774-89-0Relevant academic research and scientific papers
Utility of anthranilic acid and diethylacetylenedicarboxylate for the synthesis of nitrogenous organo/organometallic compounds as urease inhibitors
El-Zahabi, Heba S. A.,Abdulwahab, Hanan G.,Edrees, Mastoura M.,Hegab, Amany M.
, (2019/07/08)
Fumarate diester 3 was synthesized upon reacting anthranilic acid with diethylacetylenedicarboxylate. Compound 3 was reacted with different nucleophiles in mild reaction conditions. Selected reaction routes that afforded products 6, 9, 10, 11, and 12 were explained. The estimated mechanism for the reaction of 3 with ethylenediamine to afford 9 was proved by X-ray single-crystal and retro-synthetic reaction. Acetyl anthranilic acid was utilized with zinc and copper to afford the organometallic compounds 14a and 14b, respectively. Three single crystals were afforded for 3, 9 and the organocopper complex 14b. Target compounds were screened for their inhibitory potential against urease enzyme. Most compounds were more potent than thiourea as standard inhibitor, considering that oxopiperazine 9 exhibited double the activity: IC50 = 8.16 ± 0.65 μM (thiourea IC50 = 20.04 ± 0.33 μM). Docking studies were in agreement with the in vitro enzyme assay.
REACTION OF 1,2-DIAMINES WITH β-KETO ESTERS
Bagrov, F. V.
, p. 1768 - 1770 (2007/10/03)
The reaction of 1,2-diamines (o-phenylenediamine and 1,2-diaminoethane) with oxobutanedioic esters leads to the closure of a six-membered heterocycle.In the crystalline state and in solution the condensation products exist exclusively in the form of the enamine tautomer.In chloroform 1,4-di(ethoxycarbonyl)cyclopentane-2,3-dione represents a tautomeric mixture of the dienol and ketoenol in a ratio of 59:41.With 1,2-diamines it only reacts through the ketone carbonyls with the formation of piperazine derivatives, stabilized by intramolecular hydrogen bonds.
