41734-55-8

Usage

Uses

Used in Research and Pharmaceutical Industry:
5-NITROINDENE is utilized as a building block in the synthesis of various organic compounds, playing a crucial role in the development of new pharmaceuticals and other chemical products.
Used in Dye and Pigment Production:
5-NITROINDENE is employed in the production of dyes and pigments, where its chemical properties contribute to the color and stability of the final products.
Used in Pharmaceutical Intermediates:
5-NITROINDENE serves as an intermediate in the pharmaceutical industry, facilitating the creation of intermediate compounds that are essential for the synthesis of various medications.

InChI:InChI=1/C9H7NO2/c11-10(12)9-5-4-7-2-1-3-8(7)6-9/h1,3-6H,2H2

Upstream product

• 83-33-0 inden-1-one 
• 24623-24-3 6-nitroindan-1-one 
• 496-11-7 INDANE 
• 7732-18-5 water 
• 185230-66-4 6-nitro-indan-1-ylamine; hydrochloride 
• 7647-01-0 hydrogenchloride 
• 119273-81-3 6-nitro-2,3-dihydro-1H-inden-1-ol 

Downstream Products

• 24425-40-9 indan-5-amine 
• 13058-73-6 7-nitroisoquinoline 
• 16513-67-0 5-nitro-2,3-dihydro-1H-inden-2-ol 
• 75476-79-8 5-Iodoindene 
• 75476-83-4 7-Iodoisoquinoline 
• 59856-06-3 5-acetamidoindane 

Relevant academic research and scientific papers

Benzo heterocyclic derivatives, their preparation and their use in medicine (by machine translation)

The present invention relates to benzo heterocyclic derivatives, their preparation and their use in medicine. In particular, the invention relates to a general formula (I) indicated by the compound, the compound has anti-tumor of the use, the inhibition of angiogenesis and as the role of the HIF - 1 α inhibitors in the medical application. Wherein the general formula (I) of each substituent in the definition in the description of the same. (by machine translation)

Design, synthesis and evaluation of indene derivatives as retinoic acid receptor α agonists

A series of novel indene-derived retinoic acid receptor α (RARα) agonists have been designed and synthesized. The use of receptor binding, cell proliferation and cell differentiation assays demonstrated that most of these compounds exhibited moderate RARα binding activity and potent antiproliferative activity. In particular, 4-((3-isopropoxy-2,3-dihydro-1H-inden-5-yl)-carbamoyl) benzoic acid (36d), which showed a moderate binding affinity, exhibited a great potential to induce the differentiation of NB4 cells (68.88% at 5 μM). Importantly, our work established indene as a promising skeleton for the development of novel RARα agonists.

Development of a practical synthesis of an aminoindanol-derived m1 agonist

An efficient and scalable synthesis of the clinical candidate 1 is described. The first-generation synthesis built the enantioenriched nitro-aminoindanol core from 6-nitroindanone using a five-step literature route. The second-generation route used a safe aromatic nitration protocol in the presence of the unprotected alcohol to afford the requisite nitro-aminoindanol in one step. Challenges addressed in the remainder of the synthesis include a nitro group reduction to afford ppm levels of unreacted Ar-NO2 (a mutagen) and a novel amidine formation under mild conditions via DMAP/K2CO3-promoted reaction with a thioimidate-activated amide. A convenient protocol for freebasing the API was provided by stirring with solid K2CO3 and monitoring disappearance of HI by reverse-phase HPLC.

Aryl sulfonamido indane inhibitors of the Kv1.5 ion channel

A collection of aryl sulfonamido indanes based on the lead compound 1 was synthesized and evaluated for Kv1.5 inhibitory activity. Kv1.5 inhibitors have the potential to be atrium-selective agents for treatment of atrial fibrillation. (1R,2R)-1 has an IC50 of 0.033 μM against Kv1.5 and is selective against other cardiac ion channels, including hERG.

Photoaddition of Water and Alcohols to 3-Nitrostyrenes. Structure-Reactivity and Solvent Effects

The photoadditions of water and several alcohols to the triplet excited states of 3-nitrostyrenes 1, 3-5, and 8 to give the corresponding anti-Markovnikov addition products are reported.Both 3- and 4-nitrostilbenes (6 and 7, respectively) do not undergo photoaddition on direct or sensitized irradiation in aqeous or alcohol solutions; only trans to cis photoisomerisation is observed.It is proposed that for the nitrostilbenes, efficient twisting of the alkene in the triplet excited state competes favorably with photoaddition.The efficient photoaddition of the water and methanol observed for 5-nitroindene (8)-the alkene moiety of which cannot attain an orthogonal ("twisted") state-is taken as additional evidence that these photoadditions probably occur via the planar triplet state and that twisting results in only deactivation to the ground state.The use of cosolvents (CH3CN and HCONH2) on several photoadditions is also reported.For example, use of CH3CN cosolvent in aqueous solution decreases the efficiency of photohydration in the parent 3-nitrostyrene (1) but is observed to enhance the efficiency of reaction (until about 40-70 mol percent CH3CN, depending on the substrate) for 3, 4, and 8.Quantum yields for photohydration and photoaddition of alcohols are reported for several systems.