Synthesis and reactivity of formyl-substituted photochromic 3,3-diphenyl-[3H]-naphtho[2,1-b]pyrans

Chamontin, Karine; Lokshin, Vladimir; Rossollin, Valérie; Samat, A.; Guglielmetti, R.

doi:10.1016/s0040-4020(99)00245-8

Cited by 33 publications

(16 citation statements)

References 19 publications

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“…Dibenzylation of 3,4-dihydroxybenzaldehyde with potassium carbonate and benzyl bromide 24 produced aldehyde 9h , and similarly, methylation of 4-hydroxynaphthalenecarboxaldehyde with potassium carbonate and methyl iodide furnished aldehyde 10b . 25 The metallation/Vilsmeier-Haack reaction of 6-bromo-2-naphthol with sodium hydride, n -BuLi, and DMF 26 gave aldehyde 11 .…”

Section: Resultsmentioning

confidence: 99%

Inhibition of Acyl-CoA: Cholesterol Acyltransferase (ACAT), Overexpression of Cholesterol Transporter Gene, and Protection of Amyloid β (Aβ) Oligomers-Induced Neuronal Cell Death by Tricyclic Pyrone Molecules

et al. 2012

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A major effort in Alzheimer’s disease therapeutic development has targeted Aβ and downstream events. We have synthesized a small library of tricyclic pyrone compounds. Their protective action in MC65 cells and inhibition of ACAT along with the upregulation of cholesterol transporter gene were investigated. Five active compounds exhibited potencies in the nanomolar ranges. The multiple effects of the compounds on Aβ and cellular cholesterol pathways could be potential mechanisms underlying the protective effects in vivo.

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Section: Resultsmentioning

confidence: 99%

Inhibition of Acyl-CoA: Cholesterol Acyltransferase (ACAT), Overexpression of Cholesterol Transporter Gene, and Protection of Amyloid β (Aβ) Oligomers-Induced Neuronal Cell Death by Tricyclic Pyrone Molecules

et al. 2012

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“…A sample of molecular diversity bearing photochromic 3H-naphtho[2,1-b]pyran core reported in recent literatures in presented in Figure 3. Chamontin et al reported the synthesis of formyl-substituted naphthopyrans (e.g., 29) either by starting the reaction from formylated 2-naphthol or by conducting formylation on the naphthopyran products [26]. These formylated naphthopyrans can be used to produce an array of derivatives.…”

Section: Methods Of Synthesismentioning

confidence: 99%

Synthetic approaches to 3H‐naphtho[2,1‐b]pyrans and 2,3‐dihydro‐1H‐naphtho[2,1‐b]pyrans

Jha

Huang

2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Naphtho [2,1-b]pyran nuclei are prevalent in natural products with significant biological and medicinal properties. 3,3-Disubstituted 3H-naphtho[2,1-b]pyrans are photochromic and find use in electronic display systems, ophthalmic lenses, optical switches, and temporary or permanent memories. Of the various possible structural isomers of naphthopyran framework, this review is an account of reported synthetic procedures to produce 3H-naphtho[2,1-b]pyrans and their dihydro analogs, 2,3-dihydro-1H-naphtho[2,1-b]pyrans. The advantages and disadvantages of each procedure in terms of yields, complexity, formation of side-products, use of uncommon/expensive reagents, etc., are also described.

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“…For further synthetic details, see: Chakraborti & Gulhane (2003); Chamontin et al (1999); Steglich & Hö fle (1969).…”

Section: Related Literaturementioning

confidence: 99%

4′-Formylbiphenyl-4-yl acetate

Liu

Wang

et al. 2010

Acta Cryst E

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Synthesis and reactivity of formyl-substituted photochromic 3,3-diphenyl-[3H]-naphtho[2,1-b]pyrans

Cited by 33 publications

References 19 publications

Inhibition of Acyl-CoA: Cholesterol Acyltransferase (ACAT), Overexpression of Cholesterol Transporter Gene, and Protection of Amyloid β (Aβ) Oligomers-Induced Neuronal Cell Death by Tricyclic Pyrone Molecules

Inhibition of Acyl-CoA: Cholesterol Acyltransferase (ACAT), Overexpression of Cholesterol Transporter Gene, and Protection of Amyloid β (Aβ) Oligomers-Induced Neuronal Cell Death by Tricyclic Pyrone Molecules

Synthetic approaches to 3H‐naphtho[2,1‐b]pyrans and 2,3‐dihydro‐1H‐naphtho[2,1‐b]pyrans

4′-Formylbiphenyl-4-yl acetate

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