substituent at the 3-position of the isoxazoline showed considerable antitumor activities in all four cell lines with IC50 values ranging from 43 μM to 56 μM.

KW - 1,3-Dipolar cycloaddition

KW - Bioevaluation

KW - Regioselectivity

KW - Spiro-isoxazolines

KW - Stereoselective intramolecular cyclization

UR - https://www.scopus.com/pages/publications/84925510577

U2 - 10.1016/j.tetlet.2015.02.059

DO - 10.1016/j.tetlet.2015.02.059

M3 - Article

AN - SCOPUS:84925510577

SN - 0040-4039

VL - 56

SP - 1794

EP - 1797

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents

Abstract

UN SDGs

Keywords

ASJC Scopus subject areas

Access to Document

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