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Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides.

Chemical communications (Cambridge, England)

Liu X, Yin Y, Jiang Z.
PMID: 31490488
Chem Commun (Camb). 2019 Sep 24;55(77):11527-11530. doi: 10.1039/c9cc06249a.

A formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides via visible light-driven photoredox catalysis is reported. Under transition metal-free conditions using a dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst, the transformation was efficient and led to a...

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Liu X, Yin Y, Jiang Z. Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides. Chem Commun (Camb). 2019;55(77):11527-11530doi: 10.1039/c9cc06249a.
Liu, X., Yin, Y., & Jiang, Z. (2019). Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides. Chemical communications (Cambridge, England), 55(77), 11527-11530. https://doi.org/10.1039/c9cc06249a
Liu, Xiangyuan, et al. "Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides." Chemical communications (Cambridge, England) vol. 55,77 (2019): 11527-11530. doi: https://doi.org/10.1039/c9cc06249a
Liu X, Yin Y, Jiang Z. Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides. Chem Commun (Camb). 2019 Sep 24;55(77):11527-11530. doi: 10.1039/c9cc06249a. PMID: 31490488.
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Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence.

The Journal of organic chemistry

Jayaram V, Sridhar T, Sharma GVM, Berrée F, Carboni B.
PMID: 29251507
J Org Chem. 2018 Jan 19;83(2):843-853. doi: 10.1021/acs.joc.7b02831. Epub 2018 Jan 05.

An efficient and straightforward synthesis of isoquinolines is reported from internal alkenyl boronic esters, easily prepared from the corresponding 1,2-bis(boronates), via a sequential copper-catalyzed azidation/aza-Wittig condensation. This synthetic method has been used to synthesize quinisocaine, a topical anesthetic used...

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Jayaram V, Sridhar T, Sharma GVM, et al. Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence. J Org Chem. 2018;83(2):843-853doi: 10.1021/acs.joc.7b02831.
Jayaram, V., Sridhar, T., Sharma, G. V. M., Berrée, F., & Carboni, B. (2018). Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence. The Journal of organic chemistry, 83(2), 843-853. https://doi.org/10.1021/acs.joc.7b02831
Jayaram, Vankudoth, et al. "Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence." The Journal of organic chemistry vol. 83,2 (2018): 843-853. doi: https://doi.org/10.1021/acs.joc.7b02831
Jayaram V, Sridhar T, Sharma GVM, Berrée F, Carboni B. Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence. J Org Chem. 2018 Jan 19;83(2):843-853. doi: 10.1021/acs.joc.7b02831. Epub 2018 Jan 05. PMID: 29251507.
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Iodine-catalyzed oxidative multiple C-H bond functionalization of isoquinolines with methylarenes: an efficient synthesis of isoquinoline-1,3,4(2H)-triones.

Organic & biomolecular chemistry

Zhu D, Luo WK, Yang L, Ma DY.
PMID: 28825437
Org Biomol Chem. 2017 Aug 30;15(34):7112-7116. doi: 10.1039/c7ob01539a.

An iodine-catalyzed multiple C-H bond functionalization of isoquinolines with methylarenes via a successive benzylic sp

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Zhu D, Luo WK, Yang L, et al. Iodine-catalyzed oxidative multiple C-H bond functionalization of isoquinolines with methylarenes: an efficient synthesis of isoquinoline-1,3,4(2H)-triones. Org Biomol Chem. 2017;15(34):7112-7116doi: 10.1039/c7ob01539a.
Zhu, D., Luo, W. K., Yang, L., & Ma, D. Y. (2017). Iodine-catalyzed oxidative multiple C-H bond functionalization of isoquinolines with methylarenes: an efficient synthesis of isoquinoline-1,3,4(2H)-triones. Organic & biomolecular chemistry, 15(34), 7112-7116. https://doi.org/10.1039/c7ob01539a
Zhu, Di, et al. "Iodine-catalyzed oxidative multiple C-H bond functionalization of isoquinolines with methylarenes: an efficient synthesis of isoquinoline-1,3,4(2H)-triones." Organic & biomolecular chemistry vol. 15,34 (2017): 7112-7116. doi: https://doi.org/10.1039/c7ob01539a
Zhu D, Luo WK, Yang L, Ma DY. Iodine-catalyzed oxidative multiple C-H bond functionalization of isoquinolines with methylarenes: an efficient synthesis of isoquinoline-1,3,4(2H)-triones. Org Biomol Chem. 2017 Aug 30;15(34):7112-7116. doi: 10.1039/c7ob01539a. PMID: 28825437.
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Convenient synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines via silver-catalyzed oxidative radical decarboxylation.

Organic & biomolecular chemistry

Yao Q, Zhou X, Zhang X, Wang C, Wang P, Li M.
PMID: 28059413
Org Biomol Chem. 2017 Jan 25;15(4):957-971. doi: 10.1039/c6ob02331b.

A convenient and efficient protocol for the synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines has been developed. The reaction relies on the coupling of 2-isocyanobiphenyls and vinyl isonitriles with alkyl radicals formed by the silver-catalyzed decarboxylation of stoichiometric aliphatic...

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Yao Q, Zhou X, Zhang X, et al. Convenient synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines via silver-catalyzed oxidative radical decarboxylation. Org Biomol Chem. 2017;15(4):957-971doi: 10.1039/c6ob02331b.
Yao, Q., Zhou, X., Zhang, X., Wang, C., Wang, P., & Li, M. (2017). Convenient synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines via silver-catalyzed oxidative radical decarboxylation. Organic & biomolecular chemistry, 15(4), 957-971. https://doi.org/10.1039/c6ob02331b
Yao, Qian, et al. "Convenient synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines via silver-catalyzed oxidative radical decarboxylation." Organic & biomolecular chemistry vol. 15,4 (2017): 957-971. doi: https://doi.org/10.1039/c6ob02331b
Yao Q, Zhou X, Zhang X, Wang C, Wang P, Li M. Convenient synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines via silver-catalyzed oxidative radical decarboxylation. Org Biomol Chem. 2017 Jan 25;15(4):957-971. doi: 10.1039/c6ob02331b. PMID: 28059413.
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Fasudil in Combination With Bone Marrow Stromal Cells (BMSCs) Attenuates Alzheimer's Disease-Related Changes Through the Regulation of the Peripheral Immune System.

Frontiers in aging neuroscience

Yu J, Yan Y, Gu Q, Kumar G, Yu H, Zhao Y, Liu C, Gao Y, Chai Z, Chumber J, Xiao BG, Zhang GX, Zhang HT, Jiang Y, Ma CG.
PMID: 30061826
Front Aging Neurosci. 2018 Jul 16;10:216. doi: 10.3389/fnagi.2018.00216. eCollection 2018.

Alzheimer's disease (AD) is a chronic progressive neurodegenerative disease. Its mechanism is still not clear. Majority of research focused on the central nervous system (CNS) changes, while few studies emphasize on peripheral immune system modulation. Our study aimed to...

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Yu J, Yan Y, Gu Q, et al. Fasudil in Combination With Bone Marrow Stromal Cells (BMSCs) Attenuates Alzheimer's Disease-Related Changes Through the Regulation of the Peripheral Immune System. Front Aging Neurosci. 2018;10:216doi: 10.3389/fnagi.2018.00216.
Yu, J., Yan, Y., Gu, Q., Kumar, G., Yu, H., Zhao, Y., Liu, C., Gao, Y., Chai, Z., Chumber, J., Xiao, B. G., Zhang, G. X., Zhang, H. T., Jiang, Y., & Ma, C. G. (2018). Fasudil in Combination With Bone Marrow Stromal Cells (BMSCs) Attenuates Alzheimer's Disease-Related Changes Through the Regulation of the Peripheral Immune System. Frontiers in aging neuroscience, 10216. https://doi.org/10.3389/fnagi.2018.00216
Yu, Jiezhong, et al. "Fasudil in Combination With Bone Marrow Stromal Cells (BMSCs) Attenuates Alzheimer's Disease-Related Changes Through the Regulation of the Peripheral Immune System." Frontiers in aging neuroscience vol. 10 (2018): 216. doi: https://doi.org/10.3389/fnagi.2018.00216
Yu J, Yan Y, Gu Q, Kumar G, Yu H, Zhao Y, Liu C, Gao Y, Chai Z, Chumber J, Xiao BG, Zhang GX, Zhang HT, Jiang Y, Ma CG. Fasudil in Combination With Bone Marrow Stromal Cells (BMSCs) Attenuates Alzheimer's Disease-Related Changes Through the Regulation of the Peripheral Immune System. Front Aging Neurosci. 2018 Jul 16;10:216. doi: 10.3389/fnagi.2018.00216. eCollection 2018. PMID: 30061826; PMCID: PMC6054996.
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Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons.

Journal of the American Chemical Society

Chen D, Xu G, Zhou Q, Chung LW, Tang W.
PMID: 28700227
J Am Chem Soc. 2017 Jul 26;139(29):9767-9770. doi: 10.1021/jacs.7b04256. Epub 2017 Jul 14.

We herein describe a chiral diboron-templated highly diastereoselective and enantioselective reductive coupling of isoquinolines that provided expedited access to a series of chiral substituted bisisoquinolines in good yields and excellent ee's under mild conditions. The method enjoys a broad...

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Chen D, Xu G, Zhou Q, et al. Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons. J Am Chem Soc. 2017;139(29):9767-9770doi: 10.1021/jacs.7b04256.
Chen, D., Xu, G., Zhou, Q., Chung, L. W., & Tang, W. (2017). Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons. Journal of the American Chemical Society, 139(29), 9767-9770. https://doi.org/10.1021/jacs.7b04256
Chen, Dongping, et al. "Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons." Journal of the American Chemical Society vol. 139,29 (2017): 9767-9770. doi: https://doi.org/10.1021/jacs.7b04256
Chen D, Xu G, Zhou Q, Chung LW, Tang W. Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons. J Am Chem Soc. 2017 Jul 26;139(29):9767-9770. doi: 10.1021/jacs.7b04256. Epub 2017 Jul 14. PMID: 28700227.
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A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines.

Beilstein journal of organic chemistry

Melzer BC, Bracher F.
PMID: 28904605
Beilstein J Org Chem. 2017 Aug 08;13:1564-1571. doi: 10.3762/bjoc.13.156. eCollection 2017.

Oxoisoaporphine alkaloids are conveniently prepared via direct ring metalation of alkoxy-substituted isoquinolines at C-1, followed by reaction with iodine. Subsequent Suzuki cross-coupling of the resulting 1-iodoisoquinolines to methyl 2-(isoquinolin-1-yl)benzoates and intramolecular acylation of the corresponding carboxylic acids with Eaton's...

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Melzer BC, Bracher F. A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines. Beilstein J Org Chem. 2017;13:1564-1571doi: 10.3762/bjoc.13.156.
Melzer, B. C., & Bracher, F. (2017). A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines. Beilstein journal of organic chemistry, 131564-1571. https://doi.org/10.3762/bjoc.13.156
Melzer, Benedikt C, and Bracher, Franz. "A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines." Beilstein journal of organic chemistry vol. 13 (2017): 1564-1571. doi: https://doi.org/10.3762/bjoc.13.156
Melzer BC, Bracher F. A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines. Beilstein J Org Chem. 2017 Aug 08;13:1564-1571. doi: 10.3762/bjoc.13.156. eCollection 2017. PMID: 28904605; PMCID: PMC5564254.
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Base-Mediated Hydroamination of Alkynes.

Accounts of chemical research

Patel M, Saunthwal RK, Verma AK.
PMID: 28128923
Acc Chem Res. 2017 Feb 21;50(2):240-254. doi: 10.1021/acs.accounts.6b00449. Epub 2017 Jan 27.

Inter- or intramolecular hydroamination reactions are a paradigmatic example of modern sustainable organic chemistry, as they are a catalytic, 100% atom-economical, and waste-free process of fundamental simplicity in which an amine is added to an alkyne substrate. Many enamines...

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Patel M, Saunthwal RK, Verma AK. Base-Mediated Hydroamination of Alkynes. Acc Chem Res. 2017;50(2):240-254doi: 10.1021/acs.accounts.6b00449.
Patel, M., Saunthwal, R. K., & Verma, A. K. (2017). Base-Mediated Hydroamination of Alkynes. Accounts of chemical research, 50(2), 240-254. https://doi.org/10.1021/acs.accounts.6b00449
Patel, Monika, et al. "Base-Mediated Hydroamination of Alkynes." Accounts of chemical research vol. 50,2 (2017): 240-254. doi: https://doi.org/10.1021/acs.accounts.6b00449
Patel M, Saunthwal RK, Verma AK. Base-Mediated Hydroamination of Alkynes. Acc Chem Res. 2017 Feb 21;50(2):240-254. doi: 10.1021/acs.accounts.6b00449. Epub 2017 Jan 27. PMID: 28128923.
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Spectroscopic profiling, DFT computations, molecular docking and molecular dynamic simulation of biologically active 5-isoquinolinesulfonic acid.

Journal of biomolecular structure & dynamics

Saral A, Sudha P, Muthu S, Irfan A.
PMID: 34882072
J Biomol Struct Dyn. 2021 Dec 09;1-14. doi: 10.1080/07391102.2021.2011417. Epub 2021 Dec 09.

The title compound 5-isoquinolinesulfonic acid (5IQSA) is characterized using the FT-IR, FT-Raman, NMR and UV-Vis spectra. The optimized molecular geometry, vibrational assignments, infrared intensities and Raman scattering are precisely calculated using Density Functional Theory (DFT) with the B3LYP/6-311++G(d,p) basis...

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Saral A, Sudha P, Muthu S, et al. Spectroscopic profiling, DFT computations, molecular docking and molecular dynamic simulation of biologically active 5-isoquinolinesulfonic acid. J Biomol Struct Dyn. 2021;1-14doi: 10.1080/07391102.2021.2011417.
Saral, A., Sudha, P., Muthu, S., & Irfan, A. (2021). Spectroscopic profiling, DFT computations, molecular docking and molecular dynamic simulation of biologically active 5-isoquinolinesulfonic acid. Journal of biomolecular structure & dynamics, 1-14. https://doi.org/10.1080/07391102.2021.2011417
Saral, A, et al. "Spectroscopic profiling, DFT computations, molecular docking and molecular dynamic simulation of biologically active 5-isoquinolinesulfonic acid." Journal of biomolecular structure & dynamics vol. (2021): 1-14. doi: https://doi.org/10.1080/07391102.2021.2011417
Saral A, Sudha P, Muthu S, Irfan A. Spectroscopic profiling, DFT computations, molecular docking and molecular dynamic simulation of biologically active 5-isoquinolinesulfonic acid. J Biomol Struct Dyn. 2021 Dec 09;1-14. doi: 10.1080/07391102.2021.2011417. Epub 2021 Dec 09. PMID: 34882072.
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Synthesis and Anti-HIV Activity of a Novel Series of Isoquinoline-Based CXCR4 Antagonists.

Molecules (Basel, Switzerland)

Shad MS, Claes S, Goffin E, Van Loy T, Schols D, De Jonghe S, Dehaen W.
PMID: 34684878
Molecules. 2021 Oct 18;26(20). doi: 10.3390/molecules26206297.

An expansion of the structure-activity relationship study of CXCR4 antagonists led to the synthesis of a series of isoquinolines, bearing a tetrahydroquinoline or a 3-methylpyridinyl moiety as head group. All compounds were investigated for CXCR4 affinity and antagonism in...

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Shad MS, Claes S, Goffin E, et al. Synthesis and Anti-HIV Activity of a Novel Series of Isoquinoline-Based CXCR4 Antagonists. Molecules. 2021;26(20)doi: 10.3390/molecules26206297.
Shad, M. S., Claes, S., Goffin, E., Van Loy, T., Schols, D., De Jonghe, S., & Dehaen, W. (2021). Synthesis and Anti-HIV Activity of a Novel Series of Isoquinoline-Based CXCR4 Antagonists. Molecules (Basel, Switzerland), 26(20), . https://doi.org/10.3390/molecules26206297
Shad, Mastaneh Safarnejad, et al. "Synthesis and Anti-HIV Activity of a Novel Series of Isoquinoline-Based CXCR4 Antagonists." Molecules (Basel, Switzerland) vol. 26,20 (2021). doi: https://doi.org/10.3390/molecules26206297
Shad MS, Claes S, Goffin E, Van Loy T, Schols D, De Jonghe S, Dehaen W. Synthesis and Anti-HIV Activity of a Novel Series of Isoquinoline-Based CXCR4 Antagonists. Molecules. 2021 Oct 18;26(20). doi: 10.3390/molecules26206297. PMID: 34684878; PMCID: PMC8539250.
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Rhodium-catalyzed oxidative annulation of 1H-indazoles with alkynes for the synthesis of indazolo[3,2-a]isoquinolines via C-H bond functionalization.

Organic & biomolecular chemistry

Huang J, Fu Y, Deng Z, Chen W, Song Z, Peng Y.
PMID: 33295929
Org Biomol Chem. 2020 Dec 28;18(48):9863-9872. doi: 10.1039/d0ob02060e. Epub 2020 Dec 09.

A Rh(iii)-catalyzed oxidative annulation of 1H-indazoles with internal alkynes via C-C and C-N coupling for the preparation of highly functionalized indazolo[3,2-a]isoquinolines is disclosed. This reaction features the use of easily accessible starting materials, is operationally simple, has a relatively...

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Huang J, Fu Y, Deng Z, et al. Rhodium-catalyzed oxidative annulation of 1H-indazoles with alkynes for the synthesis of indazolo[3,2-a]isoquinolines via C-H bond functionalization. Org Biomol Chem. 2020;18(48):9863-9872doi: 10.1039/d0ob02060e.
Huang, J., Fu, Y., Deng, Z., Chen, W., Song, Z., & Peng, Y. (2020). Rhodium-catalyzed oxidative annulation of 1H-indazoles with alkynes for the synthesis of indazolo[3,2-a]isoquinolines via C-H bond functionalization. Organic & biomolecular chemistry, 18(48), 9863-9872. https://doi.org/10.1039/d0ob02060e
Huang, Jian, et al. "Rhodium-catalyzed oxidative annulation of 1H-indazoles with alkynes for the synthesis of indazolo[3,2-a]isoquinolines via C-H bond functionalization." Organic & biomolecular chemistry vol. 18,48 (2020): 9863-9872. doi: https://doi.org/10.1039/d0ob02060e
Huang J, Fu Y, Deng Z, Chen W, Song Z, Peng Y. Rhodium-catalyzed oxidative annulation of 1H-indazoles with alkynes for the synthesis of indazolo[3,2-a]isoquinolines via C-H bond functionalization. Org Biomol Chem. 2020 Dec 28;18(48):9863-9872. doi: 10.1039/d0ob02060e. Epub 2020 Dec 09. PMID: 33295929.
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Transition-Metal-Free One-Pot Tandem Synthesis of 3-Ketoisoquinolines from Aldehydes and Phenacyl Azides.

The Journal of organic chemistry

Prasad B, Phanindrudu M, Tiwari DK, Kamal A.
PMID: 31502837
J Org Chem. 2019 Oct 04;84(19):12334-12343. doi: 10.1021/acs.joc.9b01534. Epub 2019 Sep 23.

An efficient and transition-metal-free strategy for the synthesis of 3-keto-isoquinolines in one pot has been developed from the easily accessible 2-(formylphenyl)acrylates and phenacyl azides. Various substituted aldehydes and phenacyl azides were successfully employed in this transformation to furnish a...

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Prasad B, Phanindrudu M, Tiwari DK, et al. Transition-Metal-Free One-Pot Tandem Synthesis of 3-Ketoisoquinolines from Aldehydes and Phenacyl Azides. J Org Chem. 2019;84(19):12334-12343doi: 10.1021/acs.joc.9b01534.
Prasad, B., Phanindrudu, M., Tiwari, D. K., & Kamal, A. (2019). Transition-Metal-Free One-Pot Tandem Synthesis of 3-Ketoisoquinolines from Aldehydes and Phenacyl Azides. The Journal of organic chemistry, 84(19), 12334-12343. https://doi.org/10.1021/acs.joc.9b01534
Prasad, Budaganaboyina, et al. "Transition-Metal-Free One-Pot Tandem Synthesis of 3-Ketoisoquinolines from Aldehydes and Phenacyl Azides." The Journal of organic chemistry vol. 84,19 (2019): 12334-12343. doi: https://doi.org/10.1021/acs.joc.9b01534
Prasad B, Phanindrudu M, Tiwari DK, Kamal A. Transition-Metal-Free One-Pot Tandem Synthesis of 3-Ketoisoquinolines from Aldehydes and Phenacyl Azides. J Org Chem. 2019 Oct 04;84(19):12334-12343. doi: 10.1021/acs.joc.9b01534. Epub 2019 Sep 23. PMID: 31502837.
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Showing 25 to 36 of 274 entries