Side chain modifications of (indol-3-yl)glyoxamides as antitumor agents

Abstract

New series of analogues of N-(pyridin-4-yl)-2-[1-(4-chlorobenzyl)-indol-3-yl]glyoxamide D-24851 were synthesized, characterized and tested for their in vitro anticancer properties. In the first series, an amino acid spacer was introduced in the glyoxamide chain of D-24851. In the second series, the glyoxamide chain was moved to positions 4 and 5 of indole skeleton. These new compounds were tested on four cancer cell lines (KB, SK-OV-3, NCI-H460 and SF-268), with promising activity for the glycine derivative.

Antiproliferative Homoleptic and Heteroleptic Phosphino Silver(I) Complexes: Effect of Ligand Combination on Their Biological Mechanism of Action

“…Berners-Price and coworkers observed a selective antimitochondrial activity for the tetrahedral diphosphino [Ag(eppe) 2 ]NO 3 derivative (eppe = diethyl-diphenyldiphosphinoethane) [10], and, more recently, various silver derivatives were found able to disrupt mitochondrial homeostasis, causing its imbalance and membrane depolarization [11,12]. This behavior, together with the reported ability of inactivating enzyme thiol groups with formation of mercaptides [13], could be related to an interaction between silver compounds and redox enzymes involved in maintaining healthy mitochondria homeostasis, such the selenoenzyme thioredoxin reductase (TrxR). TrxR is considered an attractive target for development of anticancer agents as it is frequently overexpressed in aggressive cancer cells [14].…”

“…H NMR (DMSO-d 6 ): δ (ppm) 2.33 (m, 6H, CH 2 CN), 2.84 (m, 6H CH 2 P), 6.18 (t, 3H, CH pz ), 7.59 (d, 3H, CH pz ), 7.74 (d, 3H, CH pz ) 31. P{H} NMR (DMSO-d 6 ): δ (ppm) 8.0 (d) (J P-Ag 664 Hz) 13. C{H} NMR (DMSO): δ (ppm) 14.4 (d, CH 2 -P), 21.3 (d, CH 2 -N), 104.7 (s, CH pz ), 120.8 (d, CN), 136.0 (s, CH pz ), 141.6 (s, CH pz )).…”

An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry

“…For these applications, chirality is an important factor. Several methods have been reported for arylamides, including the use of enzymes and flow chemistry [57][58][59][60][61][62][63][64][65][66][67][68][69][70][71], and we believe we are reporting, for the first time, the synthesis of amino acid arylamides in water.…”

Green Synthesis: Novel method for Substituted Anilines from its Benzyl Azides

“…2-methyl-3-nitro-benzoic acid methyl ester 3 (6): To a pre cooled solution of 2-Methyl-3nitrobenzoic acid (1.0 g, 5.5 mmol, 1.0 eq) in DCM (10 mL) was added oxalyl chloride (0.58 mL, 0.84 g, 6.6 mmol, 1.2 eq) and one drop of DMF under nitrogen atmosphere. Stir at 0 o C-RT for 6 h. After completion, quenched the reaction with methanol at 0 o C. Stir at 40 o C for 15 minutes.…”