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

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1246/cl.2006.1010

Cite this

@article{fdf8adb219bb4445a7d9dc36d6dc3aa6,

title = "Synthesis and biological evaluation of pyridooxazine-tetrahydroisoquinoline derivatives as MDR modulators",

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.",

author = "Chen Ma and Liu, {Shao Jie} and Liang Xin and Qun Zhang and Kai Ding and Falck, {J R} and Shin, {Dong Soo}",

year = "2006",

month = sep,

day = "5",

doi = "10.1246/cl.2006.1010",

language = "English (US)",

volume = "35",

pages = "1010--1011",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "9",

}

TY - JOUR

T1 - Synthesis and biological evaluation of pyridooxazine-tetrahydroisoquinoline derivatives as MDR modulators

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

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=33845260990&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33845260990&partnerID=8YFLogxK

U2 - 10.1246/cl.2006.1010

DO - 10.1246/cl.2006.1010

M3 - Article

AN - SCOPUS:33845260990

SN - 0366-7022

VL - 35

SP - 1010

EP - 1011

JO - Chemistry Letters

JF - Chemistry Letters

IS - 9

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this