5,5′-(Piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiol-3-one)
Conjugates of 3H-1,2-dithiol-3-ones with various biologically active compounds are intensively investigated. Although many derivatives of this class have been described in the literature, the compounds containing two dithiole cycles have been explored much less. In this communication, it was shown t...
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| Published in | MolBank Vol. 2022; no. 3; p. M1411 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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01.09.2022
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| Abstract | Conjugates of 3H-1,2-dithiol-3-ones with various biologically active compounds are intensively investigated. Although many derivatives of this class have been described in the literature, the compounds containing two dithiole cycles have been explored much less. In this communication, it was shown that the reaction of 4,5-dichloro-3H-1,2-dithiol-3-one with piperazine can selectively lead to the mono-product, 4-chloro-5-piperazin-1-yl-3H-1,2-dithiol-3-one and bis-product, 5,5′-(piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiol-3-one). The structure of the synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy, and mass-spectrometry. |
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| AbstractList | Conjugates of 3H-1,2-dithiol-3-ones with various biologically active compounds are intensively investigated. Although many derivatives of this class have been described in the literature, the compounds containing two dithiole cycles have been explored much less. In this communication, it was shown that the reaction of 4,5-dichloro-3H-1,2-dithiol-3-one with piperazine can selectively lead to the mono-product, 4-chloro-5-piperazin-1-yl-3H-1,2-dithiol-3-one and bis-product, 5,5′-(piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiol-3-one). The structure of the synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy, and mass-spectrometry. |
| Author | Rakitin, Oleg A. Ogurtsov, Vladimir A. |
| Author_xml | – sequence: 1 givenname: Vladimir A. surname: Ogurtsov fullname: Ogurtsov, Vladimir A. – sequence: 2 givenname: Oleg A. orcidid: 0000-0001-6609-4087 surname: Rakitin fullname: Rakitin, Oleg A. |
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| Cites_doi | 10.1016/j.tetlet.2007.06.071 10.1070/RC2012v081n07ABEH004231 10.1007/s11172-022-3438-x 10.1002/jlac.19646790115 10.1016/j.ejmech.2015.07.026 10.3390/molecules26123595 10.1007/s11172-021-3127-1 10.1073/pnas.82.23.8232 10.1111/j.1471-4159.2010.06580.x 10.1128/AAC.48.8.3093-3102.2004 |
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| Copyright | 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. |
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| References | Kelloff (ref_5) 1994; 3 Prochaska (ref_7) 1985; 82 Fedorov (ref_3) 2021; 70 Fedorov (ref_12) 2022; 71 Shaquiquzzaman (ref_15) 2015; 102 Clayton (ref_10) 1997; 3 Boberg (ref_11) 1964; 679 Joule (ref_2) 2008; Volume 4 Konstantinova (ref_13) 2007; 48 ref_1 Gadalla (ref_4) 2010; 113 ref_9 Ogurtsov (ref_14) 2012; 81 Kensler (ref_6) 1998; 7 He (ref_8) 2004; 48 |
| References_xml | – volume: 48 start-page: 5851 year: 2007 ident: ref_13 article-title: Selective synthesis of bis[1,2]dithiolo[1,4]thiazines from 4-isopropylamino-5-chloro-1,2-dithiole-3-ones publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2007.06.071 contributor: fullname: Konstantinova – ident: ref_9 – volume: 81 start-page: 638 year: 2012 ident: ref_14 article-title: Reactivity of 1,2-dithioles publication-title: Russ. Chem. Revi. doi: 10.1070/RC2012v081n07ABEH004231 contributor: fullname: Ogurtsov – volume: 7 start-page: 127 year: 1998 ident: ref_6 article-title: Oltipraz chemoprevention trial in Qidong, People’s Republic of China: Modulation of serum aflatoxin albumin adduct biomarkers publication-title: Cancer Epidemiol. Biomark. Prev. contributor: fullname: Kensler – volume: 71 start-page: 489 year: 2022 ident: ref_12 article-title: Synthesis and study of thioglycoside conjugates of 4-chloro-1,2-dithiol-3-one as potential cancer-preventive substances in vitro and in vivo publication-title: Russ Chem Bull. doi: 10.1007/s11172-022-3438-x contributor: fullname: Fedorov – volume: 679 start-page: 109 year: 1964 ident: ref_11 article-title: Über 1.2-Dithia-cyclopentene, V. 4.5-Dichlor-1.2-dithia-cyclopentenon-(3) publication-title: Liebigs Ann. Chem. doi: 10.1002/jlac.19646790115 contributor: fullname: Boberg – volume: 102 start-page: 487 year: 2015 ident: ref_15 article-title: Piperazine scaffold: A remarkable tool in generation of diverse pharmacological agents publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2015.07.026 contributor: fullname: Shaquiquzzaman – ident: ref_1 doi: 10.3390/molecules26123595 – volume: 3 start-page: 783 year: 1997 ident: ref_10 article-title: Cellular kinetics of induction by oltipraz and its keto derivative of detoxication enzymes in human colon adenocarcinoma cells publication-title: Clin. Cancer Res. contributor: fullname: Clayton – volume: 3 start-page: 85 year: 1994 ident: ref_5 article-title: Chemopreventive drug development: Perspectives and progress publication-title: Cancer Epidemiol. Biomark. Prev. contributor: fullname: Kelloff – volume: Volume 4 start-page: 893 year: 2008 ident: ref_2 article-title: 1,2-Dithioles publication-title: Comprehensive Heterocyclic Chemistry III contributor: fullname: Joule – volume: 70 start-page: 573 year: 2021 ident: ref_3 article-title: Synthesis and studies of acetylthioglycoside conjugates of 4-chloro-1,2-dithiole-3-thione as potential antitumor agents publication-title: Russ. Chem. Bull. doi: 10.1007/s11172-021-3127-1 contributor: fullname: Fedorov – volume: 82 start-page: 8232 year: 1985 ident: ref_7 article-title: On the mechanisms of induction of cancer-protective enzymes: A unifying proposal publication-title: Proc. Natl. Acad. Sci. USA doi: 10.1073/pnas.82.23.8232 contributor: fullname: Prochaska – volume: 113 start-page: 14 year: 2010 ident: ref_4 article-title: Hydrogen sulfide as a gasotransmitter publication-title: J. Neurochem. doi: 10.1111/j.1471-4159.2010.06580.x contributor: fullname: Gadalla – volume: 48 start-page: 3093 year: 2004 ident: ref_8 article-title: 1,2-Dithiole-3-Ones as Potent Inhibitors of the Bacterial 3-Ketoacyl Acyl Carrier Protein Synthase III (FabH) publication-title: Antimicrob. Agents Chemother. doi: 10.1128/AAC.48.8.3093-3102.2004 contributor: fullname: He |
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| SubjectTerms | 3H-1,2-Dithiole-3-ones 5,5′-(piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiol-3-one) Cancer Chemical analysis Conflicts of interest Infrared spectroscopy NMR Nuclear magnetic resonance nucleophilic substitution piperazine Scientific imaging Solvents Spectrometry |
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| Title | 5,5′-(Piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiol-3-one) |
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