Naslov
Synthesis of Bis-substituted Amidinobenzothiazoles as Potential Anti-HIV Agents

Autori
Racane, Livio ; Tralić-Kulenović, Vesna ; Fišer-Jakić, Lelja ; Boykin, W. David ; Karminski-Zamola, Grace

Izvornik
Heterocycles (0385-5414) 55 (2001), 11; 2085-2098

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
amidines ; benzothiazoles ; furans ; thiophenes ; anti-HIV agents

Sažetak
Abstract Searching for new potencialy biologically active molecules we prepared a number of bis amidines (as free bases and dihydrochlorides). In multistep reactions the following dinitriles were obtained: 2-[4-(6-cyanobenzothiazol-2-yl)phenyl]-5-(6-cyanobenzothiazol-2-yl)furan 6a, 2-[4-(6-cyanobenzothiazol-2-yl)phenyl]-5-(6-cyanobenzothiazol-2-yl)thiophene 6b, 5-(4-cyanophenyl)-2-furancarbonitril 8, 2-(4-cyanophenyl)-5-(6-cyanobenzothiazol-2-yl)furan 12a, 2-(4-cyanophenyl)-5-(6-cyanobenzothiazol-2-yl)thiophene 12b, 2-[4-(6-cyanobenzothiazol-2-yl)phenyl]-5-furancarbonitril 18a , 2-[4-(6-cyanobenzothiazol-2-yl)phenyl]-5-thiophenecarbonitril 1, 4-bis-(6-cyanobenzothiazol-2-yl)benzene 24a, and 1, 4-bis-[2-(6-cyanobenzothiazol-2-yl)-1-ethenyl]benzene 24b. From this dinitriles via imidoylether dihydrochlorides (Pinner’s method) the corresponding substituted amidines were prepared: 5-[4-(imidazolin-2-yl)phenyl]-2-(imidazolin-2-yl)furan 9 , 2-[4-(imidazolin-2-yl)phenyl]-5-[6-imidazolin-2-yl)benzothiazol-2-yl]furan 13a, 2-[4-(imidazolin-2-yl)phenyl]-5-[6-imidazolin-2-yl)benzothiazol-2-yl]thiophene 13b, 2-[4-(N-isopropylamidino)phenyl]-5-[6-(N-isopropylamidino)benzothiazol-2-yl]furan dihydrochloride dihydrat 15a, 2-[4-(N-isopropylamidino)phenyl]-5-[6-(N-isopropylamidino)benzothiazol-2-yl]thiophene dihydrochloride dihydrat 15b, 2-{; ; 4-[6-(N-imidazolin-2-yl)benzothiazol-2-yl]phenyl}; ; -5-(imidazolin-2-yl)furan 19 and 2-{; ; 4-[6-( N-isopropylamidino)benzothiazol-2-yl]phenyl}; ; -5-(N-isopropylamidino) furan 21 The free bases 9, 13a, 13b, 19 and 21 were converted to corresponding water soluble dihydrochlorides: 5-[4- imidazolin-2-yl)phenyl]-2-(imidazolin-2-yl)furan dihydrochloride dihydrat 10, 2-[4-(imidazolin-2-yl)phenyl]-5-[6-imidazolin-2-yl)benzothiazol-2-yl]furan dihydrochloride dihydrat 14a, 2-[4-(imidazolin-2-yl)phenyl]-5-[6-imidazolin-2-yl)benzothiazol-2-yl]thiophene dihydrochloride dihydrat 14b, 2-{; ; 4-[6-(imidazolin-2-yl)benzothiazol-2-yl]phenyl}; ; -5-(imidazolin-2-yl)furan dihydrochloride dihydrat 20, and 2-{; ; 4-[6-( N-isopropylamidino)benzothiazol-2-yl]phenyl}; ; -5-(N-isopropylamidino) furan dihydrochloride dihydrat 22. The biological examination of compounds 10, 14a, 14b, 15a, 15b, 20 and 21 are in course.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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