Design, synthesis and pharmacological studies of some new quinoline Schiff bases and 2,5-(disubstituted-[1,3,4])-oxadiazoles

Bharadwaj, Swaminath; Poojary, Boja; Kumar, Shankar; Byrappa, K.; Nagananda, G.S.; Chaitanya, A. Krishna; Zaveri, Kunal; Yarla, Nagendra Sastry; Shiralgi, Yallappa; Kudva, Avinash K.; Dhananjaya, Bhadrapura Lakkappa

doi:10.1039/c6nj03913h

Cited by 13 publications

(15 citation statements)

References 63 publications

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“…Without further purification, the intermediate 3 (10 mmol) reacted directly with bromide (11 mmol) in ethanol (15 mL) to give the intermediate for 4-amino-1,2,4-triazole derivative 4 in 85–95% yields. According to the reported procedure, , the intermediate 4 (10 mmol) underwent an aldimine condensation reaction with aromatic aldehyde (11 mmol) in acetic acid (5 mL) to give the target compounds 5aa – 5bj in 60–80% yields. The CN double bond is in the E configuration. , …”

Section: Results and Discussionmentioning

confidence: 99%

“…For example, thioether-containing pyrithiobac is a powerful herbicide used in cotton fields with excellent selectivity . In addition, heterocyclic Schiff bases are known to possess a wide range of biological activities, , such as herbicidal (Figure ), − antibacterial, and antifungal activities. Schiff bases are ideal for the development of green pesticides as a result of their environmental compatibility .…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, and Herbicidal Activity of Thioether Containing 1,2,4-Triazole Schiff Bases as Transketolase Inhibitors

Wang

Yang

Huo

et al. 2021

J. Agric. Food Chem.

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Transketolase (TK) represents a potential target for novel herbicide development. To discover novel TK inhibitors with potency against resistant weeds, 36 thioether compounds containing 1,2,4-triazole Schiff bases were designed and synthesized for herbicidal activity evaluation. The results demonstrated that compounds 5av and 5aw provided excellent weed control with inhibition of over 90% against the tested weeds, even at concentrations as low as 100 mg/L in vitro. In addition, compounds 5av and 5aw exhibited higher postemergence herbicidal activity than all of the positive controls against the tested weeds at 50−90 g [active ingredient (ai)]/ha in a greenhouse, while being safe for crops of maize and wheat at 90 g (ai)/ha. Fluorescent binding experiments of At TK indicated that compounds 5av and 5aw had strong TK inhibitory activity and could tightly bind with the enzyme At TK. Also, molecular docking analyses revealed that the structures of compounds 5av and 5aw were suitable for TK inhibitory activity. Taken together, these results suggested that compounds 5av and 5aw were promising herbicide candidates for weed control in wheat and maize fields targeting TK.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Herbicidal Activity of Thioether Containing 1,2,4-Triazole Schiff Bases as Transketolase Inhibitors

Wang

Yang

Huo

et al. 2021

J. Agric. Food Chem.

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“…All the studied compounds were synthesized by using the same procedure and characterized by spectroscopic analysis. 66 , 67 The solid-state properties of the target compounds are listed in Supporting Information Table S1.…”

Section: Resultsmentioning

confidence: 99%

Efficient Synthesis and in Silico Studies of the Benzimidazole Hybrid Scaffold with the Quinolinyloxadiazole Skeleton with Potential α-Glucosidase Inhibitory, Anticoagulant, and Antiplatelet Activities for Type-II Diabetes Mellitus Management and Treating Thrombotic Disorders

et al. 2018

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The current study evaluates antidiabetic, anticoagulant, and antiplatelet activity of novel benzimidazole-containing quinolinyl oxadiazoles. These derivatives are synthesized and characterized using spectroscopy (FT-IR, 1H NMR, and mass spectroscopy) and single-crystal X-ray diffraction methods. The inhibitory effects of these compounds were evaluated by the α-glucosidase inhibitory assay and shows the activity in the range of IC50 = 0.66 ± 0.05 to 3.79 ± 0.46 μg/mL. In addition, molecular docking studies revealed that benzimidazole-containing quinolinyl oxadiazoles can correctly dock into the target receptor protein of the human intestinal α-glucosidase, while their bioavailability/drug-likeness was predicted to be acceptable but requires further optimization. On the other hand, compound 8a and 8d showed anticoagulant activity as they enhanced the clotting time from control 180–410 and 180–390 s, respectively, in platelet rich plasma and 230–460 and 230–545 s in platelet poor plasma. Furthermore, only 8a showed antiplatelet activity by inhibiting epinephrine-induced platelet aggregation, and the observed aggregation inhibition was found to be 93.4%. Compounds 8a–f show nontoxic properties because of the non-hydrolyzing properties in the RBC cells. In addition, 8a and 8d show anti-edema and anti-hemorrhagic properties in the experimental mice. These findings reveal that benzimidazole-containing quinolinyl oxadiazoles act as α-glucosidase inhibitors to develop novel therapeutics for treating type-II diabetes mellitus and can act as lead molecules in drug discovery as potential antidiabetic and antithrombotic agents.

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“…Plates were taken out of the chamber when the solvent front hat reached 3/4 th of the plate and dry at room temperature Detection of Spots: Under UV chamber the developed TLC plates were placed and spots were observed. In-vitro Anti-Inflammatory Activity: [17][18][19][20][21][22] Albumin Denaturation Assay: The test compounds were prepared in different concentrations. From the test solution, 1 ml was taken and 1 ml of 1% aqueous solution of Egg albumin fraction was added and pH was adjusted to 6.8 by using glacial acetic acid.…”

Section: Chromatogram Developmentmentioning

confidence: 99%

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2020

IJPSR

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Quinolines bears a very good synthon so that a variety of novel heterocyclic with good pharmaceutical profile can be designed. There are various biological activities for quinolones such as antibacterial, antimalarial and various drugs possessing quinolone as nucleus are ciprofloxacin (Cipro), lomefloxacin (Maxaquin), norfloxacin (Noroxin), ofloxacin (Floxin), moxifloxacin (Avelox) and levofloxacin (Levaquin). So, in the present work 2chloro quinoline 3-carbaldehyde containing quinolines were synthesized by using solvent conservation techniques like reflux technique. Various quinolines derivatives were synthesized by the condensation reaction between dimethylformamide, PoCl 3, and different substituted aniline to give 2-chloro 3carbaldehyde (1a). The reaction of 2-chloro 3-carbaldehyde with metformin gives quinolines Schiff bases as final compound (2a-2d). The obtained product was purified and structures were confirmed by TLC, MP & IR spectroscopy. All the compounds were screened for in-vitro anti-inflammatory activity using diclofenac sodium as standard by using protein denaturation method. Further, the selected compounds also studied for anti-inflammatory activity by in-vitro methods and anti-oxidant activity by hydrogen peroxide methods. Some of the compounds have shown significant activities compared to standard.

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Design, synthesis and pharmacological studies of some new quinoline Schiff bases and 2,5-(disubstituted-[1,3,4])-oxadiazoles

Abstract: G6P-Ligand (4f) and (5b) interactions as visualized using Chimera (Version 1.8).

Cited by 13 publications

References 63 publications

Design, Synthesis, and Herbicidal Activity of Thioether Containing 1,2,4-Triazole Schiff Bases as Transketolase Inhibitors

Design, Synthesis, and Herbicidal Activity of Thioether Containing 1,2,4-Triazole Schiff Bases as Transketolase Inhibitors

Efficient Synthesis and in Silico Studies of the Benzimidazole Hybrid Scaffold with the Quinolinyloxadiazole Skeleton with Potential α-Glucosidase Inhibitory, Anticoagulant, and Antiplatelet Activities for Type-II Diabetes Mellitus Management and Treating Thrombotic Disorders

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