Peroxisome proliferator-activated receptor (PPAR) agonists with 3,4-dihydro-2H-benzo[e][1,3]oxazine and 2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine skeletons: Effects of cyclization of linker moiety on ppar-agonistic activity

Kenji Ohgane; Jyun Ichi Kasuga; Takuji Ohyama; Yuko Hirakawa; Kosuke Morikawa; Makoto Makishima; Yuichi Hashimoto; Hiroyuki Miyachi

doi:10.3987/COM-08-11407

Peroxisome proliferator-activated receptor (PPAR) agonists with 3,4-dihydro-2H-benzo[e][1,3]oxazine and 2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine skeletons: Effects of cyclization of linker moiety on ppar-agonistic activity

Kenji Ohgane, Jyun Ichi Kasuga, Takuji Ohyama, Yuko Hirakawa, Kosuke Morikawa, Makoto Makishima, Yuichi Hashimoto, Hiroyuki Miyachi

Faculty of Pharmaceutical Sciences

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

2 Citations (Scopus)

Abstract

Conformationally restricted heterocyclic derivatives of KCL ((S)-2-{4-methoxy-3-[4-(trifluoromethyl)benzylcarbamoyl]benzyl}butanoic acid), which exhibit selective PPARα-agonistic activity, were prepared to examine the significance of the amide bond of KCL. In vitro transactivation assay clearly indicated that introduction of a 2-position fluorine atom enhanced PPARs-agonistic activity as expected, while cyclization of the amide bond caused a drastic decrease of PPARs-agonistic activity.

Original language	English
Pages (from-to)	2187-2192
Number of pages	6
Journal	Heterocycles
Volume	75
Issue number	9
DOIs	https://doi.org/10.3987/COM-08-11407
Publication status	Published - Dec 1 2008

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-08-11407

Fingerprint

Dive into the research topics of 'Peroxisome proliferator-activated receptor (PPAR) agonists with 3,4-dihydro-2H-benzo[e][1,3]oxazine and 2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine skeletons: Effects of cyclization of linker moiety on ppar-agonistic activity'. Together they form a unique fingerprint.

Cite this

Ohgane, K., Kasuga, J. I., Ohyama, T., Hirakawa, Y., Morikawa, K., Makishima, M., Hashimoto, Y., & Miyachi, H. (2008). Peroxisome proliferator-activated receptor (PPAR) agonists with 3,4-dihydro-2H-benzo[e][1,3]oxazine and 2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine skeletons: Effects of cyclization of linker moiety on ppar-agonistic activity. Heterocycles, 75(9), 2187-2192. https://doi.org/10.3987/COM-08-11407

Peroxisome proliferator-activated receptor (PPAR) agonists with 3,4-dihydro-2H-benzo[e][1,3]oxazine and 2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine skeletons : Effects of cyclization of linker moiety on ppar-agonistic activity. / Ohgane, Kenji; Kasuga, Jyun Ichi; Ohyama, Takuji et al.

In: Heterocycles, Vol. 75, No. 9, 01.12.2008, p. 2187-2192.

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

Ohgane, K, Kasuga, JI, Ohyama, T, Hirakawa, Y, Morikawa, K, Makishima, M, Hashimoto, Y & Miyachi, H 2008, 'Peroxisome proliferator-activated receptor (PPAR) agonists with 3,4-dihydro-2H-benzo[e][1,3]oxazine and 2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine skeletons: Effects of cyclization of linker moiety on ppar-agonistic activity', Heterocycles, vol. 75, no. 9, pp. 2187-2192. https://doi.org/10.3987/COM-08-11407

@article{df1e8d125d8247448123a81250dff502,

title = "Peroxisome proliferator-activated receptor (PPAR) agonists with 3,4-dihydro-2H-benzo[e][1,3]oxazine and 2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine skeletons: Effects of cyclization of linker moiety on ppar-agonistic activity",

abstract = "Conformationally restricted heterocyclic derivatives of KCL ((S)-2-{4-methoxy-3-[4-(trifluoromethyl)benzylcarbamoyl]benzyl}butanoic acid), which exhibit selective PPARα-agonistic activity, were prepared to examine the significance of the amide bond of KCL. In vitro transactivation assay clearly indicated that introduction of a 2-position fluorine atom enhanced PPARs-agonistic activity as expected, while cyclization of the amide bond caused a drastic decrease of PPARs-agonistic activity.",

author = "Kenji Ohgane and Kasuga, {Jyun Ichi} and Takuji Ohyama and Yuko Hirakawa and Kosuke Morikawa and Makoto Makishima and Yuichi Hashimoto and Hiroyuki Miyachi",

year = "2008",

month = dec,

day = "1",

doi = "10.3987/COM-08-11407",

language = "English",

volume = "75",

pages = "2187--2192",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "9",

}

TY - JOUR

T1 - Peroxisome proliferator-activated receptor (PPAR) agonists with 3,4-dihydro-2H-benzo[e][1,3]oxazine and 2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine skeletons

T2 - Effects of cyclization of linker moiety on ppar-agonistic activity

AU - Ohgane, Kenji

AU - Kasuga, Jyun Ichi

AU - Ohyama, Takuji

AU - Hirakawa, Yuko

AU - Morikawa, Kosuke

AU - Makishima, Makoto

AU - Hashimoto, Yuichi

AU - Miyachi, Hiroyuki

PY - 2008/12/1

Y1 - 2008/12/1

N2 - Conformationally restricted heterocyclic derivatives of KCL ((S)-2-{4-methoxy-3-[4-(trifluoromethyl)benzylcarbamoyl]benzyl}butanoic acid), which exhibit selective PPARα-agonistic activity, were prepared to examine the significance of the amide bond of KCL. In vitro transactivation assay clearly indicated that introduction of a 2-position fluorine atom enhanced PPARs-agonistic activity as expected, while cyclization of the amide bond caused a drastic decrease of PPARs-agonistic activity.

AB - Conformationally restricted heterocyclic derivatives of KCL ((S)-2-{4-methoxy-3-[4-(trifluoromethyl)benzylcarbamoyl]benzyl}butanoic acid), which exhibit selective PPARα-agonistic activity, were prepared to examine the significance of the amide bond of KCL. In vitro transactivation assay clearly indicated that introduction of a 2-position fluorine atom enhanced PPARs-agonistic activity as expected, while cyclization of the amide bond caused a drastic decrease of PPARs-agonistic activity.

UR - http://www.scopus.com/inward/record.url?scp=77954222182&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77954222182&partnerID=8YFLogxK

U2 - 10.3987/COM-08-11407

DO - 10.3987/COM-08-11407

M3 - Article

AN - SCOPUS:77954222182

SN - 0385-5414

VL - 75

SP - 2187

EP - 2192

JO - Heterocycles

JF - Heterocycles

IS - 9

ER -

Peroxisome proliferator-activated receptor (PPAR) agonists with 3,4-dihydro-2H-benzo[e][1,3]oxazine and 2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine skeletons: Effects of cyclization of linker moiety on ppar-agonistic activity

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this