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Showing 1 to 12 of 13 entries
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Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol.

Beilstein journal of organic chemistry

Mollo MC, Kilimciler NB, Bisceglia JA, Orelli LR.
PMID: 31976014
Beilstein J Org Chem. 2020 Jan 06;16:32-38. doi: 10.3762/bjoc.16.5. eCollection 2020.

A general procedure for the synthesis of 2-substituted tetrahydro-1,3-thiazepines by MW-assisted cyclization of 4-thioamidobutanols is presented. The acyclic precursors were prepared in high overall yields by an expeditious three-step diacylation/thionation/deprotection sequence from 4-aminobutanol. Microwave-assisted ring closure of 4-thioamido alcohols...

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Mollo MC, Kilimciler NB, Bisceglia JA, et al. Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol. Beilstein J Org Chem. 2020;16:32-38doi: 10.3762/bjoc.16.5.
Mollo, M. C., Kilimciler, N. B., Bisceglia, J. A., & Orelli, L. R. (2020). Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol. Beilstein journal of organic chemistry, 1632-38. https://doi.org/10.3762/bjoc.16.5
Mollo, María C, et al. "Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol." Beilstein journal of organic chemistry vol. 16 (2020): 32-38. doi: https://doi.org/10.3762/bjoc.16.5
Mollo MC, Kilimciler NB, Bisceglia JA, Orelli LR. Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol. Beilstein J Org Chem. 2020 Jan 06;16:32-38. doi: 10.3762/bjoc.16.5. eCollection 2020. PMID: 31976014; PMCID: PMC6964664.
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Direct Amine-Catalyzed Enantioselective Synthesis of Pentacyclic Dibenzo[.

The Journal of organic chemistry

Yadav J, Pawar AP, Nagare YK, Iype E, Rangan K, Ohshita J, Kumar D, Kumar I.
PMID: 33030896
J Org Chem. 2020 Nov 06;85(21):14094-14108. doi: 10.1021/acs.joc.0c02141. Epub 2020 Oct 08.

A direct protocol for the asymmetric synthesis of dibenzoxazepine/thiazepine-fused [2.2.2] isoquinuclidines is developed. The reaction proceeds through a proline-catalyzed direct Mannich reaction followed by an intramolecular aza-Michael cascade sequence between 2-cyclohexene-1-one and various tricyclic imines, like dibenzoxazepines/thiazepines, as an...

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Yadav J, Pawar AP, Nagare YK, et al. Direct Amine-Catalyzed Enantioselective Synthesis of Pentacyclic Dibenzo[. J Org Chem. 2020;85(21):14094-14108doi: 10.1021/acs.joc.0c02141.
Yadav, J., Pawar, A. P., Nagare, Y. K., Iype, E., Rangan, K., Ohshita, J., Kumar, D., & Kumar, I. (2020). Direct Amine-Catalyzed Enantioselective Synthesis of Pentacyclic Dibenzo[. The Journal of organic chemistry, 85(21), 14094-14108. https://doi.org/10.1021/acs.joc.0c02141
Yadav, Jyothi, et al. "Direct Amine-Catalyzed Enantioselective Synthesis of Pentacyclic Dibenzo[." The Journal of organic chemistry vol. 85,21 (2020): 14094-14108. doi: https://doi.org/10.1021/acs.joc.0c02141
Yadav J, Pawar AP, Nagare YK, Iype E, Rangan K, Ohshita J, Kumar D, Kumar I. Direct Amine-Catalyzed Enantioselective Synthesis of Pentacyclic Dibenzo[. J Org Chem. 2020 Nov 06;85(21):14094-14108. doi: 10.1021/acs.joc.0c02141. Epub 2020 Oct 08. PMID: 33030896.
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Unconventional approaches for the introduction of sulfur-based functional groups.

Organic & biomolecular chemistry

Lanfranco A, Moro R, Azzi E, Deagostino A, Renzi P.
PMID: 34333579
Org Biomol Chem. 2021 Aug 28;19(32):6926-6957. doi: 10.1039/d1ob01091c. Epub 2021 Aug 01.

Organosulfur compounds have a pivotal role in the functionalities of many natural products, pharmaceuticals and organic materials. For these reasons, the search for new methodologies for the formation of carbon-sulfur bonds has been the object of intensive work for...

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Lanfranco A, Moro R, Azzi E, et al. Unconventional approaches for the introduction of sulfur-based functional groups. Org Biomol Chem. 2021;19(32):6926-6957doi: 10.1039/d1ob01091c.
Lanfranco, A., Moro, R., Azzi, E., Deagostino, A., & Renzi, P. (2021). Unconventional approaches for the introduction of sulfur-based functional groups. Organic & biomolecular chemistry, 19(32), 6926-6957. https://doi.org/10.1039/d1ob01091c
Lanfranco, Alberto, et al. "Unconventional approaches for the introduction of sulfur-based functional groups." Organic & biomolecular chemistry vol. 19,32 (2021): 6926-6957. doi: https://doi.org/10.1039/d1ob01091c
Lanfranco A, Moro R, Azzi E, Deagostino A, Renzi P. Unconventional approaches for the introduction of sulfur-based functional groups. Org Biomol Chem. 2021 Aug 28;19(32):6926-6957. doi: 10.1039/d1ob01091c. Epub 2021 Aug 01. PMID: 34333579.
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Rethinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds.

The Journal of organic chemistry

Reutskaya E, Osipyan A, Sapegin A, Novikov AS, Krasavin M.
PMID: 30566355
J Org Chem. 2019 Feb 15;84(4):1693-1705. doi: 10.1021/acs.joc.8b02805. Epub 2018 Dec 24.

The previously reported ring-expansion strategy involving hydrolytically prone imidazoline rings was thought to include the formation of a hydrated imidazoline intermediate. In this work, we accessed the latter via the addition of a 2-aminoethyl side chain onto a lactam...

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Reutskaya E, Osipyan A, Sapegin A, et al. Rethinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds. J Org Chem. 2018;84(4):1693-1705doi: 10.1021/acs.joc.8b02805.
Reutskaya, E., Osipyan, A., Sapegin, A., Novikov, A. S., & Krasavin, M. (2019). Rethinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds. The Journal of organic chemistry, 84(4), 1693-1705. https://doi.org/10.1021/acs.joc.8b02805
Reutskaya, Elena, et al. "Rethinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds." The Journal of organic chemistry vol. 84,4 (2019): 1693-1705. doi: https://doi.org/10.1021/acs.joc.8b02805
Reutskaya E, Osipyan A, Sapegin A, Novikov AS, Krasavin M. Rethinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds. J Org Chem. 2019 Feb 15;84(4):1693-1705. doi: 10.1021/acs.joc.8b02805. Epub 2018 Dec 24. PMID: 30566355.
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1,4-thiazepines, 1,4-benzothiazepin-5-ones, and 1,4-benzothioxepin orthoamides via multicomponent reactions of isocyanides.

The Journal of organic chemistry

Marcaccini S, Miguel D, Torroba T, García-Valverde M.
PMID: 12688810
J Org Chem. 2003 Apr 18;68(8):3315-8. doi: 10.1021/jo026614z.

The intramolecular Ugi four-component condensation between 6-oxo-4-thiacarboxylic acids, benzylamines, and cyclohexyl isocyanide gave hexahydro-1,4-thiazepin-5-ones and 1,4-benzothiazepin-5-ones, in some cases with high stereoselectivity, and the intramolecular Passerini three-component reaction, in the presence of catalytic amine, gave tetracyclic 1,4-benzothioxepin orthoamides.

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Marcaccini S, Miguel D, Torroba T, et al. 1,4-thiazepines, 1,4-benzothiazepin-5-ones, and 1,4-benzothioxepin orthoamides via multicomponent reactions of isocyanides. J Org Chem. 2003;68(8):3315-8doi: 10.1021/jo026614z.
Marcaccini, S., Miguel, D., Torroba, T., & García-Valverde, M. (2003). 1,4-thiazepines, 1,4-benzothiazepin-5-ones, and 1,4-benzothioxepin orthoamides via multicomponent reactions of isocyanides. The Journal of organic chemistry, 68(8), 3315-8. https://doi.org/10.1021/jo026614z
Marcaccini, Stefano, et al. "1,4-thiazepines, 1,4-benzothiazepin-5-ones, and 1,4-benzothioxepin orthoamides via multicomponent reactions of isocyanides." The Journal of organic chemistry vol. 68,8 (2003): 3315-8. doi: https://doi.org/10.1021/jo026614z
Marcaccini S, Miguel D, Torroba T, García-Valverde M. 1,4-thiazepines, 1,4-benzothiazepin-5-ones, and 1,4-benzothioxepin orthoamides via multicomponent reactions of isocyanides. J Org Chem. 2003 Apr 18;68(8):3315-8. doi: 10.1021/jo026614z. PMID: 12688810.
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Expedition of sulfur-containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update.

Medicinal research reviews

Laxmikeshav K, Kumari P, Shankaraiah N.
PMID: 34453452
Med Res Rev. 2022 Jan;42(1):513-575. doi: 10.1002/med.21852. Epub 2021 Aug 28.

This review article proposes a comprehensive report of the design strategies engaged in the development of various sulfur-bearing cytotoxic agents. The outcomes of various studies depict that the sulfur heterocyclic framework is a fundamental structure in diverse synthetic analogs...

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Laxmikeshav K, Kumari P, Shankaraiah N. Expedition of sulfur-containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update. Med Res Rev. 2021;42(1):513-575doi: 10.1002/med.21852.
Laxmikeshav, K., Kumari, P., & Shankaraiah, N. (2022). Expedition of sulfur-containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update. Medicinal research reviews, 42(1), 513-575. https://doi.org/10.1002/med.21852
Laxmikeshav, Kritika, et al. "Expedition of sulfur-containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update." Medicinal research reviews vol. 42,1 (2022): 513-575. doi: https://doi.org/10.1002/med.21852
Laxmikeshav K, Kumari P, Shankaraiah N. Expedition of sulfur-containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update. Med Res Rev. 2022 Jan;42(1):513-575. doi: 10.1002/med.21852. Epub 2021 Aug 28. PMID: 34453452.
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Analysis of Drug-Induced Gastrointestinal Obstruction and Perforation Using the Japanese Adverse Drug Event Report Database.

Frontiers in pharmacology

Satake R, Matsumoto K, Tanaka M, Mukai R, Shimada K, Yoshida Y, Inoue M, Hasegawa S, Iguchi K, Ikesue H, Shimizu S, Nishida S, Suzuki A, Hashida T, Nakamura M.
PMID: 34381361
Front Pharmacol. 2021 Jul 26;12:692292. doi: 10.3389/fphar.2021.692292. eCollection 2021.

Drug-induced gastrointestinal obstruction (DIGO) and gastrointestinal perforation (DIGP) may be the result of gastrointestinal hypomotility and severe constipation, which may lead to potentially fatal complications of bowel ischemia, sepsis and perforation. We evaluated the onset profile of DIGs (DIGO...

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Satake R, Matsumoto K, Tanaka M, et al. Analysis of Drug-Induced Gastrointestinal Obstruction and Perforation Using the Japanese Adverse Drug Event Report Database. Front Pharmacol. 2021;12:692292doi: 10.3389/fphar.2021.692292.
Satake, R., Matsumoto, K., Tanaka, M., Mukai, R., Shimada, K., Yoshida, Y., Inoue, M., Hasegawa, S., Iguchi, K., Ikesue, H., Shimizu, S., Nishida, S., Suzuki, A., Hashida, T., & Nakamura, M. (2021). Analysis of Drug-Induced Gastrointestinal Obstruction and Perforation Using the Japanese Adverse Drug Event Report Database. Frontiers in pharmacology, 12692292. https://doi.org/10.3389/fphar.2021.692292
Satake, Riko, et al. "Analysis of Drug-Induced Gastrointestinal Obstruction and Perforation Using the Japanese Adverse Drug Event Report Database." Frontiers in pharmacology vol. 12 (2021): 692292. doi: https://doi.org/10.3389/fphar.2021.692292
Satake R, Matsumoto K, Tanaka M, Mukai R, Shimada K, Yoshida Y, Inoue M, Hasegawa S, Iguchi K, Ikesue H, Shimizu S, Nishida S, Suzuki A, Hashida T, Nakamura M. Analysis of Drug-Induced Gastrointestinal Obstruction and Perforation Using the Japanese Adverse Drug Event Report Database. Front Pharmacol. 2021 Jul 26;12:692292. doi: 10.3389/fphar.2021.692292. eCollection 2021. PMID: 34381361; PMCID: PMC8350341.
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Synthesis of 1,4-Thiazepines.

The Journal of organic chemistry

Kelgokmen Y, Zora M.
PMID: 29936840
J Org Chem. 2018 Aug 03;83(15):8376-8389. doi: 10.1021/acs.joc.8b01029. Epub 2018 Jul 05.

An efficient, general, and unprecedented methodology for the synthesis of 2-methylene-2,3-dihydro-1,4-thiazepines from N-propargylic β-enaminones is described. Initially, N-propargylic β-enaminones were thionated with Lawesson's reagent in good to high yields, and then the resulting N-propargylic β-enaminothiones were subjected to electrophilic...

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Kelgokmen Y, Zora M. Synthesis of 1,4-Thiazepines. J Org Chem. 2018;83(15):8376-8389doi: 10.1021/acs.joc.8b01029.
Kelgokmen, Y., & Zora, M. (2018). Synthesis of 1,4-Thiazepines. The Journal of organic chemistry, 83(15), 8376-8389. https://doi.org/10.1021/acs.joc.8b01029
Kelgokmen, Yilmaz, and Zora, Metin. "Synthesis of 1,4-Thiazepines." The Journal of organic chemistry vol. 83,15 (2018): 8376-8389. doi: https://doi.org/10.1021/acs.joc.8b01029
Kelgokmen Y, Zora M. Synthesis of 1,4-Thiazepines. J Org Chem. 2018 Aug 03;83(15):8376-8389. doi: 10.1021/acs.joc.8b01029. Epub 2018 Jul 05. PMID: 29936840.
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Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE).

The Journal of organic chemistry

Osipyan A, Sapegin A, Novikov AS, Krasavin M.
PMID: 30101583
J Org Chem. 2018 Sep 07;83(17):9707-9717. doi: 10.1021/acs.joc.8b01210. Epub 2018 Aug 22.

The hydrolytic imidazoline ring expansion (HIRE) methodology was extended to readily available tetracyclic [1,4]thiazepines as well as sulfoxide and sulfone analogs thereof. The reactions resulted in the facile formation of a rare medium-sized [1,4,7]thiazecine ring system that has an...

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Osipyan A, Sapegin A, Novikov AS, et al. Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE). J Org Chem. 2018;83(17):9707-9717doi: 10.1021/acs.joc.8b01210.
Osipyan, A., Sapegin, A., Novikov, A. S., & Krasavin, M. (2018). Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE). The Journal of organic chemistry, 83(17), 9707-9717. https://doi.org/10.1021/acs.joc.8b01210
Osipyan, Angelina, et al. "Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE)." The Journal of organic chemistry vol. 83,17 (2018): 9707-9717. doi: https://doi.org/10.1021/acs.joc.8b01210
Osipyan A, Sapegin A, Novikov AS, Krasavin M. Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE). J Org Chem. 2018 Sep 07;83(17):9707-9717. doi: 10.1021/acs.joc.8b01210. Epub 2018 Aug 22. PMID: 30101583.
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Synthesis of bicyclic 1,4-thiazepines as novel anti-.

MedChemComm

Vairoletti F, Medeiros A, Fontán P, Meléndrez J, Tabárez C, Salinas G, Franco J, Comini MA, Saldaña J, Jancik V, Mahler G, Saiz C.
PMID: 31673311
Medchemcomm. 2019 Jun 11;10(8):1481-1487. doi: 10.1039/c9md00064j. eCollection 2019 Aug 01.

1,4-Thiazepines derivatives are pharmacologically important heterocycles with different applications in medicinal chemistry. In the present work, we describe the preparation of new bicyclic thiazolidinyl-1,4-thiazepines

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Vairoletti F, Medeiros A, Fontán P, et al. Synthesis of bicyclic 1,4-thiazepines as novel anti-. Medchemcomm. 2019;10(8):1481-1487doi: 10.1039/c9md00064j.
Vairoletti, F., Medeiros, A., Fontán, P., Meléndrez, J., Tabárez, C., Salinas, G., Franco, J., Comini, M. A., Saldaña, J., Jancik, V., Mahler, G., & Saiz, C. (2019). Synthesis of bicyclic 1,4-thiazepines as novel anti-. MedChemComm, 10(8), 1481-1487. https://doi.org/10.1039/c9md00064j
Vairoletti, Franco, et al. "Synthesis of bicyclic 1,4-thiazepines as novel anti-." MedChemComm vol. 10,8 (2019): 1481-1487. doi: https://doi.org/10.1039/c9md00064j
Vairoletti F, Medeiros A, Fontán P, Meléndrez J, Tabárez C, Salinas G, Franco J, Comini MA, Saldaña J, Jancik V, Mahler G, Saiz C. Synthesis of bicyclic 1,4-thiazepines as novel anti-. Medchemcomm. 2019 Jun 11;10(8):1481-1487. doi: 10.1039/c9md00064j. eCollection 2019 Aug 01. PMID: 31673311; PMCID: PMC6786244.
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A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones.

Organic & biomolecular chemistry

Kelgokmen Y, Zora M.
PMID: 30758002
Org Biomol Chem. 2019 Feb 27;17(9):2529-2541. doi: 10.1039/c8ob03180k.

A new method for the synthesis of 2,4,5-trisubstituted pyridines from N-propargylic β-enaminothiones is reported. β-Enaminothiones were prepared by thionation of the corresponding β-enaminones with Lawesson's reagent. When treated with diisopropylamine in DMF at room temperature, N-propargylic β-enaminothiones yielded 2,4,5-trisubstituted...

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Kelgokmen Y, Zora M. A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones. Org Biomol Chem. 2019;17(9):2529-2541doi: 10.1039/c8ob03180k.
Kelgokmen, Y., & Zora, M. (2019). A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones. Organic & biomolecular chemistry, 17(9), 2529-2541. https://doi.org/10.1039/c8ob03180k
Kelgokmen, Yilmaz, and Zora, Metin. "A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones." Organic & biomolecular chemistry vol. 17,9 (2019): 2529-2541. doi: https://doi.org/10.1039/c8ob03180k
Kelgokmen Y, Zora M. A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones. Org Biomol Chem. 2019 Feb 27;17(9):2529-2541. doi: 10.1039/c8ob03180k. PMID: 30758002.
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Cyclopropyl-Fused 1,3-Thiazepines as BACE1 and BACE2 Inhibitors.

ACS medicinal chemistry letters

Blass B.
PMID: 24900681
ACS Med Chem Lett. 2013 Mar 15;4(4):379-80. doi: 10.1021/ml400060e. eCollection 2013 Apr 11.

No abstract available.

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Blass B. Cyclopropyl-Fused 1,3-Thiazepines as BACE1 and BACE2 Inhibitors. ACS Med Chem Lett. 2013;4(4):379-80doi: 10.1021/ml400060e.
Blass, B. (2013). Cyclopropyl-Fused 1,3-Thiazepines as BACE1 and BACE2 Inhibitors. ACS medicinal chemistry letters, 4(4), 379-80. https://doi.org/10.1021/ml400060e
Blass, Benjamin. "Cyclopropyl-Fused 1,3-Thiazepines as BACE1 and BACE2 Inhibitors." ACS medicinal chemistry letters vol. 4,4 (2013): 379-80. doi: https://doi.org/10.1021/ml400060e
Blass B. Cyclopropyl-Fused 1,3-Thiazepines as BACE1 and BACE2 Inhibitors. ACS Med Chem Lett. 2013 Mar 15;4(4):379-80. doi: 10.1021/ml400060e. eCollection 2013 Apr 11. PMID: 24900681; PMCID: PMC4027375.
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Showing 1 to 12 of 13 entries