Synthesis and biological evaluation of pyridooxazine-tetrahydroisoquinoline derivatives as MDR modulators

Chen Ma; Shao Jie Liu; Liang Xin; Qun Zhang; Kai Ding; J R Falck; Dong Soo Shin

doi:10.1246/cl.2006.1010

Synthesis and biological evaluation of pyridooxazine-tetrahydroisoquinoline derivatives as MDR modulators

Chen Ma, Shao Jie Liu, Liang Xin, Qun Zhang, Kai Ding, J R Falck, Dong Soo Shin

Biochemistry

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

8 Scopus citations

Abstract

Pyridooxazine-tetrahydroisoquinoline derivatives were designed and synthesized for MDR modulating activity. Pyridooxazin-2-one scaffolds were constructed in a one-pot annulation of N-substituted-2-chloroacetamides with 2-bromo-3-hydroxy pyridine via Smiles rearrangement. The Pictet-Spengler cyclization to form tetrahydroisoquinoline ring afforded target compounds in 17-37% overall yields. Some of these compounds exhibited multidrug resistance (MDR) reversing activity.

Original language	English (US)
Pages (from-to)	1010-1011
Number of pages	2
Journal	Chemistry Letters
Volume	35
Issue number	9
DOIs	https://doi.org/10.1246/cl.2006.1010
State	Published - Sep 5 2006

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Chemistry(all)

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abstract = "Pyridooxazine-tetrahydroisoquinoline derivatives were designed and synthesized for MDR modulating activity. Pyridooxazin-2-one scaffolds were constructed in a one-pot annulation of N-substituted-2-chloroacetamides with 2-bromo-3-hydroxy pyridine via Smiles rearrangement. The Pictet-Spengler cyclization to form tetrahydroisoquinoline ring afforded target compounds in 17-37% overall yields. Some of these compounds exhibited multidrug resistance (MDR) reversing activity.",

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AU - Ma, Chen

AU - Liu, Shao Jie

AU - Xin, Liang

AU - Zhang, Qun

AU - Ding, Kai

AU - Falck, J R

AU - Shin, Dong Soo

PY - 2006/9/5

Y1 - 2006/9/5

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AB - Pyridooxazine-tetrahydroisoquinoline derivatives were designed and synthesized for MDR modulating activity. Pyridooxazin-2-one scaffolds were constructed in a one-pot annulation of N-substituted-2-chloroacetamides with 2-bromo-3-hydroxy pyridine via Smiles rearrangement. The Pictet-Spengler cyclization to form tetrahydroisoquinoline ring afforded target compounds in 17-37% overall yields. Some of these compounds exhibited multidrug resistance (MDR) reversing activity.

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JO - Chemistry Letters

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ER -

Synthesis and biological evaluation of pyridooxazine-tetrahydroisoquinoline derivatives as MDR modulators

Abstract

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