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Solution-Phase Synthesis of a Combinatorial Thiohydantoin Library(1).

The Journal of organic chemistry

Sim MM, Ganesan A.
PMID: 11671708
J Org Chem. 1997 May 16;62(10):3230-3235. doi: 10.1021/jo962376u.

An efficient one-pot three-component synthesis of thiohydantoins was developed. In the first step, amino acid esters were alkylated by imine formation with aldehydes and reduction by sodium triacetoxyborohydride. In the second step, an isothiocyanate was added together with a...

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Sim MM, Ganesan A. Solution-Phase Synthesis of a Combinatorial Thiohydantoin Library(1). J Org Chem. 1997;62(10):3230-3235doi: 10.1021/jo962376u.
Sim, M. M., & Ganesan, A. (1997). Solution-Phase Synthesis of a Combinatorial Thiohydantoin Library(1). The Journal of organic chemistry, 62(10), 3230-3235. https://doi.org/10.1021/jo962376u
Sim, Mui Mui, and Ganesan, Arasu. "Solution-Phase Synthesis of a Combinatorial Thiohydantoin Library(1)." The Journal of organic chemistry vol. 62,10 (1997): 3230-3235. doi: https://doi.org/10.1021/jo962376u
Sim MM, Ganesan A. Solution-Phase Synthesis of a Combinatorial Thiohydantoin Library(1). J Org Chem. 1997 May 16;62(10):3230-3235. doi: 10.1021/jo962376u. PMID: 11671708.
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Elucidation of the atroposelectivity in the synthesis of axially chiral thiohydantoin derivatives.

Organic & biomolecular chemistry

Haslak ZP, Agopcan Cinar S, Sarigul Ozbek S, Monard G, Dogan I, Aviyente V.
PMID: 32022073
Org Biomol Chem. 2020 Mar 25;18(12):2233-2241. doi: 10.1039/c9ob02556a.

Recently, Sarigul and Dogan have synthesized a number of enantiomerically enriched axially chiral atropoisomeric 2-thiohydantoins by the reaction of l-amino acid ester salts and o-aryl isothiocyanates in the presence of triethyl amine (TEA) in dichloromethane. The non-axially chiral derivative...

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Haslak ZP, Agopcan Cinar S, Sarigul Ozbek S, et al. Elucidation of the atroposelectivity in the synthesis of axially chiral thiohydantoin derivatives. Org Biomol Chem. 2020;18(12):2233-2241doi: 10.1039/c9ob02556a.
Haslak, Z. P., Agopcan Cinar, S., Sarigul Ozbek, S., Monard, G., Dogan, I., & Aviyente, V. (2020). Elucidation of the atroposelectivity in the synthesis of axially chiral thiohydantoin derivatives. Organic & biomolecular chemistry, 18(12), 2233-2241. https://doi.org/10.1039/c9ob02556a
Haslak, Zeynep Pinar, et al. "Elucidation of the atroposelectivity in the synthesis of axially chiral thiohydantoin derivatives." Organic & biomolecular chemistry vol. 18,12 (2020): 2233-2241. doi: https://doi.org/10.1039/c9ob02556a
Haslak ZP, Agopcan Cinar S, Sarigul Ozbek S, Monard G, Dogan I, Aviyente V. Elucidation of the atroposelectivity in the synthesis of axially chiral thiohydantoin derivatives. Org Biomol Chem. 2020 Mar 25;18(12):2233-2241. doi: 10.1039/c9ob02556a. PMID: 32022073.
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Mass spectral study of the occurrence of tautomeric forms of thiohydantoins.

European journal of mass spectrometry (Chichester, England)

Alegretti PE, de las Mercedes Shiavoni M, Guzmán C, Ponzinibbio A, Furlong JJ.
PMID: 17942979
Eur J Mass Spectrom (Chichester). 2007;13(4):291-306. doi: 10.1255/ejms.885.

Mass spectrometry is used to evaluate the occurrence of thio-enol structures among the several possible tautomers of thiohydantoins and dithiohydantoins. Mass spectra of differently substituted thiohydantoins are examined looking for common mass spectral behaviors. Ion fragmentations from specific tautomers...

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Alegretti PE, de las Mercedes Shiavoni M, Guzmán C, et al. Mass spectral study of the occurrence of tautomeric forms of thiohydantoins. Eur J Mass Spectrom (Chichester). 2007;13(4):291-306doi: 10.1255/ejms.885.
Alegretti, P. E., de las Mercedes Shiavoni, M., Guzmán, C., Ponzinibbio, A., & Furlong, J. J. (2007). Mass spectral study of the occurrence of tautomeric forms of thiohydantoins. European journal of mass spectrometry (Chichester, England), 13(4), 291-306. https://doi.org/10.1255/ejms.885
Alegretti, Patricia E, et al. "Mass spectral study of the occurrence of tautomeric forms of thiohydantoins." European journal of mass spectrometry (Chichester, England) vol. 13,4 (2007): 291-306. doi: https://doi.org/10.1255/ejms.885
Alegretti PE, de las Mercedes Shiavoni M, Guzmán C, Ponzinibbio A, Furlong JJ. Mass spectral study of the occurrence of tautomeric forms of thiohydantoins. Eur J Mass Spectrom (Chichester). 2007;13(4):291-306. doi: 10.1255/ejms.885. PMID: 17942979.
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New platinum(II) complexes of cycloalkanespiro-5-(2-thiohydantoins). Synthesis and quantum chemical investigation.

Acta chimica Slovenica

Marinova P, Marinov M, Delchev V, Stoyanov N.
PMID: 25830980
Acta Chim Slov. 2015;62(1):225-32. doi: 10.17344/acsi.2014.1206.

Synthesis and characterization of new Pt(II) complexes of cyclohexanespiro-5-(2-thiohydantoin) (L1) and cycloheptanespiro-5-(2-thiohydantoin) (L2) are discussed. The new complexes are studied by elemental analysis, IR, ATR FTIR spectroscopy. The free ligands are investigated by UV-Vis, FT-IR, (1)H NMR, (13)C NMR...

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Marinova P, Marinov M, Delchev V, et al. New platinum(II) complexes of cycloalkanespiro-5-(2-thiohydantoins). Synthesis and quantum chemical investigation. Acta Chim Slov. 2015;62(1):225-32doi: 10.17344/acsi.2014.1206.
Marinova, P., Marinov, M., Delchev, V., & Stoyanov, N. (2015). New platinum(II) complexes of cycloalkanespiro-5-(2-thiohydantoins). Synthesis and quantum chemical investigation. Acta chimica Slovenica, 62(1), 225-32. https://doi.org/10.17344/acsi.2014.1206
Marinova, Petja, et al. "New platinum(II) complexes of cycloalkanespiro-5-(2-thiohydantoins). Synthesis and quantum chemical investigation." Acta chimica Slovenica vol. 62,1 (2015): 225-32. doi: https://doi.org/10.17344/acsi.2014.1206
Marinova P, Marinov M, Delchev V, Stoyanov N. New platinum(II) complexes of cycloalkanespiro-5-(2-thiohydantoins). Synthesis and quantum chemical investigation. Acta Chim Slov. 2015;62(1):225-32. doi: 10.17344/acsi.2014.1206. PMID: 25830980.
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Investigation of the antileishmanial activity and mechanisms of action of acetyl-thiohydantoins.

Chemico-biological interactions

Bortoleti BTDS, Gonçalves MD, Tomiotto-Pellissier F, Camargo PG, Assolini JP, Concato VM, Detoni MB, Bidóia DL, Bispo MLF, Lima CHDS, de Macedo FC, Conchon-Costa I, Miranda-Sapla MM, Wowk PF, Pavanelli WR.
PMID: 34637778
Chem Biol Interact. 2022 Jan 05;351:109690. doi: 10.1016/j.cbi.2021.109690. Epub 2021 Oct 09.

The currently available treatment options for leishmaniasis are associated with high costs, severe side effects, and high toxicity. In previous studies, thiohydantoins demonstrated some pharmacological activities and were shown to be potential hit compounds with antileishmanial properties. The present...

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Bortoleti BTDS, Gonçalves MD, Tomiotto-Pellissier F, et al. Investigation of the antileishmanial activity and mechanisms of action of acetyl-thiohydantoins. Chem Biol Interact. 2021;351:109690doi: 10.1016/j.cbi.2021.109690.
Bortoleti, B. T. D. S., Gonçalves, M. D., Tomiotto-Pellissier, F., Camargo, P. G., Assolini, J. P., Concato, V. M., Detoni, M. B., Bidóia, D. L., Bispo, M. L. F., Lima, C. H. D. S., de Macedo, F. C., Conchon-Costa, I., Miranda-Sapla, M. M., Wowk, P. F., & Pavanelli, W. R. (2022). Investigation of the antileishmanial activity and mechanisms of action of acetyl-thiohydantoins. Chemico-biological interactions, 351109690. https://doi.org/10.1016/j.cbi.2021.109690
Bortoleti, Bruna Taciane da Silva, et al. "Investigation of the antileishmanial activity and mechanisms of action of acetyl-thiohydantoins." Chemico-biological interactions vol. 351 (2022): 109690. doi: https://doi.org/10.1016/j.cbi.2021.109690
Bortoleti BTDS, Gonçalves MD, Tomiotto-Pellissier F, Camargo PG, Assolini JP, Concato VM, Detoni MB, Bidóia DL, Bispo MLF, Lima CHDS, de Macedo FC, Conchon-Costa I, Miranda-Sapla MM, Wowk PF, Pavanelli WR. Investigation of the antileishmanial activity and mechanisms of action of acetyl-thiohydantoins. Chem Biol Interact. 2022 Jan 05;351:109690. doi: 10.1016/j.cbi.2021.109690. Epub 2021 Oct 09. PMID: 34637778.
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Patterns of Cell Death Induced by Thiohydantoins in Human MCF-7 Breast Cancer Cells.

Anti-cancer agents in medicinal chemistry

Fagundes TR, Bortoleti B, Camargo P, Concato V, Tomiotto-Pellissier F, Carloto A, Panis C, Bispo M, Junior FM, Conchon-Costa I, Pavanelli W.
PMID: 34382528
Anticancer Agents Med Chem. 2021 Aug 10; doi: 10.2174/1871520621666210811102441. Epub 2021 Aug 10.

BACKGROUND: Conventional therapies for breast cancer is still a challenge due to use of cytotoxic drugs not highly effective with major adverse effects. Thiohydantoins, are biologically active heterocyclic compounds reported by several biological activities, including anticarcinogenic properties, i.e., this...

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Fagundes TR, Bortoleti B, Camargo P, et al. Patterns of Cell Death Induced by Thiohydantoins in Human MCF-7 Breast Cancer Cells. Anticancer Agents Med Chem. 2021;doi: 10.2174/1871520621666210811102441.
Fagundes, T. R., Bortoleti, B., Camargo, P., Concato, V., Tomiotto-Pellissier, F., Carloto, A., Panis, C., Bispo, M., Junior, F. M., Conchon-Costa, I., & Pavanelli, W. (2021). Patterns of Cell Death Induced by Thiohydantoins in Human MCF-7 Breast Cancer Cells. Anti-cancer agents in medicinal chemistry, . https://doi.org/10.2174/1871520621666210811102441
Fagundes, Tatiane Renata, et al. "Patterns of Cell Death Induced by Thiohydantoins in Human MCF-7 Breast Cancer Cells." Anti-cancer agents in medicinal chemistry vol. (2021). doi: https://doi.org/10.2174/1871520621666210811102441
Fagundes TR, Bortoleti B, Camargo P, Concato V, Tomiotto-Pellissier F, Carloto A, Panis C, Bispo M, Junior FM, Conchon-Costa I, Pavanelli W. Patterns of Cell Death Induced by Thiohydantoins in Human MCF-7 Breast Cancer Cells. Anticancer Agents Med Chem. 2021 Aug 10; doi: 10.2174/1871520621666210811102441. Epub 2021 Aug 10. PMID: 34382528.
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Investigation of the antileishmanial activity and mechanisms of action of acetyl-thiohydantoins.

Chemico-biological interactions

Bortoleti BTDS, Gonçalves MD, Tomiotto-Pellissier F, Camargo PG, Assolini JP, Concato VM, Detoni MB, Bidóia DL, Bispo MLF, Lima CHDS, de Macedo FC, Conchon-Costa I, Miranda-Sapla MM, Wowk PF, Pavanelli WR.
PMID: 34637778
Chem Biol Interact. 2021 Oct 09;351:109690. doi: 10.1016/j.cbi.2021.109690. Epub 2021 Oct 09.

The currently available treatment options for leishmaniasis are associated with high costs, severe side effects, and high toxicity. In previous studies, thiohydantoins demonstrated some pharmacological activities and were shown to be potential hit compounds with antileishmanial properties. The present...

Cite
Bortoleti BTDS, Gonçalves MD, Tomiotto-Pellissier F, et al. Investigation of the antileishmanial activity and mechanisms of action of acetyl-thiohydantoins. Chem Biol Interact. 2021;351:109690doi: 10.1016/j.cbi.2021.109690.
Bortoleti, B. T. D. S., Gonçalves, M. D., Tomiotto-Pellissier, F., Camargo, P. G., Assolini, J. P., Concato, V. M., Detoni, M. B., Bidóia, D. L., Bispo, M. L. F., Lima, C. H. D. S., de Macedo, F. C., Conchon-Costa, I., Miranda-Sapla, M. M., Wowk, P. F., & Pavanelli, W. R. (2021). Investigation of the antileishmanial activity and mechanisms of action of acetyl-thiohydantoins. Chemico-biological interactions, 351109690. https://doi.org/10.1016/j.cbi.2021.109690
Bortoleti, Bruna Taciane da Silva, et al. "Investigation of the antileishmanial activity and mechanisms of action of acetyl-thiohydantoins." Chemico-biological interactions vol. 351 (2021): 109690. doi: https://doi.org/10.1016/j.cbi.2021.109690
Bortoleti BTDS, Gonçalves MD, Tomiotto-Pellissier F, Camargo PG, Assolini JP, Concato VM, Detoni MB, Bidóia DL, Bispo MLF, Lima CHDS, de Macedo FC, Conchon-Costa I, Miranda-Sapla MM, Wowk PF, Pavanelli WR. Investigation of the antileishmanial activity and mechanisms of action of acetyl-thiohydantoins. Chem Biol Interact. 2021 Oct 09;351:109690. doi: 10.1016/j.cbi.2021.109690. Epub 2021 Oct 09. PMID: 34637778.
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Gas chromatographic identification of the thiohydantoins of degradation products of peptides and proteins.

Angewandte Chemie (International ed. in English)

Tschesche H, Obermeier R, Kupfer S.
PMID: 4993356
Angew Chem Int Ed Engl. 1970 Nov;9(11):893-4. doi: 10.1002/anie.197008931.

No abstract available.

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Tschesche H, Obermeier R, Kupfer S. Gas chromatographic identification of the thiohydantoins of degradation products of peptides and proteins. Angew Chem Int Ed Engl. 1970;9(11):893-4doi: 10.1002/anie.197008931.
Tschesche, H., Obermeier, R., & Kupfer, S. (1970). Gas chromatographic identification of the thiohydantoins of degradation products of peptides and proteins. Angewandte Chemie (International ed. in English), 9(11), 893-4. https://doi.org/10.1002/anie.197008931
Tschesche, H, et al. "Gas chromatographic identification of the thiohydantoins of degradation products of peptides and proteins." Angewandte Chemie (International ed. in English) vol. 9,11 (1970): 893-4. doi: https://doi.org/10.1002/anie.197008931
Tschesche H, Obermeier R, Kupfer S. Gas chromatographic identification of the thiohydantoins of degradation products of peptides and proteins. Angew Chem Int Ed Engl. 1970 Nov;9(11):893-4. doi: 10.1002/anie.197008931. PMID: 4993356.
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An automated C-terminal sequencing method for analysis of proteins us ing an ABI 473A sequencer.

Journal of biomolecular techniques : JBT

Tang S, Mozdzanowski J, Anumula KR.
PMID: 19499018
J Biomol Tech. 1999 Sep;10(3):144-52.

We developed a novel chemistry for C-terminal sequencing of proteins based on derivatization with acetylisothiocyanate to yield amino acid thiohydantoins (TH-AAs), and it was used for manual sequencing of biopharmaceutical products on a routine basis.This simple chemistry was automated...

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Tang S, Mozdzanowski J, Anumula KR. An automated C-terminal sequencing method for analysis of proteins us ing an ABI 473A sequencer. J Biomol Tech. 1999;10(3):144-52
Tang, S., Mozdzanowski, J., & Anumula, K. R. (1999). An automated C-terminal sequencing method for analysis of proteins us ing an ABI 473A sequencer. Journal of biomolecular techniques : JBT, 10(3), 144-52.
Tang, S, et al. "An automated C-terminal sequencing method for analysis of proteins us ing an ABI 473A sequencer." Journal of biomolecular techniques : JBT vol. 10,3 (1999): 144-52.
Tang S, Mozdzanowski J, Anumula KR. An automated C-terminal sequencing method for analysis of proteins us ing an ABI 473A sequencer. J Biomol Tech. 1999 Sep;10(3):144-52. PMID: 19499018; PMCID: PMC2291600.
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Atroposelective Synthesis of Axially Chiral Thiohydantoin Derivatives.

The Journal of organic chemistry

Sarigul S, Dogan I.
PMID: 27322739
J Org Chem. 2016 Jul 15;81(14):5895-902. doi: 10.1021/acs.joc.6b00696. Epub 2016 Jun 28.

Nonracemic axially chiral thiohydantoins were synthesized atroposelectively by the reaction of o-aryl isothiocyanates with amino acid ester salts in the presence of triethylamine (TEA). The synthesis of the nonaxially chiral derivatives, however, gave thiohydantoins racemized at C-5 of the...

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Sarigul S, Dogan I. Atroposelective Synthesis of Axially Chiral Thiohydantoin Derivatives. J Org Chem. 2016;81(14):5895-902doi: 10.1021/acs.joc.6b00696.
Sarigul, S., & Dogan, I. (2016). Atroposelective Synthesis of Axially Chiral Thiohydantoin Derivatives. The Journal of organic chemistry, 81(14), 5895-902. https://doi.org/10.1021/acs.joc.6b00696
Sarigul, Sevgi, and Dogan, Ilknur. "Atroposelective Synthesis of Axially Chiral Thiohydantoin Derivatives." The Journal of organic chemistry vol. 81,14 (2016): 5895-902. doi: https://doi.org/10.1021/acs.joc.6b00696
Sarigul S, Dogan I. Atroposelective Synthesis of Axially Chiral Thiohydantoin Derivatives. J Org Chem. 2016 Jul 15;81(14):5895-902. doi: 10.1021/acs.joc.6b00696. Epub 2016 Jun 28. PMID: 27322739.
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1-Benzyl-3-aryl-2-thiohydantoin Derivatives as New Anti-.

ACS medicinal chemistry letters

Buchynskyy A, Gillespie JR, Herbst ZM, Ranade RM, Buckner FS, Gelb MH.
PMID: 28835807
ACS Med Chem Lett. 2017 Jul 10;8(8):886-891. doi: 10.1021/acsmedchemlett.7b00230. eCollection 2017 Aug 10.

A high throughput screening and subsequent hit validation identified compound

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Buchynskyy A, Gillespie JR, Herbst ZM, et al. 1-Benzyl-3-aryl-2-thiohydantoin Derivatives as New Anti-. ACS Med Chem Lett. 2017;8(8):886-891doi: 10.1021/acsmedchemlett.7b00230.
Buchynskyy, A., Gillespie, J. R., Herbst, Z. M., Ranade, R. M., Buckner, F. S., & Gelb, M. H. (2017). 1-Benzyl-3-aryl-2-thiohydantoin Derivatives as New Anti-. ACS medicinal chemistry letters, 8(8), 886-891. https://doi.org/10.1021/acsmedchemlett.7b00230
Buchynskyy, Andriy, et al. "1-Benzyl-3-aryl-2-thiohydantoin Derivatives as New Anti-." ACS medicinal chemistry letters vol. 8,8 (2017): 886-891. doi: https://doi.org/10.1021/acsmedchemlett.7b00230
Buchynskyy A, Gillespie JR, Herbst ZM, Ranade RM, Buckner FS, Gelb MH. 1-Benzyl-3-aryl-2-thiohydantoin Derivatives as New Anti-. ACS Med Chem Lett. 2017 Jul 10;8(8):886-891. doi: 10.1021/acsmedchemlett.7b00230. eCollection 2017 Aug 10. PMID: 28835807; PMCID: PMC5554913.
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Progress on the Chemical Constituents Derived from Glucosinolates in Maca (Lepidium meyenii).

Natural products and bioprospecting

Huang YJ, Peng XR, Qiu MH.
PMID: 30151716
Nat Prod Bioprospect. 2018 Dec;8(6):405-412. doi: 10.1007/s13659-018-0185-7. Epub 2018 Aug 27.

Maca (Lepidium meyenii Walp.), a famous food supplement, has drawn an unprecedented international interest over the last two decades. It was assumed that glucosinolates, macamides, macaenes, and alkaloids are the main bioactive components of Maca before. Recently, a series...

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Huang YJ, Peng XR, Qiu MH. Progress on the Chemical Constituents Derived from Glucosinolates in Maca (Lepidium meyenii). Nat Prod Bioprospect. 2018;8(6):405-412doi: 10.1007/s13659-018-0185-7.
Huang, Y. J., Peng, X. R., & Qiu, M. H. (2018). Progress on the Chemical Constituents Derived from Glucosinolates in Maca (Lepidium meyenii). Natural products and bioprospecting, 8(6), 405-412. https://doi.org/10.1007/s13659-018-0185-7
Huang, Yan-Jie, et al. "Progress on the Chemical Constituents Derived from Glucosinolates in Maca (Lepidium meyenii)." Natural products and bioprospecting vol. 8,6 (2018): 405-412. doi: https://doi.org/10.1007/s13659-018-0185-7
Huang YJ, Peng XR, Qiu MH. Progress on the Chemical Constituents Derived from Glucosinolates in Maca (Lepidium meyenii). Nat Prod Bioprospect. 2018 Dec;8(6):405-412. doi: 10.1007/s13659-018-0185-7. Epub 2018 Aug 27. PMID: 30151716; PMCID: PMC6224809.
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Showing 1 to 12 of 19 entries