Synthesis, binding affinity and intrinsic activity of new anilide derivatives of serotonin at human 5-HT(1D) receptors

M. Perez; N. Ayerbe; C. Fourrier; I. Sigogneau; P. J. Pauwels; C. Palmier; G. W. John; J. P. Valentin; S. Halazy

doi:10.1016/S0223-5234(97)87539-3

Synthesis, binding affinity and intrinsic activity of new anilide derivatives of serotonin at human 5-HT(1D) receptors

M. Perez, N. Ayerbe, C. Fourrier, I. Sigogneau, P. J. Pauwels, C. Palmier, G. W. John, J. P. Valentin, S. Halazy

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

7 Scopus citations

Abstract

The design and synthesis of a new series of anilide derivatives of serotonin is described. Binding affinity and intrinsic activity were evaluated at cloned human 5-HT(1Dα), 5-HT(1Dβ) and 5-HT(1A) receptors. Modification of the terminal substituent on the aromatic moiety (R₁) was investigated and optimal affinity, activity and selectivity for 5-HT(1D) versus 5-HT(1A) receptors were obtained for the sulfonamide derivatives 9 and 10. Functional activity was also assessed in the New Zealand white rabbit saphenous vein contraction model, in which most of the compounds behaved as full agonists. Further structural modifications are also described, eg, replacement of the oxygen for carbon atom at the 5-position of the tryptamine moiety or terminal N-dimethylation.

Original language	English
Pages (from-to)	129-134
Number of pages	6
Journal	European Journal of Medicinal Chemistry
Volume	32
Issue number	2
DOIs	https://doi.org/10.1016/S0223-5234(97)87539-3
State	Published - 1997
Externally published	Yes

Keywords

5-HT(1D) receptor agonist
Anilide
Migraine
Serotonin
Sumatriptan

Access to Document

10.1016/S0223-5234(97)87539-3

Cite this

@article{5633560b734d4716a007af0080575511,

title = "Synthesis, binding affinity and intrinsic activity of new anilide derivatives of serotonin at human 5-HT(1D) receptors",

abstract = "The design and synthesis of a new series of anilide derivatives of serotonin is described. Binding affinity and intrinsic activity were evaluated at cloned human 5-HT(1Dα), 5-HT(1Dβ) and 5-HT(1A) receptors. Modification of the terminal substituent on the aromatic moiety (R1) was investigated and optimal affinity, activity and selectivity for 5-HT(1D) versus 5-HT(1A) receptors were obtained for the sulfonamide derivatives 9 and 10. Functional activity was also assessed in the New Zealand white rabbit saphenous vein contraction model, in which most of the compounds behaved as full agonists. Further structural modifications are also described, eg, replacement of the oxygen for carbon atom at the 5-position of the tryptamine moiety or terminal N-dimethylation.",

keywords = "5-HT(1D) receptor agonist, Anilide, Migraine, Serotonin, Sumatriptan",

author = "M. Perez and N. Ayerbe and C. Fourrier and I. Sigogneau and Pauwels, \{P. J.\} and C. Palmier and John, \{G. W.\} and Valentin, \{J. P.\} and S. Halazy",

year = "1997",

doi = "10.1016/S0223-5234(97)87539-3",

language = "English",

volume = "32",

pages = "129--134",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson s.r.l.",

number = "2",

}

TY - JOUR

T1 - Synthesis, binding affinity and intrinsic activity of new anilide derivatives of serotonin at human 5-HT(1D) receptors

AU - Perez, M.

AU - Ayerbe, N.

AU - Fourrier, C.

AU - Sigogneau, I.

AU - Pauwels, P. J.

AU - Palmier, C.

AU - John, G. W.

AU - Valentin, J. P.

AU - Halazy, S.

PY - 1997

Y1 - 1997

N2 - The design and synthesis of a new series of anilide derivatives of serotonin is described. Binding affinity and intrinsic activity were evaluated at cloned human 5-HT(1Dα), 5-HT(1Dβ) and 5-HT(1A) receptors. Modification of the terminal substituent on the aromatic moiety (R1) was investigated and optimal affinity, activity and selectivity for 5-HT(1D) versus 5-HT(1A) receptors were obtained for the sulfonamide derivatives 9 and 10. Functional activity was also assessed in the New Zealand white rabbit saphenous vein contraction model, in which most of the compounds behaved as full agonists. Further structural modifications are also described, eg, replacement of the oxygen for carbon atom at the 5-position of the tryptamine moiety or terminal N-dimethylation.

AB - The design and synthesis of a new series of anilide derivatives of serotonin is described. Binding affinity and intrinsic activity were evaluated at cloned human 5-HT(1Dα), 5-HT(1Dβ) and 5-HT(1A) receptors. Modification of the terminal substituent on the aromatic moiety (R1) was investigated and optimal affinity, activity and selectivity for 5-HT(1D) versus 5-HT(1A) receptors were obtained for the sulfonamide derivatives 9 and 10. Functional activity was also assessed in the New Zealand white rabbit saphenous vein contraction model, in which most of the compounds behaved as full agonists. Further structural modifications are also described, eg, replacement of the oxygen for carbon atom at the 5-position of the tryptamine moiety or terminal N-dimethylation.

KW - 5-HT(1D) receptor agonist

KW - Anilide

KW - Migraine

KW - Serotonin

KW - Sumatriptan

UR - https://www.scopus.com/pages/publications/0031050731

U2 - 10.1016/S0223-5234(97)87539-3

DO - 10.1016/S0223-5234(97)87539-3

M3 - Article

AN - SCOPUS:0031050731

SN - 0223-5234

VL - 32

SP - 129

EP - 134

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 2

ER -

Synthesis, binding affinity and intrinsic activity of new anilide derivatives of serotonin at human 5-HT(1D) receptors

Abstract

Keywords

Access to Document

Fingerprint

Cite this