Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents

Abstract

The synthesis and antiallergic activity of a series of novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles are described. A number of the compounds inhibit the release of histamine from anti-IgE stimulated basophils obtained from allergic donors. Optimal inhibition is exhibited in benzothiophenes with a 3-alkoxy substituent in combination with a 5-methoxy, 6-methoxy, or a 5,6-dimethoxy group. Compound 13c (CI-959) also inhibited respiratory burst of human neutrophils and the release of mediators from anti-IgE-stimulated human chopped lung.

Palladium(II) Catalyzed Cyclization-Carbonylation-Cyclization Coupling Reaction of (ortho-Alkynyl Phenyl) (Methoxymethyl) Sulfides Using Molecular Oxygen as the Terminal Oxidant

“…We are currently investigating further biological studies of the synthesized compounds 2. Benzo [b]thiophene skeletons are an important class of S-heterocycles [15][16][17][18] and are found in a variety of drugs, pesticides, and biologically active compounds that exhibit various interesting biological properties [19][20][21][22][23][24]. Diaryl ketone scaffolds are also important motifs in natural products and pharmaceuticals [25][26][27][28][29][30] (Figure 1).…”

Copper- versus palladium-catalyzed aromatization of 2-(methoxycarbonyl) tetralones: synthesis of methyl 1-hydroxy-2-naphthoates

“…In the case of 7-methoxy substituted α-tetralone 5b naphthoate 1b was obtained in a higher 94% yield under CuI catalyzed conditions ( Table 2, entry 3). However, by using Pd 2 (dba) 3 (1 mol%) the addition of Bu t 3 PHBF 4 (4 mol%) was necessary to achieve a 40% yield (Table 2, entry 4). Naphthoate 1c, with a methoxy group at the 5-position was also obtained in higher yield when CuI was used as catalyst (89% versus 70%, Table 2, entries 5 and 6).…”

“…12 Although, the most direct way for the preparation of these 1-hydroxy-2-naphthoates is the brominationdehydrobromination of 2-substituted α-tetralones 5 bearing an ester group at the 2-position. 2,3,13 Alternatively, dehydrogenation reactions of compounds 5 using an excess of an α-iodoxybenzoic acid derivative 14 or 5% palladium on carbon in refluxing pcymene 6 have been used. We communicate here the first catalyzed direct aromatization 2-(methoxycarbonyl)-α-tetralones (5) to methyl 1-hydroxy-2-naphthoates (1) under very simple and mild conditions using CuI or Pd 2 (dba) 3 as catalysts.…”

Annulation of Eight- to Ten-Membered Oxaza Rings to the Benzo[b]thiophene System by Intramolecular Nucleophilic Displacement

“…Substitution of the 3-chloro group in acid chlorides of type 2 is readily achieved by a nucleophilic addition/elimination sequence. [16] Thus reaction of 2 with sodium methoxide gave the 3-methoxy substituted methyl ester 3, [17] from which the corresponding acid 4 [17] could be obtained by standard alkaline hydrolysis. Amide derivatisation was then achieved via dicyclohexylcarbodiimide-mediated reaction of methyl β-alinate 5 (Y=COOCH 3 , n = 2) with the acid 4 in the case of 6a, and with the commercially available acetal 5 (Y=CH(OCH 2 CH 3 ) 2 , n=3) or the alcohol 5 (Y=CH 2 OH, n= 4), to afford 6c and 6f respectively.…”