1,2-Benzisoxazole-3-acetamide derivatives as dual agents for DPP-IV inhibition and anticancer activity

Karandikar, Shubhendu; Soni, Rina; Soman, Shubhangi S.; Umar, Shweta; Balakrishnan, Suresh

doi:10.1080/00397911.2018.1508723

Cited by 9 publications

(4 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Besides that, Karandikar et al 18 revealed that derivatives of benzisoxazole acetamide 7 containing pyrrolidin-2-amine group have also shown potential as DPP-IV inhibitor at 25-200 µM concentrations. The amide group in the pyrrolidine ring seems essential in DPP-IV activity, as replacing the amide group at 7 with the ester or cyano group resulted in the loss of DPP-IV inhibitory activity.…”

Section: -1 Antidiabeticmentioning

confidence: 99%

Five-Membered Nitrogen Heterocycles as New Lead Compounds in Drug Discovery

Sazali Hamzah,

Fazli Mohammat,

Wibowo

et al. 2022

HETEROCYCLES

View full text Add to dashboard Cite

Five-membered nitrogen heterocyclic compounds are a very important group with various pharmaceutical properties. The different substitutions and functionalization of these compounds contributed to various biological activities.Five-membered nitrogen heterocyclic scaffolds are used for synthesizing numerous natural and synthetic compounds with a significant biological application. They include antidiabetic, anticancer, antimalarial, antiviral, antimicrobial, antiinflammatory, antibacterial, and anti-neurodegenerative agents. This mini-review provides an overview of the biological activities and the synthetic methods for preparing the five-membered nitrogen heterocyclic scaffolds and their functionalization. In the final part, this mini-review also listed some commercial drugs containing five-membered nitrogen heterocyclic motifs, highlighting the versatility of the five-membered nitrogen heterocyclic core in drug discovery. CONTENTS 1. Introduction 2. Biological activities and synthetic methodology of five-membered nitrogen heterocyclic compounds 2-1. Antidiabetic 2-2. Anticancer 2-3. Antibacterial 2-4. Antiviral244

show abstract

Section: -1 Antidiabeticmentioning

confidence: 99%

Five-Membered Nitrogen Heterocycles as New Lead Compounds in Drug Discovery

Sazali Hamzah,

Fazli Mohammat,

Wibowo

et al. 2022

HETEROCYCLES

View full text Add to dashboard Cite

show abstract

“…17 Pyrimidinethione are frequently incorporated into metal-based medications intended to specifically address various biological processes or medical conditions. 18 Previously we have investigated various biological activities of these benzisoxazole derivatives aspromising class of heterocyclic compounds and show biological and pharmacological properties such as antitumor, antithrombotic, analgesic antioxidant, antimicrobial, anticancer, anticonvulsant, antipsychotic and anti-inflammatory agents [13][14] . With the broad biological and pharmacological uses of O-glucosides, thiopyrimidines, benzisoxazolesandextended research on heterocyclic compounds previously carried out, we produced a variety of pyrimidine and O-glucoside and examined their abilities to fight off microbes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biofunctional Evaluation of Novel Isoxazole, C-Nucleoside, and Thioxopyrimidine Derivatives

K. Wanare,

R. Tayade,

A. Sukhadeve

et al. 2023

Orient. J. Chem

View full text Add to dashboard Cite

Thioxopyrimidines are an important class of compounds in the fields of biology and chemistry that play significant roles in drug discovery, nucleic acid chemistry, enzyme inhibition, and various other fields of science and technology. Their structural diversity and potential bioactivities make them valuable tools for researchers. This work presents a thorough synthesis and analysis and bio-functional assessment of a variety of isoxazole C-Nucleoside, and thioxopyrimidine derivative. The structural characterization of the synthesized compounds was achieved through spectral analyses, including IR, 1H NMR, and mass spectra and also deals with its antibacterial and antifungal activity.

show abstract

“…Naturally occurring and synthetic benzisoxazoles [ 1 ], particularly their 3-substituted representatives [ 2 ], are important pharmacophores and serve as valuable tools for drug design and discovery, having a high number of positive hits in biological screens. Because of their versatile properties and potential as selective ligands for a variety of macromolecular targets, these bicyclic aromatic ring systems constitute the essential structural motif in a wide range of pharmacologically active compounds, including a number of potential anticancer agents ( Figure 1 ) [ 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. Furthermore, the benzisoxazole scaffold is often used as a bioisosteric replacement for the benzoyl group of biologically active molecules [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

“… Benzisoxazoles ( I – VI ) [ 3 , 4 , 5 , 6 , 7 , 8 ] and steroidal isoxazoles ( VII , VIII ) [ 13 , 15 ] with anticancer activity and the proposed E2-benzisoxazole hybrids. …”

Section: Introductionmentioning

confidence: 99%

Substitutional Diversity-Oriented Synthesis and In Vitro Anticancer Activity of Framework-Integrated Estradiol-Benzisoxazole Chimeras

et al. 2022

View full text Add to dashboard Cite

Hybridization of steroids and other pharmacophores often modifies the bioactivity of the parent compounds, improving selectivity and side effect profile. In this study, estradiol and 3′-(un)substituted benzisoxazole moieties were combined into novel molecules by structural integration of their aromatic rings. Simple estrogen starting materials, such as estrone, estradiol and estradiol-3-methylether were used for the multistep transformations. Some of the heterocyclic derivatives were prepared from the estrane precursor by a formylation or Friedel–Crafts acylation—oximation—cyclization sequence, whereas others were obtained by a functional group interconversion strategy. The antiproliferative activities of the synthesized compounds were assessed on various human cervical, breast and prostate cancer cell lines (HeLa, MCF-7, PC3, DU-145) and non-cancerous MRC-5 fibroblast cells. Based on the primary cytotoxicity screens, the most effective cancer-selective compounds were selected, their IC50 values were determined and their apoptosis-inducing potential was evaluated by quantitative real-time PCR. Pharmacological studies revealed a strong structure–function relationship, where derivatives with a hydroxyl group on C-17 exhibited stronger anticancer activity compared to the 17-acetylated counterparts. The present study concludes that novel estradiol-benzisoxazole hybrids exert remarkable cancer cell-specific antiproliferative activity and trigger apoptosis in cancer cells.

show abstract

1,2-Benzisoxazole-3-acetamide derivatives as dual agents for DPP-IV inhibition and anticancer activity

Cited by 9 publications

References 23 publications

Five-Membered Nitrogen Heterocycles as New Lead Compounds in Drug Discovery

Five-Membered Nitrogen Heterocycles as New Lead Compounds in Drug Discovery

Synthesis and Biofunctional Evaluation of Novel Isoxazole, C-Nucleoside, and Thioxopyrimidine Derivatives

Substitutional Diversity-Oriented Synthesis and In Vitro Anticancer Activity of Framework-Integrated Estradiol-Benzisoxazole Chimeras

Contact Info

Product

Resources

About