6633-28-9Relevant academic research and scientific papers
An atom economical method for the direct synthesis of quinoline derivatives from substituted o-nitrotoluenes
Liu, Guiyan,Yi, Maocong,Liu, Lu,Wang, Jingjing,Wang, Jianhui
, p. 2911 - 2914 (2015/02/19)
A highly efficient one-pot procedure for the preparation of substituted quinolines from substituted o-nitrotoluenes with electron-withdrawing groups and olefins (acrylic esters and acrylonitriles) using a cesium catalyst has been developed. A plausible [2+4] cycloaddition mechanism is proposed. This method uses nitroaromatic compounds as the starting materials to give quinoline derivatives in good to high yields under mild conditions with no transition metal catalysis. It provides an atom economical pathway for the synthesis of quinoline derivatives which could be used in industrial processes.
Synthesis and biological evaluation of substituted N-alkylphenyl-3,5- dinitrobenzamide analogs as anti-TB agents
Munagala, Gurunadham,Yempalla, Kushalava Reddy,Aithagani, Sravan Kumar,Kalia, Nitin Pal,Ali, Furqan,Ali, Intzar,Rajput, Vikrant Singh,Rani, Chitra,Chib, Reena,Mehra, Rukmankesh,Nargotra, Ami,Khan, Inshad Ali,Vishwakarma, Ram A.,Singh, Parvinder Pal
, p. 521 - 527 (2014/04/17)
Here, a medicinal chemistry study of an N-alkylphenyl-3,5-dinitrobenzamide (DNB) scaffold as a potent anti-TB agent is presented. A series of chemical modifications were performed and forty-three new molecules were synthesized to study the structure-activity relationship (SAR) by evaluating against a sensitive strain (H37Rv) of Mycobacterium tuberculosis (MTB). Potent DNB analogs 4b, 7a, 7c, 7d, 7j, 7r and 9a were further tested against resistant strains of MTB. Their intracellular as well as bactericidal potential was also evaluated. Cytotoxicity and in vivo pharmacokinetic studies suggested that DNB analogs have an acceptable safety index, in vivo stability and bio-availability. From the present work, two compounds 7a and 7d have shown nanomolar to sub micro-molar MIC in extracellular and intracellular assays.
Aspartic protease inhibitors via C1-homologation of peptidic aldehydes and studies on reduced amide isosteres
Braun, Hannes A.,Zall, Andrea,Brockhaus, Manfred,Schütz, Marco,Meusinger, Reinhard,Schmidt, Boris
, p. 7990 - 7993 (2008/03/14)
(R)-Configured isophthalic hydroxyethylamines play an important role in the inhibition of β-secretase (BACE1). We present the synthesis of a number of (S)-configured hydroxyethylamine derivatives via 2-iodoethanol intermediates and the comparison with the
A reevaluation of the Hofmann rearrangement in electron deficient systems: Preparation of 2-(15N)amino-4,6-dinitrotoluene and 4-(15N)- amino-2,6dinitrotoluene
Spanggord, Ronald J.,Clizbe, Lane A.
, p. 615 - 621 (2007/10/03)
The Hofmann rearrangement is an excellent synthetic method to introduce amino functions into aromatic molecules; however, it becomes less efficient in electron-deficient systems because of competitive hydrolytic reactions. This report describes the preparation of the aminodinitrotoluenes (ADNTs) 2- (15N)amino-4,6-dinitrotoluene and 4-(15N)-amino-2,6-dinitrotoluene by developing conditions using HPLC as a reaction monitoring technique. Both ADNTs were prepared in >70% yield and >95% isotopic purity by using organic solvents and controlling pH during the formation of N-chlorobenzamides and then performing the rearrangement.
