56461-20-2

Usage

Uses

Used in Pharmaceutical Industry:
1-Oxo-indan-4-carboxylic acid is used as a reactant for the preparation of dihydroindenopyrazoles, which are multitargeted receptor tyrosine kinase inhibitors. These inhibitors play a crucial role in the development of targeted therapies for various diseases, including cancer, by blocking the activity of specific enzymes involved in cell signaling pathways.

InChI:InChI=1S/C10H8O3/c11-9-5-4-6-7(9)2-1-3-8(6)10(12)13/h1-3H,4-5H2,(H,12,13)

Upstream product

• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 612-40-8 2-carboxycinnamic acid 
• 447-53-0 1,2-Dihydronaphthalene 
• 91-20-3 naphthalene 
• 612-17-9 1,4-dihydronaphthalene 
• 15115-60-3 4-bromo-2,3-dihydroinden-1-one 

Downstream Products

• 56461-76-8 4-p-Fluorbenzoyl-1-indanon 
• 56461-77-9 4-p-Brombenzoyl-1-indanon 
• 68569-88-0 4-p-t-Butylbenzoyl-1-indanon 
• 56461-16-6 4-(p-chlorobenzoyl)indan-1-one 
• 56461-09-7 4-(p-toluoyl)indan-1-one 
• 56461-74-6 4-(2',4',6'-Trimethylbenzoyl)-1-indanon 
• 56461-08-6 4-benzoylindan-1-one 
• 55934-10-6 methyl 1-oxo-2,3-dihydro-1H-indene-4-carboxylate 
• 1213591-14-0 1-amino-2,3-dihydro-1H-indene-4-carbonitrile 
• 1213099-69-4 (S)-(1-amino-2,3-dihydro-1H-indene-1-yl)-4-carbonitrile 
• 68569-94-8 4-(2,4,6-Trimethyl-benzoyl)-1-indancarbonsaeure 
• 56461-39-3 4-p-t-Butylbenzoyl-1-indancarbonsaeure 
• 56461-47-3 4-(2,4,6-Trimethylbenzoyl)-1-indancarboxamid 
• 56461-38-2 4-(3'-Methyl-4'-chlor-benzoyl)-1-indancarbonsaeure 

Relevant academic research and scientific papers

Synthesis, biological evaluation and molecular docking studies of indeno [1, 2-c] pyrazol derivatives as inhibitors of mitochondrial malate dehydrogenase 2 (MDH2)

Hypoxia inducible factor-1 (HIF-1) is a pivotal transcription factor, which is strongly correlated with the induction of angiogenesis, tumor survival, metastasis, and cell proliferation, making it a pivotal therapeutic target for solid tumor therapeutic agents. Herein, a new series of multi-functional chemical probes were designed including principal groups, viz. adamantyl and indene, at various locations of the parent compound LW6. Molecular docking studies were performed on the designed compounds and their relationship with HIF-1α and malate dehydrogenase 2 (MDH2). Inhibition of MDH2 by our compounds was expected to decrease the NADH level. Indeed, treatment of the breast cancer cell line 4T1 led to a strong reduction of the NADH concentration. The greatest reduction in NADH production in mitochondria was observed with (E)-3-(4-((3r, 5r, 7r)-adamantan-1-yl) phenoxy)-N-(5-(piperidine-1-carbonyl)-1, 4-dihydroindeno [1, 2-c] pyrazol-3-yl) acrylamide (18: IC50 = 59 nM), and has the best inhibitory potential under hypoxic conditions (MCF-7: IC50 = 57 nM). This compound also gave one of the highest docking “higher than the score obtained with LW6 in parallel (?31.63 kcal/mol) in the initial docking runs (PDB Code: 4WLO). Other related compounds with good yields were also synthesized from docking results, and all the synthesized compounds (14, 18, 22, 26, 29, 30) were evaluated in vitro on human adenocarcinoma cell lines.

Chemoenzymatic Synthesis of a Chiral Ozanimod Key Intermediate Starting from Naphthalene as Cheap Petrochemical Feedstock

Ozanimod represents a recently developed, promising active pharmaceutical ingredient (API) molecule in combating multiple sclerosis. Addressing the goal of a scalable, economically attractive, and technically feasible process for the manufacture of this drug, a novel alternative synthetic approach toward (S)-4-cyano-1-aminoindane as a chiral key intermediate for ozanimod has been developed. The total synthesis of this intermediate is based on the utilization of naphthalene as a readily accessible, economically attractive, and thus favorable petrochemical starting material. At first, naphthalene is transformed into 4-carboxy-indanone within a four-step process by means of an initial Birch reduction, followed by an isomerization of the C=C double bond, oxidative C=C cleavage, and intramolecular Friedel-Crafts acylation. The transformation of the 4-carboxy-indanone into (S)-4-cyano-1-aminoindane then represents the key step for introducing the chirality and the desired absolute S configuration. When evaluating complementary biocatalytic approaches based on the use of a lipase and transaminase, respectively, the combination of a chemical reductive amination of the 4-carboxyindanone followed by a subsequent lipase-catalyzed resolution turned out to be the most efficient route, leading to the desired key intermediate (S)-4-cyano-1-aminoindane in satisfactory yield and with excellent enantiomeric excess of 99%.

SUBSTITUTED BICYCLIC COMPOUNDS AS INHIBITORS OF EZH2

The present invention provides compounds of formula 1, isotopic forms, stereoisomers or tautomers thereof, or pharmaceutically acceptable salts, solvates, N-oxides, S-oxides and polymorphs thereof, and processes for their preparation. The invention further relates to pharmaceutical compositions containing said compounds and their use in the treatment of diseases or disorders mediated by EZH2 (enhancer of zeste homolog 2), particularly cancer.

Synthesis and biological evaluation of 5-substituted 1,4-dihydroindeno[1,2-c]pyrazoles as multitargeted receptor tyrosine kinase inhibitors

We report the synthesis and biological evaluation of 5-substituted 1,4-dihydroindeno[1,2-c]pyrazoles as multitargeted kinase inhibitors. Initial efforts focused on the development of selective KDR inhibitors, while later strategies involved the improvement of potency toward multiple kinase targets. Thus, several compounds were identified as potent KDR, Flt1, Flt3, and c-Kit inhibitors.

TRICYCLIC PYRAZOLE KINASE INHIBITORS

Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

5H, 10H-IMIDAZO[1,2-A]INDENO[1,2-E] PYRAZIN-4-ONE DERIVATIVES, PREPARATION THEREOF, AND DRUGS CONTAINING SAID DERIVATIVES

Compounds of formula (I), wherein R is a hydrogen atom or a carboxy, alkoxycarbonyl,--CO--NR 4 R 5,--PO 3 H 2 or--CH 2 OH radical, and R 1 is an-alk-NH 2,-alk-NH--CO--R 3,-alk-COOR 4,-alk-CO--NR 5 R 6 or--CO--NH--R 7 radical. The compounds of formula (I) have valuable pharmacological properties and are antagonists of the α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor also known as the quisqualate receptor. Furthermore, the compounds of formula (I) are non-competitive antagonists of the N-methyl-D-aspartame (NMDA) receptor and more specifically are ligands for NMDA receptor glycine modulator sites.

Synthesis based on Cyclohexadienes. Part-271. Synthesis of Functionalized Tricyclo[5.2.2.01,5]undecanes

A new methodology for the construction of tricyclo[5.2.2.01,5]undecanes is described from indane-4-carboxylic acids. Birch reduction of indane-4-carboxylic acids followed by conjugation and cycloaddition with α-ehloroacrylonitrile and hydrolysi