Synthesis and antioxidant assay of new nicotinonitrile analogues clubbed thiazole, pyrazole and/or pyridine ring systems

Abumelha, Hana M.

doi:10.1002/jhet.3820

Cited by 14 publications

(10 citation statements)

References 39 publications

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“…[38] The most potent 7), were prepared starting from nicotinonitrile in a multistep reaction and were evaluated as antioxidant agents. [53] The free radical used in the study was 2,2'-Azino-Bis(3-ethyl-benzoThiazoline-6-Sulfonic acid) (ABTS), compound 93 was the most potent among other compounds reported in the same study, with 86 percent scavenging activity (See Table 3). Next compound with very close results was 94 with 84.9 % efficiency in comparison to the standard, Ascorbic acid, 88 %.…”

Section: Antioxidant Potentialsmentioning

confidence: 97%

Pyridine Derivatives as Biologically Active Precursors; Organics and Selected Coordination Complexes

Khan

2021

ChemistrySelect

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Pyridine (py) is an important heterocyclic compound and is an integral part of various natural products. There are various medicines containing py ring system being available in the market to combat different human ailments. Observing the medicine market, Omeprazole, a widely used py-based drug in medicinal market since 1998. Netupitant (an antiemitic drug, since 2014) is used in combination with another drug to prevent acute and delayed vomiting and nausea associated with cancer chemotherapy led the run towards development of anticancer drugs. Several drugs have been approved by FDA for the treatment of cancer in recent years such as, Abemaciclib (2015), Lorlatinib (2018), Apalutamide (2018) and Ivosidenib (2019). Research on py on the bases of these advancements is an evergreen field and associated with greater hopes to address several disease related issues. Several compounds are in the process of clinical trials and are expected to serve various purposes in days to come. This review article deals with recent findings in py chemistry and its coordination complexes. The medicinal efficiency has been argued for organic and inorganic derivatives. Selected biological applications are hereby discussed as follow up study of our report in 2015. Suitable literature prior to 2015 has also been incorporated in appropriate places in order to cover the scope in broader sense.

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Section: Antioxidant Potentialsmentioning

confidence: 97%

Pyridine Derivatives as Biologically Active Precursors; Organics and Selected Coordination Complexes

Khan

2021

ChemistrySelect

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“…[38] The reaction of pyrazolyl-thiophene derivative 3 with three different diazotized anilines (namely, 4-toluidine, 4-anisidine and 4-chloroaniline) was carried in pyridine at 0 C to 5 C to furnish the corresponding 4-amino-5-(4-arylhydrazono-5-oxo-1H-pyrazol-3-yl)-thiophene-3-carboxamides 4a-c. In an attempt to separate the Knoevenagel product [39] (intermediate C) through heating of pyrazolyl-thiophene derivative 3 with different types of substituted benzaldehyde, fortunately the isolated product in each case was tricyclic ring system, pyrazolo [3,4-d]thieno [3,2-b]pyridine 5. The reaction seems to proceed by intramolecular cyclization of the intermediate C via attack the amino group on the unsaturated part (β-carbon) followed by oxidation (dehydrogenation).…”

Section: Chemistrymentioning

confidence: 99%

Convenient synthesis and anticancer evaluation of novel pyrazolyl‐thiophene, thieno[3,2‐b]pyridine, pyrazolo[3,4‐d]thieno[3,2‐b]pyridine and pyrano[2,3‐d]thieno[3,2‐b]pyridine derivatives

Masaret

2021

Journal of Heterocyclic Chem

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The newly synthesized 3-(3-amino-5-(phenylamino)-4-(phenylcarbamoyl) thiophen-2-yl)-3-oxopropanoate was utilized as a precursor for the synthesis of pyrazolyl-thiophene derivative, which undergoes cyclization upon treatment with benzaldehyde derivatives to provide pyrazolo [3,4-d]thieno[3,2-b]pyridines. Basic treatment of pyrazolyl-thiophene derivative with phenyl isothiocyanate followed by subsequent addition of chloroacetone and/or ethyl bromoacetate yielded the thiazolylidene-pyrazolyl thiophenes. In addition, the building block 3-(3-amino-5-(phenylamino)-4-(phenylcarbamoyl)thiophen-2-yl)-3-oxopropanoate was converted into the corresponding thieno[3,2-b] pyridine compounds through its reactions with (DMF-DMA) and/or heating in sodium ethoxide. Moreover, the reaction of 7-hydroxy-5-oxo-N-phenyl-2-(phenylamino)-4,5-dihydrothieno[3,2-b]pyridine-3-carboxamide with 2-arylidenemalononitrile produced the new annulated pyrano[2,3-d]thieno[3,2-b]pyridines. The prepared thiophene-based compounds were evaluated against HepG2, PC3, and MCF-7 cancer cells, and normal fibroblast cell (WI38). The pyrazolo [3,4-d]thieno[3,2-b]pyridine and pyrano [2,3-d]thieno[3,2-b]pyridine compounds substituted with chlorophenyl group presented promising cytotoxic activities against HepG2 cancer cell line without any human toxicity. Docking study for the synthesized thiophene compounds delivered valuable insights about the binding interactions with the crystal structure of NS5B enzyme with PDB ID (4TLR).

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“…Abumelha [24] reported the synthesis of new nicotinonitrile-thiazole derivatives utilizing nicotinonitrilelinked N-phenyl thiosemicarbazide derivative. Some of the prior hybrids displayed promising antioxidant activity (see Figure 2).…”

Section: Introductionmentioning

confidence: 99%

“…In addition, they can be used in the treatment of multiple sclerosis by inhibition of sphingosine 1-phosphate lyase enzyme [38]. They also act as potent inhibitors of dipeptidyl peptidase-IV [34], acetylcholinesterase [39,40], and COX-2 enzymes [24]. Some biologically active hybrids linked to nicotinonitrile units are presented in Figure 2 [24,[40][41][42].…”

Section: Introductionmentioning

confidence: 99%

Pyridine‐2(1H)‐thiones: Versatile precursors for one‐pot synthesis of new nicotinonitrile‐thiazole hybrids

Sanad

Mekky

Said

et al. 2021

Journal of Heterocyclic Chem

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In the current study, we report a facile procedure for the preparation of a new series of nicotinonitrile-thiazoles, in excellent isolated yields. For this purpose, pyridine-2(1H)-thiones were investigated as key building blocks for the synthesis of new nicotinonitrile-linked 2-hydroxybenzaldehyde derivatives. To prepare the target thiazole hybrids, a facile one-pot procedure was developed involving amine-mediated reaction of the prior aldehydes, thiosemicarbazide, and the appropriate of hydrazonyl chlorides. The reaction conditions of this one-pot protocol were optimized by repeating the reaction using different solvents and amines. The optimized conditions were conducting the reaction in dioxane containing triethylamine at 100 C for 5 h. The prior protocol gave, in each case, new series of nicotinonitrile-linked thiazole and thiazol-4(5H)-one hybrids, bearing aryldiazenyl or arylhydrazineylidene units. Repeating the prior one-pot protocol using the appropriate halogen containing reagents instead of hydrazonyl chlorides afforded the target thiazoles in excellent isolated yields. By considering their elemental analyses and spectral findings, the structures of the new hybrids were clarified.

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Synthesis and antioxidant assay of new nicotinonitrile analogues clubbed thiazole, pyrazole and/or pyridine ring systems

Cited by 14 publications

References 39 publications

Pyridine Derivatives as Biologically Active Precursors; Organics and Selected Coordination Complexes

Pyridine Derivatives as Biologically Active Precursors; Organics and Selected Coordination Complexes

Convenient synthesis and anticancer evaluation of novel pyrazolyl‐thiophene, thieno[3,2‐b]pyridine, pyrazolo[3,4‐d]thieno[3,2‐b]pyridine and pyrano[2,3‐d]thieno[3,2‐b]pyridine derivatives

Pyridine‐2(1H)‐thiones: Versatile precursors for one‐pot synthesis of new nicotinonitrile‐thiazole hybrids

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