51927-26-5

Upstream product

• 17496-14-9 2,3-dihydro-2-methyl-1H-inden-1-one 

Downstream Products

• 54553-61-6 5-Amino-2-methylindan 
• 911300-78-2 N-(2-methyl-2,3-dihydro-1H-inden-5-yl)acetamide 

Relevant academic research and scientific papers

Tricyclic [1,2,4]triazine 1,4-dioxides as hypoxia selective cytotoxins

A series of novel tricyclic triazine-di-N-oxides (TTOs) related to tirapazamine have been designed and prepared. A wide range of structural arrangements with cycloalkyl, oxygen-, and nitrogen-containing saturated rings fused to the triazine core, coupled with various side chains linked to either hemisphere, resulted in TTO analogues that displayed hypoxia-selective cytotoxicity in vitro. Optimal rates of hypoxic metabolism and tissue diffusion coefficients were achieved with fused cycloalkyl rings in combination with both the 3-aminoalkyl or 3-alkyl substituents linked to weakly basic soluble amines. The selection was further refined using pharmacokinetic/pharmacodynamic model predictions of the in vivo hypoxic potency (AUCreq) and selectivity (HCD) with 12 TTO analogues predicted to be active in vivo, subject to the achievement of adequate plasma pharmacokinetics.

Indene-based scaffolds. Design and synthesis of novel serotonin 5-HT 6 receptor ligands

A series of novel indene derivatives designed by a scaffold selection gave access to several examples of (Z)-arylmethylideneindenes and indenylsulfonamides that acted as serotonin 5-HT6 receptor ligands. Different synthetic multistep routes could be applied to these target compounds, each with their own complexity and limitations. A reasonable route involved the (3-indenyl)acetic acids as the key intermediates, and two alternatives were also examined. The first protocol used was a two-step sequence employing a modified Horner-Wadsworth-Emmons reaction, but better results were obtained with a procedure based on the condensation of indanones with the lithium salt of ethyl acetate, followed immediately by dehydration with acid and hydrolysis/ isomerization under basic catalysis. (3-Indenyl)acetic acids were transformed to the corresponding acetamides, which were effectively reduced to indenylsulfonamides 13-17 using an optimized procedure with AlH 3-NMe2Et. The binding at the 5-HT6 receptor was with moderate affinity (Ki = 216.5 nM) for the (Z)- benzylideneindenylsulfonamide 12 and enhanced affinity for the simple indenylsulfonamide counterpart 13 (Ki = 50.6 nM). Selected indenylsulfonamides 14-17 were then tested, showing Ki values as low as 20.2 nM. The Royal Society of Chemistry 2008.

TRICYCLIC 1,2,4-TRIAZINE OXIDES AND COMPOSITIONS THEREFROM FOR THERAPEUTIC USE IN CANCER TREATMENTS

The invention relates to novel tricyclic 1,2,4-triazine-1-oxides and novel tricyclic 1,2,4-triazine-1,4-dioxides of formula: (I); and to related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.