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Crystal structure of 2-[9-(2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetic acid.

Acta crystallographica. Section E, Crystallographic communications

Akkurt M, Jasinski JP, Mohamed SK, Allah OA, Tamam AH, Albayati MR.
PMID: 26870552
Acta Crystallogr E Crystallogr Commun. 2015 Nov 21;71:o963-4. doi: 10.1107/S2056989015021611. eCollection 2015 Dec 01.

The title compound, C21H21NO5, crystallizes with two mol-ecules in the asymmetric unit. In each mol-ecule, the central 1,4-di-hydro-pyridine ring adopts a shallow sofa conformations (with the C atom bearing the phenol ring as the flap), whereas the pendant cyclo-hexene...

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Akkurt M, Jasinski JP, Mohamed SK, et al. Crystal structure of 2-[9-(2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetic acid. Acta Crystallogr E Crystallogr Commun. 2015;71:o963-4doi: 10.1107/S2056989015021611.
Akkurt, M., Jasinski, J. P., Mohamed, S. K., Allah, O. A., Tamam, A. H., & Albayati, M. R. (2015). Crystal structure of 2-[9-(2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetic acid. Acta crystallographica. Section E, Crystallographic communications, 71o963-4. https://doi.org/10.1107/S2056989015021611
Akkurt, Mehmet, et al. "Crystal structure of 2-[9-(2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetic acid." Acta crystallographica. Section E, Crystallographic communications vol. 71 (2015): o963-4. doi: https://doi.org/10.1107/S2056989015021611
Akkurt M, Jasinski JP, Mohamed SK, Allah OA, Tamam AH, Albayati MR. Crystal structure of 2-[9-(2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetic acid. Acta Crystallogr E Crystallogr Commun. 2015 Nov 21;71:o963-4. doi: 10.1107/S2056989015021611. eCollection 2015 Dec 01. PMID: 26870552; PMCID: PMC4719924.
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Crystal structure of ethyl 2-[9-(5-bromo-2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetate.

Acta crystallographica. Section E, Crystallographic communications

Mohamed SK, Akkurt M, Jasinski JP, Abdelhamid AA, Tamam AH, Albayati MR.
PMID: 26870566
Acta Crystallogr E Crystallogr Commun. 2015 Nov 25;71:o989-90. doi: 10.1107/S2056989015022240. eCollection 2015 Dec 01.

In the title compound, C23H24BrNO5, the central 1,4-di-hydro-pyridine ring of the 1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine ring system adopts a half-chair conformation. The two cyclo-hexene rings fused to the central ring both have a twisted-boat conformation. The mean planes of the bromo-hydroxy-phenyl ring...

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Mohamed SK, Akkurt M, Jasinski JP, et al. Crystal structure of ethyl 2-[9-(5-bromo-2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetate. Acta Crystallogr E Crystallogr Commun. 2015;71:o989-90doi: 10.1107/S2056989015022240.
Mohamed, S. K., Akkurt, M., Jasinski, J. P., Abdelhamid, A. A., Tamam, A. H., & Albayati, M. R. (2015). Crystal structure of ethyl 2-[9-(5-bromo-2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetate. Acta crystallographica. Section E, Crystallographic communications, 71o989-90. https://doi.org/10.1107/S2056989015022240
Mohamed, Shaaban K, et al. "Crystal structure of ethyl 2-[9-(5-bromo-2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetate." Acta crystallographica. Section E, Crystallographic communications vol. 71 (2015): o989-90. doi: https://doi.org/10.1107/S2056989015022240
Mohamed SK, Akkurt M, Jasinski JP, Abdelhamid AA, Tamam AH, Albayati MR. Crystal structure of ethyl 2-[9-(5-bromo-2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetate. Acta Crystallogr E Crystallogr Commun. 2015 Nov 25;71:o989-90. doi: 10.1107/S2056989015022240. eCollection 2015 Dec 01. PMID: 26870566; PMCID: PMC4719938.
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First Whole-Genome Sequence of a .

Genome announcements

Giufrè M, Cardines R, Cerquetti M.
PMID: 28360180
Genome Announc. 2017 Mar 30;5(13). doi: 10.1128/genomeA.00059-17.

In the present era of conjugate vaccines against

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Giufrè M, Cardines R, Cerquetti M. First Whole-Genome Sequence of a . Genome Announc. 2017;5(13)doi: 10.1128/genomeA.00059-17.
Giufrè, M., Cardines, R., & Cerquetti, M. (2017). First Whole-Genome Sequence of a . Genome announcements, 5(13), . https://doi.org/10.1128/genomeA.00059-17
Giufrè, Maria, et al. "First Whole-Genome Sequence of a ." Genome announcements vol. 5,13 (2017). doi: https://doi.org/10.1128/genomeA.00059-17
Giufrè M, Cardines R, Cerquetti M. First Whole-Genome Sequence of a . Genome Announc. 2017 Mar 30;5(13). doi: 10.1128/genomeA.00059-17. PMID: 28360180; PMCID: PMC5374224.
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Whole-Genome Sequences of Nonencapsulated Haemophilus influenzae Strains Isolated in Italy.

Genome announcements

Giufrè M, De Chiara M, Censini S, Guidotti S, Torricelli G, De Angelis G, Cardines R, Pizza M, Muzzi A, Cerquetti M, Soriani M.
PMID: 25814593
Genome Announc. 2015 Mar 26;3(2). doi: 10.1128/genomeA.00110-15.

Haemophilus influenzae is an important human pathogen involved in invasive disease. Here, we report the whole-genome sequences of 11 nonencapsulated H. influenzae (ncHi) strains isolated from both invasive disease and healthy carriers in Italy. This genomic information will enrich...

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Giufrè M, De Chiara M, Censini S, et al. Whole-Genome Sequences of Nonencapsulated Haemophilus influenzae Strains Isolated in Italy. Genome Announc. 2015;3(2)doi: 10.1128/genomeA.00110-15.
Giufrè, M., De Chiara, M., Censini, S., Guidotti, S., Torricelli, G., De Angelis, G., Cardines, R., Pizza, M., Muzzi, A., Cerquetti, M., & Soriani, M. (2015). Whole-Genome Sequences of Nonencapsulated Haemophilus influenzae Strains Isolated in Italy. Genome announcements, 3(2), . https://doi.org/10.1128/genomeA.00110-15
Giufrè, Maria, et al. "Whole-Genome Sequences of Nonencapsulated Haemophilus influenzae Strains Isolated in Italy." Genome announcements vol. 3,2 (2015). doi: https://doi.org/10.1128/genomeA.00110-15
Giufrè M, De Chiara M, Censini S, Guidotti S, Torricelli G, De Angelis G, Cardines R, Pizza M, Muzzi A, Cerquetti M, Soriani M. Whole-Genome Sequences of Nonencapsulated Haemophilus influenzae Strains Isolated in Italy. Genome Announc. 2015 Mar 26;3(2). doi: 10.1128/genomeA.00110-15. PMID: 25814593; PMCID: PMC4384133.
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Intracellular distribution of 3,6-bis(3-alkylguanidino)acridines determines their cytotoxicity.

Neoplasma

Krajnakova L, Paulikova H, Bacova Z, Bakos J, Janovec L, Imrich J, Hunakova L.
PMID: 25563372
Neoplasma. 2015;62(1):98-107. doi: 10.4149/neo_2015_012.

UNLABELLED: Cytotoxicity of two derivatives of 3,6-bis(3-alkylguanidino)acridines (GNDAs; pentyl- and hexyl-GNDA) was determined against three cell lines: a murine immortalized fibroblast cell line NIH-3T3, a human ovarian carcinoma cell line A2780, and a human neuroblastoma cell line SH-SY5Y. We...

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Krajnakova L, Paulikova H, Bacova Z, et al. Intracellular distribution of 3,6-bis(3-alkylguanidino)acridines determines their cytotoxicity. Neoplasma. 2015;62(1):98-107doi: 10.4149/neo_2015_012.
Krajnakova, L., Paulikova, H., Bacova, Z., Bakos, J., Janovec, L., Imrich, J., & Hunakova, L. (2015). Intracellular distribution of 3,6-bis(3-alkylguanidino)acridines determines their cytotoxicity. Neoplasma, 62(1), 98-107. https://doi.org/10.4149/neo_2015_012
Krajnakova, L, et al. "Intracellular distribution of 3,6-bis(3-alkylguanidino)acridines determines their cytotoxicity." Neoplasma vol. 62,1 (2015): 98-107. doi: https://doi.org/10.4149/neo_2015_012
Krajnakova L, Paulikova H, Bacova Z, Bakos J, Janovec L, Imrich J, Hunakova L. Intracellular distribution of 3,6-bis(3-alkylguanidino)acridines determines their cytotoxicity. Neoplasma. 2015;62(1):98-107. doi: 10.4149/neo_2015_012. PMID: 25563372.
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ATTEMPTS TO PROTECT AGAINST INFLUENZA VIRUS WITH VARIOUS SULFONAMIDES, ACRIDINES AND ANTIBIOTICS.

Science (New York, N.Y.)

[No authors listed]
PMID: 17794469
Science. 1943 Oct 15;98(2546):348-9. doi: 10.1126/science.98.2546.348.

No abstract available.

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ATTEMPTS TO PROTECT AGAINST INFLUENZA VIRUS WITH VARIOUS SULFONAMIDES, ACRIDINES AND ANTIBIOTICS. Science. 1943;98(2546):348-9doi: 10.1126/science.98.2546.348.
(1943). ATTEMPTS TO PROTECT AGAINST INFLUENZA VIRUS WITH VARIOUS SULFONAMIDES, ACRIDINES AND ANTIBIOTICS. Science (New York, N.Y.), 98(2546), 348-9. https://doi.org/10.1126/science.98.2546.348
"ATTEMPTS TO PROTECT AGAINST INFLUENZA VIRUS WITH VARIOUS SULFONAMIDES, ACRIDINES AND ANTIBIOTICS." Science (New York, N.Y.) vol. 98,2546 (1943): 348-9. doi: https://doi.org/10.1126/science.98.2546.348
ATTEMPTS TO PROTECT AGAINST INFLUENZA VIRUS WITH VARIOUS SULFONAMIDES, ACRIDINES AND ANTIBIOTICS. Science. 1943 Oct 15;98(2546):348-9. doi: 10.1126/science.98.2546.348. PMID: 17794469.
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Reactivity of pyrido[4,3,2-kl]acridines: regioselective formation of 6-substituted derivatives.

The Journal of organic chemistry

Bouffier L, Demeunynck M, Milet A, Dumy P.
PMID: 15527309
J Org Chem. 2004 Nov 12;69(23):8144-7. doi: 10.1021/jo0487855.

Pyrido[4,3,2-kl]acridines represent a new class of heterocycles, isomers of marine alkaloids. The 7H-pyrido[4,3,2-kl]acridine reacts as an electron rich heterocycle, and in particular via electrophilic substitution such as H/D exchange and the Vilsmeier-Haack reaction. The reaction is fully regioselective and...

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Bouffier L, Demeunynck M, Milet A, et al. Reactivity of pyrido[4,3,2-kl]acridines: regioselective formation of 6-substituted derivatives. J Org Chem. 2004;69(23):8144-7doi: 10.1021/jo0487855.
Bouffier, L., Demeunynck, M., Milet, A., & Dumy, P. (2004). Reactivity of pyrido[4,3,2-kl]acridines: regioselective formation of 6-substituted derivatives. The Journal of organic chemistry, 69(23), 8144-7. https://doi.org/10.1021/jo0487855
Bouffier, Laurent, et al. "Reactivity of pyrido[4,3,2-kl]acridines: regioselective formation of 6-substituted derivatives." The Journal of organic chemistry vol. 69,23 (2004): 8144-7. doi: https://doi.org/10.1021/jo0487855
Bouffier L, Demeunynck M, Milet A, Dumy P. Reactivity of pyrido[4,3,2-kl]acridines: regioselective formation of 6-substituted derivatives. J Org Chem. 2004 Nov 12;69(23):8144-7. doi: 10.1021/jo0487855. PMID: 15527309.
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The concept of privileged structures in rational drug design: focus on acridine and quinoline scaffolds in neurodegenerative and protozoan diseases.

Expert opinion on drug discovery

Bongarzone S, Bolognesi ML.
PMID: 22647203
Expert Opin Drug Discov. 2011 Mar;6(3):251-68. doi: 10.1517/17460441.2011.550914. Epub 2011 Jan 18.

INTRODUCTION: For nearly 20 years, privileged structures have offered an optimal source of core scaffolds and capping fragments for the design of combinatorial libraries directed at a broad spectrum of targets. From describing structures promiscuous within a given target...

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Bongarzone S, Bolognesi ML. The concept of privileged structures in rational drug design: focus on acridine and quinoline scaffolds in neurodegenerative and protozoan diseases. Expert Opin Drug Discov. 2011;6(3):251-68doi: 10.1517/17460441.2011.550914.
Bongarzone, S., & Bolognesi, M. L. (2011). The concept of privileged structures in rational drug design: focus on acridine and quinoline scaffolds in neurodegenerative and protozoan diseases. Expert opinion on drug discovery, 6(3), 251-68. https://doi.org/10.1517/17460441.2011.550914
Bongarzone, Salvatore, and Bolognesi, Maria Laura. "The concept of privileged structures in rational drug design: focus on acridine and quinoline scaffolds in neurodegenerative and protozoan diseases." Expert opinion on drug discovery vol. 6,3 (2011): 251-68. doi: https://doi.org/10.1517/17460441.2011.550914
Bongarzone S, Bolognesi ML. The concept of privileged structures in rational drug design: focus on acridine and quinoline scaffolds in neurodegenerative and protozoan diseases. Expert Opin Drug Discov. 2011 Mar;6(3):251-68. doi: 10.1517/17460441.2011.550914. Epub 2011 Jan 18. PMID: 22647203.
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Unexpected cyclization of tritylamines promoted by copper salt through C-H and C-N bond cleavages to produce acridine derivatives.

Chemistry (Weinheim an der Bergstrasse, Germany)

Morioka R, Hirano K, Satoh T, Miura M.
PMID: 25196267
Chemistry. 2014 Sep 26;20(40):12720-4. doi: 10.1002/chem.201404656. Epub 2014 Sep 04.

Herein, we demonstrate that tritylamines undergo an unprecedented copper-mediated cyclization involving the cleavages of two C-H bonds and one C-N bond to give 9-arylacridine derivatives. This kind of acridines is of interest due to their biological properties and their...

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Morioka R, Hirano K, Satoh T, et al. Unexpected cyclization of tritylamines promoted by copper salt through C-H and C-N bond cleavages to produce acridine derivatives. Chemistry. 2014;20(40):12720-4doi: 10.1002/chem.201404656.
Morioka, R., Hirano, K., Satoh, T., & Miura, M. (2014). Unexpected cyclization of tritylamines promoted by copper salt through C-H and C-N bond cleavages to produce acridine derivatives. Chemistry (Weinheim an der Bergstrasse, Germany), 20(40), 12720-4. https://doi.org/10.1002/chem.201404656
Morioka, Ryosuke, et al. "Unexpected cyclization of tritylamines promoted by copper salt through C-H and C-N bond cleavages to produce acridine derivatives." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,40 (2014): 12720-4. doi: https://doi.org/10.1002/chem.201404656
Morioka R, Hirano K, Satoh T, Miura M. Unexpected cyclization of tritylamines promoted by copper salt through C-H and C-N bond cleavages to produce acridine derivatives. Chemistry. 2014 Sep 26;20(40):12720-4. doi: 10.1002/chem.201404656. Epub 2014 Sep 04. PMID: 25196267.
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Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction.

The Journal of organic chemistry

Zhao Y, Yuan Y, Wang X, Li Y.
PMID: 28967752
J Org Chem. 2017 Oct 20;82(20):11198-11205. doi: 10.1021/acs.joc.7b01614. Epub 2017 Oct 09.

A novel methodology for stereoselective synthesis of benzo[b]indolo[3,2,1-de]acridines through the tandem reaction of propargylic compounds with organoboron is described, and only one diastereoisomer was obtained. The sequential procedure was triggered by Pd(0)-catalyzed allenylation of propargyl carbonate. Then, Diels-Alder cyclization...

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Zhao Y, Yuan Y, Wang X, et al. Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction. J Org Chem. 2017;82(20):11198-11205doi: 10.1021/acs.joc.7b01614.
Zhao, Y., Yuan, Y., Wang, X., & Li, Y. (2017). Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction. The Journal of organic chemistry, 82(20), 11198-11205. https://doi.org/10.1021/acs.joc.7b01614
Zhao, Yulei, et al. "Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction." The Journal of organic chemistry vol. 82,20 (2017): 11198-11205. doi: https://doi.org/10.1021/acs.joc.7b01614
Zhao Y, Yuan Y, Wang X, Li Y. Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction. J Org Chem. 2017 Oct 20;82(20):11198-11205. doi: 10.1021/acs.joc.7b01614. Epub 2017 Oct 09. PMID: 28967752.
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Site-Selective RNA Activation by Acridine-Modified Oligodeoxynucleotides in Metal-Ion Catalyzed Hydrolysis: A Comprehensive Study.

ACS omega

Kuzuya A, Machida K, Shi Y, Tanaka K, Komiyama M.
PMID: 31457805
ACS Omega. 2017 Sep 01;2(9):5370-5377. doi: 10.1021/acsomega.7b00966. eCollection 2017 Sep 30.

Various types of acridine were conjugated to DNA and used for site-selective RNA scission together with another unmodified DNA and a Lu(III) ion. The target phosphodiester linkage in the substrate RNA was selectively and efficiently activated, and was hydrolyzed...

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Kuzuya A, Machida K, Shi Y, et al. Site-Selective RNA Activation by Acridine-Modified Oligodeoxynucleotides in Metal-Ion Catalyzed Hydrolysis: A Comprehensive Study. ACS Omega. 2017;2(9):5370-5377doi: 10.1021/acsomega.7b00966.
Kuzuya, A., Machida, K., Shi, Y., Tanaka, K., & Komiyama, M. (2017). Site-Selective RNA Activation by Acridine-Modified Oligodeoxynucleotides in Metal-Ion Catalyzed Hydrolysis: A Comprehensive Study. ACS omega, 2(9), 5370-5377. https://doi.org/10.1021/acsomega.7b00966
Kuzuya, Akinori, et al. "Site-Selective RNA Activation by Acridine-Modified Oligodeoxynucleotides in Metal-Ion Catalyzed Hydrolysis: A Comprehensive Study." ACS omega vol. 2,9 (2017): 5370-5377. doi: https://doi.org/10.1021/acsomega.7b00966
Kuzuya A, Machida K, Shi Y, Tanaka K, Komiyama M. Site-Selective RNA Activation by Acridine-Modified Oligodeoxynucleotides in Metal-Ion Catalyzed Hydrolysis: A Comprehensive Study. ACS Omega. 2017 Sep 01;2(9):5370-5377. doi: 10.1021/acsomega.7b00966. eCollection 2017 Sep 30. PMID: 31457805; PMCID: PMC6644747.
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Doped but Stable: Spirobisacridine Hole Transporting Materials for Hysteresis-Free and Stable Perovskite Solar Cells.

Journal of the American Chemical Society

Drigo N, Roldan-Carmona C, Franckevičius M, Lin KH, Gegevičius R, Kim H, Schouwink PA, Sutanto AA, Olthof S, Sohail M, Meerholz K, Gulbinas V, Corminboeuf C, Paek S, Nazeeruddin MK.
PMID: 31865703
J Am Chem Soc. 2020 Jan 29;142(4):1792-1800. doi: 10.1021/jacs.9b07166. Epub 2020 Jan 13.

Four spirobisacridine (SBA) hole-transporting materials were synthesized and employed in perovskite solar cells (PSCs). The molecules bear electronically inert alkyl chains of different length and bulkiness, attached to in-plane N atoms of nearly orthogonal spiro-connected acridines. Di-

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Drigo N, Roldan-Carmona C, Franckevičius M, et al. Doped but Stable: Spirobisacridine Hole Transporting Materials for Hysteresis-Free and Stable Perovskite Solar Cells. J Am Chem Soc. 2020;142(4):1792-1800doi: 10.1021/jacs.9b07166.
Drigo, N., Roldan-Carmona, C., Franckevičius, M., Lin, K. H., Gegevičius, R., Kim, H., Schouwink, P. A., Sutanto, A. A., Olthof, S., Sohail, M., Meerholz, K., Gulbinas, V., Corminboeuf, C., Paek, S., & Nazeeruddin, M. K. (2020). Doped but Stable: Spirobisacridine Hole Transporting Materials for Hysteresis-Free and Stable Perovskite Solar Cells. Journal of the American Chemical Society, 142(4), 1792-1800. https://doi.org/10.1021/jacs.9b07166
Drigo, Nikita, et al. "Doped but Stable: Spirobisacridine Hole Transporting Materials for Hysteresis-Free and Stable Perovskite Solar Cells." Journal of the American Chemical Society vol. 142,4 (2020): 1792-1800. doi: https://doi.org/10.1021/jacs.9b07166
Drigo N, Roldan-Carmona C, Franckevičius M, Lin KH, Gegevičius R, Kim H, Schouwink PA, Sutanto AA, Olthof S, Sohail M, Meerholz K, Gulbinas V, Corminboeuf C, Paek S, Nazeeruddin MK. Doped but Stable: Spirobisacridine Hole Transporting Materials for Hysteresis-Free and Stable Perovskite Solar Cells. J Am Chem Soc. 2020 Jan 29;142(4):1792-1800. doi: 10.1021/jacs.9b07166. Epub 2020 Jan 13. PMID: 31865703.
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