New urea and thiourea derivatives of piperazine doped with febuxostat: synthesis and evaluation of anti-TMV and antimicrobial activities.
A series of new 4-(5-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-2-carbonyl)-N-(substituted phenyl)piperazine-1-carboxamides 8(a-e)/carbothioamides 8(f-j) were accomplished for biological interest by the simple addition of active functionalized arylisocyanates 7(a-e)/arylisothiocyanates 7(f-j) with 2-isobutoxy-5-(4-methyl-2-(piperazine-1-carbonyl)thiazol-5-yl)benzonitrile (4). Compound 4 was synthesized in high yields (94%) by the condensation reaction of febuxostat (1) with piperazine using a selective reagent such as propylphosphonic anhydride (T3P). Antiviral activity against Tobacco mosaic virus (TMV) and antimicrobial activity of the synthesized compounds were evaluated. Biological data revealed that 4-nitrophenyl substituted urea 8d, and 3-bromophenyl substituted thiourea 8f exhibited promising antiviral activities. Moreover, 4-fluorophenyl substituted urea 8a, 4-nitrophenyl substituted urea 8d, 3-bromophenyl substituted thiourea 8f, and 2,4-dichlorophenyl substituted thiourea 8j exhibited potent antimicrobial activity.
Department of Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh-517 502, India.
Reddivari Chenna
RC
Krishna Reddy
Department of Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh-517 502, India.
Syed
S
Rasheed
Department of Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh-517 502, India.
Devineni
D
Subba Rao
Department of Biochemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh-517 502, India.
Shaik
S
Adam
Department of Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh-517 502, India.
Yellala
Y
Venkata Rami Reddy
Department of Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh-517 502, India.
Chamarthi Naga
CN
Raju
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D018407:Bacterial Physiological Phenomena / Q000187:drug effects*; D000069465:Febuxostat; D000077489:Piperazine; D010879:Piperazines / Q000138:chemical synthesis* / Q000494:pharmacology*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D013890:Thiourea / Q000031:analogs & derivatives; D014027:Tobacco Mosaic Virus / Q000187:drug effects* / Q000502:physiology*; D014508:Urea / Q000031:analogs & derivatives
D000890:Anti-Infective Agents; D000998:Antiviral Agents; D010879:Piperazines; D013844:Thiazoles; D000069465:Febuxostat; D000077489:Piperazine; D014508:Urea; D013890:Thiourea