1-Indancarboxylic acids. I. Electrophilic substitution reactions of 1-indancarboxylic acid and synthesis of 6-substituted 1-indancarboxylic acids as potential antiinflammatory agents.

Aono, Tetsuya; Kishimoto, Shinji; Araki, Yoshiaki; Noguchi, Shunsaku

doi:10.1248/cpb.25.3198

Cited by 8 publications

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“…The chloroindane methyl ester 34 was prepared by direct chlorination of the indane acid 32 (ref. [24][25][26] and selective recrystallization of 33 (see ESI †) followed by esterication. Coupling with the quinazoline 4b was accomplished via the enolate addition/decarboxylation procedure (vide supra) to give racemic 23b, and chiral HPLC resolution afforded the nal product 27.…”

Section: Resultsmentioning

confidence: 99%

Small-molecule phosphodiesterase probes: discovery of potent and selective CNS-penetrable quinazoline inhibitors of PDE1

et al. 2014

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Section: Resultsmentioning

confidence: 99%

Small-molecule phosphodiesterase probes: discovery of potent and selective CNS-penetrable quinazoline inhibitors of PDE1

et al. 2014

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“…Substituted 3-oxo-indan-1-carboxylic acid (2) have been converted to the corresponding indan-1-carboxylic acid (3) by Clemmensen reaction employing zinc amalgam, a hazardous reagent, as the reducing reagent 2,6,7 . Olah 8 had reported trifluoromethanesulfonic acid/triethylsilane as a hydrogenation reagent for the reduction of diaryl and alkyl, aryl ketones to hydrocarbons.…”

Section: Resultsmentioning

confidence: 99%

An Improved Synthesis of Substituted Indan-1-Carboxylic Acid

Zhang

Cao

et al. 2011

Journal of Chemical Research

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Substituted indan-1-carboxylic acid compounds have been prepared by clyclisation of the phenyl succinic acid and reduction of the indanon-1-carboxylic acid with triethylsilane in trifluoracetic acid.Keyword: indan-1-carboxylic acid, anti-inflammatory, analgesic, triethylsilane Compounds containing indan or 2,3-dihydro-1H-inden-1-one ring systems have been studied recently in the context of the synthesis of compounds with anti-inflammatory and analgesic properties. Juby et al. 1 had reported that a series of indan-1carboxylic acid derivatives, especially the compound TAI-284 (Brand name, Clidanac), exhibited potent anti-inflammatory, analgesic and antipyretic activity. It was introduced as an antiinflammatory and analgesic drug in 1981. Das 2 observed that the writhing of Swiss albino mice induced by acetic acid was significantly reduced by 6-fluoro-3-oxoindan-1-carboxylic acid and 6-fluoroindan-1-carboxylic acid, in a dose dependent manner. In addition, halogen substituted 5-(indan-1'-yl)-tetrazoles prepared from substituted indan-1-carboxylic acid by Bachar 3 were also found to possess analgesic activity. The preparation of substituted indan-1-carboxylic acids has become increasingly important and we wished to develop a convenient synthetic route to indan derivatives.The synthesis of substituted indan-1-carboxylic acids reported by several workers 2,4-6 was mainly focused on a procedure starting from substituted phenylsuccinic acids (Scheme 1). This route had several weak points involving time-consuming procedures and inconvenient operations. Moreover, some * Correspondent.Scheme 1 Synthesis of substituted indan-1-carboxylic acid from the appropriate phenylsuccinic acid.Scheme 2 An improved and convenient synthesis of substituted indan-1-carboxylic acids.

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“…4-Chloroindan-1-carboxylic acid (4a), 5-chloroindan-1-carboxylic acid (4b), 6-chloroindan-1-carboxylic acid (4c), 7-chloroindan-1-carboxylic acid (4d), 4-bromoindan-1-carboxylic acid (6b) and 6-bromoindan-1-carboxylic acid (6a) were synthesized by Aono et al [19].…”

Section: Indan-1-carboxylic Acidsmentioning

confidence: 99%

“…Synthesis of various chloroindan-1-carboxylic acids Aono et al [19] also reported the synthesis of chloroindan-1-carboxylic acids (4a-d) using a different synthetic approach (Scheme 2). Chlorination of indan-1-carboxylic acid (5) produced these compounds.…”

Section: Indan-1-carboxylic Acidsmentioning

confidence: 99%

“…Indan-1-acetic acid (18a), 6-methoxyindan-1-acetic acid (18b) and 5,6-dimethoxyindan-1-acetic acid (18c) were refluxed with SOCl2 to obtain various indan-1-acetyl chlorides (19), which were then dissolved in dry ether, added slowly to a cold ethereal solution of diazomethane (CH2N2) under reflux. The mixtures were stirred continuously and kept below 5°C during addition, and allowed to stand overnight at r.t.…”

Section: Indan-1-acetic Acidsmentioning

confidence: 99%

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Synthesis and structure-activity-relationships of indan acid derivatives as analgesic and anti-inflammatory agents

2016

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1-Indancarboxylic acids. I. Electrophilic substitution reactions of 1-indancarboxylic acid and synthesis of 6-substituted 1-indancarboxylic acids as potential antiinflammatory agents.

Cited by 8 publications

References 0 publications

Small-molecule phosphodiesterase probes: discovery of potent and selective CNS-penetrable quinazoline inhibitors of PDE1

Small-molecule phosphodiesterase probes: discovery of potent and selective CNS-penetrable quinazoline inhibitors of PDE1

An Improved Synthesis of Substituted Indan-1-Carboxylic Acid

Synthesis and structure-activity-relationships of indan acid derivatives as analgesic and anti-inflammatory agents

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