Synthesis and pharmacological profile of a series of 2,5-substituted-N,N-dimethyltryptamine derivatives as novel antagonists for the vascular 5-HT1B-like receptor

Recent developments in indole ring synthesis—methodology and applications

“…Both 2-and 3-methylindole can be synthesized in good yields (70%, 69%) from the corresponding o-nitrostyrenes, and indole is obtained in 55% yield. This research group has also used this methodology to synthesize the indole alkaloids cryptosanguinolentine (33) and cryptotackieine (34) from the common starting azide 32 (Scheme 41). 157 A very similar strategy to synthesize the alkaloids 33 and 34 was reported earlier by Timári et al 158 Depending on the solvent, the photolysis of 2-amino-2Јazidobiphenyl yields small amounts of 4-aminocarbazole and 4,10-dihydroazepino[2,3-b]indole, amongst two non-indolic products.…”

Synthesis of 5-alkynylated d4T Analogues as Potential HIV-1 Reverse Transcriptase Inhibitors

“…Condensation of 5 0 -O-acetyl-5-iodo-d4U 1 with N-trifluoroacetyl propargylamine 14 28 gave as major product the expected C-5 substituted d4U 16 isolated in 47% yield after purification by chromatography. Using the N-Boc propargylamine 15 29 , we similarly obtained compound 17 in 53% yield. All structures were confirmed by analytical and spectroscopic data (see chemical procedures in experimental section).…”

X‐ray Structures and Thermodynamics of the Interaction of PA‐IIL from Pseudomonas aeruginosa with Disaccharide Derivatives

“…135.3, 137.1, 137.7, 138.3, 138.4, 165.9, 167.6, 171.5 ppm. ESI-MS: À4 mol) and N-Boc-protected propargylamine 5 [29] (32.1 mg, 2.1 10 À4 mol, 1.2 equiv) in a mixture tert-butanol/water (v/v 1:1, 0.04 m). The solution was milky white.…”

“…1 tert-Butyl [1-(tri-O-benzyl-a-l-fucopyranosyl-(1!4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-b-d-glucopyranosyl)-1H-1,2,3-triazol-4yl]methylcarbamate 9. Copper sulfate (8.6 mg, 3.4 10 À5 mol, 0.2 equiv) and ascorbic acid (13.6 mg, 6.9 10 À5 mol, 0.4 equiv) was added to a solution of the disaccharide 3 (150.0 mg, 1.7 10 À4 mol) and N-Boc-protected propargylamine 5 [29] (32.1 mg, 2.1 10 À4 mol, 1.2 equiv) in a mixture tert-butanol/water (v/ v 1:1, 0.04 m). The solution was milky white.…”

“…Next, the regioselective cycloadditions were done under the improved copper(I)-catalyzed conditions which allowed the clean formation of the 1,4-regioisomers. [28] Thus, addition of an aqueous solution of copper(II) sulfate-sodium ascorbate to a mixture of disaccharide 3 and alkynes 4, 5, [29] or 6 (1.2 equiv) in tert-butanol/water (v/v 1:1) at room temperature, resulted in the clean formation of the 1,4-regioisomers 7, 9, and 10, respectively. As the reactions were carried out at room temperature, the reactions between 3 and propargyl alcohol 4 or N-Boc-propargylamine 5 were complete after 16-18 h, providing 7 and 9 in good yields (80 % and 89 %, respectively).…”