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Synthesis of the Naphthalenic Bioisostere of Indorenate. Synthese des Naphthalin‐Bioisosters von Indorenat
Author(s) -
Yous Said,
Depreux Patrick,
Renard Pierre
Publication year - 1993
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19933260210
Subject(s) - bioisostere , chemistry , serotonergic , indole test , stereochemistry , serotonin , agonist , 5 ht receptor , receptor , pharmacology , chemical synthesis , biochemistry , in vitro , biology
The relationships between some physiological processes and central nervous system or peripheral activity of serotonin (5‐HT; A) has resulted in extensive studies of the chemistry and biological properties of many serotoninergic (agonists or antagonists) compounds 1) and the existence of multiple serotoninergic receptors subtypes is supported by pharmacological evidence 2) . So, central 5‐HT binding sites can be classified into 5‐HT 1 (1A, 1B, 1C, 1D), 5‐HT 2 , 5‐HT 3 and 5‐HT 4 subtypes 3,4) There is some basis for considering that central serotoninergic agonists might be antihypertensives acting via 5‐HT 1A receptors 5,6,7) Indorenate ( B ), a synthetic indole. closely related to serotonin, has antihypertensive properties resulting from agonist activity at central serotoninergic receptors with a relatively high affinity for 5‐HT 1A sites 8) . A possible approach in the design of new serotoninergic ligands and more generally new drug candidates may consist in the application of the bioisosteric theory. So, the NH group is a classical bioisostere of the vinyl increment and the naphthalene nacleus could be considered as a bioisostere of the indole ring. Few examples of the naphthalene‐indole bioisosterism have emerged in the lit. 9,10,11) Here we describe the synthesis of the naphthalenic bioisostere C of B (Scheme 1).