Non-competitive and selective dipeptidyl peptidase IV inhibitors with phenethylphenylphthalimide skeleton derived from thalidomide-related α-glucosidase inhibitors and liver X receptor antagonists

Kazunori Motoshima; Kazuyuki Sugita; Yuichi Hashimoto; Minoru Ishikawa

doi:10.1016/j.bmcl.2011.03.026

Non-competitive and selective dipeptidyl peptidase IV inhibitors with phenethylphenylphthalimide skeleton derived from thalidomide-related α-glucosidase inhibitors and liver X receptor antagonists

Kazunori Motoshima, Kazuyuki Sugita, Yuichi Hashimoto, Minoru Ishikawa

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

15 Citations (Scopus)

Abstract

Novel dipeptidyl peptidase IV (DPP-IV) inhibitors with a phenethylphenylphthalimide skeleton were prepared based on α-glucosidase inhibitors and liver X receptor (LXR) antagonists derived from thalidomide. Representative compounds showed non-competitive inhibition of DPP-IV and 28a exhibited 10-fold selectivity for DPP-IV over DPP-8. Compound 28a is the first non-competitive, selective DPP-IV inhibitor.

Original language	English
Pages (from-to)	3041-3045
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	10
DOIs	https://doi.org/10.1016/j.bmcl.2011.03.026
Publication status	Published - 2011 May 15
Externally published	Yes

Keywords

Dipeptidyl peptidase IV
Enzyme inhibitor
Non-competitive inhibition
Phthalimide
Subtype selectivity

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmcl.2011.03.026

Cite this

Non-competitive and selective dipeptidyl peptidase IV inhibitors with phenethylphenylphthalimide skeleton derived from thalidomide-related α-glucosidase inhibitors and liver X receptor antagonists. / Motoshima, Kazunori; Sugita, Kazuyuki; Hashimoto, Yuichi et al.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 21, No. 10, 15.05.2011, p. 3041-3045.

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

Motoshima, K, Sugita, K, Hashimoto, Y & Ishikawa, M 2011, 'Non-competitive and selective dipeptidyl peptidase IV inhibitors with phenethylphenylphthalimide skeleton derived from thalidomide-related α-glucosidase inhibitors and liver X receptor antagonists', Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 10, pp. 3041-3045. https://doi.org/10.1016/j.bmcl.2011.03.026

@article{85781843282a4c67a30e0edc38ddd46c,

title = "Non-competitive and selective dipeptidyl peptidase IV inhibitors with phenethylphenylphthalimide skeleton derived from thalidomide-related α-glucosidase inhibitors and liver X receptor antagonists",

abstract = "Novel dipeptidyl peptidase IV (DPP-IV) inhibitors with a phenethylphenylphthalimide skeleton were prepared based on α-glucosidase inhibitors and liver X receptor (LXR) antagonists derived from thalidomide. Representative compounds showed non-competitive inhibition of DPP-IV and 28a exhibited 10-fold selectivity for DPP-IV over DPP-8. Compound 28a is the first non-competitive, selective DPP-IV inhibitor.",

keywords = "Dipeptidyl peptidase IV, Enzyme inhibitor, Non-competitive inhibition, Phthalimide, Subtype selectivity",

author = "Kazunori Motoshima and Kazuyuki Sugita and Yuichi Hashimoto and Minoru Ishikawa",

note = "Funding Information: The work described in this paper was partially supported by Grants-in-Aid for Scientific Research from The Ministry of Education, Culture, Sports, Science and Technology , Japan, and the Japan Society for the Promotion of Science . ",

year = "2011",

month = may,

day = "15",

doi = "10.1016/j.bmcl.2011.03.026",

language = "English",

volume = "21",

pages = "3041--3045",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "10",

}

TY - JOUR

T1 - Non-competitive and selective dipeptidyl peptidase IV inhibitors with phenethylphenylphthalimide skeleton derived from thalidomide-related α-glucosidase inhibitors and liver X receptor antagonists

AU - Motoshima, Kazunori

AU - Sugita, Kazuyuki

AU - Hashimoto, Yuichi

AU - Ishikawa, Minoru

N1 - Funding Information: The work described in this paper was partially supported by Grants-in-Aid for Scientific Research from The Ministry of Education, Culture, Sports, Science and Technology , Japan, and the Japan Society for the Promotion of Science .

PY - 2011/5/15

Y1 - 2011/5/15

N2 - Novel dipeptidyl peptidase IV (DPP-IV) inhibitors with a phenethylphenylphthalimide skeleton were prepared based on α-glucosidase inhibitors and liver X receptor (LXR) antagonists derived from thalidomide. Representative compounds showed non-competitive inhibition of DPP-IV and 28a exhibited 10-fold selectivity for DPP-IV over DPP-8. Compound 28a is the first non-competitive, selective DPP-IV inhibitor.

AB - Novel dipeptidyl peptidase IV (DPP-IV) inhibitors with a phenethylphenylphthalimide skeleton were prepared based on α-glucosidase inhibitors and liver X receptor (LXR) antagonists derived from thalidomide. Representative compounds showed non-competitive inhibition of DPP-IV and 28a exhibited 10-fold selectivity for DPP-IV over DPP-8. Compound 28a is the first non-competitive, selective DPP-IV inhibitor.

KW - Dipeptidyl peptidase IV

KW - Enzyme inhibitor

KW - Non-competitive inhibition

KW - Phthalimide

KW - Subtype selectivity

UR - http://www.scopus.com/inward/record.url?scp=79955551684&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79955551684&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2011.03.026

DO - 10.1016/j.bmcl.2011.03.026

M3 - Article

C2 - 21478015

AN - SCOPUS:79955551684

VL - 21

SP - 3041

EP - 3045

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 10

ER -

Non-competitive and selective dipeptidyl peptidase IV inhibitors with phenethylphenylphthalimide skeleton derived from thalidomide-related α-glucosidase inhibitors and liver X receptor antagonists

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this