Thiazole 2-dimethylamino

Thiazole, 2-cyano-4,6-dinitrobenzene-l,5 -azo-2 -dimethylamino-4 -phenyl-visible, 1, 343 (78C323)... 

Dimethylamino-phenylazo)-3-methyl-2,3-dihydro-1,3-henzo thiazol... 

A (3-lactam ring substituted by a thiazole moiety has been reported to be formed simultaneously and under mild condition during the course of a multicomponent reaction [200]. When the 3-dimethylamino-2-isocyanoacrylate was reacted with the aldehyde in the presence of a (3-aminothiocarboxylic acid, substituted l-thiazole-2-yl-methyl-azetidin-2-one was smoothly formed (Scheme 92). Plausible reaction intermediates have been proposed. 

The reaction of 2-(phenylamino)- and 2-(dimethylamino)-thiazoles (38) with DMAD produced dimethyl 6-(phenylamino)- and 6-(dimethylamino)-3,4-pyridinedicarboxyl-ates exclusively. The intermediate 2 + 2-cycloadduct (39) undergoes ring opening, 6jr-electrocyclization with the extrusion of sulfur to produce the final pyridine derivatives (40) (Scheme ll).38... 

Aminothiocarboxylic acids react with aldehydes and 3-dimethylamino-2-isocyanoacrylic acid methyl ester following the pathway described for /7-aminoacids, affording, after ring contraction of the seven-membered intermediate 87, Michael-type cyclization and /7-elimination, /7-lactam 88 equipped with a thiazole... 

Most compounds within this group are partially saturated and are dealt with in that section. Azine approach. In the reaction between ethyl bromo(pyridin-2-yl)acetate (435) and tetramethylthiourea the first formed tetramethylthiouronium salt is cyclized to the thiazole (436). The 3-dimethylamino group is readily hydrolyzed yielding the corresponding lactam... 

A novel multicomponent reaction of (3-aminothiocarboxylic acids, aldehydes, and 3-dimethylamino-2-isocyanoacrylates, which involves a remarkable increase in molecular complexity, has been used for the preparation of substituted l-thiazol-2-ylmethyl-2-azetidinones 12 <02TL6897>. 

Dimethylamino-pyrrolidin-1 -yl)-[2-(7 -methyl-1H-indazol-3-yl)-5-(6-methyl-pyridin-3-yl)-thiazol-4-yl]-methanone 1 H Vs >"CN °... 

Different activity of 5-[2-(dimethylamino)ethyl]-9-phenyl-47/-benzo[,y) ]thiazolo[5,4-g]isoquinoline-4,6(5/f)-dione derivatives as photonucleases may arise from the impact of substituents on the 2-phenyl ring of thiazole on the electron population of the excited triple state according to AMI semi-empirical calculations <2004TL1247>. 

A new family of photonucleases, 5-[2-(dimethylamino)ethyl]-9-phenyl-4//-benzo[rA]thiazolo[5,4-g]isoquinoline-4,6(57/)-dione derivatives, 544, was synthesized and evaluated. These compounds intercalated into DNA efficiently and damaged DNA photochemically at concentrations as low as 5pM. Mechanistic studies suggested that a novel naphthalimide-thiazole radical produced via an excited triple state might be involved in the DNA photodamage <2004TL1247>. 

Nitrosation of 2-(dimethylamino)thiazoles under acid conditions gives 5-nitroso-derivatives... 

In a similar way, the dipeptide (449) reacts with the thiazole amino acid (450) in the presence of benzotriazol-l-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) to give the corresponding tripeptide (451) (Equation (93)) <92CLI005>. 

Fig. 13. Chemical structures for allosteric and ATP-competitive Eg5 inhibitors, (a) Monastrol ((S)-ethyl 1,2,3,4-tetrahydro-4-(3-hydroxyphenyl)-6-methyl-2-thioxopyrimidine-5-carboxylate), the first compound discovered which bound to the allosteric pocket the compound has an IC50 of 22 uM. (b) CK-f 06023 (N-((R)-f-(3-benzyl-7-chloro-3,4-dihydro-4-oxoquinazolin-2-yl)propyl)-4-bromo-N-(3-(dimethylamino)propyl) benzamide), which binds to the same allosteric pocket as Monastrol and has a Ki of f 2 nM. (c) CK-238273 N-(3-aminopropyl)-N-((R)-f -(3-benzyl-7-chloro-3,4-dihydro-4-oxoquinazolin-2-yl)-2-methylpropyl)-4-methylbenzamide), an optimized analog of CK-f 06023 which is in phase II and has a Ki of f. 7 nM. (d) 4-(2-(f -phenylethyl)thiazol-4-yl)pyridine, an ATP-competitive thiazole compound which was an initial hit from the Merck compound collection the compound has an IC50 of f f uM. (e) 4-(2-(f -(4-chlorophenyl)cyclo-propyl)thiazol-4-yl)pyridine, an optimized ATP-competitive thiazole compound with an IC50 of 290 nM.

Zur Herstellung von 2-Amino-5-nitro-l,3-thiazol (83% Schmp. 198°) wird Thioharnstoff mit l-Brom-2-dimethylamino-l-nitro-ethen umgesetzt625. 

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