ChemInform Abstract: ANTIVIRAL DRUGS. XVIII. 2‐AMINOTHIAZOLES BY CLEAVAGE OF THE S‐S BOND OF DISULFIDODICARBAMIDINE

Kreutzberger, A.; Schimmelpfennig, H.

doi:10.1002/chin.198134220

Cited by 4 publications

(4 citation statements)

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“…1-(2-Amino-4-ethylthiazol-5-yl)propan-1-one 14. 24 An absolute ethanol solution of bromine (453 µL, 8.82 mmol) was added dropwise at room temperature to an absolute ethanol solution of 3,5-heptanedione (1.13 g, 8.82 mmol), and thiourea (5.11g, 8.82 mmol). The resulting reaction mixture was refluxed overnight, at which point the ethanol was evaporated in vacuo and the residue was triturated with a small quantity of DCM.…”

Section: N-(3-(2-bromoacetyl)phenyl)pivalamidementioning

confidence: 99%

Potent s-cis-Locked Bithiazole Correctors of ΔF508 Cystic Fibrosis Transmembrane Conductance Regulator Cellular Processing for Cystic Fibrosis Therapy

Yoo

Yang

et al. 2008

J. Med. Chem.

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N-(5-(2-(5-Chloro-2-methoxyphenylamino)thiazol-4-yl)-4-methylthiazol-2-yl)pivalamide 1 (compound 15Jf) was found previously to correct defective cellular processing of the cystic fibrosis protein ΔF508-CFTR. Eight C4′-C5 C,C-bond-controlling bithiazole analogs of 1 were designed, synthesized, and evaluated to establish that constraining rotation about the bithiazole-tethering has a significant effect on corrector activity. For example, constraining the C4′-C5 bithiazole tether in the s-cis conformation [N-(2-(5-chloro-2-methoxyphenyl-amino)-7,8-dihydro-6H-cyclohepta[1,2-d:3,4-d′]bithiazole-2′-yl)pivalamide; 29] results in improved corrector activity. Heteroatom placement in the bithaizole core is also critical as evidenced by the decisive loss of corrector activity with s-cis constrained N-(2-(5-chloro-2-methoxyphenylamino)-5,6-dihydro-4H-cyclohepta[1,2-d:3,4-d′]bithiazole-2′-yl)pivalamide 33. In addition, computational models were utilized to examine the conformational preferences for select model systems. Following our analysis, the “s-cis locked” cycloheptathiazolothiazole 29 was found to be the most potent bithiazole corrector, with an IC50 of ~450 nM.

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Section: N-(3-(2-bromoacetyl)phenyl)pivalamidementioning

confidence: 99%

Potent s-cis-Locked Bithiazole Correctors of ΔF508 Cystic Fibrosis Transmembrane Conductance Regulator Cellular Processing for Cystic Fibrosis Therapy

Yoo

Yang

et al. 2008

J. Med. Chem.

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“…Azo compounds are of great importance due to their versatile application in various fields, such as the dyeing of textile fibers, coloring of different materials, biomedical studies, and advanced applications in organic synthesis [1][2][3][4]. In continuation of our previous work [5][6][7][8] on the synthesis of S/N heterocyclic azo compounds with different applications, such as dyeing polyester fabrics and bioactive function, the present work describes the synthesis of several new S/N heterocyclic mono azo compounds based on the 2-aminothiazole moiety, and their applications as biologically active materials.…”

Section: Introductionmentioning

confidence: 99%

“…In continuation of our previous work [5][6][7][8] on the synthesis of S/N heterocyclic azo compounds with different applications, such as dyeing polyester fabrics and bioactive function, the present work describes the synthesis of several new S/N heterocyclic mono azo compounds based on the 2-aminothiazole moiety, and their applications as biologically active materials. Diverse biological activities have been found to be associated with thiazolidine derivatives, including anesthetic [3], antiviral [4], antimicrobial [9], bactericidal [10], anti-inflammatory [11], fungicidal [12,13], and anticonvulsant [14][15][16] properties. It is well known that 2-aminothiazole can exhibit amino-imino tautomeric configurations in nature, and the amino configuration is the predominant tautomer [17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 2-amino-5-arylazothiazol derivatives and their biological impacts: Assessment of toxicity and antioxidant enzymes activities

Khalifa

Mohamed

Alshehri

2015

Maced. J. Chem. Chem. Eng.

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A reactivity study of both the amino group and the aryl substituent of a newly synthesized 2-amino-5-(4-acetylphenylazo)-thiazole compound and its derivatives via various electrophilic reagents was performed to obtain new bioactive chalcone, imine, and pyrazole-thiazolidine derivatives. The synthesized compounds were chemically elucidated by analytical and spectral methods, and biologically evaluated in vitro and in vivo for their toxicity and antioxidant activity based on liver function enzymes.Keywords: 2-aminothiazole; chalcone; imine; pyrazole; azo coupling; biological activities СИНТЕЗА НА НОВИ ДЕРИВАТИ НА 2-АМИНО-5-АРИЛТИАЗОЛ И НИВНА БИОЛОШКА АКТИВНОСТ: ПРОЦЕНА НА НИВНАТА ТОКСИЧНОСТ И АНТИОКСИДАТИВНА ЕНЗИМСКА АКТИВНОСТИзвршено е испитување како на аминогрупата така и на арилсупституентот на ново синтетизирано соедиенние на 2-амино-5-(4-ацетилфенилазо)-тиазол и неговите деривати преку разни електрофилни реагенси за да се добијат нови биоактивни халконски, имински и пиразолти-азолидински деривати. Синтетизираните соединенија беа идентификувани преку аналитички и спектрални методи, а потоа беа и биолошки евалуирани in vitro и in vivo за нивната токсичност и антиоксидативна активност преку ензими од црниот дроб.

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“…2-A minothiazo les are known main ly as biologically active co mpounds with a broad range of activity and as intermed iates in the synthesis of antibiotics and dyes [2]. Several papers have been published on the use of these compounds as antimicrobial [3], antifungal [4], anti-inflammatory activity [5], anesthetic [6] and antiviral drugs [7]. 2-A minothiazoles and their derivatives are also used in the syntheses of various types of dyes [8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New 5-Arylazothiazole Derivatives as Disperse Dyes for Dyeing Polyester Fibers

Khalifa¹,

Abdel‐Latif²,

Amer³

et al. 2013

TEXTILE

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A series of 5-arylazo-2-(arylidenehydrazino)-2-th iazo lin -4-one dyes 3 and 4 was prepared by cyclocondensation of hydrazonoyl bro mides 2 with various thiosemicarbazone derivatives 1. While the synthesis of 3-amino-N-(5-aryla zo-2-thiazo lyl)-thieno[2,3-b]pyrid ine-2-carbo xamide dyes 8 was achieved by the reaction of 2-(N-chloroacetyl)-5-ary lazo -thiazo le derivatives 5 with 4,6-dimethyl-2-mercaptonicotinonitrile fo llowed by heterocyclizat ion of the obtained sulfide derivatives 7 in a solution of ethanol containing sodium etho xide. These dyes were applied as disperse dyes for dyeing polyester fibers and their characteristics and fastness properties have been measured. The dyed fibers exh ibit very good to excellent washing, perspiration and sublimat ion fastness properties, with little variation in good to excellent rubbing and light fastness.

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ChemInform Abstract: ANTIVIRAL DRUGS. XVIII. 2‐AMINOTHIAZOLES BY CLEAVAGE OF THE S‐S BOND OF DISULFIDODICARBAMIDINE

Abstract: Die Reaktion der β‐Diketone (I) mit Disulfidocarbamidin (II) führt zu den Aminothiazolen (III).

Cited by 4 publications

References 1 publication

Potent s-cis-Locked Bithiazole Correctors of ΔF508 Cystic Fibrosis Transmembrane Conductance Regulator Cellular Processing for Cystic Fibrosis Therapy

Potent s-cis-Locked Bithiazole Correctors of ΔF508 Cystic Fibrosis Transmembrane Conductance Regulator Cellular Processing for Cystic Fibrosis Therapy

Synthesis of novel 2-amino-5-arylazothiazol derivatives and their biological impacts: Assessment of toxicity and antioxidant enzymes activities

Synthesis of Some New 5-Arylazothiazole Derivatives as Disperse Dyes for Dyeing Polyester Fibers

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