A Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Witting Reagent (I): A Synthesis of Methoxy- and Hydroxycoumarins

Harayama, Takashi; Katsuno, Keiko; Nishioka, Hiromi; Fujii, Masako; Nishita, Yoshitaka; Ishii, Hisashi; Kaneko, Yasuko

doi:10.3987/com-94-s(b)54

Cited by 33 publications

(19 citation statements)

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“…The same type of reaction was performed by Harayama et al [153], for the synthesis of bromo and methoxycarbonylcoumarins. This type of reaction was conducted in the presence or absence of solvent and was also adequate to obtain methoxy-, hydroxy-, nitro-and 3,4-unsubstituted coumarins [154,155]. A convenient synthesis of coumarins involving a combination of lithiation and Wittig reaction was also published [156].…”

Section: Knoevenagel Reactionmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

890

458

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Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The structural diversity found in this family of compounds led to the division into different categories, from simple coumarins to many other kinds of policyclic coumarins, such as furocoumarins and pyranocoumarins. Simple coumarins and analogues are a large class of compounds that have attracted their interest for a long time due to their biological activities: they have shown to be useful as antitumoural, anti-HIV agents and as CNS-active compounds. Furthermore, they have been reported to have multiple biological activities (anticoagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics of this field of research. The present work is to survey the information published or abstracted from 1990 till 2003, which is mainly related to the occurrence, synthesis and biological importance of simple coumarins and some analogues, such as biscoumarins and triscoumarins. Data are also highlighted, concerning the development of new synthetic strategies that could help in drug design and in the work on SAR or QSAR.

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Section: Knoevenagel Reactionmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

890

458

View full text Add to dashboard Cite

show abstract

“…6,7-Dimethoxy-3-hydroxycoumarin was prepared from esculetin according to a reported synthetic pathway, [32] with slight modifications; 5-and 8-hydroxycoumarin were synthesized by a Wittig olefination of a suitable hydroxysalicylaldehyde with ethyl (triphenylphosphoranylidene)acetate followed by intramolecular cyclization of the resulting cinnamate ester under very harsh conditions according to a reported procedure, [33] with slight modifications. 7-Hydroxy-3,4-annulated coumarin intermediates 1 a and 1 d were prepared according to the reaction pathway shown in Scheme 1.…”

Section: Chemistrymentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Coumarin Derivatives Tethered to an Edrophonium‐like Fragment as Highly Potent and Selective Dual Binding Site Acetylcholinesterase Inhibitors

et al. 2010

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A large series of substituted coumarins linked through an appropriate spacer to 3-hydroxy-N,N-dimethylanilino or 3-hydroxy-N,N,N-trialkylbenzaminium moieties were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors. The highest AChE inhibitory potency in the 3-hydroxy-N,N-dimethylanilino series was observed with a 6,7-dimethoxy-3-substituted coumarin derivative, which, along with an outstanding affinity (IC(50)=0.236 nM) exhibits excellent AChE/BChE selectivity (SI>300 000). Most of the synthesized 3-hydroxy-N,N,N-trialkylbenzaminium salts display an AChE affinity in the sub-nanomolar to picomolar range along with excellent AChE/BChE selectivities (SI values up to 138 333). The combined use of docking and molecular dynamics simulations permitted us to shed light on the observed structure-affinity and structure-selectivity relationships, to detect two possible alternative binding modes, and to assess the critical role of pi-pi stacking interactions in the AChE peripheral binding site.

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“…To a soln. of 6-hydroxycoumarin ( 6-hydroxy-2H-1-benzopyran-2-one) [24] (2.43 g, 15 mmol) in acetone (80 ml), K 2 CO 3 (2.07 g, 15 mmol), KI (0.50 g, 3 mmol), and 1-bromo-3-methylbut-2-ene (2.24 g, 15 mmol) were added. The resulting mixture was refluxed for 5 h ( TLC monitoring).…”

Section: Experimental Partmentioning

confidence: 99%

“…± The g-[(E)-1-methylprop-1-enyl]-a-methylidene-gbutyrolactones 7 ± 9 were prepared from 6-hydroxycoumarin [24], 7-hydroxycoumarin [25], and 3-chloro-7-hydroxy-4-methylcoumarin [26], respectively, via 1 ± 3 and 4 ± 6 (Scheme). Thus, 6-hydroxycoumarin (from 2,5-dihydroxybenzaldehyde) was alkylated with 1-bromo-3-methylbut-2-ene to give 6-(3-methylbut-2-enyloxy)-2H-1-benzopyran-2-one (1).…”

mentioning

confidence: 99%

Geiparvarin Analogues: Synthesis and Anticancer Evaluation ofα-Methylidene-γ-butyrolactone-Bearing Coumarins

Chen

Wang

Tzeng

et al. 1999

HCA

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A Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Witting Reagent (I): A Synthesis of Methoxy- and Hydroxycoumarins

Cited by 33 publications

References 0 publications

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Design, Synthesis, and Biological Evaluation of Coumarin Derivatives Tethered to an Edrophonium‐like Fragment as Highly Potent and Selective Dual Binding Site Acetylcholinesterase Inhibitors

Geiparvarin Analogues: Synthesis and Anticancer Evaluation ofα-Methylidene-γ-butyrolactone-Bearing Coumarins

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