Design, Synthesis, and Anti-Inflammatory Activity of Some Coumarin Schiff Base Derivatives: In silico and in vitro Study

Hamid, Shokhan J; Salih, Twana

doi:10.2147/dddt.s364746

Cited by 44 publications

(21 citation statements)

References 76 publications

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“…Coumarins are the most widely accepted and exploited natural compound reported for several types of biological activities including antibacterial, [15,16] anticoagulant, [17] anticancer, [18] antiinflammatory, [19] and antifungal. [20] The combination of phytochemicals along with the existing drugs has reshaped the face of the medical fraternity.…”

Section: Coumarin-sulfonamide As a Core Ring For Anticancer Drug Deve...mentioning

confidence: 99%

Coumaryl‐sulfonamide moiety: Unraveling their synthetic strategy and specificity toward hCA IX/XII, facilitating anticancer drug development

Mahapatra

Mekap

Mal

et al. 2023

Archiv der Pharmazie

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Currently, cancer is the most grieving threat to society. The cancer-related death rate has had an ascending trend, despite the implementation of numerous treatment strategies or the discovery of an array of potent molecules against several pathways of cancer growth. The need of the hour is to prevent the multidrug resistance toll, and the current efforts have been bestowed upon a versatile small molecule scaffold, coumarin (benz[α]pyrone), a natural compound possessing interesting affinity toward the cancer target human carbonic anhydrase (hCA), focusing on hCA I, II, IX, and XII. Along with coumarin, the age-old known antibacterial drug sulfonamide, when conjugated at positions 3, 7, and 8 of coumarin either with a linker group or as a single entity, has been reported to enhance the affinity of coumarin toward the overexpressed enzymes in tumor cell lines. The sulfonamides have been listed as obsolete drugs due to the severe side effects caused by them; however, their affinity toward the hCA-zinc-binding core has attracted the attention of researchers. Hence, in the process of drug development, coumarin and sulfonamides have remained the choice of last resort. To unveil the synthetic strategy of coumarin-sulfonamide conjugation, their rationale for inhibiting cancer cells/enzymes, and their affinity toward various types of carcinoma have been the sole goal of the researchers. This review specifically focuses on the mechanism of action and the structure-activity relationship through synthetic strategies and the binding affinity of coumarylsulfonamide conjugates with the anticancer targets possessing the highest enzyme affinity, since 2008.

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Section: Coumarin-sulfonamide As a Core Ring For Anticancer Drug Deve...mentioning

confidence: 99%

Coumaryl‐sulfonamide moiety: Unraveling their synthetic strategy and specificity toward hCA IX/XII, facilitating anticancer drug development

Mahapatra

Mekap

Mal

et al. 2023

Archiv der Pharmazie

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“…Schiff bases show biological activities like nematicidal [20], insecticidal [21], antibacterial [22], antifungal [23], antileukaemia [24], anti-inflammatory [25], anti-HIV activity [26], antimycobacterial activity [27], antioxidant [28], anticancer [29], and plant growth regulatory activity [30] among others. Besides biological applications, Schiff base and their metal complexes have enormous applications in analytical chemistry [31], dye industry [32], and corrosion inhibitors [33].…”

Section: Introductionmentioning

confidence: 99%

Schiff Bases and Their Metal Complexes: Synthesis, Structural Characteristics and Applications

Meena¹,

Meena²,

Kumari³

et al. 2023

Schiff Base in Organic, Inorganic and Physical Chemistry

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The development of Schiff base was a major step forward in the area of coordination chemistry. Schiff bases, a class of organic compounds, carry the imine or azomethine (>C=N–) functional group. Schiff bases played an influencing role in the development of coordination chemistry and were a key point in the development of inorganic, bioinorganic chemistry and optical materials. Schiff bases, widely used in inorganic, organic, and analytical chemistry, account for a significant portion of the more commonly employed classes of organic molecules. The ability of Schiff base ligands to form stable metal complexes with a wide range of transition and other metal ions makes them extremely useful. Condensation of a primary amine with an aldehyde or ketone yields a Schiff bases. In this chapter, we focused on introducing Schiff bases, classified them and their metal complexes, and discussed several synthesis methods, including conventional and green approaches. This chapter also elaborated on the industries’ applications, such as the food industry, agrochemical industry, dye industry, analytical chemistry, catalysis, energy storage, environmental, chemo-sensing, bio-sensing, and biomedical applications of novel Schiff bases and their metal complexes.

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“…The function of inflammation in human and animal diseases has drawn global interest. Inflammatory disorders are responsible for causing numerous diseases. , Synthesizing and developing novel and more potent anti-inflammatory drugs with no or fewer side effects are crucial due to the side effects of existing drugs that have caused serious clinical issues . Schiff bases have an azomethine linkage, which has sparked the interest of pharmacists due to its predicted efficiency .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral Characterization, Thermal Investigation, Computational Studies, Molecular Docking, and In Vitro Biological Activities of a New Schiff Base Derived from 2-Chloro Benzaldehyde and 3,3′-Dimethyl-[1,1′-biphenyl]-4,4′-diamine

Thakor,

Patel,

Giri

et al. 2023

ACS Omega

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The current research involves the synthesis of a new Schiff base through the reaction between 2-chlorobenzaldehyde and 3,3′-dimethyl-[1,1′-biphenyl]-4,4′-diamine by using a natural acid catalyst and a synthesized compound physicochemically characterized by X-ray diffraction, Fourier transform infrared spectroscopy, 1H- and 13C-nuclear magnetic resonance, and liquid chromatography–mass spectrometry. Thermal studies were conducted using thermogravimetric, differential thermal analysis, and differential thermogravimetric curves. These curves were obtained in an inert nitrogen environment from ambient temperature to 1263 K using heating rates of 10, 15, and 20 K·min–1. Using thermocurve data, model-free isoconversional techniques such as Kissinger–Akahira–Sunose, Flynn–Wall–Ozawa, and Friedman are used to determine kinetic parameters. These parameters include activation energy, phonon frequency factor, activation enthalpy, activation entropy, and Gibb’s free energy change. All of the results have been thoroughly investigated. The molecule’s anti-inflammatory and antidiabetic properties were also examined. To learn more about the potential of the Schiff base and how successfully it can suppress the amylase enzyme, a molecular docking experiment was also conducted. For in silico research, the Swiss Absorption, Distribution, Metabolism, Excretion, and Toxicity algorithms were used to calculate the theoretical pharmacokinetic properties, oral bioavailability, toxic effects, and biological activities of the synthesized molecule. Moreover, the cytotoxicity tests against a human lung cancer cell line (A549) using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay demonstrated that the synthesized Schiff base exhibited significant anticancer properties.

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Design, Synthesis, and Anti-Inflammatory Activity of Some Coumarin Schiff Base Derivatives: In silico and in vitro Study

Cited by 44 publications

References 76 publications

Coumaryl‐sulfonamide moiety: Unraveling their synthetic strategy and specificity toward hCA IX/XII, facilitating anticancer drug development

Coumaryl‐sulfonamide moiety: Unraveling their synthetic strategy and specificity toward hCA IX/XII, facilitating anticancer drug development

Schiff Bases and Their Metal Complexes: Synthesis, Structural Characteristics and Applications

Synthesis, Spectral Characterization, Thermal Investigation, Computational Studies, Molecular Docking, and In Vitro Biological Activities of a New Schiff Base Derived from 2-Chloro Benzaldehyde and 3,3′-Dimethyl-[1,1′-biphenyl]-4,4′-diamine

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