Synthesis of 3-Nitrosoimidazo[1,2-a]pyridine Derivatives as Potential Antiretroviral Agents

Abstract

Ten 2‐aryl or heteroaryl‐3‐nitrosoimidazo[1,2‐a]pyridine derivatives were synthesised as potential antiretroviral agents. The new compounds were characterized by elemental analysis, 1H NMR, and by crystallography for (14). The compounds were devoid of any activity against HIV‐1 or HIV‐2.

4′-Methyl-3-(4-nitrophenyl)-4-phenyl-4,5,1′,2′,3′,4′-hexahydrospiro[isoxazole-5,2′-naphthalen]-1′-one

“…For the crystal structure of a very similar compound, 3-(4chlorophenyl)-4-(4-phenyl-3 0 ,4 0 -dihydro-1 0 H,4H-spiro[isoxazole-5,2 0 -naphthalen]-1 0 -one, see: Subbiah Pandi et al (2001). For related literature, see: Anaflous et al (2004); Arnold et al (1947); Bakavoli et al (2005); Chaouni-Benabdallah et al (2001); Chenera et al (1993); Debaerdemaeker et al (1977); Ellis (1997); Howe & Shelton (1990); Katritzky et al (2003); Kerbal et al (1990); Kooijman et al (1984); Seifert et al (1976); Smietana et al (1999).…”

4′-(4-Methoxyphenyl)-3′-phenylspiro[1H-isothiachroman-3,5′-isoxazolidin]-4(2H)-one

“…Many 4-chromanone derivatives are versatile intermediates for the synthesis of natural products such as brazillin, hematoxylin, ripariochromene, clausenin, calonlide A and inophyllum B (Kooijman et al, 1984;Chenera et al, 1993). Chromanone heterocycles have also attracted much attention owing to their important pharmacological properties (Chaouni-Benabdallah et al, 2001). Their high synthetic utility and pharmacological importance have prompted us to synthesize some biologically active spiroisoxazoline derivatives, one of which is the title compound, (I).…”

A Simple One‐Pot Synthesis of Fully Substituted 1H‐Pyridone[1,2‐a]‐Fused‐1,3‐Diazaheterocycles

“…The pyrido[1,2‐ a ]pyrimidines and imidazo[1,2‐ a ]pyridines nucleuses show a wide range of biological and medicinal activities and use as valuable building blocks for further synthetic transformations . For example, these scaffolds show antiviral , anti‐tumoral , anti‐inflammatory , antibacterial , anti‐ulcer , antifungal , antiprotozoal , and antiretroviral activities. Although a diversity of methodologies and protocols has been reported by a number of pharmaceutical or synthetic chemists , but the importance of these heterocycles led to the development of numerous methods for their preparation .…”