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Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier.

Angewandte Chemie (International ed. in English)

Chen XW, Zhao H, Chen CL, Jiang HF, Zhang M.
PMID: 28926172
Angew Chem Int Ed Engl. 2017 Nov 06;56(45):14232-14236. doi: 10.1002/anie.201707702. Epub 2017 Oct 05.

A general catalytic hydrogen transfer-mediated α-functionalization of 1,8-naphthyridines is reported for the first time that benefits from a hydrogen transfer-mediated activation mode for non-activated pyridyl cores. The pyridyl α-site selectively couples with the C8-site of various tetrahydroquinolines (THQs) to...

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Chen XW, Zhao H, Chen CL, et al. Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier. Angew Chem Int Ed Engl. 2017;56(45):14232-14236doi: 10.1002/anie.201707702.
Chen, X. W., Zhao, H., Chen, C. L., Jiang, H. F., & Zhang, M. (2017). Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier. Angewandte Chemie (International ed. in English), 56(45), 14232-14236. https://doi.org/10.1002/anie.201707702
Chen, Xiu-Wen, et al. "Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier." Angewandte Chemie (International ed. in English) vol. 56,45 (2017): 14232-14236. doi: https://doi.org/10.1002/anie.201707702
Chen XW, Zhao H, Chen CL, Jiang HF, Zhang M. Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier. Angew Chem Int Ed Engl. 2017 Nov 06;56(45):14232-14236. doi: 10.1002/anie.201707702. Epub 2017 Oct 05. PMID: 28926172.
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2,8-Disubstituted-1,6-Naphthyridines and 4,6-Disubstituted-Isoquinolines with Potent, Selective Affinity for CDK8/19.

ACS medicinal chemistry letters

Mallinger A, Schiemann K, Rink C, Sejberg J, Honey MA, Czodrowski P, Stubbs M, Poeschke O, Busch M, Schneider R, Schwarz D, Musil D, Burke R, Urbahns K, Workman P, Wienke D, Clarke PA, Raynaud FI, Eccles SA, Esdar C, Rohdich F, Blagg J.
PMID: 27326329
ACS Med Chem Lett. 2016 Mar 28;7(6):573-8. doi: 10.1021/acsmedchemlett.6b00022. eCollection 2016 Jun 09.

We demonstrate a designed scaffold-hop approach to the discovery of 2,8-disubstituted-1,6-naphthyridine- and 4,6-disubstituted-isoquinoline-based dual CDK8/19 ligands. Optimized compounds in both series exhibited rapid aldehyde oxidase-mediated metabolism, which could be abrogated by introduction of an amino substituent at C5 of...

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Mallinger A, Schiemann K, Rink C, et al. 2,8-Disubstituted-1,6-Naphthyridines and 4,6-Disubstituted-Isoquinolines with Potent, Selective Affinity for CDK8/19. ACS Med Chem Lett. 2016;7(6):573-8doi: 10.1021/acsmedchemlett.6b00022.
Mallinger, A., Schiemann, K., Rink, C., Sejberg, J., Honey, M. A., Czodrowski, P., Stubbs, M., Poeschke, O., Busch, M., Schneider, R., Schwarz, D., Musil, D., Burke, R., Urbahns, K., Workman, P., Wienke, D., Clarke, P. A., Raynaud, F. I., Eccles, S. A., Esdar, C., Rohdich, F., & Blagg, J. (2016). 2,8-Disubstituted-1,6-Naphthyridines and 4,6-Disubstituted-Isoquinolines with Potent, Selective Affinity for CDK8/19. ACS medicinal chemistry letters, 7(6), 573-8. https://doi.org/10.1021/acsmedchemlett.6b00022
Mallinger, Aurélie, et al. "2,8-Disubstituted-1,6-Naphthyridines and 4,6-Disubstituted-Isoquinolines with Potent, Selective Affinity for CDK8/19." ACS medicinal chemistry letters vol. 7,6 (2016): 573-8. doi: https://doi.org/10.1021/acsmedchemlett.6b00022
Mallinger A, Schiemann K, Rink C, Sejberg J, Honey MA, Czodrowski P, Stubbs M, Poeschke O, Busch M, Schneider R, Schwarz D, Musil D, Burke R, Urbahns K, Workman P, Wienke D, Clarke PA, Raynaud FI, Eccles SA, Esdar C, Rohdich F, Blagg J. 2,8-Disubstituted-1,6-Naphthyridines and 4,6-Disubstituted-Isoquinolines with Potent, Selective Affinity for CDK8/19. ACS Med Chem Lett. 2016 Mar 28;7(6):573-8. doi: 10.1021/acsmedchemlett.6b00022. eCollection 2016 Jun 09. PMID: 27326329; PMCID: PMC4904262.
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Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives.

The Journal of organic chemistry

Alonso C, González M, Palacios F, Rubiales G.
PMID: 28537387
J Org Chem. 2017 Jun 16;82(12):6379-6387. doi: 10.1021/acs.joc.7b00977. Epub 2017 Jun 05.

Both experimental and computational studies for the cycloaddition reaction between N-(3-pyridyl)aldimines and acetylenes where 1,5-naphthyridines are obtained are reported. The reaction of benzaldimine with a methoxycarbonyl group in position 2 with phenyl acetylene, styrene, and indene afforded polycyclic isoindolone...

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Alonso C, González M, Palacios F, et al. Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives. J Org Chem. 2017;82(12):6379-6387doi: 10.1021/acs.joc.7b00977.
Alonso, C., González, M., Palacios, F., & Rubiales, G. (2017). Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives. The Journal of organic chemistry, 82(12), 6379-6387. https://doi.org/10.1021/acs.joc.7b00977
Alonso, Concepción, et al. "Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives." The Journal of organic chemistry vol. 82,12 (2017): 6379-6387. doi: https://doi.org/10.1021/acs.joc.7b00977
Alonso C, González M, Palacios F, Rubiales G. Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives. J Org Chem. 2017 Jun 16;82(12):6379-6387. doi: 10.1021/acs.joc.7b00977. Epub 2017 Jun 05. PMID: 28537387.
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Cytotoxicity and Structure-activity Relationships of Naphthyridine Derivatives in Human Cervical Cancer, Leukemia, and Prostate Cancer.

The Korean journal of physiology & pharmacology : official journal of the Korean Physiological Society and the Korean Society of Pharmacology

Hwang YJ, Chung ML, Sohn UD, Im C.
PMID: 24381501
Korean J Physiol Pharmacol. 2013 Dec;17(6):517-23. doi: 10.4196/kjpp.2013.17.6.517. Epub 2013 Dec 16.

Naphthyridine compounds are important, because they exhibit various biological activities including anticancer, antimicrobial, and anti-inflammatory activity. Some naphthyridines have antimitotic effects or demonstrate anticancer activity by inhibiting topoisomerase II. These compounds have been investigated as potential anticancer agents, and...

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Hwang YJ, Chung ML, Sohn UD, et al. Cytotoxicity and Structure-activity Relationships of Naphthyridine Derivatives in Human Cervical Cancer, Leukemia, and Prostate Cancer. Korean J Physiol Pharmacol. 2013;17(6):517-23doi: 10.4196/kjpp.2013.17.6.517.
Hwang, Y. J., Chung, M. L., Sohn, U. D., & Im, C. (2013). Cytotoxicity and Structure-activity Relationships of Naphthyridine Derivatives in Human Cervical Cancer, Leukemia, and Prostate Cancer. The Korean journal of physiology & pharmacology : official journal of the Korean Physiological Society and the Korean Society of Pharmacology, 17(6), 517-23. https://doi.org/10.4196/kjpp.2013.17.6.517
Hwang, Yu Jin, et al. "Cytotoxicity and Structure-activity Relationships of Naphthyridine Derivatives in Human Cervical Cancer, Leukemia, and Prostate Cancer." The Korean journal of physiology & pharmacology : official journal of the Korean Physiological Society and the Korean Society of Pharmacology vol. 17,6 (2013): 517-23. doi: https://doi.org/10.4196/kjpp.2013.17.6.517
Hwang YJ, Chung ML, Sohn UD, Im C. Cytotoxicity and Structure-activity Relationships of Naphthyridine Derivatives in Human Cervical Cancer, Leukemia, and Prostate Cancer. Korean J Physiol Pharmacol. 2013 Dec;17(6):517-23. doi: 10.4196/kjpp.2013.17.6.517. Epub 2013 Dec 16. PMID: 24381501; PMCID: PMC3874439.
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Oxacalixarenes and oxacyclophanes containing 1,8-naphthyridines: a new class of molecular tweezers with concave-surface functionality.

Chemical communications (Cambridge, England)

Katz JL, Geller BJ, Foster PD.
PMID: 17325794
Chem Commun (Camb). 2007 Mar 14;(10):1026-8. doi: 10.1039/b615336d. Epub 2007 Feb 02.

The first examples of oxacalix[4]arenes and [1(4)]oxacyclophanes bearing 1,8-naphthyridine units are reported, and these systems function as molecular tweezers containing inner-cavity hydrogen bond acceptors.

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Katz JL, Geller BJ, Foster PD. Oxacalixarenes and oxacyclophanes containing 1,8-naphthyridines: a new class of molecular tweezers with concave-surface functionality. Chem Commun (Camb). 2007;(10):1026-8doi: 10.1039/b615336d.
Katz, J. L., Geller, B. J., & Foster, P. D. (2007). Oxacalixarenes and oxacyclophanes containing 1,8-naphthyridines: a new class of molecular tweezers with concave-surface functionality. Chemical communications (Cambridge, England), (10), 1026-8. https://doi.org/10.1039/b615336d
Katz, Jeffrey L, et al. "Oxacalixarenes and oxacyclophanes containing 1,8-naphthyridines: a new class of molecular tweezers with concave-surface functionality." Chemical communications (Cambridge, England) vol. ,10 (2007): 1026-8. doi: https://doi.org/10.1039/b615336d
Katz JL, Geller BJ, Foster PD. Oxacalixarenes and oxacyclophanes containing 1,8-naphthyridines: a new class of molecular tweezers with concave-surface functionality. Chem Commun (Camb). 2007 Mar 14;(10):1026-8. doi: 10.1039/b615336d. Epub 2007 Feb 02. PMID: 17325794.
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1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development.

Tetrahedron

Woo GH, Beeler AB, Snyder JK.
PMID: 19112520
Tetrahedron. 2007 Jun 18;63(25):5649-5655. doi: 10.1016/j.tet.2007.04.003.

The chemistry of 1,2,3,4-tetrahydro-1,5-naphthyridines and 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines has been explored with the goal of discovering reactions at N1 suitable for library development. Epoxide openings, palladium-catalyzed N-arylations, DEPBT-promoted acylations, and urea formation through the reaction with isocyanates were all successful. The...

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Woo GH, Beeler AB, Snyder JK. 1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development. Tetrahedron. 2007;63(25):5649-5655doi: 10.1016/j.tet.2007.04.003.
Woo, G. H., Beeler, A. B., & Snyder, J. K. (2007). 1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development. Tetrahedron, 63(25), 5649-5655. https://doi.org/10.1016/j.tet.2007.04.003
Woo, Grace H C, et al. "1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development." Tetrahedron vol. 63,25 (2007): 5649-5655. doi: https://doi.org/10.1016/j.tet.2007.04.003
Woo GH, Beeler AB, Snyder JK. 1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development. Tetrahedron. 2007 Jun 18;63(25):5649-5655. doi: 10.1016/j.tet.2007.04.003. PMID: 19112520; PMCID: PMC2608727.
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Room temperature, copper-catalyzed amination of bromonaphthyridines with aqueous ammonia.

The Journal of organic chemistry

Anderson CA, Taylor PG, Zeller MA, Zimmerman SC.
PMID: 20550204
J Org Chem. 2010 Jul 16;75(14):4848-51. doi: 10.1021/jo100476x.

Room temperature, copper-catalyzed amination of amido-bromo-1,8-naphthyridines is reported. Use of Cu(2)O and aqueous ammonia at ambient temperature affords amination products in 10-87% yield. Bromonaphthyridines are prepared in 15-65% yield via treatment of amidonaphthyridinones with phosphorus tribromide. This methodology provides...

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Anderson CA, Taylor PG, Zeller MA, et al. Room temperature, copper-catalyzed amination of bromonaphthyridines with aqueous ammonia. J Org Chem. 2010;75(14):4848-51doi: 10.1021/jo100476x.
Anderson, C. A., Taylor, P. G., Zeller, M. A., & Zimmerman, S. C. (2010). Room temperature, copper-catalyzed amination of bromonaphthyridines with aqueous ammonia. The Journal of organic chemistry, 75(14), 4848-51. https://doi.org/10.1021/jo100476x
Anderson, Cyrus A, et al. "Room temperature, copper-catalyzed amination of bromonaphthyridines with aqueous ammonia." The Journal of organic chemistry vol. 75,14 (2010): 4848-51. doi: https://doi.org/10.1021/jo100476x
Anderson CA, Taylor PG, Zeller MA, Zimmerman SC. Room temperature, copper-catalyzed amination of bromonaphthyridines with aqueous ammonia. J Org Chem. 2010 Jul 16;75(14):4848-51. doi: 10.1021/jo100476x. PMID: 20550204.
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Rh(III)-Catalyzed Synthesis of 3-Amino-4-arylisoquinolinones from 4-Diazoisochroman-3-imines and N-Methoxybenzamides.

Organic letters

Li Z, Wu L, Chang B, Lu P, Wang Y.
PMID: 30763110
Org Lett. 2019 Mar 01;21(5):1497-1501. doi: 10.1021/acs.orglett.9b00290. Epub 2019 Feb 14.

A Rh(III)-catalyzed reaction of N-methoxybenzamides and 4-diazoisochroman-3-imines is described. This method offers a rapid entry to 3-amino-4-arylisoquinolinone architectures from readily available starting materials under mild reaction conditions. A one-pot cascade C-H bond activation/formal [4 + 2] cycloaddition mechanism is...

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Li Z, Wu L, Chang B, et al. Rh(III)-Catalyzed Synthesis of 3-Amino-4-arylisoquinolinones from 4-Diazoisochroman-3-imines and N-Methoxybenzamides. Org Lett. 2019;21(5):1497-1501doi: 10.1021/acs.orglett.9b00290.
Li, Z., Wu, L., Chang, B., Lu, P., & Wang, Y. (2019). Rh(III)-Catalyzed Synthesis of 3-Amino-4-arylisoquinolinones from 4-Diazoisochroman-3-imines and N-Methoxybenzamides. Organic letters, 21(5), 1497-1501. https://doi.org/10.1021/acs.orglett.9b00290
Li, Zhenmin, et al. "Rh(III)-Catalyzed Synthesis of 3-Amino-4-arylisoquinolinones from 4-Diazoisochroman-3-imines and N-Methoxybenzamides." Organic letters vol. 21,5 (2019): 1497-1501. doi: https://doi.org/10.1021/acs.orglett.9b00290
Li Z, Wu L, Chang B, Lu P, Wang Y. Rh(III)-Catalyzed Synthesis of 3-Amino-4-arylisoquinolinones from 4-Diazoisochroman-3-imines and N-Methoxybenzamides. Org Lett. 2019 Mar 01;21(5):1497-1501. doi: 10.1021/acs.orglett.9b00290. Epub 2019 Feb 14. PMID: 30763110.
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Dibenzopyrrolo[1,2-a][1,8]naphthyridines: Synthesis and Structural Modification of Fluorescent L-Shaped Heteroarenes.

The Journal of organic chemistry

Tateno K, Ogawa R, Sakamoto R, Tsuchiya M, Kutsumura N, Otani T, Ono K, Kawai H, Saito T.
PMID: 29231717
J Org Chem. 2018 Jan 19;83(2):690-702. doi: 10.1021/acs.joc.7b02674. Epub 2017 Dec 29.

The L-shaped, π-extended pentacycle dibenzopyrrolo[1,2-a][1,8]naphthyridine and its derivatives were synthesized using two methods: fully intramolecular [2 + 2 + 2] cycloaddition and oxidative aromatization using substituted carbodiimide and modification of an electron-rich indole ring of an L-shaped skeleton via...

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Tateno K, Ogawa R, Sakamoto R, et al. Dibenzopyrrolo[1,2-a][1,8]naphthyridines: Synthesis and Structural Modification of Fluorescent L-Shaped Heteroarenes. J Org Chem. 2017;83(2):690-702doi: 10.1021/acs.joc.7b02674.
Tateno, K., Ogawa, R., Sakamoto, R., Tsuchiya, M., Kutsumura, N., Otani, T., Ono, K., Kawai, H., & Saito, T. (2018). Dibenzopyrrolo[1,2-a][1,8]naphthyridines: Synthesis and Structural Modification of Fluorescent L-Shaped Heteroarenes. The Journal of organic chemistry, 83(2), 690-702. https://doi.org/10.1021/acs.joc.7b02674
Tateno, Kotaro, et al. "Dibenzopyrrolo[1,2-a][1,8]naphthyridines: Synthesis and Structural Modification of Fluorescent L-Shaped Heteroarenes." The Journal of organic chemistry vol. 83,2 (2018): 690-702. doi: https://doi.org/10.1021/acs.joc.7b02674
Tateno K, Ogawa R, Sakamoto R, Tsuchiya M, Kutsumura N, Otani T, Ono K, Kawai H, Saito T. Dibenzopyrrolo[1,2-a][1,8]naphthyridines: Synthesis and Structural Modification of Fluorescent L-Shaped Heteroarenes. J Org Chem. 2018 Jan 19;83(2):690-702. doi: 10.1021/acs.joc.7b02674. Epub 2017 Dec 29. PMID: 29231717.
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Combined effect of hydrogen bonding interactions and freezing of rotameric equilibrium on the enhancement of photostability.

Physical chemistry chemical physics : PCCP

Golec B, Nawara K, Gorski A, Thummel RP, Herbich J, Waluk J.
PMID: 29717306
Phys Chem Chem Phys. 2018 May 16;20(19):13306-13315. doi: 10.1039/c8cp00726h.

The photophysics and photostability of 12,13-dihydro-5H-indolo[3,2-c]acridine (IA), a rigid bifunctional indole derivative with proton donor/acceptor functionalities, can be drastically changed by the environment. The formation of hydrogen bonds with alcohols leads to a significant decrease of the triplet formation...

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Golec B, Nawara K, Gorski A, et al. Combined effect of hydrogen bonding interactions and freezing of rotameric equilibrium on the enhancement of photostability. Phys Chem Chem Phys. 2018;20(19):13306-13315doi: 10.1039/c8cp00726h.
Golec, B., Nawara, K., Gorski, A., Thummel, R. P., Herbich, J., & Waluk, J. (2018). Combined effect of hydrogen bonding interactions and freezing of rotameric equilibrium on the enhancement of photostability. Physical chemistry chemical physics : PCCP, 20(19), 13306-13315. https://doi.org/10.1039/c8cp00726h
Golec, Barbara, et al. "Combined effect of hydrogen bonding interactions and freezing of rotameric equilibrium on the enhancement of photostability." Physical chemistry chemical physics : PCCP vol. 20,19 (2018): 13306-13315. doi: https://doi.org/10.1039/c8cp00726h
Golec B, Nawara K, Gorski A, Thummel RP, Herbich J, Waluk J. Combined effect of hydrogen bonding interactions and freezing of rotameric equilibrium on the enhancement of photostability. Phys Chem Chem Phys. 2018 May 16;20(19):13306-13315. doi: 10.1039/c8cp00726h. PMID: 29717306.
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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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1,6-Naphthyridin-2(1.

Pharmaceuticals (Basel, Switzerland)

Oliveras JM, Puig de la Bellacasa R, Estrada-Tejedor R, Teixidó J, Borrell JI.
PMID: 34681253
Pharmaceuticals (Basel). 2021 Oct 09;14(10). doi: 10.3390/ph14101029.

Naphthyridines, also known as diazanaphthalenes, are a group of heterocyclic compounds that include six isomeric bicyclic systems containing two pyridine rings. 1,6-Naphthyridines are one of the members of such a family capable of providing ligands for several receptors in...

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Oliveras JM, Puig de la Bellacasa R, Estrada-Tejedor R, et al. 1,6-Naphthyridin-2(1. Pharmaceuticals (Basel). 2021;14(10)doi: 10.3390/ph14101029.
Oliveras, J. M., Puig de la Bellacasa, R., Estrada-Tejedor, R., Teixidó, J., & Borrell, J. I. (2021). 1,6-Naphthyridin-2(1. Pharmaceuticals (Basel, Switzerland), 14(10), . https://doi.org/10.3390/ph14101029
Oliveras, Juan Marcos, et al. "1,6-Naphthyridin-2(1." Pharmaceuticals (Basel, Switzerland) vol. 14,10 (2021). doi: https://doi.org/10.3390/ph14101029
Oliveras JM, Puig de la Bellacasa R, Estrada-Tejedor R, Teixidó J, Borrell JI. 1,6-Naphthyridin-2(1. Pharmaceuticals (Basel). 2021 Oct 09;14(10). doi: 10.3390/ph14101029. PMID: 34681253; PMCID: PMC8539032.
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