Synthesis, azo-hydrazone tautomerism and antitumor screening of N-(3-ethoxycarbonyl-4,5,6,7-tetrahydro-benzo[b]thien-2-yl)-2-arylhydrazono-3-oxobutanamide derivatives

Abstract

A series of new N- (3-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)-2-aryl hydrazono-3-oxobutanamide derivatives 4a-i were synthesized and the acid dissociation constants (pK a s) for the series prepared were determined and correlated by the Hammett-type equation using the enhanced substituent constants σ x -. The results of such correlation together with the spectral data indicated that the studied compounds exist predominantly in the hydrazone tautomeric form. Some of these derivatives exhibit high antitumor activity.

Unexpected Formation of N-(1-(2-Aryl-hydrazono)isoindolin-2-yl)benzamides and Their Conversion into 1,2-(Bis-1,3,4-oxadiazol-2-yl)benzenes

“…Thus, we presume that the formation of the five member ring takes place in the canonical form I of the acyclic isomer 10A by the nucleophilic attack of a negatively charged nitrogen to the electrophilic double bonded CH. Next, the azo form III undergoes an azo-hydrazone tautomerism 35 reaction with the formation of the isolated cyclic isomer 10C.…”

Synthesis and characterization of azobenzene derived from 8-aminoquinoline in aqueous media

“…Azobenzenes are an important class of organic compounds that are widely used as organic dyes (1, 2), protein probes (3,4), chemosensors (5,6), cosmetics (7)(8)(9), nanotubes (10,11) and polymers (12)(13)(14). Due to the presence of N-N linkages, they have been used for pharmacological applications such as antiviral, anti-inflammatory, antimicrobial, antitumor, antidiabetics, and antituberculotic (15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25). Beyond their potential in these application areas, azo-compounds are mostly used as dyes.…”

A novel azo compound derived from ethyl-4-amino benzoate: synthesis, nonlinear optical properties and DFT investigations

“…Further, the azo compounds are reactive compounds, which were reported for their pharmaceutical importance as antineoplastic, antidiabetic [34], anticancer [35] and antibacterial [29]. The theoretical studies on the structure of each synthetic azo compounds were also carried to describe the relation among the molecular structure and the compounds properties [36,37].…”