Uma série de novos carbamatos de zidovudina (AZT, 1) foi sintetizada, caracterizada e avaliada em relação a sua atividade anti-HIV e citotoxicidade. O grupo hidroxila da posição 5' do AZT foi derivatizado usando-se N, N'-carbonildiimidazol e diferentes aminas para gerar os respectivos 5'-O-carbamatos. Além disso, dois derivados já conhecidos foram sintetizados, um 5'-O-tosilato e um derivado tricíclico (AZT-Cycl), empregando-se métodos mais rápidos e simples do que os previamente reportados. Embora os novos derivados tenham apresentado menor toxicidade do que o AZT, essa redução na citotoxicidade foi concomitante com a marcada diminuição para inibir a replicação do vírus, com exceção do AZT-Cycl, o qual, mesmo apresentando IC 50 = 1 µmol L -1 , não demonstrou sinais de citotoxicidade com valores de CCID 50 (µmol L -1 ) > 1000.A series of zidovudine (AZT, 1) derivatives have been synthesized and their anti-HIV activity and cytotoxicity have been determined. The 5'-OH function of AZT was derivatized using N, N'-carbonyldiimidazole and different amine compounds leading to their 5'-O-carbamates. In addition, two known AZT derivatives 5'-O-tosylate and a tricyclic one (AZT-Cycl) were also obtained by a simpler procedure than those previously reported. Although these AZT derivatives were less toxic than AZT, their reduced cytotoxicity was concomitant with an inability to inhibit HIV-1 replication, except in the case of AZT-Cycl, which showed an IC 50 = 1 µmol L -1 without cytotoxicity with values of CCID 50 (µmol L -1 ) > 1000.
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