Synthesis and Antioxidant Activity of Amido‐Linked Benzoxazolyl/Benzothiazolyl/Benzimidazolyl‐Pyrazoles and Isoxazoles

Durgamma, Suram; Reddy, P. Ramachandra; Padmavathi, V.; Padmaja, A.

doi:10.1002/jhet.2347

Cited by 20 publications

(8 citation statements)

References 41 publications

(38 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For the last couple of years we have been actively engaged on the development of functionalized heterocycles linked by amide and sulfonamide moieties. In fact, we have reported the reaction between heteroaryl acids and heteroaryl amines to develop amide linkage using 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU)/ N,N-diisopropylethylamine (DIPEA)/ N,N-dimethylformamide (DMF), 16 N,N'dicyclohexylcarbodiimide (DCC)/ 4-dimethylaminopyridine (DMAP)/ Dioxane, 17,18 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo [4,5-b]pyridinium-3-oxidehexafluorophosphate (HATU)/ DIPEA/DMF. 19 In this communication we have adopted simple, eco-friendly methodology for the development of amide and sulfonamide linked heterocycles © ARKAT USA, Inc directly by amidation and sulfonamidation of heteroaldehydes with heteroaryl amines and sulfonylamines.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of carboxamide and sulfonyl carboxamide linked heterocycles under green conditions

Gaddam¹,

Thata²,

Adivireddy³

et al. 2019

Arkivoc

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of carboxamide and sulfonyl carboxamide linked heterocycles under green conditions

Gaddam¹,

Thata²,

Adivireddy³

et al. 2019

Arkivoc

View full text Add to dashboard Cite

show abstract

“…The isoxazole structures considered as potential pharmacological agents constitute the most promising five-membered heterocyclic units [74]. Some isoxazoles and related compounds are known to exhibit antitumor [75], anti-HIV [76], anti-inflammatory [77], antioxidant [78], antiviral [79], antimicrobial activities [80] and insecticidal [81]. Currently, there is no approved drug for the treatment of coronaviral disease, although Chloroquine has in vitro activity against SARS-CoV-2.…”

Section: Molecular Dockingmentioning

confidence: 99%

Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions

et al. 2021

View full text Add to dashboard Cite

The regioselectvity and the mechanism of the (32CA) cycloadditions reactions of 1-bromo-4-vinylbenzene 1 and 1-chloro-4-vinylbenzene 2 with benzonitrile oxide 3 were investigated under the molecular electron density theory (MEDT) at the B3LYP/6-311++G(d,p) computational level. Evaluation of the ELF reveals that these zwitterionic type (zw-type) 32CA reactions take place in a two-stage one-step mechanism. This MEDT study shows that the meta isoxazolines are kinetically and thermodynamically favored over the ortho ones, these 32CA reactions being completely regioselective, in agreement with experimental outcomes. In addition, the efficiency of isoxazolines against SARS-CoV-2 have been also investigated. According to the docking analysis, the present study concludes that 5-(p-bromophenyl)-3-phenyl-2-isoxazoline (B-m) shows better interactions for the inhibition of SARS-CoV-2 in comparison to chloroquine.

show abstract

“…On the other hand, isoxazoles possess an extensive lineup of biological activities as well as forming an integrate of varied biodynamic agents [13,14]. A number of isoxazoles and related compounds are known to exhibit antitumor [15], anti-HIV [16], anti-inflammatory [17], antioxidant [18], antiviral [19], and antimicrobial activities [20]. Various biological activities of pyrazoles and isoxazole pharmacophores led to the search for new bioactive compounds of this class [21].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Docking, and Biological Evaluation of Pyrazole 1-Carbothiamide Incorporated Isoxazole Derivatives

Tumma

Vamaraju

2019

Asian J Pharm Clin Res

View full text Add to dashboard Cite

Objectives: Novel isoxazole incorporated pyrazole carbothiamide 5 (a-r) was designed and synthesized, docked and evaluated for anticancer activity Michigan Cancer Foundation-7 (MCF-7), and breast cancer cell lines. Materials and Methods: Designed compounds were synthesized by the condensation of 1-(5-methyl-3-(4-nitrophenyl) isoxazole-4-yl) -3-(substitutedphenyl) prop-2-en-1-one (4) with thiosemicarbazides and substituted thiosemicarbazides to give the target molecules 5 (a-r). To predict the affinity and activity of the ligand molecule, the docking program Accelrys Discovery Studio 2.1 was employed to generate different bioactive binding poses of designing molecules at the active site of human Dihydrofolate Reductase (DHFR) (PDB ID: 1KMS). All the synthesized compounds were characterized based on the spectral and elemental analysis data. Antiproliferative activity was performed against MCF-7 breast cancer cell lines. Results: All the synthesized compounds showed the characteristic peaks in Fourier-transform infrared,1H C13NMR, and mass spectral analysis. During docking, all the synthesized compounds 5 (a-r) exhibited higher fitness scores with minimum three bonding interaction with the active site human DHFR (PDB ID: 1KMS). In the MTT assay based on MCF-7 breast cancer cell lines, most of the compounds exhibited significant activity. In the antiproliferative assay against MCF-7 cell lines, most of the compounds exhibited potent activity with IC50 values in micromolar concentrations. Compounds 5a, 5b, 5f, 5h, and 5k have exhibited significant anticancer activity. Conclusions: The derivatives were synthesized in quantitative yields. New derivatives possess the antiproliferative activity and antitubercular activity.

show abstract

Synthesis and Antioxidant Activity of Amido‐Linked Benzoxazolyl/Benzothiazolyl/Benzimidazolyl‐Pyrazoles and Isoxazoles

Abstract: A new class of amido‐linked bis heterocycles‐benzoxazolyl/benzothiazolyl/benzimidazolyl‐pyrazoles and isoxazoles were prepared from benzoxazolyl /benzothiazolyl/benzimidazolyl‐cinnamamides and tested for antioxidant activity.

Cited by 20 publications

References 41 publications

Synthesis of carboxamide and sulfonyl carboxamide linked heterocycles under green conditions

Synthesis of carboxamide and sulfonyl carboxamide linked heterocycles under green conditions

Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions

Design, Synthesis, Molecular Docking, and Biological Evaluation of Pyrazole 1-Carbothiamide Incorporated Isoxazole Derivatives

Contact Info

Product

Resources

About