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Use of Flavonoids and Cinnamates, the Main Photoprotectors with Natural Origin.

Advances in pharmacological sciences

Nunes AR, Vieira ÍGP, Queiroz DB, Leal ALAB, Maia Morais S, Muniz DF, Calixto-Junior JT, Coutinho HDM.
PMID: 30622564
Adv Pharmacol Sci. 2018 Nov 28;2018:5341487. doi: 10.1155/2018/5341487. eCollection 2018.

Many pathological problems are initiated by ultraviolet radiation (UVR), such as skin cancer, the most commonly diagnosed cancer worldwide. The UVA (320-400 nm) and UVB (290-320 nm) wavelengths may cause effects such as photoaging, DNA damage, and a series...

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Nunes AR, Vieira ÍGP, Queiroz DB, et al. Use of Flavonoids and Cinnamates, the Main Photoprotectors with Natural Origin. Adv Pharmacol Sci. 2018;2018:5341487doi: 10.1155/2018/5341487.
Nunes, A. R., Vieira, �. �. G. P., Queiroz, D. B., Leal, A. L. A. B., Maia Morais, S., Muniz, D. F., Calixto-Junior, J. T., & Coutinho, H. D. M. (2018). Use of Flavonoids and Cinnamates, the Main Photoprotectors with Natural Origin. Advances in pharmacological sciences, 20185341487. https://doi.org/10.1155/2018/5341487
Nunes, Alesandra R, et al. "Use of Flavonoids and Cinnamates, the Main Photoprotectors with Natural Origin." Advances in pharmacological sciences vol. 2018 (2018): 5341487. doi: https://doi.org/10.1155/2018/5341487
Nunes AR, Vieira ÍGP, Queiroz DB, Leal ALAB, Maia Morais S, Muniz DF, Calixto-Junior JT, Coutinho HDM. Use of Flavonoids and Cinnamates, the Main Photoprotectors with Natural Origin. Adv Pharmacol Sci. 2018 Nov 28;2018:5341487. doi: 10.1155/2018/5341487. eCollection 2018. PMID: 30622564; PMCID: PMC6304211.
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An intramolecular Heck reaction of enol ethers involving β-alkoxyl elimination followed by the β-hydride elimination process: access to (Z)-ortho-formyl/keto-cinnamates.

Chemical communications (Cambridge, England)

Sun M, Wu H, Wu H, Wang Z.
PMID: 31720626
Chem Commun (Camb). 2019 Nov 28;55(96):14422-14425. doi: 10.1039/c9cc08133j.

A highly regio- and stereoselective intramolecular Heck reaction of enol ethers involving β-alkoxyl elimination followed by the β-hydride elimination process has been developed. Various o-iodobenzyl enol ethers derived from allenoates or alkynoates are found to be efficient substrates for...

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Sun M, Wu H, Wu H, et al. An intramolecular Heck reaction of enol ethers involving β-alkoxyl elimination followed by the β-hydride elimination process: access to (Z)-ortho-formyl/keto-cinnamates. Chem Commun (Camb). 2019;55(96):14422-14425doi: 10.1039/c9cc08133j.
Sun, M., Wu, H., Wu, H., & Wang, Z. (2019). An intramolecular Heck reaction of enol ethers involving β-alkoxyl elimination followed by the β-hydride elimination process: access to (Z)-ortho-formyl/keto-cinnamates. Chemical communications (Cambridge, England), 55(96), 14422-14425. https://doi.org/10.1039/c9cc08133j
Sun, Manman, et al. "An intramolecular Heck reaction of enol ethers involving β-alkoxyl elimination followed by the β-hydride elimination process: access to (Z)-ortho-formyl/keto-cinnamates." Chemical communications (Cambridge, England) vol. 55,96 (2019): 14422-14425. doi: https://doi.org/10.1039/c9cc08133j
Sun M, Wu H, Wu H, Wang Z. An intramolecular Heck reaction of enol ethers involving β-alkoxyl elimination followed by the β-hydride elimination process: access to (Z)-ortho-formyl/keto-cinnamates. Chem Commun (Camb). 2019 Nov 28;55(96):14422-14425. doi: 10.1039/c9cc08133j. PMID: 31720626.
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The direct observation of the doorway .

Physical chemistry chemical physics : PCCP

Kinoshita SN, Inokuchi Y, Onitsuka Y, Kohguchi H, Akai N, Shiraogawa T, Ehara M, Yamazaki K, Harabuchi Y, Maeda S, Ebata T.
PMID: 31259349
Phys Chem Chem Phys. 2019 Sep 18;21(36):19755-19763. doi: 10.1039/c9cp02914a.

The electronic states and photochemistry including nonradiative decay (NRD) and trans(E) → cis(Z) isomerization of methylcinnamate (MC) and its hydrogen-bonded complex with methanol have been investigated under jet-cooled conditions. S1(1nπ*) and S2(1ππ*) are directly observed in MC. This is...

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Kinoshita SN, Inokuchi Y, Onitsuka Y, et al. The direct observation of the doorway . Phys Chem Chem Phys. 2019;21(36):19755-19763doi: 10.1039/c9cp02914a.
Kinoshita, S. N., Inokuchi, Y., Onitsuka, Y., Kohguchi, H., Akai, N., Shiraogawa, T., Ehara, M., Yamazaki, K., Harabuchi, Y., Maeda, S., & Ebata, T. (2019). The direct observation of the doorway . Physical chemistry chemical physics : PCCP, 21(36), 19755-19763. https://doi.org/10.1039/c9cp02914a
Kinoshita, Shin-Nosuke, et al. "The direct observation of the doorway ." Physical chemistry chemical physics : PCCP vol. 21,36 (2019): 19755-19763. doi: https://doi.org/10.1039/c9cp02914a
Kinoshita SN, Inokuchi Y, Onitsuka Y, Kohguchi H, Akai N, Shiraogawa T, Ehara M, Yamazaki K, Harabuchi Y, Maeda S, Ebata T. The direct observation of the doorway . Phys Chem Chem Phys. 2019 Sep 18;21(36):19755-19763. doi: 10.1039/c9cp02914a. PMID: 31259349.
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Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines.

Chemical communications (Cambridge, England)

Ametovski J, Dutta U, Burchill L, Maiti D, Lupton DW, Hooper JF.
PMID: 29165450
Chem Commun (Camb). 2017 Dec 05;53(97):13071-13074. doi: 10.1039/c7cc08252e.

The (5 + 1) annulation of ynone/cinnamates and related substrates with protected primary amines gives rise to isoquinolones, pyrrolidinones and pyrrolopiperazines in good to excellent yields under phosphine catalysis. The reaction is viable with chiral phosphines, although the selectivity...

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Ametovski J, Dutta U, Burchill L, et al. Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines. Chem Commun (Camb). 2017;53(97):13071-13074doi: 10.1039/c7cc08252e.
Ametovski, J., Dutta, U., Burchill, L., Maiti, D., Lupton, D. W., & Hooper, J. F. (2017). Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines. Chemical communications (Cambridge, England), 53(97), 13071-13074. https://doi.org/10.1039/c7cc08252e
Ametovski, Jhi, et al. "Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines." Chemical communications (Cambridge, England) vol. 53,97 (2017): 13071-13074. doi: https://doi.org/10.1039/c7cc08252e
Ametovski J, Dutta U, Burchill L, Maiti D, Lupton DW, Hooper JF. Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines. Chem Commun (Camb). 2017 Dec 05;53(97):13071-13074. doi: 10.1039/c7cc08252e. PMID: 29165450.
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Fe(III)-Catalyzed Hydroallylation of Unactivated Alkenes with Morita-Baylis-Hillman Adducts.

Organic letters

Qi J, Zheng J, Cui S.
PMID: 29457733
Org Lett. 2018 Mar 02;20(5):1355-1358. doi: 10.1021/acs.orglett.8b00108. Epub 2018 Feb 19.

An Fe(III)-catalyzed hydroallylation of unactivated alkenes with Morita-Baylis-Hillman adducts via an Fe-catalyzed process is described. A variety of alkenes, including mono-, di-, and trisubstituted alkenes, could all smoothly convert to structural diversified cinnamates in this protocol. Interestingly, when the...

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Qi J, Zheng J, Cui S. Fe(III)-Catalyzed Hydroallylation of Unactivated Alkenes with Morita-Baylis-Hillman Adducts. Org Lett. 2018;20(5):1355-1358doi: 10.1021/acs.orglett.8b00108.
Qi, J., Zheng, J., & Cui, S. (2018). Fe(III)-Catalyzed Hydroallylation of Unactivated Alkenes with Morita-Baylis-Hillman Adducts. Organic letters, 20(5), 1355-1358. https://doi.org/10.1021/acs.orglett.8b00108
Qi, Jifeng, et al. "Fe(III)-Catalyzed Hydroallylation of Unactivated Alkenes with Morita-Baylis-Hillman Adducts." Organic letters vol. 20,5 (2018): 1355-1358. doi: https://doi.org/10.1021/acs.orglett.8b00108
Qi J, Zheng J, Cui S. Fe(III)-Catalyzed Hydroallylation of Unactivated Alkenes with Morita-Baylis-Hillman Adducts. Org Lett. 2018 Mar 02;20(5):1355-1358. doi: 10.1021/acs.orglett.8b00108. Epub 2018 Feb 19. PMID: 29457733.
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Asymmetric Lewis acid organocatalysis of the Diels-Alder reaction by a silylated C-H acid.

Science (New York, N.Y.)

Gatzenmeier T, van Gemmeren M, Xie Y, Höfler D, Leutzsch M, List B.
PMID: 26917765
Science. 2016 Feb 26;351(6276):949-52. doi: 10.1126/science.aae0010.

Silylium ion equivalents have shown promise as Lewis acid catalysts for a range of important C-C bond-forming reactions. Here we describe chiral C-H acids that upon in situ silylation, generate silylium-carbanion pairs, which are extremely active Lewis acid catalysts...

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Gatzenmeier T, van Gemmeren M, Xie Y, et al. Asymmetric Lewis acid organocatalysis of the Diels-Alder reaction by a silylated C-H acid. Science. 2016;351(6276):949-52doi: 10.1126/science.aae0010.
Gatzenmeier, T., van Gemmeren, M., Xie, Y., Höfler, D., Leutzsch, M., & List, B. (2016). Asymmetric Lewis acid organocatalysis of the Diels-Alder reaction by a silylated C-H acid. Science (New York, N.Y.), 351(6276), 949-52. https://doi.org/10.1126/science.aae0010
Gatzenmeier, Tim, et al. "Asymmetric Lewis acid organocatalysis of the Diels-Alder reaction by a silylated C-H acid." Science (New York, N.Y.) vol. 351,6276 (2016): 949-52. doi: https://doi.org/10.1126/science.aae0010
Gatzenmeier T, van Gemmeren M, Xie Y, Höfler D, Leutzsch M, List B. Asymmetric Lewis acid organocatalysis of the Diels-Alder reaction by a silylated C-H acid. Science. 2016 Feb 26;351(6276):949-52. doi: 10.1126/science.aae0010. PMID: 26917765.
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Photoisomerization of ionic liquid ammonium cinnamates: one-pot synthesis-isolation of Z-cinnamic acids.

Organic letters

Salum ML, Robles CJ, Erra-Balsells R.
PMID: 20873819
Org Lett. 2010 Nov 05;12(21):4808-11. doi: 10.1021/ol1019508.

Photoisomerization presents the only direct method for contra-thermodynamic E-Z isomerization of olefins. Synthetic applications of this method have been limited by its reversible nature, which leads to a photostationary-state mixture of both isomers. For the first time, a highly...

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Salum ML, Robles CJ, Erra-Balsells R. Photoisomerization of ionic liquid ammonium cinnamates: one-pot synthesis-isolation of Z-cinnamic acids. Org Lett. 2010;12(21):4808-11doi: 10.1021/ol1019508.
Salum, M. L., Robles, C. J., & Erra-Balsells, R. (2010). Photoisomerization of ionic liquid ammonium cinnamates: one-pot synthesis-isolation of Z-cinnamic acids. Organic letters, 12(21), 4808-11. https://doi.org/10.1021/ol1019508
Salum, María L, et al. "Photoisomerization of ionic liquid ammonium cinnamates: one-pot synthesis-isolation of Z-cinnamic acids." Organic letters vol. 12,21 (2010): 4808-11. doi: https://doi.org/10.1021/ol1019508
Salum ML, Robles CJ, Erra-Balsells R. Photoisomerization of ionic liquid ammonium cinnamates: one-pot synthesis-isolation of Z-cinnamic acids. Org Lett. 2010 Nov 05;12(21):4808-11. doi: 10.1021/ol1019508. PMID: 20873819.
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Photophysical characterization of cinnamates.

Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology

Karpkird TM, Wanichweacharungruang S, Albinsson B.
PMID: 19789816
Photochem Photobiol Sci. 2009 Oct;8(10):1455-60. doi: 10.1039/b909695g. Epub 2009 Aug 05.

The photophysical properties of five methoxy-substituted 2-ethylhexylcinnamates were studied with experimental and theoretical methods. It was found that the fluorescence quantum yields varied strongly with the substitution pattern of the phenyl ring. A methoxy substitution at the meta position...

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Karpkird TM, Wanichweacharungruang S, Albinsson B. Photophysical characterization of cinnamates. Photochem Photobiol Sci. 2009;8(10):1455-60doi: 10.1039/b909695g.
Karpkird, T. M., Wanichweacharungruang, S., & Albinsson, B. (2009). Photophysical characterization of cinnamates. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 8(10), 1455-60. https://doi.org/10.1039/b909695g
Karpkird, Thitinun Monhaphol, et al. "Photophysical characterization of cinnamates." Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology vol. 8,10 (2009): 1455-60. doi: https://doi.org/10.1039/b909695g
Karpkird TM, Wanichweacharungruang S, Albinsson B. Photophysical characterization of cinnamates. Photochem Photobiol Sci. 2009 Oct;8(10):1455-60. doi: 10.1039/b909695g. Epub 2009 Aug 05. PMID: 19789816.
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Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae).

Bioorganic & medicinal chemistry

Bezerra França S, Carine Barros de Lima L, Rychard da Silva Cunha C, Santos Anunciação D, Ferreira da Silva-Júnior E, Ester de Sá Barreto Barros M, José da Paz Lima D.
PMID: 34225166
Bioorg Med Chem. 2021 Aug 15;44:116299. doi: 10.1016/j.bmc.2021.116299. Epub 2021 Jun 28.

Cinnamic acid derivatives (CAD's) represent a great alternative in the search for insecticides against Aedes aegypti mosquitoes since they have antimicrobial and insecticide properties. Ae. aegypti is responsible for transmitting Dengue, Chikungunya, and Zika viruses, among other arboviruses associated...

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Bezerra França S, Carine Barros de Lima L, Rychard da Silva Cunha C, et al. Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae). Bioorg Med Chem. 2021;44:116299doi: 10.1016/j.bmc.2021.116299.
Bezerra França, S., Carine Barros de Lima, L., Rychard da Silva Cunha, C., Santos Anunciação, D., Ferreira da Silva-Júnior, E., Ester de Sá Barreto Barros, M., & José da Paz Lima, D. (2021). Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae). Bioorganic & medicinal chemistry, 44116299. https://doi.org/10.1016/j.bmc.2021.116299
Bezerra França, Saraliny, et al. "Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae)." Bioorganic & medicinal chemistry vol. 44 (2021): 116299. doi: https://doi.org/10.1016/j.bmc.2021.116299
Bezerra França S, Carine Barros de Lima L, Rychard da Silva Cunha C, Santos Anunciação D, Ferreira da Silva-Júnior E, Ester de Sá Barreto Barros M, José da Paz Lima D. Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae). Bioorg Med Chem. 2021 Aug 15;44:116299. doi: 10.1016/j.bmc.2021.116299. Epub 2021 Jun 28. PMID: 34225166.
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2-Oxoglutarate-dependent dioxygenases in the biosynthesis of simple coumarins.

Frontiers in plant science

Shimizu B.
PMID: 25404933
Front Plant Sci. 2014 Nov 03;5:549. doi: 10.3389/fpls.2014.00549. eCollection 2014.

Coumarins are natural plant products that have been the subject of extensive phytochemical and pharmacological research studies in the past few decades. The core structure of coumarins is derived from the respective cinnamates via ortho-hydroxylation of the aromatic ring,...

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Shimizu B. 2-Oxoglutarate-dependent dioxygenases in the biosynthesis of simple coumarins. Front Plant Sci. 2014;5:549doi: 10.3389/fpls.2014.00549.
Shimizu, B. (2014). 2-Oxoglutarate-dependent dioxygenases in the biosynthesis of simple coumarins. Frontiers in plant science, 5549. https://doi.org/10.3389/fpls.2014.00549
Shimizu, Bun-Ichi. "2-Oxoglutarate-dependent dioxygenases in the biosynthesis of simple coumarins." Frontiers in plant science vol. 5 (2014): 549. doi: https://doi.org/10.3389/fpls.2014.00549
Shimizu B. 2-Oxoglutarate-dependent dioxygenases in the biosynthesis of simple coumarins. Front Plant Sci. 2014 Nov 03;5:549. doi: 10.3389/fpls.2014.00549. eCollection 2014. PMID: 25404933; PMCID: PMC4217350.
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Stacking and Electrostatic Interactions Drive the Stereoselectivity of Silylium-Ion Asymmetric Counteranion-Directed Catalysis.

Angewandte Chemie (International ed. in English)

Seguin TJ, Wheeler SE.
PMID: 27860103
Angew Chem Int Ed Engl. 2016 Dec 19;55(51):15889-15893. doi: 10.1002/anie.201609095. Epub 2016 Nov 17.

Computational analysis shows that the enantioselectivity of asymmetric Lewis-acid organocatalysis of the Diels-Alder cycloaddition of cyclopentadiene to cinnamates arises from stacking interactions that favor the addition of the diene to the more hindered face of the dienophile, while electrostatic...

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Seguin TJ, Wheeler SE. Stacking and Electrostatic Interactions Drive the Stereoselectivity of Silylium-Ion Asymmetric Counteranion-Directed Catalysis. Angew Chem Int Ed Engl. 2016;55(51):15889-15893doi: 10.1002/anie.201609095.
Seguin, T. J., & Wheeler, S. E. (2016). Stacking and Electrostatic Interactions Drive the Stereoselectivity of Silylium-Ion Asymmetric Counteranion-Directed Catalysis. Angewandte Chemie (International ed. in English), 55(51), 15889-15893. https://doi.org/10.1002/anie.201609095
Seguin, Trevor J, and Wheeler, Steven E. "Stacking and Electrostatic Interactions Drive the Stereoselectivity of Silylium-Ion Asymmetric Counteranion-Directed Catalysis." Angewandte Chemie (International ed. in English) vol. 55,51 (2016): 15889-15893. doi: https://doi.org/10.1002/anie.201609095
Seguin TJ, Wheeler SE. Stacking and Electrostatic Interactions Drive the Stereoselectivity of Silylium-Ion Asymmetric Counteranion-Directed Catalysis. Angew Chem Int Ed Engl. 2016 Dec 19;55(51):15889-15893. doi: 10.1002/anie.201609095. Epub 2016 Nov 17. PMID: 27860103.
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Aminobromination of olefins with TsNH(2) and NBS as the nitrogen and bromine sources mediated by hypervalent iodine in a ball mill.

Organic & biomolecular chemistry

Wu XL, Xia JJ, Wang GW.
PMID: 18219426
Org Biomol Chem. 2008 Feb 07;6(3):548-53. doi: 10.1039/b717333d. Epub 2007 Dec 18.

A series of olefins including alpha,beta-unsaturated ketones, cinnamates, cinnamides and styrenes have been aminobrominated with good yields and excellent diastereoselectivities under mechanical milling conditions, using TsNH(2) and NBS as the nitrogen and bromine sources, promoted by (diacetoxyiodo)benzene.

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Wu XL, Xia JJ, Wang GW. Aminobromination of olefins with TsNH(2) and NBS as the nitrogen and bromine sources mediated by hypervalent iodine in a ball mill. Org Biomol Chem. 2007;6(3):548-53doi: 10.1039/b717333d.
Wu, X. L., Xia, J. J., & Wang, G. W. (2008). Aminobromination of olefins with TsNH(2) and NBS as the nitrogen and bromine sources mediated by hypervalent iodine in a ball mill. Organic & biomolecular chemistry, 6(3), 548-53. https://doi.org/10.1039/b717333d
Wu, Xue-Liang, et al. "Aminobromination of olefins with TsNH(2) and NBS as the nitrogen and bromine sources mediated by hypervalent iodine in a ball mill." Organic & biomolecular chemistry vol. 6,3 (2008): 548-53. doi: https://doi.org/10.1039/b717333d
Wu XL, Xia JJ, Wang GW. Aminobromination of olefins with TsNH(2) and NBS as the nitrogen and bromine sources mediated by hypervalent iodine in a ball mill. Org Biomol Chem. 2008 Feb 07;6(3):548-53. doi: 10.1039/b717333d. Epub 2007 Dec 18. PMID: 18219426.
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Showing 13 to 24 of 61 entries