Synthesis and antimicrobial evaluation of novel 4-amino-6-(1,3,4-oxadiazolo/1,3,4-thiadiazolo)-pyrimidine derivatives.
A series of novel 4-amino-6-(1,3,4-oxadiazolo/1,3,4-thiadiazolo)-pyrimidine derivatives of biological interest were prepared by sequential amination, hydrazide formation, and hydrazine carbothioamidination followed by cyclization. All the synthesized compounds (6a-6h and 7a-7f) were screened for antibacterial and antifungal activity. From this group, compound 7f (MIC (μg/mL μg/mL )/Inhibition (mm): 6.25/23-30) showed good antibacterial and antifungal activity. Reagents and conditions: (a) Ethyl acetoacetate, 60% NaH, 1,4-dioxane, 60°C, 6 h; (b) DIPEA, 1,4-dioxane, 100°C, 14 h; (c) NH2NH2 ⋅ H2O, EtOH, reflux, 14 h; (d) Tolyl isothiocyanatobenzene, DMF, RT, 2 h; (e) (if X = O) EDC⋅ HCl, TEA, DMF, RT, 14 h; (f) (if X = S) Conc. H2O4, RT, 14h.
Department of Chemistry, Srinivas School of Engineering, Mukka, Mangalore, 574146, India.
Poornima
P
Shetty
Department of Chemistry, Srinivas School of Engineering, Mukka, Mangalore, 574146, India. bm.praveen@yahoo.co.in.
B M
BM
Praveen
Department of Chemistry, Government Pre-University College, Kanasawadi, Doddaballapura taluk, Bangalore-Rural, Karnataka, India.
M
M
Raghavendra
Department of Chemistry, Nagarjuna College of Engineering & Technology, Devanahalli taluk, Bangalore, 562 110, India.
K
K
Manjunath
Department of Chemistry, Srinivas School of Engineering, Mukka, Mangalore, 574146, India.
Srinivas
S
Cheruku
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D011743:Pyrimidines; C030986:pyrimidine
1, 3, 4-Oxadiazole; 1, 3, 4-Thiadiazole; Antibacterial; Antifungal; Pyrimidine; Thiosemicarbazide