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Organophosphorus-mediated N-N bond formation: facile access to 3-amino-2H-indazoles.

Organic & biomolecular chemistry

Bel Abed H, Schoene J, Christmann M, Nazaré M.
PMID: 27541713
Org Biomol Chem. 2016 Sep 28;14(36):8520-8. doi: 10.1039/c6ob01544a. Epub 2016 Aug 19.

A convenient and efficient strategy has been devised to access 3-amino-2H-indazole derivatives in two steps from readily available starting materials. The conversion of 2-nitrobenzonitriles to substituted benzamidines followed by an organophosphorus-mediated reductive cyclization and a subsequent N-N bond formation...

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Bel Abed H, Schoene J, Christmann M, et al. Organophosphorus-mediated N-N bond formation: facile access to 3-amino-2H-indazoles. Org Biomol Chem. 2016;14(36):8520-8doi: 10.1039/c6ob01544a.
Bel Abed, H., Schoene, J., Christmann, M., & Nazaré, M. (2016). Organophosphorus-mediated N-N bond formation: facile access to 3-amino-2H-indazoles. Organic & biomolecular chemistry, 14(36), 8520-8. https://doi.org/10.1039/c6ob01544a
Bel Abed, Hassen, et al. "Organophosphorus-mediated N-N bond formation: facile access to 3-amino-2H-indazoles." Organic & biomolecular chemistry vol. 14,36 (2016): 8520-8. doi: https://doi.org/10.1039/c6ob01544a
Bel Abed H, Schoene J, Christmann M, Nazaré M. Organophosphorus-mediated N-N bond formation: facile access to 3-amino-2H-indazoles. Org Biomol Chem. 2016 Sep 28;14(36):8520-8. doi: 10.1039/c6ob01544a. Epub 2016 Aug 19. PMID: 27541713.
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One-pot synthesis of highly substituted polyheteroaromatic compounds by rhodium(III)-catalyzed multiple C-H activation and annulation.

Angewandte Chemie (International ed. in English)

Jayakumar J, Parthasarathy K, Chen YH, Lee TH, Chuang SC, Cheng CH.
PMID: 25044327
Angew Chem Int Ed Engl. 2014 Sep 08;53(37):9889-92. doi: 10.1002/anie.201405183. Epub 2014 Jul 17.

A new method for the synthesis of highly substituted naphthyridine-based polyheteroaromatic compounds in high yields proceeds through rhodium(III)-catalyzed multiple C-H bond cleavage and C-C and C-N bond formation in a one-pot process. Such highly substituted polyheteroaromatic compounds have attracted...

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Jayakumar J, Parthasarathy K, Chen YH, et al. One-pot synthesis of highly substituted polyheteroaromatic compounds by rhodium(III)-catalyzed multiple C-H activation and annulation. Angew Chem Int Ed Engl. 2014;53(37):9889-92doi: 10.1002/anie.201405183.
Jayakumar, J., Parthasarathy, K., Chen, Y. H., Lee, T. H., Chuang, S. C., & Cheng, C. H. (2014). One-pot synthesis of highly substituted polyheteroaromatic compounds by rhodium(III)-catalyzed multiple C-H activation and annulation. Angewandte Chemie (International ed. in English), 53(37), 9889-92. https://doi.org/10.1002/anie.201405183
Jayakumar, Jayachandran, et al. "One-pot synthesis of highly substituted polyheteroaromatic compounds by rhodium(III)-catalyzed multiple C-H activation and annulation." Angewandte Chemie (International ed. in English) vol. 53,37 (2014): 9889-92. doi: https://doi.org/10.1002/anie.201405183
Jayakumar J, Parthasarathy K, Chen YH, Lee TH, Chuang SC, Cheng CH. One-pot synthesis of highly substituted polyheteroaromatic compounds by rhodium(III)-catalyzed multiple C-H activation and annulation. Angew Chem Int Ed Engl. 2014 Sep 08;53(37):9889-92. doi: 10.1002/anie.201405183. Epub 2014 Jul 17. PMID: 25044327.
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Palladacycles bearing tridentate CNS-type benzamidinate ligands as catalysts for cross-coupling reactions.

Dalton transactions (Cambridge, England : 2003)

Wang WC, Peng KF, Chen MT, Chen CT.
PMID: 22278632
Dalton Trans. 2012 Mar 14;41(10):3022-9. doi: 10.1039/c2dt11097k. Epub 2012 Jan 25.

Three pendant benzamidines, [Ph-C(=NC(6)H(5))-{NH(E)}] [E = -(CH(2))(2)SMe (1); -(CH(2))(2)S(t)Bu (2); -o-C(6)H(4)SMe (3)], are described. Reactions of 1, 2 or 3 with one molar equivalent of Pd(OAc)(2) in CH(2)Cl(2) give the palladacyclic complexes, [Ph-C{-NH(η(1)-C(6)H(4))}{=N(E)}]Pd(OAc) [E = -(CH(2))(2)SMe (4); -(CH(2))(2)S(t)Bu (5);...

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Wang WC, Peng KF, Chen MT, et al. Palladacycles bearing tridentate CNS-type benzamidinate ligands as catalysts for cross-coupling reactions. Dalton Trans. 2012;41(10):3022-9doi: 10.1039/c2dt11097k.
Wang, W. C., Peng, K. F., Chen, M. T., & Chen, C. T. (2012). Palladacycles bearing tridentate CNS-type benzamidinate ligands as catalysts for cross-coupling reactions. Dalton transactions (Cambridge, England : 2003), 41(10), 3022-9. https://doi.org/10.1039/c2dt11097k
Wang, Wei-Chi, et al. "Palladacycles bearing tridentate CNS-type benzamidinate ligands as catalysts for cross-coupling reactions." Dalton transactions (Cambridge, England : 2003) vol. 41,10 (2012): 3022-9. doi: https://doi.org/10.1039/c2dt11097k
Wang WC, Peng KF, Chen MT, Chen CT. Palladacycles bearing tridentate CNS-type benzamidinate ligands as catalysts for cross-coupling reactions. Dalton Trans. 2012 Mar 14;41(10):3022-9. doi: 10.1039/c2dt11097k. Epub 2012 Jan 25. PMID: 22278632.
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Efficient and Accurate Free Energy Calculations on Trypsin Inhibitors.

Journal of chemical theory and computation

de Ruiter A, Oostenbrink C.
PMID: 26593013
J Chem Theory Comput. 2012 Oct 09;8(10):3686-95. doi: 10.1021/ct200750p. Epub 2012 Feb 03.

Several combinations of free energy calculation methods have been applied to determine the relative free energies of binding between eight para-substituted benzamidines in complex with the serine protease trypsin. With the aim to improve efficiency and maintain accuracy, the...

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de Ruiter A, Oostenbrink C. Efficient and Accurate Free Energy Calculations on Trypsin Inhibitors. J Chem Theory Comput. 2012;8(10):3686-95doi: 10.1021/ct200750p.
de Ruiter, A., & Oostenbrink, C. (2012). Efficient and Accurate Free Energy Calculations on Trypsin Inhibitors. Journal of chemical theory and computation, 8(10), 3686-95. https://doi.org/10.1021/ct200750p
de Ruiter, Anita, and Oostenbrink, Chris. "Efficient and Accurate Free Energy Calculations on Trypsin Inhibitors." Journal of chemical theory and computation vol. 8,10 (2012): 3686-95. doi: https://doi.org/10.1021/ct200750p
de Ruiter A, Oostenbrink C. Efficient and Accurate Free Energy Calculations on Trypsin Inhibitors. J Chem Theory Comput. 2012 Oct 09;8(10):3686-95. doi: 10.1021/ct200750p. Epub 2012 Feb 03. PMID: 26593013.
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3,1-Benzothiazines, 1,4-Benzodioxines and 1,4-Benzoxazines as Inhibitors of Matriptase-2: Outcome of a Focused Screening Approach.

Pharmaceuticals (Basel, Switzerland)

Roydeva PG, Beckmann AM, Stirnberg M, Cesar J, Kikelj D, Ilaš J, Gütschow M.
PMID: 26771619
Pharmaceuticals (Basel). 2016 Jan 13;9(1). doi: 10.3390/ph9010002.

The liver enzyme matriptase-2 is a multi-domain, transmembrane serine protease with an extracellular, C-terminal catalytic domain. Synthetic low-molecular weight inhibitors of matriptase-2 have potential as therapeutics to treat iron overload syndromes, in particular in patients with β-thalassemia. A sub-library...

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Roydeva PG, Beckmann AM, Stirnberg M, et al. 3,1-Benzothiazines, 1,4-Benzodioxines and 1,4-Benzoxazines as Inhibitors of Matriptase-2: Outcome of a Focused Screening Approach. Pharmaceuticals (Basel). 2016;9(1)doi: 10.3390/ph9010002.
Roydeva, P. G., Beckmann, A. M., Stirnberg, M., Cesar, J., Kikelj, D., Ilaš, J., & Gütschow, M. (2016). 3,1-Benzothiazines, 1,4-Benzodioxines and 1,4-Benzoxazines as Inhibitors of Matriptase-2: Outcome of a Focused Screening Approach. Pharmaceuticals (Basel, Switzerland), 9(1), . https://doi.org/10.3390/ph9010002
Roydeva, Polya G, et al. "3,1-Benzothiazines, 1,4-Benzodioxines and 1,4-Benzoxazines as Inhibitors of Matriptase-2: Outcome of a Focused Screening Approach." Pharmaceuticals (Basel, Switzerland) vol. 9,1 (2016). doi: https://doi.org/10.3390/ph9010002
Roydeva PG, Beckmann AM, Stirnberg M, Cesar J, Kikelj D, Ilaš J, Gütschow M. 3,1-Benzothiazines, 1,4-Benzodioxines and 1,4-Benzoxazines as Inhibitors of Matriptase-2: Outcome of a Focused Screening Approach. Pharmaceuticals (Basel). 2016 Jan 13;9(1). doi: 10.3390/ph9010002. PMID: 26771619; PMCID: PMC4812366.
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Catalytic Synthesis of Luminescent Pyrimidines via Acceptor-less Dehydrogenative Coupling.

The Journal of organic chemistry

Mondal R, Lozada IB, Stotska O, Herbert DE.
PMID: 33095015
J Org Chem. 2020 Nov 06;85(21):13747-13756. doi: 10.1021/acs.joc.0c01882. Epub 2020 Oct 23.

A simple catalytic synthesis of luminescent pyrimidines from benzamidines and alcohols is reported. These one-pot, acceptor-less dehydrogenative coupling reactions are catalyzed by a ruthenium hydrido chloride complex (

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Mondal R, Lozada IB, Stotska O, et al. Catalytic Synthesis of Luminescent Pyrimidines via Acceptor-less Dehydrogenative Coupling. J Org Chem. 2020;85(21):13747-13756doi: 10.1021/acs.joc.0c01882.
Mondal, R., Lozada, I. B., Stotska, O., & Herbert, D. E. (2020). Catalytic Synthesis of Luminescent Pyrimidines via Acceptor-less Dehydrogenative Coupling. The Journal of organic chemistry, 85(21), 13747-13756. https://doi.org/10.1021/acs.joc.0c01882
Mondal, Rajarshi, et al. "Catalytic Synthesis of Luminescent Pyrimidines via Acceptor-less Dehydrogenative Coupling." The Journal of organic chemistry vol. 85,21 (2020): 13747-13756. doi: https://doi.org/10.1021/acs.joc.0c01882
Mondal R, Lozada IB, Stotska O, Herbert DE. Catalytic Synthesis of Luminescent Pyrimidines via Acceptor-less Dehydrogenative Coupling. J Org Chem. 2020 Nov 06;85(21):13747-13756. doi: 10.1021/acs.joc.0c01882. Epub 2020 Oct 23. PMID: 33095015.
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Ru(ii)-Catalyzed annulation of benzamidines and alkynes by C-H/N-H activation: a facile synthesis of 1-aminoisoquinolines.

Organic & biomolecular chemistry

Kaishap PP, Duarah G, Chetia D, Gogoi S.
PMID: 28387398
Org Biomol Chem. 2017 Apr 18;15(16):3491-3498. doi: 10.1039/c7ob00389g.

An inexpensive Ru(ii) complex catalyzes the oxidative annulation reaction of disubstituted alkynes with benzamidines to provide highly valuable 1-aminoisoquinolines in high yields. The reaction also features excellent regioselectivity with some unsymmetrical alkynes.

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Kaishap PP, Duarah G, Chetia D, et al. Ru(ii)-Catalyzed annulation of benzamidines and alkynes by C-H/N-H activation: a facile synthesis of 1-aminoisoquinolines. Org Biomol Chem. 2017;15(16):3491-3498doi: 10.1039/c7ob00389g.
Kaishap, P. P., Duarah, G., Chetia, D., & Gogoi, S. (2017). Ru(ii)-Catalyzed annulation of benzamidines and alkynes by C-H/N-H activation: a facile synthesis of 1-aminoisoquinolines. Organic & biomolecular chemistry, 15(16), 3491-3498. https://doi.org/10.1039/c7ob00389g
Kaishap, P P, et al. "Ru(ii)-Catalyzed annulation of benzamidines and alkynes by C-H/N-H activation: a facile synthesis of 1-aminoisoquinolines." Organic & biomolecular chemistry vol. 15,16 (2017): 3491-3498. doi: https://doi.org/10.1039/c7ob00389g
Kaishap PP, Duarah G, Chetia D, Gogoi S. Ru(ii)-Catalyzed annulation of benzamidines and alkynes by C-H/N-H activation: a facile synthesis of 1-aminoisoquinolines. Org Biomol Chem. 2017 Apr 18;15(16):3491-3498. doi: 10.1039/c7ob00389g. PMID: 28387398.
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A new catalytic cross-coupling approach for the synthesis of protected aryl and heteroaryl amidines.

Organic letters

Kusturin CL, Liebeskind LS, Neumann WL.
PMID: 11893202
Org Lett. 2002 Mar 21;4(6):983-5. doi: 10.1021/ol025547s.

[reaction: see text] A new method for the synthesis of protected benzamidines is described. The commercially available 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea guanidylation reagent, after SEM-protection, functions as an amidine-forming cross-coupling partner under Liebeskind-Srogl conditions. In the presence of copper(I) thiophenecarboxylate (CuTC), the...

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Kusturin CL, Liebeskind LS, Neumann WL. A new catalytic cross-coupling approach for the synthesis of protected aryl and heteroaryl amidines. Org Lett. 2002;4(6):983-5doi: 10.1021/ol025547s.
Kusturin, C. L., Liebeskind, L. S., & Neumann, W. L. (2002). A new catalytic cross-coupling approach for the synthesis of protected aryl and heteroaryl amidines. Organic letters, 4(6), 983-5. https://doi.org/10.1021/ol025547s
Kusturin, Carrie L, et al. "A new catalytic cross-coupling approach for the synthesis of protected aryl and heteroaryl amidines." Organic letters vol. 4,6 (2002): 983-5. doi: https://doi.org/10.1021/ol025547s
Kusturin CL, Liebeskind LS, Neumann WL. A new catalytic cross-coupling approach for the synthesis of protected aryl and heteroaryl amidines. Org Lett. 2002 Mar 21;4(6):983-5. doi: 10.1021/ol025547s. PMID: 11893202.
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N1-substituted tetra-benzamidines - inhibition of DNA-protein interactions and invitro tumor-cell growth.

International journal of oncology

Feriotto G, Nastruzzi C, Mischiati C, Gambari R.
PMID: 21584542
Int J Oncol. 1992 Aug;1(3):277-81. doi: 10.3892/ijo.1.3.277.

The pharmacological-mediated inhibition of the interaction between regulatory proteins and target DNA sequences could represent a potential experimental strategy to control growth of neoplastic cells, viral DNA replication and biological life cycle of infectious microorganisms. Aromatic polyamidines are powerful...

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Feriotto G, Nastruzzi C, Mischiati C, et al. N1-substituted tetra-benzamidines - inhibition of DNA-protein interactions and invitro tumor-cell growth. Int J Oncol. 1992;1(3):277-81doi: 10.3892/ijo.1.3.277.
Feriotto, G., Nastruzzi, C., Mischiati, C., & Gambari, R. (1992). N1-substituted tetra-benzamidines - inhibition of DNA-protein interactions and invitro tumor-cell growth. International journal of oncology, 1(3), 277-81. https://doi.org/10.3892/ijo.1.3.277
Feriotto, G, et al. "N1-substituted tetra-benzamidines - inhibition of DNA-protein interactions and invitro tumor-cell growth." International journal of oncology vol. 1,3 (1992): 277-81. doi: https://doi.org/10.3892/ijo.1.3.277
Feriotto G, Nastruzzi C, Mischiati C, Gambari R. N1-substituted tetra-benzamidines - inhibition of DNA-protein interactions and invitro tumor-cell growth. Int J Oncol. 1992 Aug;1(3):277-81. doi: 10.3892/ijo.1.3.277. PMID: 21584542.
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A Convenient, TiCl 4 /SnCl 4 -Mediated Synthesis of N-Phenyl or N-Aryl Benzamidines and N-Phenylpicolinamidines.

ISRN organic chemistry

Patil UD, Mahulikar PP.
PMID: 24052858
ISRN Org Chem. 2012 Jul 29;2012:963195. doi: 10.5402/2012/963195. eCollection 2012.

A new, TiCl4-or SnCl4-mediated, solvent-free method was developed for the synthesis of N-Aryl benzamidines and N-phenylpicolinamidines, in moderate-to-good yield, using suitable amines and nitriles as starting materials.

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Patil UD, Mahulikar PP. A Convenient, TiCl 4 /SnCl 4 -Mediated Synthesis of N-Phenyl or N-Aryl Benzamidines and N-Phenylpicolinamidines. ISRN Org Chem. 2012;2012:963195doi: 10.5402/2012/963195.
Patil, U. D., & Mahulikar, P. P. (2012). A Convenient, TiCl 4 /SnCl 4 -Mediated Synthesis of N-Phenyl or N-Aryl Benzamidines and N-Phenylpicolinamidines. ISRN organic chemistry, 2012963195. https://doi.org/10.5402/2012/963195
Patil, Umesh D, and Mahulikar, Pramod P. "A Convenient, TiCl 4 /SnCl 4 -Mediated Synthesis of N-Phenyl or N-Aryl Benzamidines and N-Phenylpicolinamidines." ISRN organic chemistry vol. 2012 (2012): 963195. doi: https://doi.org/10.5402/2012/963195
Patil UD, Mahulikar PP. A Convenient, TiCl 4 /SnCl 4 -Mediated Synthesis of N-Phenyl or N-Aryl Benzamidines and N-Phenylpicolinamidines. ISRN Org Chem. 2012 Jul 29;2012:963195. doi: 10.5402/2012/963195. eCollection 2012. PMID: 24052858; PMCID: PMC3767339.
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Showing 1 to 10 of 10 entries