Reference

Synthesis and narcotic agonist-antagonist evaluation of some 2,6-methano-3-benzazocine-11-propanols

Synthesis and narcotic agonist-antagonist evaluation of some 2,6-methano-3-benzazocine-11-propanols. Analogs of the ring C bridged oripavine-7-methanols. Michne, William F.; Salsbury, Ronald L.; Michalec, Stephen J. (Sterling-Winthrop Res. Inst., Rensselaer, N.Some commonly used reagents like 62249-93-8 and 62215-86-5 are used in this experiment. Y., USA). J. Med. Chem., 20(5), 682-6 (English) 1977. CODEN: JMCMAR. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacodynamics) Section cross-reference(s): 31 Eighteen title compds. (I:R1=Me, Et, Pr, Bu, tert-Bu; R2=Me, cyclopropylmethyl; R3=H, Me) were prepd. from 4-methyl- [23662-66-0] or3,4-dimethyl-1-(phenylmethyl)pyridinium chloride [22185-44-0] by Grignard reaction with 4-methoxyphenylmethyl chloride [824-94-2] followed by cyclization reaction with CH2:CHCO2Et, cyclization withHF to the methanolbenzoquinoline deriv., sapon., reaction with MeLi to give a ketone, ring cleavage, reaction with alkyl Li to give a carbinol, deprotection, and N-alkylation. In the mouse acetylcholine writhing test for narcotic agonist activity and the rat phenazocine antagonism test, the compds. were generally weak agonists but potent antagonists. Structure-activity relations are discussed. .

Relationship between the electrophilicity of substituting agents and substrate selectivity in Friedel-Crafts reactions

Meneses, L.; Fuentealba, P.; Contreras, R. 824-94-2 and 35730-09-7 are also occured in this study. (Departamento de Quimica, Facultad de Ciencias, Universidad de Chile, CasillaSantiago 653, Chile). Tetrahedron, 61(4), 831-836 (English) 2005 Elsevier B.V. CODEN: TETRAB. ISSN: 0040-4020. DOCUMENT TYPE: Journal CA Section: 22 (Physical Organic Chemistry) The global electrophilicity index evaluated at the ground state of benzylating and acylating agents shows a quant. linear relationship with the exptl. substrate selectivity index evaluated for a series of Friedel-Crafts reactions. The theor. scale correctly accounts for the electrophilic activation/deactivation effects promoted by electron withdrawing and electron releasing substituents in these mols. The predicted substrate selectivity values estd. from the knowledge of the electrophilicity index may become accurate to within 10% and less. .