Optimization of the Reaction Conditions for the Synthesis of Dihydrobenzofuran Neolignans

Dias, Herbert Júnior; Rodrigues, Matheus Leandro; Crotti, Antônio Eduardo Miller

doi:10.21577/0103-5053.20200149

Cited by 6 publications

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“…This methodology allows for obtaining the structure core of DBNs in one single synthetic step in moderate yields (40–60%) [ 38 ]. Recently, Dias and co-workers achieved a considerable reduction in the reaction time (from 24 h to 4 h) by using acetonitrile as the reaction solvent, thus introducing an additional advantage to this methodology [ 20 ].…”

Section: Resultsmentioning

confidence: 99%

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Exploring Synthetic Dihydrobenzofuran and Benzofuran Neolignans as Antiprotozoal Agents against Trypanosoma cruzi

et al. 2023

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Chagas disease is a neglected tropical disease that affects more than 8 million people. Although there are therapies against this disease, the search for new drugs is important because the current treatments show limited effectiveness and high toxicity. In this work, eighteen dihydrobenzofuran-type neolignans (DBNs) and two benzofuran-type neolignans (BNs) were synthesized and evaluated against amastigote forms of two Trypanosoma cruzi strains. The in vitro cytotoxicity and hemolytic activity of the most active compounds were also evaluated and their relationships with T. cruzi tubulin DBNs were investigated by an in silico approach. Four DBNs demonstrated activity against the T. cruzi Tulahuen lac-Z strain (IC50 from 7.96 to 21.12 µM), and DBN 1 exhibited the highest activity against the amastigote forms of the T. cruzi Y strain (IC50 3.26 μM). Compounds 1–4 showed CC50 values higher than antitrypanosomal activities, except for DBN 3. All DBNs with antitrypanosomal activity demonstrated CH50 higher than 100 µM. The in silico results indicated that DBNs 1, 2, and 4 are capable of destabilizing the dynamics of the tubulin-microtubule from the vinca site. These compounds displayed promising in vitro activity against T. cruzi, especially compound 1, and can be considered molecular prototypes for the development of new antiparasitic drugs.

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Section: Resultsmentioning

confidence: 99%

“…DBNs 1 , 2 , and 3 were synthesized by oxidative coupling of methyl p -coumarate ( a ), methyl ferulate ( b ), and methyl caffeate ( c ), respectively ( Scheme 1 ), as previously reported [ 19 , 20 ]. Compounds 4 – 20 were synthesized from 1 or 2 by the previously reported methodologies [ 21 , 22 , 23 ].…”

Section: Methodsmentioning

confidence: 99%

Exploring Synthetic Dihydrobenzofuran and Benzofuran Neolignans as Antiprotozoal Agents against Trypanosoma cruzi

et al. 2023

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“…Methyl p ‐coumarate was synthesized by esterification of p ‐coumaric acid in the presence of sulfuric acid, as catalyst, as previously reported [21,34] …”

Section: Methodsmentioning

confidence: 99%

“…Methyl p-coumarate was synthesized by esterification of p-coumaric acid in the presence of sulfuric acid, as catalyst, as previously reported. [21,34] . Compounds 1-4 were synthesized by alkylating methyl p-coumarate according to the methodology employed by Patra and coworkers [3] with modifications (Scheme 2).…”

Section: Synthesis Of Prenylated P-coumaric Acid Derivatives 1-8mentioning

confidence: 99%

In vitro Evaluation of the Antileishmanial and Antischistosomal Activities of p‐Coumaric Acid Prenylated Derivatives

Vieira,

Barco,

Paula

et al. 2024

Chemistry & Biodiversity

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We have evaluated eight p‐coumaric acid prenylated derivatives in vitro for their antileishmanial activity against Leishmania amazonensis promastigotes and their antischistosomal activity against Schistosoma mansoni adult worms. Compound 7 ((E)‐3,4‐diprenyl‐4‐isoprenyloxycinnamic alcohol) was the most active against L. amazonensis (IC50 = 45.92 µM) and S. mansoni (IC50 = 64.25 µM). Data indicated that the number of prenyl groups, the presence of hydroxyl at C9, and a single bond between C7 and C8 are important structural features for the antileishmanial activity of p‐coumaric acid prenylated derivatives.

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“…In 2021, Dias and coworkers 130 also optimized a silver-catalyzed method for the synthesis of 2,3-dihydrobenzofuran neolignans 269 and 270 via oxidative coupling strategy. In their synthetic approach, methyl p -coumarates 267 and methyl ferulates 268 were transformed into 269 and 270 , respectively, in the presence of Ag 2 O (used as catalyst) and azobisisobutyronitrile (as radical inhibitor) in acetonitrile.…”

Section: Review Of Literaturementioning

confidence: 99%

Development of novel transition metal-catalyzed synthetic approaches for the synthesis of a dihydrobenzofuran nucleus: a review

Ashraf,

Zahoor,

Ali

et al. 2024

RSC Adv.

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Optimization of the Reaction Conditions for the Synthesis of Dihydrobenzofuran Neolignans

Cited by 6 publications

References 0 publications

Exploring Synthetic Dihydrobenzofuran and Benzofuran Neolignans as Antiprotozoal Agents against Trypanosoma cruzi

Exploring Synthetic Dihydrobenzofuran and Benzofuran Neolignans as Antiprotozoal Agents against Trypanosoma cruzi

In vitro Evaluation of the Antileishmanial and Antischistosomal Activities of p‐Coumaric Acid Prenylated Derivatives

Development of novel transition metal-catalyzed synthetic approaches for the synthesis of a dihydrobenzofuran nucleus: a review

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