Synthesis of a unique dimethyl thiazoline containing intermediate of novel peroxisome proliferator-activated receptors(PPAR)δ agonists

Tara Man Kadayat; Geumwoo Lee; Kyungjin Jung; Hee Jong Hwang; Jeongmin Joo; Dongyup Hahn; Hayoung Hwang; Keun Gyu Park; Sung Jin Cho; Kyung Hee Kim; Jungwook Chin

doi:10.1016/j.tetlet.2018.10.051

Synthesis of a unique dimethyl thiazoline containing intermediate of novel peroxisome proliferator-activated receptors(PPAR)δ agonists

Tara Man Kadayat, Geumwoo Lee, Kyungjin Jung, Hee Jong Hwang, Jeongmin Joo, Dongyup Hahn, Hayoung Hwang, Keun Gyu Park, Sung Jin Cho, Kyung Hee Kim, Jungwook Chin

School of Food Science & Biotechnology

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

3 Scopus citations

Abstract

Peroxisome proliferator-activated receptor delta (PPARδ) is considered as a promising biological target for the development of new drugs to treat metabolic syndrome including hyperlipidemia. In this study, a simple and efficient method for the preparation of a unique dimethyl thiazoline containing intermediate (13) of new PPARδ agonists as GW501516 analogue is described. The intermediate 13 was readily obtained by coupling reaction of 4-(chloromethyl)-5,5-dimethyl-2-(4-(trifluoromethyl)phenyl)-4,5-dihydrothiazole (11) with 4-mercapto-2-methylphenol (12) in the presence of tetrabutylammonium hydrogensulfate (TBAHS) and Cs₂CO₃ in DMF at 80 °C for 1 h. This unique intermediate could be useful for the synthesis of various novel PPARδ agonists to understand the structural and biological significance of PPARδ.

Original language	English
Pages (from-to)	4384-4386
Number of pages	3
Journal	Tetrahedron Letters
Volume	59
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2018.10.051
State	Published - 12 Dec 2018

Keywords

4-Mercapto-2-methylphenol
D-Penicillamine
GW501516
PPAR agonists
TBAHS catalyst

Access to Document

10.1016/j.tetlet.2018.10.051

Cite this

@article{f19516b1cb3546f68fa02461e14717a4,

title = "Synthesis of a unique dimethyl thiazoline containing intermediate of novel peroxisome proliferator-activated receptors(PPAR)δ agonists",

abstract = "Peroxisome proliferator-activated receptor delta (PPARδ) is considered as a promising biological target for the development of new drugs to treat metabolic syndrome including hyperlipidemia. In this study, a simple and efficient method for the preparation of a unique dimethyl thiazoline containing intermediate (13) of new PPARδ agonists as GW501516 analogue is described. The intermediate 13 was readily obtained by coupling reaction of 4-(chloromethyl)-5,5-dimethyl-2-(4-(trifluoromethyl)phenyl)-4,5-dihydrothiazole (11) with 4-mercapto-2-methylphenol (12) in the presence of tetrabutylammonium hydrogensulfate (TBAHS) and Cs2CO3 in DMF at 80 °C for 1 h. This unique intermediate could be useful for the synthesis of various novel PPARδ agonists to understand the structural and biological significance of PPARδ.",

keywords = "4-Mercapto-2-methylphenol, D-Penicillamine, GW501516, PPAR agonists, TBAHS catalyst",

author = "{Man Kadayat}, Tara and Geumwoo Lee and Kyungjin Jung and Hwang, {Hee Jong} and Jeongmin Joo and Dongyup Hahn and Hayoung Hwang and Park, {Keun Gyu} and Cho, {Sung Jin} and Kim, {Kyung Hee} and Jungwook Chin",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = dec,

day = "12",

doi = "10.1016/j.tetlet.2018.10.051",

language = "English",

volume = "59",

pages = "4384--4386",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "50",

}

TY - JOUR

T1 - Synthesis of a unique dimethyl thiazoline containing intermediate of novel peroxisome proliferator-activated receptors(PPAR)δ agonists

AU - Man Kadayat, Tara

AU - Lee, Geumwoo

AU - Jung, Kyungjin

AU - Hwang, Hee Jong

AU - Joo, Jeongmin

AU - Hahn, Dongyup

AU - Hwang, Hayoung

AU - Park, Keun Gyu

AU - Cho, Sung Jin

AU - Kim, Kyung Hee

AU - Chin, Jungwook

PY - 2018/12/12

Y1 - 2018/12/12

N2 - Peroxisome proliferator-activated receptor delta (PPARδ) is considered as a promising biological target for the development of new drugs to treat metabolic syndrome including hyperlipidemia. In this study, a simple and efficient method for the preparation of a unique dimethyl thiazoline containing intermediate (13) of new PPARδ agonists as GW501516 analogue is described. The intermediate 13 was readily obtained by coupling reaction of 4-(chloromethyl)-5,5-dimethyl-2-(4-(trifluoromethyl)phenyl)-4,5-dihydrothiazole (11) with 4-mercapto-2-methylphenol (12) in the presence of tetrabutylammonium hydrogensulfate (TBAHS) and Cs2CO3 in DMF at 80 °C for 1 h. This unique intermediate could be useful for the synthesis of various novel PPARδ agonists to understand the structural and biological significance of PPARδ.

AB - Peroxisome proliferator-activated receptor delta (PPARδ) is considered as a promising biological target for the development of new drugs to treat metabolic syndrome including hyperlipidemia. In this study, a simple and efficient method for the preparation of a unique dimethyl thiazoline containing intermediate (13) of new PPARδ agonists as GW501516 analogue is described. The intermediate 13 was readily obtained by coupling reaction of 4-(chloromethyl)-5,5-dimethyl-2-(4-(trifluoromethyl)phenyl)-4,5-dihydrothiazole (11) with 4-mercapto-2-methylphenol (12) in the presence of tetrabutylammonium hydrogensulfate (TBAHS) and Cs2CO3 in DMF at 80 °C for 1 h. This unique intermediate could be useful for the synthesis of various novel PPARδ agonists to understand the structural and biological significance of PPARδ.

KW - 4-Mercapto-2-methylphenol

KW - D-Penicillamine

KW - GW501516

KW - PPAR agonists

KW - TBAHS catalyst

UR - http://www.scopus.com/inward/record.url?scp=85056275125&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2018.10.051

DO - 10.1016/j.tetlet.2018.10.051

M3 - Article

AN - SCOPUS:85056275125

SN - 0040-4039

VL - 59

SP - 4384

EP - 4386

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Synthesis of a unique dimethyl thiazoline containing intermediate of novel peroxisome proliferator-activated receptors(PPAR)δ agonists

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this