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Thermodynamic characterization of halide-π interactions in solution using "two-wall" aryl extended calix[4]pyrroles as model system.

Journal of the American Chemical Society

Adriaenssens L, Gil-Ramírez G, Frontera A, Quiñonero D, Escudero-Adán EC, Ballester P.
PMID: 24494711
J Am Chem Soc. 2014 Feb 26;136(8):3208-18. doi: 10.1021/ja412098v. Epub 2014 Feb 17.

Herein, we report our latest experimental investigations of halide-π interactions in solution. We base this research on the thermodynamic characterization of a series of 1:1 complexes formed between halides (Cl(-), Br(-), and I(-)) and several α,α-isomers of "two-wall" calix[4]pyrrole...

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Adriaenssens L, Gil-Ramírez G, Frontera A, et al. Thermodynamic characterization of halide-π interactions in solution using "two-wall" aryl extended calix[4]pyrroles as model system. J Am Chem Soc. 2014;136(8):3208-18doi: 10.1021/ja412098v.
Adriaenssens, L., Gil-Ramírez, G., Frontera, A., Quiñonero, D., Escudero-Adán, E. C., & Ballester, P. (2014). Thermodynamic characterization of halide-π interactions in solution using "two-wall" aryl extended calix[4]pyrroles as model system. Journal of the American Chemical Society, 136(8), 3208-18. https://doi.org/10.1021/ja412098v
Adriaenssens, Louis, et al. "Thermodynamic characterization of halide-π interactions in solution using "two-wall" aryl extended calix[4]pyrroles as model system." Journal of the American Chemical Society vol. 136,8 (2014): 3208-18. doi: https://doi.org/10.1021/ja412098v
Adriaenssens L, Gil-Ramírez G, Frontera A, Quiñonero D, Escudero-Adán EC, Ballester P. Thermodynamic characterization of halide-π interactions in solution using "two-wall" aryl extended calix[4]pyrroles as model system. J Am Chem Soc. 2014 Feb 26;136(8):3208-18. doi: 10.1021/ja412098v. Epub 2014 Feb 17. PMID: 24494711.
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Influence of structural and solvation factors on the spectral-fluorescent properties of alkyl-substituted BODIPYs in solutions.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy

Bumagina NA, Antina EV, Berezin MB, Kalyagin AA.
PMID: 27665190
Spectrochim Acta A Mol Biomol Spectrosc. 2017 Feb 15;173:228-234. doi: 10.1016/j.saa.2016.09.026. Epub 2016 Sep 20.

The spectral-fluorescent properties of alkyl-substituted BODIPYs 1-5 in organic solvents were investigated. The alkyl-substituted BODIPYs 1-5 exhibit intense chromophoric properties (lgε=4.60-5.00). Relative fluorescence quantum yield of studied compounds reaches 66-100% and weakly dependent on the structural and solvation effects....

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Bumagina NA, Antina EV, Berezin MB, et al. Influence of structural and solvation factors on the spectral-fluorescent properties of alkyl-substituted BODIPYs in solutions. Spectrochim Acta A Mol Biomol Spectrosc. 2016;173:228-234doi: 10.1016/j.saa.2016.09.026.
Bumagina, N. A., Antina, E. V., Berezin, M. B., & Kalyagin, A. A. (2017). Influence of structural and solvation factors on the spectral-fluorescent properties of alkyl-substituted BODIPYs in solutions. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 173228-234. https://doi.org/10.1016/j.saa.2016.09.026
Bumagina, Natalia A, et al. "Influence of structural and solvation factors on the spectral-fluorescent properties of alkyl-substituted BODIPYs in solutions." Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy vol. 173 (2017): 228-234. doi: https://doi.org/10.1016/j.saa.2016.09.026
Bumagina NA, Antina EV, Berezin MB, Kalyagin AA. Influence of structural and solvation factors on the spectral-fluorescent properties of alkyl-substituted BODIPYs in solutions. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Feb 15;173:228-234. doi: 10.1016/j.saa.2016.09.026. Epub 2016 Sep 20. PMID: 27665190.
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Calix[4]pyrroles with Shortest Possible Strap: Exclusively Selective toward Fluoride Ion.

Organic letters

Samanta R, Kumar BS, Panda PK.
PMID: 26313641
Org Lett. 2015 Sep 04;17(17):4140-3. doi: 10.1021/acs.orglett.5b01866. Epub 2015 Aug 27.

Four new calix[4]pyrroles with the shortest possible strap so far through ortho-linking of the aromatic unit have been synthesized, including a naphthalene-derived fluorescent receptor. They show exclusive selectivity toward the fluoride ion as confirmed by (1)H NMR, isothermal titration...

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Samanta R, Kumar BS, Panda PK. Calix[4]pyrroles with Shortest Possible Strap: Exclusively Selective toward Fluoride Ion. Org Lett. 2015;17(17):4140-3doi: 10.1021/acs.orglett.5b01866.
Samanta, R., Kumar, B. S., & Panda, P. K. (2015). Calix[4]pyrroles with Shortest Possible Strap: Exclusively Selective toward Fluoride Ion. Organic letters, 17(17), 4140-3. https://doi.org/10.1021/acs.orglett.5b01866
Samanta, Ritwik, et al. "Calix[4]pyrroles with Shortest Possible Strap: Exclusively Selective toward Fluoride Ion." Organic letters vol. 17,17 (2015): 4140-3. doi: https://doi.org/10.1021/acs.orglett.5b01866
Samanta R, Kumar BS, Panda PK. Calix[4]pyrroles with Shortest Possible Strap: Exclusively Selective toward Fluoride Ion. Org Lett. 2015 Sep 04;17(17):4140-3. doi: 10.1021/acs.orglett.5b01866. Epub 2015 Aug 27. PMID: 26313641.
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Targeting Oncogenic Mutant p53 for Cancer Therapy.

Frontiers in oncology

Parrales A, Iwakuma T.
PMID: 26732534
Front Oncol. 2015 Dec 21;5:288. doi: 10.3389/fonc.2015.00288. eCollection 2015.

Among genetic alterations in human cancers, mutations in the tumor suppressor p53 gene are the most common, occurring in over 50% of human cancers. The majority of p53 mutations are missense mutations and result in the accumulation of dysfunctional...

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Parrales A, Iwakuma T. Targeting Oncogenic Mutant p53 for Cancer Therapy. Front Oncol. 2015;5:288doi: 10.3389/fonc.2015.00288.
Parrales, A., & Iwakuma, T. (2015). Targeting Oncogenic Mutant p53 for Cancer Therapy. Frontiers in oncology, 5288. https://doi.org/10.3389/fonc.2015.00288
Parrales, Alejandro, and Iwakuma, Tomoo. "Targeting Oncogenic Mutant p53 for Cancer Therapy." Frontiers in oncology vol. 5 (2015): 288. doi: https://doi.org/10.3389/fonc.2015.00288
Parrales A, Iwakuma T. Targeting Oncogenic Mutant p53 for Cancer Therapy. Front Oncol. 2015 Dec 21;5:288. doi: 10.3389/fonc.2015.00288. eCollection 2015. PMID: 26732534; PMCID: PMC4685147.
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Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles.

Chemical communications (Cambridge, England)

Wippich J, Schnapperelle I, Bach T.
PMID: 25605647
Chem Commun (Camb). 2015 Feb 21;51(15):3166-8. doi: 10.1039/c4cc10144h.

A total of 19 alkylated heterocycles (thiophenes, benzothiophenes, pyrroles, furans) were prepared (36-99% yield) from the respective pyridin-2-yl-substituted precursors employing alkylboronic acids as the C-H alkylating reagents in an oxidative (Ag2CO3 and 2,6-dimethyl-1,4-benzoquinone as oxidants) Pd-catalysed coupling reaction.

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Wippich J, Schnapperelle I, Bach T. Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles. Chem Commun (Camb). 2015;51(15):3166-8doi: 10.1039/c4cc10144h.
Wippich, J., Schnapperelle, I., & Bach, T. (2015). Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles. Chemical communications (Cambridge, England), 51(15), 3166-8. https://doi.org/10.1039/c4cc10144h
Wippich, Julian, et al. "Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles." Chemical communications (Cambridge, England) vol. 51,15 (2015): 3166-8. doi: https://doi.org/10.1039/c4cc10144h
Wippich J, Schnapperelle I, Bach T. Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles. Chem Commun (Camb). 2015 Feb 21;51(15):3166-8. doi: 10.1039/c4cc10144h. PMID: 25605647.
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Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis.

Royal Society open science

Arimori S, Matsubara O, Takada M, Shiro M, Shibata N.
PMID: 27293790
R Soc Open Sci. 2016 May 25;3(5):160102. doi: 10.1098/rsos.160102. eCollection 2016 May.

Difluoromethanesulfonyl hypervalent iodonium ylides 2 were developed as electrophilic difluoromethylthiolation reagents for a wide range of nucleophiles. Enamines, indoles, β-keto esters, silyl enol ethers and pyrroles were effectively reacted with 2 affording desired difluoromethylthio (SCF2H)-substituted compounds in good to...

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Arimori S, Matsubara O, Takada M, et al. Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis. R Soc Open Sci. 2016;3(5):160102doi: 10.1098/rsos.160102.
Arimori, S., Matsubara, O., Takada, M., Shiro, M., & Shibata, N. (2016). Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis. Royal Society open science, 3(5), 160102. https://doi.org/10.1098/rsos.160102
Arimori, Sadayuki, et al. "Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis." Royal Society open science vol. 3,5 (2016): 160102. doi: https://doi.org/10.1098/rsos.160102
Arimori S, Matsubara O, Takada M, Shiro M, Shibata N. Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis. R Soc Open Sci. 2016 May 25;3(5):160102. doi: 10.1098/rsos.160102. eCollection 2016 May. PMID: 27293790; PMCID: PMC4892452.
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Selective Rhodium-Catalyzed Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes with a Tetraphosphoramidite Ligand.

Organic letters

Zhang Z, Wang Q, Chen C, Han Z, Dong XQ, Zhang X.
PMID: 27333272
Org Lett. 2016 Jul 01;18(13):3290-3. doi: 10.1021/acs.orglett.6b01605. Epub 2016 Jun 22.

A tetraphosphoramidite ligand was successfully applied to a Rh-catalyzed hydroformylation of various symmetrical and unsymmetrical alkynes to afford corresponding α,β-unsaturated aldehyde products in good to excellent yields (up to 97% yield). Excellent chemo- and regioselectivities and high activities (up...

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Zhang Z, Wang Q, Chen C, et al. Selective Rhodium-Catalyzed Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes with a Tetraphosphoramidite Ligand. Org Lett. 2016;18(13):3290-3doi: 10.1021/acs.orglett.6b01605.
Zhang, Z., Wang, Q., Chen, C., Han, Z., Dong, X. Q., & Zhang, X. (2016). Selective Rhodium-Catalyzed Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes with a Tetraphosphoramidite Ligand. Organic letters, 18(13), 3290-3. https://doi.org/10.1021/acs.orglett.6b01605
Zhang, Zongpeng, et al. "Selective Rhodium-Catalyzed Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes with a Tetraphosphoramidite Ligand." Organic letters vol. 18,13 (2016): 3290-3. doi: https://doi.org/10.1021/acs.orglett.6b01605
Zhang Z, Wang Q, Chen C, Han Z, Dong XQ, Zhang X. Selective Rhodium-Catalyzed Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes with a Tetraphosphoramidite Ligand. Org Lett. 2016 Jul 01;18(13):3290-3. doi: 10.1021/acs.orglett.6b01605. Epub 2016 Jun 22. PMID: 27333272.
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Hydrogen Bonding: HOC=O· · ·H-N vs. HOC=O· · ·H-C.

Monatshefte fur chemie

Dey SK, Datta S, Lightner DA.
PMID: 25745269
Monatsh Chem. 2014 Oct 01;145(10):1595-1609. doi: 10.1007/s00706-014-1257-y.

A chloroform-soluble dipyrrinone, 8,9-bis-(5-carboxypentyl)-2,3-bis-(2-methoxyethoxy)-10

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Dey SK, Datta S, Lightner DA. Hydrogen Bonding: HOC=O· · ·H-N vs. HOC=O· · ·H-C. Monatsh Chem. 2014;145(10):1595-1609doi: 10.1007/s00706-014-1257-y.
Dey, S. K., Datta, S., & Lightner, D. A. (2014). Hydrogen Bonding: HOC=O· · ·H-N vs. HOC=O· · ·H-C. Monatshefte fur chemie, 145(10), 1595-1609. https://doi.org/10.1007/s00706-014-1257-y
Dey, Sanjeev K, et al. "Hydrogen Bonding: HOC=O· · ·H-N vs. HOC=O· · ·H-C." Monatshefte fur chemie vol. 145,10 (2014): 1595-1609. doi: https://doi.org/10.1007/s00706-014-1257-y
Dey SK, Datta S, Lightner DA. Hydrogen Bonding: HOC=O· · ·H-N vs. HOC=O· · ·H-C. Monatsh Chem. 2014 Oct 01;145(10):1595-1609. doi: 10.1007/s00706-014-1257-y. PMID: 25745269; PMCID: PMC4346226.
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Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles.

The Journal of organic chemistry

Yugandar S, Konda S, Ila H.
PMID: 26842134
J Org Chem. 2016 Mar 04;81(5):2035-52. doi: 10.1021/acs.joc.5b02902. Epub 2016 Feb 18.

An efficient route to multisubstituted indoles has been developed through intramolecular oxidative C-H activation-amination of readily available 2-(het)aryl-3-(het)aryl/alkyl-3-(het)aryl/acylaminoacrylonitrile/enaminone precursors in the presence of either palladium acetate/cupric acetate catalytic system under oxygen atmosphere or palladium acetate/silver carbonate in the presence...

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Yugandar S, Konda S, Ila H. Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles. J Org Chem. 2016;81(5):2035-52doi: 10.1021/acs.joc.5b02902.
Yugandar, S., Konda, S., & Ila, H. (2016). Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles. The Journal of organic chemistry, 81(5), 2035-52. https://doi.org/10.1021/acs.joc.5b02902
Yugandar, Somaraju, et al. "Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles." The Journal of organic chemistry vol. 81,5 (2016): 2035-52. doi: https://doi.org/10.1021/acs.joc.5b02902
Yugandar S, Konda S, Ila H. Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles. J Org Chem. 2016 Mar 04;81(5):2035-52. doi: 10.1021/acs.joc.5b02902. Epub 2016 Feb 18. PMID: 26842134.
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Stabilized pyrrolyl iodonium salts and metal-free oxidative cross-coupling.

Organic & biomolecular chemistry

Morimoto K, Ohnishi Y, Koseki D, Nakamura A, Dohi T, Kita Y.
PMID: 27722732
Org Biomol Chem. 2016 Sep 26;14(38):8947-8951. doi: 10.1039/c6ob01764a.

Pyrrole-aryl derivatives are important due to their unique biological activities in medicinal chemistry. We now report a new oxidative biaryl coupling for pyrroles and indoles toward various arenes using a hypervalent iodine reagent and an appropriate stabilizer for pyrrolyl...

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Morimoto K, Ohnishi Y, Koseki D, et al. Stabilized pyrrolyl iodonium salts and metal-free oxidative cross-coupling. Org Biomol Chem. 2016;14(38):8947-8951doi: 10.1039/c6ob01764a.
Morimoto, K., Ohnishi, Y., Koseki, D., Nakamura, A., Dohi, T., & Kita, Y. (2016). Stabilized pyrrolyl iodonium salts and metal-free oxidative cross-coupling. Organic & biomolecular chemistry, 14(38), 8947-8951. https://doi.org/10.1039/c6ob01764a
Morimoto, Koji, et al. "Stabilized pyrrolyl iodonium salts and metal-free oxidative cross-coupling." Organic & biomolecular chemistry vol. 14,38 (2016): 8947-8951. doi: https://doi.org/10.1039/c6ob01764a
Morimoto K, Ohnishi Y, Koseki D, Nakamura A, Dohi T, Kita Y. Stabilized pyrrolyl iodonium salts and metal-free oxidative cross-coupling. Org Biomol Chem. 2016 Sep 26;14(38):8947-8951. doi: 10.1039/c6ob01764a. PMID: 27722732.
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Synthesis of Polysubstituted Pyrroles through a Formal [4 + 1] Cycloaddition/E1cb Elimination/Aromatization Sequence of Sulfur Ylides and α,β-Unsaturated Imines.

The Journal of organic chemistry

Cheng BY, Wang YN, Li TR, Lu LQ, Xiao WJ.
PMID: 29087199
J Org Chem. 2017 Dec 01;82(23):12134-12140. doi: 10.1021/acs.joc.7b01931. Epub 2017 Nov 09.

A reaction sequence comprising a formal [4 + 1] cycloaddition, an E1cb elimination, and an aromatization process is described in this work. By doing so, polysubstituted pyrroles were achieved from easily available chemicals, sulfur ylides, and α,β-unsaturated imines. This...

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Cheng BY, Wang YN, Li TR, et al. Synthesis of Polysubstituted Pyrroles through a Formal [4 + 1] Cycloaddition/E1cb Elimination/Aromatization Sequence of Sulfur Ylides and α,β-Unsaturated Imines. J Org Chem. 2017;82(23):12134-12140doi: 10.1021/acs.joc.7b01931.
Cheng, B. Y., Wang, Y. N., Li, T. R., Lu, L. Q., & Xiao, W. J. (2017). Synthesis of Polysubstituted Pyrroles through a Formal [4 + 1] Cycloaddition/E1cb Elimination/Aromatization Sequence of Sulfur Ylides and α,β-Unsaturated Imines. The Journal of organic chemistry, 82(23), 12134-12140. https://doi.org/10.1021/acs.joc.7b01931
Cheng, Bei-Yi, et al. "Synthesis of Polysubstituted Pyrroles through a Formal [4 + 1] Cycloaddition/E1cb Elimination/Aromatization Sequence of Sulfur Ylides and α,β-Unsaturated Imines." The Journal of organic chemistry vol. 82,23 (2017): 12134-12140. doi: https://doi.org/10.1021/acs.joc.7b01931
Cheng BY, Wang YN, Li TR, Lu LQ, Xiao WJ. Synthesis of Polysubstituted Pyrroles through a Formal [4 + 1] Cycloaddition/E1cb Elimination/Aromatization Sequence of Sulfur Ylides and α,β-Unsaturated Imines. J Org Chem. 2017 Dec 01;82(23):12134-12140. doi: 10.1021/acs.joc.7b01931. Epub 2017 Nov 09. PMID: 29087199.
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Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles.

The Journal of organic chemistry

Miao M, Luo Y, Xu H, Jin M, Chen Z, Xu J, Ren H.
PMID: 29058419
J Org Chem. 2017 Dec 01;82(23):12224-12237. doi: 10.1021/acs.joc.7b02087. Epub 2017 Oct 30.

The tunable nucleophilic nitration of 3-cyclopropylideneprop-2-en-1-ones with cheap sodium nitrite is described. This transformation proceeds with the assistance of a strained cyclopropane ring and allows for a divergent route to various synthetically useful β,γ-dinitro or γ-mononitro adducts in high...

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Miao M, Luo Y, Xu H, et al. Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles. J Org Chem. 2017;82(23):12224-12237doi: 10.1021/acs.joc.7b02087.
Miao, M., Luo, Y., Xu, H., Jin, M., Chen, Z., Xu, J., & Ren, H. (2017). Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles. The Journal of organic chemistry, 82(23), 12224-12237. https://doi.org/10.1021/acs.joc.7b02087
Miao, Maozhong, et al. "Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles." The Journal of organic chemistry vol. 82,23 (2017): 12224-12237. doi: https://doi.org/10.1021/acs.joc.7b02087
Miao M, Luo Y, Xu H, Jin M, Chen Z, Xu J, Ren H. Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles. J Org Chem. 2017 Dec 01;82(23):12224-12237. doi: 10.1021/acs.joc.7b02087. Epub 2017 Oct 30. PMID: 29058419.
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