Synthesis and dopamine receptor modulating activity of unsubstituted and substituted triproline analogues of L-prolyl-L-leucyl-glycinamide (PLG)

Paul W. Baures; Ashish Pradhan; William H. Ojala; William B. Gleason; Ram K. Mishra; Rodney L. Johnson

doi:10.1016/S0960-894X(99)00386-8

Synthesis and dopamine receptor modulating activity of unsubstituted and substituted triproline analogues of L-prolyl-L-leucyl-glycinamide (PLG)

Paul W. Baures
, Ashish Pradhan
, William H. Ojala
, William B. Gleason
, Ram K. Mishra
, Rodney L. Johnson

Medicinal Chemistry

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

19 Scopus citations

Abstract

Triprolines Pro-Pro-Pro-NH₂ (4), Pro-Pro-D-Pro-NH₂ (5), Pro-Pro(trans- 3-Me)-D-Pro-NH₂ (6), and Pro-Pro(cis-3-Me)-D-Pro-NH₂ (7) were made as conformationally constrained analogues of Pro-Leu-Gly-NH₂. Triprolines 4-6 produced significant increases in the high- and low-affinity state ratio (R(H)/R(L)) of the dopamine receptor, but only 4 was found to increase apomorphine induced rotations in 6-hydroxydopamine-lesioned rats.

Original language	English (US)
Pages (from-to)	2349-2352
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	9
Issue number	16
DOIs	https://doi.org/10.1016/S0960-894X(99)00386-8
State	Published - Aug 16 1999

Bibliographical note

Funding Information:
Acknowledgment: This work was supportedin part by an NIH grant (NS20036)t o R.L.J. and an NIH predoctoratrl aineeshi(pG M07994)t o P.W.B. The authorsth ankT om Crick for masss pectraal nalyses.

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title = "Synthesis and dopamine receptor modulating activity of unsubstituted and substituted triproline analogues of L-prolyl-L-leucyl-glycinamide (PLG)",

abstract = "Triprolines Pro-Pro-Pro-NH2 (4), Pro-Pro-D-Pro-NH2 (5), Pro-Pro(trans- 3-Me)-D-Pro-NH2 (6), and Pro-Pro(cis-3-Me)-D-Pro-NH2 (7) were made as conformationally constrained analogues of Pro-Leu-Gly-NH2. Triprolines 4-6 produced significant increases in the high- and low-affinity state ratio (R(H)/R(L)) of the dopamine receptor, but only 4 was found to increase apomorphine induced rotations in 6-hydroxydopamine-lesioned rats.",

author = "Baures, \{Paul W.\} and Ashish Pradhan and Ojala, \{William H.\} and Gleason, \{William B.\} and Mishra, \{Ram K.\} and Johnson, \{Rodney L.\}",

note = "Funding Information: Acknowledgment: This work was supportedin part by an NIH grant (NS20036)t o R.L.J. and an NIH predoctoratrl aineeshi(pG M07994)t o P.W.B. The authorsth ankT om Crick for masss pectraal nalyses.",

year = "1999",

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doi = "10.1016/S0960-894X(99)00386-8",

language = "English (US)",

volume = "9",

pages = "2349--2352",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Synthesis and dopamine receptor modulating activity of unsubstituted and substituted triproline analogues of L-prolyl-L-leucyl-glycinamide (PLG)

AU - Baures, Paul W.

AU - Pradhan, Ashish

AU - Ojala, William H.

AU - Gleason, William B.

AU - Mishra, Ram K.

AU - Johnson, Rodney L.

N1 - Funding Information: Acknowledgment: This work was supportedin part by an NIH grant (NS20036)t o R.L.J. and an NIH predoctoratrl aineeshi(pG M07994)t o P.W.B. The authorsth ankT om Crick for masss pectraal nalyses.

PY - 1999/8/16

Y1 - 1999/8/16

N2 - Triprolines Pro-Pro-Pro-NH2 (4), Pro-Pro-D-Pro-NH2 (5), Pro-Pro(trans- 3-Me)-D-Pro-NH2 (6), and Pro-Pro(cis-3-Me)-D-Pro-NH2 (7) were made as conformationally constrained analogues of Pro-Leu-Gly-NH2. Triprolines 4-6 produced significant increases in the high- and low-affinity state ratio (R(H)/R(L)) of the dopamine receptor, but only 4 was found to increase apomorphine induced rotations in 6-hydroxydopamine-lesioned rats.

AB - Triprolines Pro-Pro-Pro-NH2 (4), Pro-Pro-D-Pro-NH2 (5), Pro-Pro(trans- 3-Me)-D-Pro-NH2 (6), and Pro-Pro(cis-3-Me)-D-Pro-NH2 (7) were made as conformationally constrained analogues of Pro-Leu-Gly-NH2. Triprolines 4-6 produced significant increases in the high- and low-affinity state ratio (R(H)/R(L)) of the dopamine receptor, but only 4 was found to increase apomorphine induced rotations in 6-hydroxydopamine-lesioned rats.

UR - https://www.scopus.com/pages/publications/0033575676

UR - https://www.scopus.com/pages/publications/0033575676#tab=citedBy

U2 - 10.1016/S0960-894X(99)00386-8

DO - 10.1016/S0960-894X(99)00386-8

M3 - Article

C2 - 10476867

AN - SCOPUS:0033575676

SN - 0960-894X

VL - 9

SP - 2349

EP - 2352

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 16

ER -

Synthesis and dopamine receptor modulating activity of unsubstituted and substituted triproline analogues of L-prolyl-L-leucyl-glycinamide (PLG)

Abstract

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