Novel amalgamation of phthalazine–quinolines as biofilm inhibitors: One-pot synthesis, biological evaluation and in silico ADME prediction with favorable metabolic fate

Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs

“…50 Acetylation of aromatic amines 14a-m (dissolved in HCl) with acetic anhydride gave the corresponding substituted Nphenylacetamides 15a-m, which aer treatment with Vilsmeier's reagent afforded the substituted 2-chloro-3formylquinolines 16a-m following the methods reported by Meth-Cohn (Scheme 1). 5,49,[51][52][53][54][55][56] The better method for the synthesis of quinolines depending on the nature of the substituents in order to obtain the best yields. Aneesa et al, 57 have reported the effect of transition metal ions such as Cu(II), Ni(II), Co(II), and Cd(II) on the synthesis of quinolines through the Vilsmeier reagent with acetanilides 15.…”

“…Tetrazolo[1,5-a]quinoline-4-carbaldehydes 93a-f were prepared through reactions of 2-chloroquinoline-3-carbaldehydes 16 with sodium azide in acetic acid (Scheme 24). 55,75,76 Reduction of tetrazolo[1,5-a]quinoline-4-carbaldehyde (93a) with sodium borohydride in methanol yielded the corresponding alcohol 94 which aer methylation with methanesulfonyl chloride in dichloromethane containing catalytic triethylamine . The products 100a-r were obtained through a one-pot Ugiazide method, nucleophilic substitution and ring chain azidotautomerization.…”

Strategies and Approaches for Discovery of Small Molecule Disruptors of Biofilm Physiology

“…One major group of biofilm inhibitors, inspired by scaffolds found in natural products with reported activity, are a diverse range of heterocyclic containing families, which include indoles [ 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 ], 2-aminoimidazoles [ 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 ], phenazines [ 90 , 91 , 92 , 93 , 94 , 95 , 96 , 97 , 98 ], and quinolines [ 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 ]. These lead molecules are the results of significant medicinal chemistry effort to improve potency and other drug-like properties.…”

In‐house chemical library repurposing: A case example for Pseudomonas aeruginosa antibiofilm activity and quorum sensing inhibition

“…Recently, at 156 μM, benzimidazole was shown to inhibit S. aureus biofilm formation without bactericidal activity by binding to the biofilm proteins (Shrestha et al, 2016). Another One of the phthalazine-quinoline hybrids showed anti-biofilm activity at 30.0 μM and antimicrobial activity at 45.0 μg/mL (Zaheer, Khan, Sangshetti, Patil, & Lohar, 2016). Previously, many researcher's in the area of anti-biofilm drug discovery have shown that variety of derivatives of hydrazine carbothioamide can inhibit the growth of broad-spectrum microbes (Staphylococcus aureus, Escherichia coli, Proteus vulgaris, Pseudomonas sp, and Klebsiella pneumoniae) (Al-Amiery, Al-Majedy, Abdulreazak, & Abood, 2011).…”