Synthesis and bioactivity of substituted indan-1-ylideneaminoguanidine derivatives

Zhang, Rui; Dong, Jin; Xu, Yungen; Hua, Weiming; You, Qidong

doi:10.1016/j.ejmech.2009.04.036

Cited by 7 publications

(2 citation statements)

References 16 publications

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“…The various protocols of α-bromination of cyclopentenone derivatives and its closest analoguesindanoneshave been developed including the basic method using Br 2 in acetic acid, − in ether, − and in some other solvents. − The unfriendly and dangerous nature of bromine, however, urged on the invention of milder conditions making use of manageable reagents such as N -bromosuccinimide (NBS). NBS is known to be a superior brominating agent in terms of the ease of handling and to be used increasingly for α-bromination of carbonyl compounds, including indanone and cyclopentenone derivatives in different solvents and in the presence of a radical initiator such as azabisisobutyronitrile (AIBN) or dibenzoyl peroxide (BPO) , or some acid catalysts such as toluene-4-sulfonic acid, trimethylsilyltrifluoromethanesulfonate. − Tetra - n -butylammonium tribromide, copper(II) bromide, pyridinium tribromide, and some other brominating reagents are less commonly used in the bromination of alkyl carbonyl compounds. − However, despite many methods for the α-bromination of carbonyl compounds the choice of an effective technique of bromination of diarylcyclopentenones bearing thiophene ring is complicated by the presence of several active centers (double bond, π-donor aromatic systems, active methylene groups).…”

Section: Resultsmentioning

confidence: 99%

Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones

et al. 2012

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The bromination of 2,3-diarylcyclopent-2-en-1-ones under various conditions has been studied. It was found that depending on the brominating reagent and nature of solvent the bromine atom can be introduced at the 4- or 5-position of the ethene "bridge", as well as into the aryl moieties. Aryl group bromination is accomplished with such reagents as molecular bromine, N-bromosuccinimide, or tetrabutylammonium tribromide. 5-Bromocyclopentenones with very high efficiency can be obtained by the reaction with copper(II) bromide in methanol, while 4-bromoketones are prepared in n-propyl acetate. The developed methods can be highly useful for the synthesis of bromo-substituted 2-cyclopenten-1-ones and their close analogues, which are important synthons in organic synthesis and for the preparation of a variety of useful substances.

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Section: Resultsmentioning

confidence: 99%

Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones

et al. 2012

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“…Our synthesis of the tricyclic luliconazole analogue 5 starts from 3-(2,4-dichlorophenyl)propionic acid (7), 19 which is cyclized to the dichloroindanone 8 by Friedel-Crafts acylation. 20,21 After the regioselective α-keto-bromination to 9, 22 the reduction of the carbonyl function with sodium borohydride delivers the bicyclic bromohydrin 10. This indanol derivative is then converted into the unstable α-bromomesylate 11, which was then added to the freshly prepared dipotassium dithiolate 14 freshly prepared from 1H-imidazol-1-yl-ylacetonitrile (13), 23,24 carbon disulfide and potassium hydroxide.…”

Section: Figure 1 Lanoconazole (1) and Luliconazole (2) As Well As Their Fungicidally Active Analogues 3-6mentioning

confidence: 99%

Synthesis of Conformationally Locked and C-Linked Analogues of Imidazole-Based Ketene Dithioacetal Fungicides

Gagnepain

Jeanmart²,

Bonvalot³

et al. 2018

Synlett

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First examples with the unknown tricyclic 4,8b-dihydro-3aH-indeno[1,2-d][1,3]dithiole ring system have been prepared. Also, imidazoles linked in ring position 5 to a ketene dithioacetal and 1,3-dithiane derivatives with an exocyclic cyano- and imidazole-substituted C–C double bond are completely new. All these compounds are either conformationally locked, C-linked or six-ring analogues of the antifungal agent luliconazole. Synthesis and fungicidal activity of these sterol biosynthesis inhibitors are reported.

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ChemInform Abstract: Synthesis and Bioactivity of Substituted Indan‐1‐ylidene Aminoguanidine Derivatives.

Zhang

Dong

et al. 2009

ChemInform

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Indan derivatives Q 1050Synthesis and Bioactivity of Substituted Indan-1-ylidene Aminoguanidine Derivatives. -Twenty-one title derivatives like (VI) (no yields given) are prepared to increase the Na + /H + exchangers (NHE) inhibitory activity and to improve the stability of an initial lead compound. Most of the tested compounds possess NHE1 inhibitory effects and derivatives (VI) are markedly superior to cariporide in NHE1 inhibition. Derivative (VIc) also displays superior cardioprotective effects in vivo. -(ZHANG, R.; DONG, J.; XU*, Y.-G.; HUA, W.-Y.; WEN, N.; YOU, Q.-D.; Eur.

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Synthesis and bioactivity of substituted indan-1-ylideneaminoguanidine derivatives

Cited by 7 publications

References 16 publications

Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones

Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones

Synthesis of Conformationally Locked and C-Linked Analogues of Imidazole-Based Ketene Dithioacetal Fungicides

ChemInform Abstract: Synthesis and Bioactivity of Substituted Indan‐1‐ylidene Aminoguanidine Derivatives.

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