Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors

Ligaya M. Simpkins; Scott Bolton; Zulan Pi; James C. Sutton; Chet Kwon; Guohua Zhao; David R. Magnin; David J. Augeri; Timur Gungor; David P. Rotella; Zhong Sun; Yajun Liu; William S. Slusarchyk; Jovita Marcinkeviciene; James G. Robertson; Aiying Wang; Jeffrey A. Robl; Karnail S. Atwal; Robert L. Zahler; Rex A. Parker; Mark S. Kirby; Lawrence G. Hamann

doi:10.1016/j.bmcl.2007.09.090

Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors

Ligaya M. Simpkins
, Scott Bolton
, Zulan Pi
, James C. Sutton
, Chet Kwon
, Guohua Zhao
, David R. Magnin
, David J. Augeri
, Timur Gungor
, David P. Rotella
, Zhong Sun
, Yajun Liu
, William S. Slusarchyk
, Jovita Marcinkeviciene
, James G. Robertson
, Aiying Wang
, Jeffrey A. Robl
, Karnail S. Atwal
, Robert L. Zahler
, Rex A. Parker

Mark S. Kirby, Lawrence G. Hamann

Chemistry and Biochemistry

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

27 Scopus citations

Abstract

The synthesis and structure-activity relationships of novel dipeptidyl peptidase IV inhibitors replacing the classical cyanopyrrolidine P1 group with other small nitrogen heterocycles are described. A unique potency enhancement was achieved with β-branched natural and unnatural amino acids, particularly adamantylglycines, linked to a (2S,3R)-2,3-methanopyrrolidine based scaffold.

Original language	English
Pages (from-to)	6476-6480
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	17
Issue number	23
DOIs	https://doi.org/10.1016/j.bmcl.2007.09.090
State	Published - 1 Dec 2007

Keywords

DPP4
Diabetes
GLP-1
Non-nitrile
Serine protease

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmcl.2007.09.090

Cite this

Simpkins, L. M., Bolton, S., Pi, Z., Sutton, J. C., Kwon, C., Zhao, G., Magnin, D. R., Augeri, D. J., Gungor, T., Rotella, D. P., Sun, Z., Liu, Y., Slusarchyk, W. S., Marcinkeviciene, J., Robertson, J. G., Wang, A., Robl, J. A., Atwal, K. S., Zahler, R. L., ... Hamann, L. G. (2007). Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors. Bioorganic and Medicinal Chemistry Letters, 17(23), 6476-6480. https://doi.org/10.1016/j.bmcl.2007.09.090

@article{834935d968aa412b833e500146b960b4,

title = "Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors",

abstract = "The synthesis and structure-activity relationships of novel dipeptidyl peptidase IV inhibitors replacing the classical cyanopyrrolidine P1 group with other small nitrogen heterocycles are described. A unique potency enhancement was achieved with β-branched natural and unnatural amino acids, particularly adamantylglycines, linked to a (2S,3R)-2,3-methanopyrrolidine based scaffold.",

keywords = "DPP4, Diabetes, GLP-1, Non-nitrile, Serine protease",

author = "Simpkins, \{Ligaya M.\} and Scott Bolton and Zulan Pi and Sutton, \{James C.\} and Chet Kwon and Guohua Zhao and Magnin, \{David R.\} and Augeri, \{David J.\} and Timur Gungor and Rotella, \{David P.\} and Zhong Sun and Yajun Liu and Slusarchyk, \{William S.\} and Jovita Marcinkeviciene and Robertson, \{James G.\} and Aiying Wang and Robl, \{Jeffrey A.\} and Atwal, \{Karnail S.\} and Zahler, \{Robert L.\} and Parker, \{Rex A.\} and Kirby, \{Mark S.\} and Hamann, \{Lawrence G.\}",

year = "2007",

month = dec,

day = "1",

doi = "10.1016/j.bmcl.2007.09.090",

language = "English",

volume = "17",

pages = "6476--6480",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "23",

}

Simpkins, LM, Bolton, S, Pi, Z, Sutton, JC, Kwon, C, Zhao, G, Magnin, DR, Augeri, DJ, Gungor, T, Rotella, DP, Sun, Z, Liu, Y, Slusarchyk, WS, Marcinkeviciene, J, Robertson, JG, Wang, A, Robl, JA, Atwal, KS, Zahler, RL, Parker, RA, Kirby, MS & Hamann, LG 2007, 'Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors', Bioorganic and Medicinal Chemistry Letters, vol. 17, no. 23, pp. 6476-6480. https://doi.org/10.1016/j.bmcl.2007.09.090

TY - JOUR

T1 - Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors

AU - Simpkins, Ligaya M.

AU - Bolton, Scott

AU - Pi, Zulan

AU - Sutton, James C.

AU - Kwon, Chet

AU - Zhao, Guohua

AU - Magnin, David R.

AU - Augeri, David J.

AU - Gungor, Timur

AU - Rotella, David P.

AU - Sun, Zhong

AU - Liu, Yajun

AU - Slusarchyk, William S.

AU - Marcinkeviciene, Jovita

AU - Robertson, James G.

AU - Wang, Aiying

AU - Robl, Jeffrey A.

AU - Atwal, Karnail S.

AU - Zahler, Robert L.

AU - Parker, Rex A.

AU - Kirby, Mark S.

AU - Hamann, Lawrence G.

PY - 2007/12/1

Y1 - 2007/12/1

N2 - The synthesis and structure-activity relationships of novel dipeptidyl peptidase IV inhibitors replacing the classical cyanopyrrolidine P1 group with other small nitrogen heterocycles are described. A unique potency enhancement was achieved with β-branched natural and unnatural amino acids, particularly adamantylglycines, linked to a (2S,3R)-2,3-methanopyrrolidine based scaffold.

AB - The synthesis and structure-activity relationships of novel dipeptidyl peptidase IV inhibitors replacing the classical cyanopyrrolidine P1 group with other small nitrogen heterocycles are described. A unique potency enhancement was achieved with β-branched natural and unnatural amino acids, particularly adamantylglycines, linked to a (2S,3R)-2,3-methanopyrrolidine based scaffold.

KW - DPP4

KW - Diabetes

KW - GLP-1

KW - Non-nitrile

KW - Serine protease

UR - https://www.scopus.com/pages/publications/35648984498

U2 - 10.1016/j.bmcl.2007.09.090

DO - 10.1016/j.bmcl.2007.09.090

M3 - Article

C2 - 17937986

AN - SCOPUS:35648984498

SN - 0960-894X

VL - 17

SP - 6476

EP - 6480

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 23

ER -

Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors

Abstract

Keywords

UN SDGs

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