Convenient synthesis and biological evaluation of modafinil derivatives: Benzhydrylsulfanyl and benzhydrylsulfinyl [1,2,3]triazol-4-yl-methyl esters

Jae Chul Jung; Yeonju Lee; Jee Young Son; Eunyoung Lim; Mankil Jung; Seikwan Oh

doi:10.3390/molecules161210409

Convenient synthesis and biological evaluation of modafinil derivatives: Benzhydrylsulfanyl and benzhydrylsulfinyl [1,2,3]triazol-4-yl-methyl esters

Jae Chul Jung, Yeonju Lee, Jee Young Son, Eunyoung Lim, Mankil Jung, Seikwan Oh

Department of Molecular Medicine

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

4 Scopus citations

Abstract

Simple synthesis and biological activities of modafinil derivatives are described. The key reactions include condensation of acid and propargyl alcohol, subsequent 1,3-dipolar cycloaddition reaction of alkynes and (3-azido-propyl)cyclohexane or (4-azidobutyl) benzene in the presence of sodium ascorbate and CuSO ₄·5H ₂O in excellent yield. They were then evaluated for the suppression of LPS-induced NO generation in vitro. It was found that all compounds showed moderate effects for suppression of LPS-induced NO generation.

Original language	English
Pages (from-to)	10409-10419
Number of pages	11
Journal	Molecules
Volume	16
Issue number	12
DOIs	https://doi.org/10.3390/molecules161210409
State	Published - Dec 2011

Keywords

1,3-dipolar cycloaddition reaction
Benzhydrylsulfanyl-[1,2,3]triazol-4-yl-methyl ester
Benzhydrylsulfinyl-1,2, 3]triazol-4-yl-methyl ester
Condensation
NO-generation

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title = "Convenient synthesis and biological evaluation of modafinil derivatives: Benzhydrylsulfanyl and benzhydrylsulfinyl [1,2,3]triazol-4-yl-methyl esters",

abstract = "Simple synthesis and biological activities of modafinil derivatives are described. The key reactions include condensation of acid and propargyl alcohol, subsequent 1,3-dipolar cycloaddition reaction of alkynes and (3-azido-propyl)cyclohexane or (4-azidobutyl) benzene in the presence of sodium ascorbate and CuSO 4·5H 2O in excellent yield. They were then evaluated for the suppression of LPS-induced NO generation in vitro. It was found that all compounds showed moderate effects for suppression of LPS-induced NO generation.",

keywords = "1,3-dipolar cycloaddition reaction, Benzhydrylsulfanyl-[1,2,3]triazol-4-yl-methyl ester, Benzhydrylsulfinyl-1,2, 3]triazol-4-yl-methyl ester, Condensation, NO-generation",

author = "Jung, \{Jae Chul\} and Yeonju Lee and Son, \{Jee Young\} and Eunyoung Lim and Mankil Jung and Seikwan Oh",

year = "2011",

month = dec,

doi = "10.3390/molecules161210409",

language = "English",

volume = "16",

pages = "10409--10419",

journal = "Molecules",

issn = "1420-3049",

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TY - JOUR

T1 - Convenient synthesis and biological evaluation of modafinil derivatives

T2 - Benzhydrylsulfanyl and benzhydrylsulfinyl [1,2,3]triazol-4-yl-methyl esters

AU - Jung, Jae Chul

AU - Lee, Yeonju

AU - Son, Jee Young

AU - Lim, Eunyoung

AU - Jung, Mankil

AU - Oh, Seikwan

PY - 2011/12

Y1 - 2011/12

N2 - Simple synthesis and biological activities of modafinil derivatives are described. The key reactions include condensation of acid and propargyl alcohol, subsequent 1,3-dipolar cycloaddition reaction of alkynes and (3-azido-propyl)cyclohexane or (4-azidobutyl) benzene in the presence of sodium ascorbate and CuSO 4·5H 2O in excellent yield. They were then evaluated for the suppression of LPS-induced NO generation in vitro. It was found that all compounds showed moderate effects for suppression of LPS-induced NO generation.

AB - Simple synthesis and biological activities of modafinil derivatives are described. The key reactions include condensation of acid and propargyl alcohol, subsequent 1,3-dipolar cycloaddition reaction of alkynes and (3-azido-propyl)cyclohexane or (4-azidobutyl) benzene in the presence of sodium ascorbate and CuSO 4·5H 2O in excellent yield. They were then evaluated for the suppression of LPS-induced NO generation in vitro. It was found that all compounds showed moderate effects for suppression of LPS-induced NO generation.

KW - 1,3-dipolar cycloaddition reaction

KW - Benzhydrylsulfanyl-[1,2,3]triazol-4-yl-methyl ester

KW - Benzhydrylsulfinyl-1,2, 3]triazol-4-yl-methyl ester

KW - Condensation

KW - NO-generation

UR - https://www.scopus.com/pages/publications/84555196147

U2 - 10.3390/molecules161210409

DO - 10.3390/molecules161210409

M3 - Article

C2 - 22173334

AN - SCOPUS:84555196147

SN - 1420-3049

VL - 16

SP - 10409

EP - 10419

JO - Molecules

JF - Molecules

IS - 12

ER -

Convenient synthesis and biological evaluation of modafinil derivatives: Benzhydrylsulfanyl and benzhydrylsulfinyl [1,2,3]triazol-4-yl-methyl esters

Abstract

Keywords

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