Synthesis and contractile of new acetylenic and allenic analogues of leukotrienes C4 and D4: Importance of the Z-11, 12 double bond

J. P. Lellouche; F. Aubert; J. P. Beaucourt; E. Rechencq; G. Niel; J. P. Girard; J. C. Rossi; M. Boucard

doi:10.1016/0090-6980(89)90034-8

Synthesis and contractile of new acetylenic and allenic analogues of leukotrienes C₄ and D₄: Importance of the Z-11, 12 double bond

J. P. Lellouche, F. Aubert, J. P. Beaucourt, E. Rechencq, G. Niel, J. P. Girard, J. C. Rossi, M. Boucard

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2 Scopus citations

Abstract

The (5S,6R) isomers of new acetylenic and allenic analogues of leukotrienes C₄ and D₄ were synthesized for comparative pharmacological studies on intestinal smooth muscle preparations. These new analogues are poor spasmogenic agonists, the replacement of the 11,12-ene with a relatively more stable triple bond causing an important reduction in intrinsic activity. They did not show any significant antagonist activity. Unexpectedly, these results prove that the 11,12 portion in the triene structure of the lipophilic chain is critical for an agonist activity.

Original language	English
Pages (from-to)	93-103
Number of pages	11
Journal	Prostaglandins
Volume	37
Issue number	1
DOIs	https://doi.org/10.1016/0090-6980(89)90034-8
State	Published - Jan 1989
Externally published	Yes

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title = "Synthesis and contractile of new acetylenic and allenic analogues of leukotrienes C4 and D4: Importance of the Z-11, 12 double bond",

abstract = "The (5S,6R) isomers of new acetylenic and allenic analogues of leukotrienes C4 and D4 were synthesized for comparative pharmacological studies on intestinal smooth muscle preparations. These new analogues are poor spasmogenic agonists, the replacement of the 11,12-ene with a relatively more stable triple bond causing an important reduction in intrinsic activity. They did not show any significant antagonist activity. Unexpectedly, these results prove that the 11,12 portion in the triene structure of the lipophilic chain is critical for an agonist activity.",

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year = "1989",

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AU - Aubert, F.

AU - Beaucourt, J. P.

AU - Rechencq, E.

AU - Niel, G.

AU - Girard, J. P.

AU - Rossi, J. C.

AU - Boucard, M.

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AB - The (5S,6R) isomers of new acetylenic and allenic analogues of leukotrienes C4 and D4 were synthesized for comparative pharmacological studies on intestinal smooth muscle preparations. These new analogues are poor spasmogenic agonists, the replacement of the 11,12-ene with a relatively more stable triple bond causing an important reduction in intrinsic activity. They did not show any significant antagonist activity. Unexpectedly, these results prove that the 11,12 portion in the triene structure of the lipophilic chain is critical for an agonist activity.

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Synthesis and contractile of new acetylenic and allenic analogues of leukotrienes C₄ and D₄: Importance of the Z-11, 12 double bond

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