63786-62-9

Usage

Chemical structure

Derived from indane-1,3-dione and contains a benzimidazole ring.

Physical appearance

Yellow solid.

Molecular weight

276.29 g/mol.

Potential applications

Medicinal chemistry and pharmacology.

Reasons for interest

Interesting structural features and potential biological activities.

Research status

Further research and investigation needed to fully understand properties and potential uses.

InChI:InChI=1/C16H10N2O2/c19-14-9-5-1-2-6-10(9)15(20)13(14)16-17-11-7-3-4-8-12(11)18-16/h1-8,17-18H

Upstream product

• 615-15-6 2-Methyl-1H-benzimidazole 
• 85-44-9 phthalic anhydride 

Downstream Products

• 136953-27-0 (C₆H₄N₂HCC(CO)2C₆H₄)2Ni(P(C₄H₉)3)2 

Relevant academic research and scientific papers

Synthesis and pharmacological evaluation of 2-(2 and 4- pyridinyl)indane-1,3-diones and structuraly related compounds exerting potential anti-inflammatory and antitumoral activities

Our on going work in the series of enamido-diketones issued from 2- azaarylindane-1,3-diones led us to synthesize and experiment N and C2- substituted derivatives of 2-(2 and 4-pyridinyl)indane-1,3-diones as well as of structurally related compounds resulting from the replacement of pyridine by quinoline and benzimidazole. Pharmacological evaluation of their anti- inflammatory activity (by inhibition of carrageenan foot edema) and their anticoagulant activity (by prothombin assay) led to the conclusion of the possibility of achieving a selective antiinflammatory effect. It has been previously established that anticoagulants are liable to exert a protective effect in the development of cancer metastasis. Nevertheless none of the six experimented 2-(pyridin-2-yl)indane-1,3-diones extended survival time of mice treated by P388 lymphocytic leukemia.

Indane-1,3-diones IX. Synthesis and antiinflammatory activity of 2-polyaza-arylindane-1,3-diones and their N- or O-substituted derivatives

A series of 2 polyaza-arylindane-1,3-diones diversely substituted on the heterocycle and the homocycle were synthetized in order to study their anti-inflammatory activity. These enaminodiketones give in alkaline medium polydent anions which can undergo, in presence of electrophilic agents, C, N or O-substitution. The Mitsunobu reaction proved to be the most useful method in attempts to gain regiospecific attack at nitrogen. Pharmacomodulation by the introduction of an ethyl group on the nitrogen of the basic molecule, eventually coupled with 5-methoxylation on the homocycle, proved to be fruitful in the pyridazinyl, pyrimidinyl and tetrazolyl series. Among the 3 most active molecules 31, 43 and 50, the second one was selected for a more detailed pharmacological study.