Synthesis and antiviral activity of 4-quinolinecarboxylic acid hydrazides

Abstract

Antiviral agents were sought by using ethyl esters of 2-R-4-quinolinecarboxylic acids to synthesize the corresponding aryl (heteryl) hydrazides. 2-Methyl-4-quinolinecarboxylic acid hydrazide was used to synthesize vinylogs containing a nitro group in the substituent. The resulting compounds were tested for antiviral activity against ECHO virus type 6. 571 0091-150X/08/4210-0571

Synthesis of Optically Active 2H‐Thiopyrano[2,3‐b]quinolines with Three Contiguous Stereocenters via an Organocatalytic Asymmetric Tandem Michael–Henry Reaction

“…The quinoline scaffold is prevalent in a variety of pharmacologically active synthetic and natural compounds 1. Over the past two decades, functionalized quinolines and benzo‐/hetero‐fused quinolines have attracted much attention due to their considerable biological and pharmacological activities, such as use as antimalarial,2 antiasthmatic,3 antibacterial,4 antiviral,5 anti‐inflammatory,6 antitumor agents,7 potential HIV‐integrase inhibitors,8 and as potent melanin‐concentrating hormone 1 receptor (MCH1R) antagonists 9. Among them, 2 H ‐thiopyrano[2,3‐ b ]quinolines are tricyclic ring systems containing a thiopyran moiety condensed with a quinoline nucleus, and are currently found to be associated with some interesting bioactivities.…”

Synthesis and Antibacterial, Antioxidant, and Molecular Docking Analysis of Some Novel Quinoline Derivatives

“…Besides fluoroquinolone-based drugs, 2-chloroquinoline-3-carbaldehyde derivatives have also attracted much attention due to their considerable biological and pharmacological activities including antimicrobial [8], anti-inflammatory [11][12][13], antimalarial [14,15], anticancer [16], antiviral [17,18], and antifungal activities [19,20]. Inspired by these reports, we have designed and synthesized various quinoline-3-carbaldehyde derivatives and evaluated their antibacterial and radical scavenging activities.…”

Enantioselective Organocatalytic Domino Michael/Aldol Reactions: An Efficient Procedure for the Stereocontrolled Construction of 2H‐Thiopyrano[2,3‐b]quinoline Scaffolds

“…The experimental results, as listed in Table 4, revealed that the electronic nature and the substitution pattern of 2-mercaptoquinoline-3-carbaldehyde (1) had minimal impact on the efficiency and enantioselectivity of the Michael/aldol reaction ( Table 4, entries [1][2][3][4][5][6][7][8][9][10][11][12]. The experimental results, as listed in Table 4, revealed that the electronic nature and the substitution pattern of 2-mercaptoquinoline-3-carbaldehyde (1) had minimal impact on the efficiency and enantioselectivity of the Michael/aldol reaction ( Table 4, entries [1][2][3][4][5][6][7][8][9][10][11][12].…”

“…Compounds that possess these types of ring systems have demonstrated interesting bioactivities. [10] Therefore, it is not surprising that many methods have been developed for their synthesis, for A survey of nine acidic co-catalysts revealed that they play a definite role in governing the reaction yields and enantioselectivities (Table 2, entries [1][2][3][4][5][6][7][8][9]. The use of trifluoroacetic acid as a co-catalyst resulted in a very sluggish reaction, which may be attributed to its strong acidity (Table 2, entry 2).…”

“…To further demonstrate the scope of this organocatalytic cascade Michael/Henry reaction, a range of 2-mercaptoquinoline-3-carbaldehydes (1) were evaluated in the reactions with (E)-4-methylpent-2-enal (2 k) and trans-cinnamaldehyde (2 a) under the optimal reaction conditions. The experimental results, as listed in Table 4, revealed that the electronic nature and the substitution pattern of 2-mercaptoquinoline-3-carbaldehyde (1) had minimal impact on the efficiency and enantioselectivity of the Michael/aldol reaction ( Table 4, entries [1][2][3][4][5][6][7][8][9][10][11][12]. In each case, either with (E)-4-methylpent-2-enal (2 k; Table 4, entries 1-7) or trans-cinnamaldehyde (2 a; Table 4, entries [8][9][10][11][12] as the reaction partner, the reaction proceeds smoothly to generate the corresponding 2H-thiopyranoA C H T U N G T R E N N U N G [2,3-b]quinoline derivatives in high yields (83-98 %) and with excellent enantiomeric excesses (90-98 %).…”