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Shortcut Syntheses of Naturally Occurring 5-Alkylresorcinols with DNA-Cleaving Properties.

The Journal of organic chemistry

Fürstner A, Seidel G.
PMID: 11671563
J Org Chem. 1997 Apr 18;62(8):2332-2336. doi: 10.1021/jo962423i.

Resorcinols such as 1-5 bearing long alkyl- or alkenyl substituents at the C-5 position, including bola-formed bis-resorcinol derivatives, have recently been isolated from natural sources and were shown to exhibit exceptional DNA-cleaving properties under oxidative conditions. Previous synthetic approaches...

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Fürstner A, Seidel G. Shortcut Syntheses of Naturally Occurring 5-Alkylresorcinols with DNA-Cleaving Properties. J Org Chem. 1997;62(8):2332-2336doi: 10.1021/jo962423i.
Fürstner, A., & Seidel, G. (1997). Shortcut Syntheses of Naturally Occurring 5-Alkylresorcinols with DNA-Cleaving Properties. The Journal of organic chemistry, 62(8), 2332-2336. https://doi.org/10.1021/jo962423i
Fürstner, Alois, and Seidel, Günter. "Shortcut Syntheses of Naturally Occurring 5-Alkylresorcinols with DNA-Cleaving Properties." The Journal of organic chemistry vol. 62,8 (1997): 2332-2336. doi: https://doi.org/10.1021/jo962423i
Fürstner A, Seidel G. Shortcut Syntheses of Naturally Occurring 5-Alkylresorcinols with DNA-Cleaving Properties. J Org Chem. 1997 Apr 18;62(8):2332-2336. doi: 10.1021/jo962423i. PMID: 11671563.
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Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules.

The Journal of organic chemistry

Alonso E, Ramón DJ, Yus M.
PMID: 11671418
J Org Chem. 1997 Jan 24;62(2):417-421. doi: 10.1021/jo9610624.

The reaction of 3,5-dimethoxybenzyl trimethylsilyl ether (3) with different aldehydes (n-PrCHO, n-C(11)H(23)CHO, MeCHO, PhCHO) in the presence of lithium powder and a catalytic amount of naphthalene (4 mol %) gave, after hydrolysis, the expected alcohols 4 in moderate yields....

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Alonso E, Ramón DJ, Yus M. Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules. J Org Chem. 1997;62(2):417-421doi: 10.1021/jo9610624.
Alonso, E., Ramón, D. J., & Yus, M. (1997). Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules. The Journal of organic chemistry, 62(2), 417-421. https://doi.org/10.1021/jo9610624
Alonso, Emma, et al. "Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules." The Journal of organic chemistry vol. 62,2 (1997): 417-421. doi: https://doi.org/10.1021/jo9610624
Alonso E, Ramón DJ, Yus M. Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules. J Org Chem. 1997 Jan 24;62(2):417-421. doi: 10.1021/jo9610624. PMID: 11671418.
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Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO.

Chemical communications (Cambridge, England)

Brancour C, Fukuyama T, Ohta Y, Ryu I, Dhimane AL, Fensterbank L, Malacria M.
PMID: 20585695
Chem Commun (Camb). 2010 Aug 14;46(30):5470-2. doi: 10.1039/c0cc00747a. Epub 2010 Jun 29.

A novel [5+1] type carbonylative cycloaddition reaction has been developed using a Rh complex as catalyst. This reaction can convert readily available 3-acyloxy-1,4-enynes and CO to a wide range of functionalized resorcinols in good yields. A mechanism involving Rh-catalyzed...

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Brancour C, Fukuyama T, Ohta Y, et al. Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO. Chem Commun (Camb). 2010;46(30):5470-2doi: 10.1039/c0cc00747a.
Brancour, C., Fukuyama, T., Ohta, Y., Ryu, I., Dhimane, A. L., Fensterbank, L., & Malacria, M. (2010). Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO. Chemical communications (Cambridge, England), 46(30), 5470-2. https://doi.org/10.1039/c0cc00747a
Brancour, Célia, et al. "Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO." Chemical communications (Cambridge, England) vol. 46,30 (2010): 5470-2. doi: https://doi.org/10.1039/c0cc00747a
Brancour C, Fukuyama T, Ohta Y, Ryu I, Dhimane AL, Fensterbank L, Malacria M. Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO. Chem Commun (Camb). 2010 Aug 14;46(30):5470-2. doi: 10.1039/c0cc00747a. Epub 2010 Jun 29. PMID: 20585695.
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Metal and Oxidant-Free Brønsted Acid-Mediated Cascade Reaction to Substituted Benzofurans.

The Journal of organic chemistry

Mari G, Ciccolini C, De Crescentini L, Favi G, Santeusanio S, Mancinelli M, Mantellini F.
PMID: 31407579
J Org Chem. 2019 Sep 06;84(17):10814-10824. doi: 10.1021/acs.joc.9b01363. Epub 2019 Aug 23.

Substituted hydroxy-benzofurans are easily accessible by treatment of resorcinols and 1,2-diaza-1,3-dienes (DDs) under acidic conditions. The reaction happens through an uncommon Michael reaction between aromatic derivatives as aromatic C(sp

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Mari G, Ciccolini C, De Crescentini L, et al. Metal and Oxidant-Free Brønsted Acid-Mediated Cascade Reaction to Substituted Benzofurans. J Org Chem. 2019;84(17):10814-10824doi: 10.1021/acs.joc.9b01363.
Mari, G., Ciccolini, C., De Crescentini, L., Favi, G., Santeusanio, S., Mancinelli, M., & Mantellini, F. (2019). Metal and Oxidant-Free Brønsted Acid-Mediated Cascade Reaction to Substituted Benzofurans. The Journal of organic chemistry, 84(17), 10814-10824. https://doi.org/10.1021/acs.joc.9b01363
Mari, Giacomo, et al. "Metal and Oxidant-Free Brønsted Acid-Mediated Cascade Reaction to Substituted Benzofurans." The Journal of organic chemistry vol. 84,17 (2019): 10814-10824. doi: https://doi.org/10.1021/acs.joc.9b01363
Mari G, Ciccolini C, De Crescentini L, Favi G, Santeusanio S, Mancinelli M, Mantellini F. Metal and Oxidant-Free Brønsted Acid-Mediated Cascade Reaction to Substituted Benzofurans. J Org Chem. 2019 Sep 06;84(17):10814-10824. doi: 10.1021/acs.joc.9b01363. Epub 2019 Aug 23. PMID: 31407579.
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Regioselective photoreactions within a series of mixed co-crystals containing isosteric dihalogenated resorcinols with 4-stilbazole.

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

Grobelny AL, Rath NP, Groeneman RH.
PMID: 30849166
Photochem Photobiol Sci. 2019 May 15;18(5):989-992. doi: 10.1039/c9pp00004f.

The formation and photoreactivity of a series of mixed co-crystals containing 4-stilbazole along with both 4,6-dichlororesorcinol and 4,6-dibromoresorcinol at various ratios is reported. In all cases, the quantitative [2 + 2] cycloaddition reaction yields an identical head-to-tail photoproduct, namely...

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Grobelny AL, Rath NP, Groeneman RH. Regioselective photoreactions within a series of mixed co-crystals containing isosteric dihalogenated resorcinols with 4-stilbazole. Photochem Photobiol Sci. 2019;18(5):989-992doi: 10.1039/c9pp00004f.
Grobelny, A. L., Rath, N. P., & Groeneman, R. H. (2019). Regioselective photoreactions within a series of mixed co-crystals containing isosteric dihalogenated resorcinols with 4-stilbazole. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 18(5), 989-992. https://doi.org/10.1039/c9pp00004f
Grobelny, Anna L, et al. "Regioselective photoreactions within a series of mixed co-crystals containing isosteric dihalogenated resorcinols with 4-stilbazole." Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology vol. 18,5 (2019): 989-992. doi: https://doi.org/10.1039/c9pp00004f
Grobelny AL, Rath NP, Groeneman RH. Regioselective photoreactions within a series of mixed co-crystals containing isosteric dihalogenated resorcinols with 4-stilbazole. Photochem Photobiol Sci. 2019 May 15;18(5):989-992. doi: 10.1039/c9pp00004f. PMID: 30849166.
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Direct Synthesis of the Phenanthroviridone Skeleton Using a Highly Regioselective Nitroquinone Diels-Alder Reaction.

ACS omega

Yu H, Fought EL, Windus TL, Kraus GA.
PMID: 32363281
ACS Omega. 2020 Apr 17;5(16):9311-9315. doi: 10.1021/acsomega.0c00201. eCollection 2020 Apr 28.

A variety of nucleophiles react efficiently with in situ generated nitroquinones. The reaction with substituted resorcinols led to the direct synthesis of the phenanthroviridinone and lagumycin skeleton via a highly regioselective Diels-Alder reaction.

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Yu H, Fought EL, Windus TL, et al. Direct Synthesis of the Phenanthroviridone Skeleton Using a Highly Regioselective Nitroquinone Diels-Alder Reaction. ACS Omega. 2020;5(16):9311-9315doi: 10.1021/acsomega.0c00201.
Yu, H., Fought, E. L., Windus, T. L., & Kraus, G. A. (2020). Direct Synthesis of the Phenanthroviridone Skeleton Using a Highly Regioselective Nitroquinone Diels-Alder Reaction. ACS omega, 5(16), 9311-9315. https://doi.org/10.1021/acsomega.0c00201
Yu, Huangchao, et al. "Direct Synthesis of the Phenanthroviridone Skeleton Using a Highly Regioselective Nitroquinone Diels-Alder Reaction." ACS omega vol. 5,16 (2020): 9311-9315. doi: https://doi.org/10.1021/acsomega.0c00201
Yu H, Fought EL, Windus TL, Kraus GA. Direct Synthesis of the Phenanthroviridone Skeleton Using a Highly Regioselective Nitroquinone Diels-Alder Reaction. ACS Omega. 2020 Apr 17;5(16):9311-9315. doi: 10.1021/acsomega.0c00201. eCollection 2020 Apr 28. PMID: 32363281; PMCID: PMC7191567.
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Study of antiradical mechanisms with dihydroxybenzenes using reaction force and reaction electronic flux.

Physical chemistry chemical physics : PCCP

Ortega-Moo C, Durán R, Herrera B, Gutiérrez-Oliva S, Toro-Labbé A, Vargas R.
PMID: 28537305
Phys Chem Chem Phys. 2017 Jun 07;19(22):14512-14519. doi: 10.1039/c7cp01304c.

Phenolic compounds represent an important category of antioxidants because they help inhibit the oxidation process of organic compounds, while also acting as antiradicals in many biological processes. In this work, we analyze the transfer mechanisms for a set of...

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Ortega-Moo C, Durán R, Herrera B, et al. Study of antiradical mechanisms with dihydroxybenzenes using reaction force and reaction electronic flux. Phys Chem Chem Phys. 2017;19(22):14512-14519doi: 10.1039/c7cp01304c.
Ortega-Moo, C., Durán, R., Herrera, B., Gutiérrez-Oliva, S., Toro-Labbé, A., & Vargas, R. (2017). Study of antiradical mechanisms with dihydroxybenzenes using reaction force and reaction electronic flux. Physical chemistry chemical physics : PCCP, 19(22), 14512-14519. https://doi.org/10.1039/c7cp01304c
Ortega-Moo, Cristina, et al. "Study of antiradical mechanisms with dihydroxybenzenes using reaction force and reaction electronic flux." Physical chemistry chemical physics : PCCP vol. 19,22 (2017): 14512-14519. doi: https://doi.org/10.1039/c7cp01304c
Ortega-Moo C, Durán R, Herrera B, Gutiérrez-Oliva S, Toro-Labbé A, Vargas R. Study of antiradical mechanisms with dihydroxybenzenes using reaction force and reaction electronic flux. Phys Chem Chem Phys. 2017 Jun 07;19(22):14512-14519. doi: 10.1039/c7cp01304c. PMID: 28537305.
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Oxygen reduction reaction catalyzed by nickel complexes based on thiophosphorylated calix[4]resorcinols and immobilized in the membrane electrode assembly of fuel cells.

Dalton transactions (Cambridge, England : 2003)

Kadirov MK, Knyazeva IR, Nizameev IR, Safiullin RA, Matveeva VI, Kholin KV, Khrizanforova VV, Ismaev TI, Burilov AR, Budnikova YH, Sinyashin OG.
PMID: 27711779
Dalton Trans. 2016 Oct 18;45(41):16157-16161. doi: 10.1039/c6dt02881k.

The catalytic activity of the nickel complexes of thiophosphorylated calix[4]resorcinols for oxygen reduction in a polymer electrolyte membrane fuel cell (PEMFC) has been studied. The conformation of the macrocyclic ligand determines the morphology and catalytic properties of the resulting...

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Kadirov MK, Knyazeva IR, Nizameev IR, et al. Oxygen reduction reaction catalyzed by nickel complexes based on thiophosphorylated calix[4]resorcinols and immobilized in the membrane electrode assembly of fuel cells. Dalton Trans. 2016;45(41):16157-16161doi: 10.1039/c6dt02881k.
Kadirov, M. K., Knyazeva, I. R., Nizameev, I. R., Safiullin, R. A., Matveeva, V. I., Kholin, K. V., Khrizanforova, V. V., Ismaev, T. I., Burilov, A. R., Budnikova, Y. H., & Sinyashin, O. G. (2016). Oxygen reduction reaction catalyzed by nickel complexes based on thiophosphorylated calix[4]resorcinols and immobilized in the membrane electrode assembly of fuel cells. Dalton transactions (Cambridge, England : 2003), 45(41), 16157-16161. https://doi.org/10.1039/c6dt02881k
Kadirov, M K, et al. "Oxygen reduction reaction catalyzed by nickel complexes based on thiophosphorylated calix[4]resorcinols and immobilized in the membrane electrode assembly of fuel cells." Dalton transactions (Cambridge, England : 2003) vol. 45,41 (2016): 16157-16161. doi: https://doi.org/10.1039/c6dt02881k
Kadirov MK, Knyazeva IR, Nizameev IR, Safiullin RA, Matveeva VI, Kholin KV, Khrizanforova VV, Ismaev TI, Burilov AR, Budnikova YH, Sinyashin OG. Oxygen reduction reaction catalyzed by nickel complexes based on thiophosphorylated calix[4]resorcinols and immobilized in the membrane electrode assembly of fuel cells. Dalton Trans. 2016 Oct 18;45(41):16157-16161. doi: 10.1039/c6dt02881k. PMID: 27711779.
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A single grain screening technique for breeding alkylresorcinol-poor rye.

TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik

Hoffmann F, Wenzel G.
PMID: 24407491
Theor Appl Genet. 1977 Jan;50(1):1-2. doi: 10.1007/BF00273789.

A quick and simple semi-quantitative method of selecting single seeds of rye for their content of 5-alkyl-resorcinols is presented. The resorcinols are extracted from whole, intact caryopses with acetone. Under the conditions described the germination rate is hardly decreased....

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Hoffmann F, Wenzel G. A single grain screening technique for breeding alkylresorcinol-poor rye. Theor Appl Genet. 1977;50(1):1-2doi: 10.1007/BF00273789.
Hoffmann, F., & Wenzel, G. (1977). A single grain screening technique for breeding alkylresorcinol-poor rye. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik, 50(1), 1-2. https://doi.org/10.1007/BF00273789
Hoffmann, F, and Wenzel, G. "A single grain screening technique for breeding alkylresorcinol-poor rye." TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik vol. 50,1 (1977): 1-2. doi: https://doi.org/10.1007/BF00273789
Hoffmann F, Wenzel G. A single grain screening technique for breeding alkylresorcinol-poor rye. Theor Appl Genet. 1977 Jan;50(1):1-2. doi: 10.1007/BF00273789. PMID: 24407491.
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Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents.

Monatshefte fur chemie

Matysiak J, Juszczak M, Karpińska MM, Langner E, Walczak K, Lemieszek M, Skrzypek A, Rzeski W, Niewiadomy A.
PMID: 26190864
Monatsh Chem. 2015;146(8):1315-1327. doi: 10.1007/s00706-015-1453-4. Epub 2015 Apr 02.

No abstract available.

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Matysiak J, Juszczak M, Karpińska MM, et al. Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents. Monatsh Chem. 2015;146(8):1315-1327doi: 10.1007/s00706-015-1453-4.
Matysiak, J., Juszczak, M., Karpińska, M. M., Langner, E., Walczak, K., Lemieszek, M., Skrzypek, A., Rzeski, W., & Niewiadomy, A. (2015). Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents. Monatshefte fur chemie, 146(8), 1315-1327. https://doi.org/10.1007/s00706-015-1453-4
Matysiak, Joanna, et al. "Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents." Monatshefte fur chemie vol. 146,8 (2015): 1315-1327. doi: https://doi.org/10.1007/s00706-015-1453-4
Matysiak J, Juszczak M, Karpińska MM, Langner E, Walczak K, Lemieszek M, Skrzypek A, Rzeski W, Niewiadomy A. Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents. Monatsh Chem. 2015;146(8):1315-1327. doi: 10.1007/s00706-015-1453-4. Epub 2015 Apr 02. PMID: 26190864; PMCID: PMC4498246.
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Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols .

Advanced synthesis & catalysis

Bryant LA, Shankland K, Straker HE, Johnston CD, Lees NR, Cobb AJA.
PMID: 34594164
Adv Synth Catal. 2021 Aug 13;363(16):4067-4074. doi: 10.1002/adsc.202100647. Epub 2021 Jul 12.

The organocatalytic transformation of resorcinols is extremely rare. In this article, we report a highly enantioselective, organocatalytic intramolecular cyclization of these systems by a Friedel-Crafts-type 1,4-addition using a Jørgensen-Hayashi-like organocatalyst with a large silyl protecting group, and show that...

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Bryant LA, Shankland K, Straker HE, et al. Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols . Adv Synth Catal. 2021;363(16):4067-4074doi: 10.1002/adsc.202100647.
Bryant, L. A., Shankland, K., Straker, H. E., Johnston, C. D., Lees, N. R., & Cobb, A. J. A. (2021). Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols . Advanced synthesis & catalysis, 363(16), 4067-4074. https://doi.org/10.1002/adsc.202100647
Bryant, Laura A, et al. "Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols ." Advanced synthesis & catalysis vol. 363,16 (2021): 4067-4074. doi: https://doi.org/10.1002/adsc.202100647
Bryant LA, Shankland K, Straker HE, Johnston CD, Lees NR, Cobb AJA. Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols . Adv Synth Catal. 2021 Aug 13;363(16):4067-4074. doi: 10.1002/adsc.202100647. Epub 2021 Jul 12. PMID: 34594164; PMCID: PMC8457227.
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Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability.

ACS medicinal chemistry letters

Kinney WA, McDonnell ME, Zhong HM, Liu C, Yang L, Ling W, Qian T, Chen Y, Cai Z, Petkanas D, Brenneman DE.
PMID: 27096053
ACS Med Chem Lett. 2016 Feb 10;7(4):424-8. doi: 10.1021/acsmedchemlett.6b00009. eCollection 2016 Apr 14.

Cannabidiol is the nonpsychoactive natural component of C. sativa that has been shown to be neuroprotective in multiple animal models. Our interest is to advance a therapeutic candidate for the orphan indication hepatic encephalopathy (HE). HE is a serious...

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Kinney WA, McDonnell ME, Zhong HM, et al. Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability. ACS Med Chem Lett. 2016;7(4):424-8doi: 10.1021/acsmedchemlett.6b00009.
Kinney, W. A., McDonnell, M. E., Zhong, H. M., Liu, C., Yang, L., Ling, W., Qian, T., Chen, Y., Cai, Z., Petkanas, D., & Brenneman, D. E. (2016). Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability. ACS medicinal chemistry letters, 7(4), 424-8. https://doi.org/10.1021/acsmedchemlett.6b00009
Kinney, William A, et al. "Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability." ACS medicinal chemistry letters vol. 7,4 (2016): 424-8. doi: https://doi.org/10.1021/acsmedchemlett.6b00009
Kinney WA, McDonnell ME, Zhong HM, Liu C, Yang L, Ling W, Qian T, Chen Y, Cai Z, Petkanas D, Brenneman DE. Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability. ACS Med Chem Lett. 2016 Feb 10;7(4):424-8. doi: 10.1021/acsmedchemlett.6b00009. eCollection 2016 Apr 14. PMID: 27096053; PMCID: PMC4834656.
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