Towards Asymmetrical Methylene Blue Analogues: Synthesis and Reactivity of 3-<i<N</i<′-Arylaminophenothiazines

The search for new ways to obtain analogues of the well-known Methylene Blue dye is an important synthetic task. Herein, we proposed and developed an approach to the synthesis of 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines. T...
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Autor*in:	Alena Khadieva [verfasserIn] Mansur Rayanov [verfasserIn] Ksenia Shibaeva [verfasserIn] Alexandr Piskunov [verfasserIn] Pavel Padnya [verfasserIn] Ivan Stoikov [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2022

Schlagwörter:	Methylene Blue phenothiazine synthesis reactivity DFT

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 27(2022), 9, p 3024
Übergeordnetes Werk:	volume:27 ; year:2022 ; number:9, p 3024

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules27093024

Katalog-ID:	DOAJ029852323

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allfields	10.3390/molecules27093024 doi (DE-627)DOAJ029852323 (DE-599)DOAJ27398a8b500942d38fdda20c20788b1a DE-627 ger DE-627 rakwb eng QD241-441 Alena Khadieva verfasserin aut Towards Asymmetrical Methylene Blue Analogues: Synthesis and Reactivity of 3-<i<N</i<′-Arylaminophenothiazines 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The search for new ways to obtain analogues of the well-known Methylene Blue dye is an important synthetic task. Herein, we proposed and developed an approach to the synthesis of 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines. This approach included the optimization of synthetic strategy by quantification analysis of the positive charge distribution in the cation of 3-<i<N</i<′-arylaminophenothiazine derivative. The obtained experimental data are confirmed by DFT studies. Two synthetic routes for asymmetrical phenothiazine diarylamino derivatives were suggested and verified. The developed convenient and versatile synthetic approach makes it easy to obtain aromatic Methylene Blue isostructural analogues with various substituents. As a result, a series of novel 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines containing ester, <i<tert</i<-butoxycarbonyl, sulfonic acid, hydroxyl and amine groups were obtained in high yields. Methylene Blue phenothiazine synthesis reactivity DFT Organic chemistry Mansur Rayanov verfasserin aut Ksenia Shibaeva verfasserin aut Alexandr Piskunov verfasserin aut Pavel Padnya verfasserin aut Ivan Stoikov verfasserin aut In Molecules MDPI AG, 2003 27(2022), 9, p 3024 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:9, p 3024 https://doi.org/10.3390/molecules27093024 kostenfrei https://doaj.org/article/27398a8b500942d38fdda20c20788b1a kostenfrei https://www.mdpi.com/1420-3049/27/9/3024 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 9, p 3024
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allfieldsSound	10.3390/molecules27093024 doi (DE-627)DOAJ029852323 (DE-599)DOAJ27398a8b500942d38fdda20c20788b1a DE-627 ger DE-627 rakwb eng QD241-441 Alena Khadieva verfasserin aut Towards Asymmetrical Methylene Blue Analogues: Synthesis and Reactivity of 3-<i<N</i<′-Arylaminophenothiazines 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The search for new ways to obtain analogues of the well-known Methylene Blue dye is an important synthetic task. Herein, we proposed and developed an approach to the synthesis of 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines. This approach included the optimization of synthetic strategy by quantification analysis of the positive charge distribution in the cation of 3-<i<N</i<′-arylaminophenothiazine derivative. The obtained experimental data are confirmed by DFT studies. Two synthetic routes for asymmetrical phenothiazine diarylamino derivatives were suggested and verified. The developed convenient and versatile synthetic approach makes it easy to obtain aromatic Methylene Blue isostructural analogues with various substituents. As a result, a series of novel 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines containing ester, <i<tert</i<-butoxycarbonyl, sulfonic acid, hydroxyl and amine groups were obtained in high yields. Methylene Blue phenothiazine synthesis reactivity DFT Organic chemistry Mansur Rayanov verfasserin aut Ksenia Shibaeva verfasserin aut Alexandr Piskunov verfasserin aut Pavel Padnya verfasserin aut Ivan Stoikov verfasserin aut In Molecules MDPI AG, 2003 27(2022), 9, p 3024 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:9, p 3024 https://doi.org/10.3390/molecules27093024 kostenfrei https://doaj.org/article/27398a8b500942d38fdda20c20788b1a kostenfrei https://www.mdpi.com/1420-3049/27/9/3024 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 9, p 3024
language	English
source	In Molecules 27(2022), 9, p 3024 volume:27 year:2022 number:9, p 3024
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topic_facet	Methylene Blue phenothiazine synthesis reactivity DFT Organic chemistry
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authorswithroles_txt_mv	Alena Khadieva @@aut@@ Mansur Rayanov @@aut@@ Ksenia Shibaeva @@aut@@ Alexandr Piskunov @@aut@@ Pavel Padnya @@aut@@ Ivan Stoikov @@aut@@
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callnumber-first	Q - Science
author	Alena Khadieva
spellingShingle	Alena Khadieva misc QD241-441 misc Methylene Blue misc phenothiazine misc synthesis misc reactivity misc DFT misc Organic chemistry Towards Asymmetrical Methylene Blue Analogues: Synthesis and Reactivity of 3-<i<N</i<′-Arylaminophenothiazines
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topic_title	QD241-441 Towards Asymmetrical Methylene Blue Analogues: Synthesis and Reactivity of 3-<i<N</i<′-Arylaminophenothiazines Methylene Blue phenothiazine synthesis reactivity DFT
topic	misc QD241-441 misc Methylene Blue misc phenothiazine misc synthesis misc reactivity misc DFT misc Organic chemistry
topic_unstemmed	misc QD241-441 misc Methylene Blue misc phenothiazine misc synthesis misc reactivity misc DFT misc Organic chemistry
topic_browse	misc QD241-441 misc Methylene Blue misc phenothiazine misc synthesis misc reactivity misc DFT misc Organic chemistry
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title	Towards Asymmetrical Methylene Blue Analogues: Synthesis and Reactivity of 3-<i<N</i<′-Arylaminophenothiazines
ctrlnum	(DE-627)DOAJ029852323 (DE-599)DOAJ27398a8b500942d38fdda20c20788b1a
title_full	Towards Asymmetrical Methylene Blue Analogues: Synthesis and Reactivity of 3-<i<N</i<′-Arylaminophenothiazines
author_sort	Alena Khadieva
journal	Molecules
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author_browse	Alena Khadieva Mansur Rayanov Ksenia Shibaeva Alexandr Piskunov Pavel Padnya Ivan Stoikov
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title_sort	towards asymmetrical methylene blue analogues: synthesis and reactivity of 3-<i<n</i<′-arylaminophenothiazines
callnumber	QD241-441
title_auth	Towards Asymmetrical Methylene Blue Analogues: Synthesis and Reactivity of 3-<i<N</i<′-Arylaminophenothiazines
abstract	The search for new ways to obtain analogues of the well-known Methylene Blue dye is an important synthetic task. Herein, we proposed and developed an approach to the synthesis of 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines. This approach included the optimization of synthetic strategy by quantification analysis of the positive charge distribution in the cation of 3-<i<N</i<′-arylaminophenothiazine derivative. The obtained experimental data are confirmed by DFT studies. Two synthetic routes for asymmetrical phenothiazine diarylamino derivatives were suggested and verified. The developed convenient and versatile synthetic approach makes it easy to obtain aromatic Methylene Blue isostructural analogues with various substituents. As a result, a series of novel 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines containing ester, <i<tert</i<-butoxycarbonyl, sulfonic acid, hydroxyl and amine groups were obtained in high yields.
abstractGer	The search for new ways to obtain analogues of the well-known Methylene Blue dye is an important synthetic task. Herein, we proposed and developed an approach to the synthesis of 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines. This approach included the optimization of synthetic strategy by quantification analysis of the positive charge distribution in the cation of 3-<i<N</i<′-arylaminophenothiazine derivative. The obtained experimental data are confirmed by DFT studies. Two synthetic routes for asymmetrical phenothiazine diarylamino derivatives were suggested and verified. The developed convenient and versatile synthetic approach makes it easy to obtain aromatic Methylene Blue isostructural analogues with various substituents. As a result, a series of novel 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines containing ester, <i<tert</i<-butoxycarbonyl, sulfonic acid, hydroxyl and amine groups were obtained in high yields.
abstract_unstemmed	The search for new ways to obtain analogues of the well-known Methylene Blue dye is an important synthetic task. Herein, we proposed and developed an approach to the synthesis of 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines. This approach included the optimization of synthetic strategy by quantification analysis of the positive charge distribution in the cation of 3-<i<N</i<′-arylaminophenothiazine derivative. The obtained experimental data are confirmed by DFT studies. Two synthetic routes for asymmetrical phenothiazine diarylamino derivatives were suggested and verified. The developed convenient and versatile synthetic approach makes it easy to obtain aromatic Methylene Blue isostructural analogues with various substituents. As a result, a series of novel 3-<i<N</i<′-arylaminophenothiazines and asymmetrical 3,7-di(<i<N</i<′-arylamino)phenothiazines containing ester, <i<tert</i<-butoxycarbonyl, sulfonic acid, hydroxyl and amine groups were obtained in high yields.
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container_issue	9, p 3024
title_short	Towards Asymmetrical Methylene Blue Analogues: Synthesis and Reactivity of 3-<i<N</i<′-Arylaminophenothiazines
url	https://doi.org/10.3390/molecules27093024 https://doaj.org/article/27398a8b500942d38fdda20c20788b1a https://www.mdpi.com/1420-3049/27/9/3024 https://doaj.org/toc/1420-3049
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author2	Mansur Rayanov Ksenia Shibaeva Alexandr Piskunov Pavel Padnya Ivan Stoikov
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up_date	2024-07-04T00:39:54.736Z
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Towards Asymmetrical Methylene Blue Analogues: Synthesis and Reactivity of 3-<i<N</i<′-Arylaminophenothiazines

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