35970-06-0

Usage

InChI:InChI=1/C15H10N2O/c18-15-12-7-3-2-6-11(12)14-16-13-8-4-1-5-10(13)9-17(14)15/h1-8H,9H2

Upstream product

• 85-44-9 phthalic anhydride 
• 4403-69-4 2-amino-1-benzylamine 
• 1021434-11-6 N-benzyl-N-cyano-2-iodobenzamide 

Relevant academic research and scientific papers

Synthesis of batracylin and its N-sulfonamido analogues in [b-3C-im][NTf2] ionic liquid

Starting with commercial and inexpensive reagents, a high-yielding chemical process carried out in [b-3C-im][NTf2] ionic liquid was achieved to afford the synthesis of batracylin and its N-sulfonamido analogues. Among all compounds synthesized, compounds 1, 11, and 14 exhibit potent inhibitory activity against human topoisomerase 1 (hTop1).

Unprecedented aromatic homolytic substitutions and cyclization of amide-iminyl radicals: Experimental and theoretical study

Amide-iminyl radicals are versatile and efficient intermediates in cascade radical cyclizations of N-acylcyanamides. They are easily trapped by alkenes or (hetero-)aromatic rings and cyclize into a series of new heterocyclic compounds which bear a pyrroloquinazoline moiety. As an illustration of the synthetic importance of these compounds, the total synthesis of the natural antitumor compound luotonin A was achieved through a tin-free radical cascade cyclization process. Not only do amide-iminyl radicals lead to new tetracyclic heterocycles but these nitrogen-centered radical species also react in aromatic homolytic substitutions. Indeed, the amide-iminyl radical moiety unprecedentedly displaces methyl, methoxy, and fluorine radicals from an aromatic carbon atom. This seminal reaction in the field of radical chemistry has been developed experimentally and its mechanism has additionally been investigated by a theoretical study.

Synthesis and pharmacological evaluation of isoindolo[1,2-b]quinazolinone and isoindolo[2,1-a]benzimidazole derivatives related to the antitumor agent batracylin

The synthesis and pharmacological activity of isoindolo[1,2-b]quinazolin- 12(10H)-ones and isoindolo[2,1-a]benzimidazoles related to batracylin are described. The acute toxicity of batracyclin has been associated with the formation of its N-acetyl metabolite which is a potent inducer of unscheduled DNA synthesis in rat hepatocytes. The desamino derivative and the 8-aza analog of batracylin retained the ability to inhibit topoisomerase II but did not induce unscheduled DNA synthesis. While less active than batracylin, these analogs were cytotoxic to CCRF CEM leukemia cells. The isoindolo[2,1- a]benzimidazole derivatives were inactive as topoisomerase II inhibitors and, in general, failed to exhibit comparable antitumor activity or to induce unscheduled DNA synthesis.