Synthesis, spectral analysis, antibacterial and antifungal activities of some 4,6-diaryl-4,5-dihydro-3-hydroxy-2[H]-indazole—a novel fused indazole derivative

Abstract

A novel class of 4,6-diaryl-4,5-dihydro-3-hydroxy-2[H]-indazoles 25-32 were synthesized and evaluated for their in vitro antibacterial and antifungal activities. Four Compounds, which all possessed electron withdrawing functional groups (ZCl, ZNO 2 , ZBr) 27, 28, 30 and 32 were more potent against the tested bacterial/fungal strains than the standard bacterial and fungal drugs ciprofloxacin and fluconazole respectively.

Synthesis, spectral characterization, and in vitro antibacterial and antifungal activities of novel 1,3-thiazine-2-amines comprising morpholine nucleus

“…(E)-1-(4-Morpholinophenyl)-3-aryl-prop-2-en-1-ones (11)(12)(13)(14)(15)(16)(17)(18)(19) were synthesized by the Claisen-Schmidt condensation of 1-(4-morpholinophenyl) ethanone and substituted benzaldehydes in the presence of alcoholic sodium hydroxide. Treatment of (E)-1-(4-morpholinophenyl)-3-aryl-prop-2-en-1-ones (11)(12)(13)(14)(15)(16)(17)(18)(19) with thiourea in the presence of potassium hydroxide in refluxing ethanol (Scheme 2, Table 1) afforded the respective target molecules (20)(21)(22)(23)(24)(25)(26)(27)(28). The structures of these compounds were confirmed by melting points, FT-IR, MS, 1 H NMR, and 13 C NMR spectral studies, and elemental analysis.…”

“…Table 1. Physical and analytical data of (E)-1-4-morpholinophenyl)-3-aryl-prop-2-en-1-ones (11-19) and 4-(4-morpholinophenyl)-6-aryl-6H-1,3-thiazin-2-amines (20)(21)(22)(23)(24)(25)(26)(27)(28) Compound 20, which has no substitution at the para position of the phenyl rings attached to C-4 and C-6 carbons of the pyrimidine moiety, exerted two-fold increased activity at a MIC value of 12.5 μg/mL against E. coli, and showed moderate activity against all other tested bacterial strains. Compound 21, with electron-donating methyl substitution at the para position of the phenyl rings attached to C-4 and C-6 carbons of the pyrimidine moiety, showed four-fold increased activity against P. aeruginosa at a MIC value of 6.25 μg/mL, and showed moderate activity against all other tested bacterial strains with a varied range of 100-25 μg/mL.…”

“…The respective test compounds (20)(21)(22)(23)(24)(25)(26)(27)(28) were dissolved in DMSO to obtain 1 mg/mL stock solution. Seeded broth (broth containing microbial spores) was prepared in nutrient broth (NB) from 24-h-old bacterial cultures on nutrient agar (HiMedia, Mumbai) at 37 ± 1°C, while fungal spores from 1-to 7-dayold Sabouraud agar (HiMedia, Mumbai) slant cultures were suspended in Sabouraud dextrose broth (SDB).…”

“…As part of our research program aimed at the synthesis of structurally diverse nitrogen/sulfur and selenium containing heterocycles [24][25][26][27][28][29] comprising piperidino 1,2,3-selenadiazoles, 1,2,3-thiadiazoles, 1,2,4-triazolidine-3-thiones, diazepans, 1,2,4,5-tetrazinan-3-thiones, and indazoles, we performed the synthesis of 4-(4-morpholinophenyl)-6-aryl-2H-1,3-thiazine-2-amines (20)(21)(22)(23)(24)(25)(26)(27)(28) from (E)-1-(4-morpholinophenyl)-3-aryl-prop-2-en-1-ones (11)(12)(13)(14)(15)(16)(17)(18)(19) and evaluated their in vitro antibacterial and antifungal activities.…”

Activated fly ash catalyzed facile synthesis of novel spiro imidazolidine derivatives as potential antibacterial and antifungal agents

“…The present study describes the use of 6-carbethoxy-3,5-diarylcyclohex-2-enone 23 as a key intermediate with three versative functional groups i.e., ketone, olefin, and ester for the synthesis of imidazolidine derivatives. Owing to our interest in synthesis of fascinating biologically active hybrid heterocyclic compounds [24][25][26] and as part of our research program, herein we planned to design a spiro imidazolidine derivatives bearing a cyclohexene substituent on the carbon between the nitrogen centers to give a new series of spiro imidazolidine heterocycles because most bio-active imidazolidine derivatives bear a substituent (aryl or alkyl group) on the carbon between the nitrogen centers [18][19][20][21] .…”