Benzothiazoles 2-amino

Hutchinson, I., S. A. Jennings, B. R. Vishnuvajjala, A. D. VNfestwell, and M. F. G Stevens. 2002. Antitumor ben-zothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugsd. Med. Chem45 744-747. 

Benzacridines, amino-, 408 Benzoic acids, o-(2-thenoyl)-, 66, 67 Benzol rlindolizines, 157-159 Benzopirridines, adduct with dimethyl acetylenedicarbo late, 144 Benzoquinoline, amino-, 408 Benzo[ ]quinol-4-one, 350 Benzo-l,2,4-thiadiazine 1,1-dioxides, 387 Benzothiazoles, amino-, 334 Benzo-l,2,4-triazin-3-one, 388 2,2 -Bithienyl, 56, 69, 74, 110, 118, 119 2,3 -Bithienyl, 56, 74 3,3 -Bithienyl, 23, 42, 75... 

Benzothiazole, 2-amino-6-thiocyanato-azo dyes from, 1, 328 Benzothiazole, 2-aryl-synthesis, 6, 321 Benzothiazole, 2-arylamino-synthesis, 6, 323 Benzothiazole, 2-aryloxy-Fries rearrangement, 6, 289 Benzothiazole, 2-benzyl-picrate, 6, 252 Benzothiazole, 2-chloro-dyes from, 1, 321-322 synthesis, 6, 323 Benzothiazole, 2,3-dihydro-oxidation, 6, 272 Benzothiazole, 2-dimethylamino-synthesis, 5, 128... 

The relative ease of preparation of condensed thiazole derivatives is a consequence of facile thiazole ring closure, and therefore also benzothiazole amines with an amino group on the benzene ring (except for the weakly regioselective nitration of benzothiazoles) are very easily accessible and useful substrates for the Gould-Jacobs reaction. 

Unlike the products of condensation of 1,2-diaminoethane and 1-amino-2-hydroxyethane with aminobutynones, which exist almost exclusively in the enole form, benzoxazoles 359,361 and benzothiazoles 360,362 are present in the solution as a tautomeric mixture of the ketone (359, 360) and enole (361,362) forms. This seems to be related to weakening of the imine nitrogen basicity due to adjacent oxygen and sulfur atoms. 

An interesting rearrangement was found by Davies and Kirby (1967) in the diazo-tization of 7-amino-benzothiazole (6.68). As Scheme 6-45 shows, the diazonium ion formed initially rearranges under hydrolytic conditions into 7-amino-l,2,3-benzo-thiadiazole (6.69). 

Nitro-l-thiocyanato-benzol liefert bei der Elektrolyse an Quecksilber-Kathoden (in 0,5 nHCl) bis 88% d. Th. 2-Amino-1,3-benzothiazol-3-oxidl. An Blei-Kathoden wird als Hauptprodukt 2-Amino-l, 3-benzthiazol neben 2-Amino-thiophenol1 2, an Kupfer-Ka-thoden ausschlicBlich 3-Amino-4-thiocyanato-phenol gebildet. 

A recent patent application from Roche [352] described a 2-amino-benzothiazole series. Roche claimed that compound (605) exhibited an IC50 value of 0.73 uM at CBi, and showed in excess of 10-fold selectivity over the CB2 receptor. The compounds were described as being of potential use in the treatment of a range of diseases, including CNS and psychiatric disorders, type-2 diabetes, gastrointestinal diseases, cardiovascular disorders, infertility disorders, inflammation, cancer, atherosclerosis, cerebral vascular incidents and cranial trauma. 

Heterocyclic amino compounds including, for instance, 2-aminothiazoles or 2-amino-benzothiazoles, which contain a nitrogen in the ring capable of forming tautomeric structures, yielded the corresponding amides, although in general in lower than usual yield 11381... 

Benzonitrile, 2,6-dimethoxy-, 22, 35 Benzophenone, 23, 99 Benzophenone azine, 24, 55 Benzophenone hydrazone, 24, 54 Benzopyrrole, 23, 42 Benzothiazole, I-amino-5-methyl-,... 

Fig. 12.2. Comparison of ATP-dependent transport activity between rats and humans determined in isolated bile canalicular membrane vesicles. Key 1, SN-38 glucuronide (carboxylate) 2, SN-38 glucuronide (lactone) 3, E3040 (6-hydroxy-5,7-dimethyl-2-methyl-amino-4-(3-pyridylmethyl) benzothiazole) glucuronide 4, 170 estradiol-170-D-glucuro-nide 5, grepafloxacin glucuronide 6, leuko-...

A wide variety of different classes of fluorescent molecules has been investigated in the peroxyoxalate chemiluminescent systems. Among those screened were fluorescent dyes such as rhodamines and fluoresceins, heterocyclic compounds such as benzoxazoles and benzothiazoles, and a number of polycyclic aromatic hydrocarbons such as anthracenes, tetracenes, and perylenes. The polycyclic aromatic hydrocarbons and some of their amino derivatives appear to be the best acceptors as they combine high fluorescence efficiency with high excitation efficiency in the chemiluminescent reaction [28],... 

Treatment of l- 6-[(/>-nitrophenyl)thio]-benzothiazol-2-yl thiourea 298 with bromine in chloroform yields 2-amino-7-[(/>-nitrophenyl)thio][l,2,4]thiadiazolo[3,2-/)]benzothiazolium bromide 299 (Equation 44) <2002MI15>. 

Kriplani et al. <2005HC0527> published that Schiff bases formed from 2-amino-benzothiazoles 228 easily undergo ring closure to fused triazine-thiones 229 when treated with ammonium thiocyanate in dioxane under heating. The products were obtained in medium to good yields (49-70%). 

The starting benzothiazole carboxylic ester 387 was subjected to a Anamination by using mesityl hydroxylamine to give an A -amino salt 388, which was treated with a tertiary amine to give the deprotonated intermediate 389. This species when reacted with phenylisocyanate yielded the final product 390 in moderate yield <2001JOC8528>. 

Aminoimidazo[2,l-b]benzothiazoles 8-Aminothiazolo[3,4,5-[Pg.364]

The condensation of 5-chloro-2-amino-benzothiazoles and -benzoxazoles with a-bromoketones, PhCOCH(Br)R (R = H, Me, Et, 4-C6H4S02Me), produces a range of fused heterocyclesthe mechanisms involved have been investigated by isotopic labelling. 

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