Study of reactivity of cyanoacetohydrazonoethyl-<i>N</i>-ethyl-<i>N</i>-methyl benzenesulfonamide: preparation of novel anticancer and antimicrobial active heterocyclic benzenesulfonamide derivatives and their molecular docking against dihydrofolate reductase

Debbabi, Khaled; Al‐Harbi, Sami A.; Al-Saidi, Hamed M.; Aljuhani, Enas; El‐Gilil, Shimaa M. Abd; Bashandy, Mahmoud S.

doi:10.1080/14756366.2016.1217851

Cited by 13 publications

(8 citation statements)

References 42 publications

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“…By intermolecular cyclization reactions between 2-cyanoacetamide derivative 56 and chloroacetonitrile, in the presence of triethylamine (TEA), under reflux in 1,4-dioxane for 5 h, Debbabi et al [ 55 ] synthesized a series of N -ethyl- N -methyl benzenesulfonamides. Among these, derivative 57 (Fig.…”

Section: Pyrrolidine Derivatives Obtained By Ring Synthesismentioning

confidence: 99%

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

et al. 2021

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The five-membered pyrrolidine ring is one of the nitrogen heterocycles used widely by medicinal chemists to obtain compounds for the treatment of human diseases. The great interest in this saturated scaffold is enhanced by (1) the possibility to efficiently explore the pharmacophore space due to sp3-hybridization, (2) the contribution to the stereochemistry of the molecule, (3) and the increased three-dimensional (3D) coverage due to the non-planarity of the ring—a phenomenon called “pseudorotation”. In this review, we report bioactive molecules with target selectivity characterized by the pyrrolidine ring and its derivatives, including pyrrolizines, pyrrolidine-2-one, pyrrolidine-2,5-diones and prolinol described in the literature from 2015 to date. After a comparison of the physicochemical parameters of pyrrolidine with the parent aromatic pyrrole and cyclopentane, we investigate the influence of steric factors on biological activity, also describing the structure–activity relationship (SAR) of the studied compounds. To aid the reader’s approach to reading the manuscript, we have planned the review on the basis of the synthetic strategies used: (1) ring construction from different cyclic or acyclic precursors, reporting the synthesis and the reaction conditions, or (2) functionalization of preformed pyrrolidine rings, e.g., proline derivatives. Since one of the most significant features of the pyrrolidine ring is the stereogenicity of carbons, we highlight how the different stereoisomers and the spatial orientation of substituents can lead to a different biological profile of drug candidates, due to the different binding mode to enantioselective proteins. We believe that this work can guide medicinal chemists to the best approach in the design of new pyrrolidine compounds with different biological profiles.

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Section: Pyrrolidine Derivatives Obtained By Ring Synthesismentioning

confidence: 99%

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

et al. 2021

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“…The phenyl thiazole based coumarin sulfonamide scaffold (30) exhibited remarkably high activity against HepG2 cells with an IC 50 value of 3.48 ± 0.28 µM when compared to the reference drug Doxorubicin which had an IC 50 value of 5.43 ± 0.24 µM. Debbabi, et al[62] synthesized cyanoacetohydrazonoethyl-N-ethyl-N-methyl benzene sulfonamide analogues and determined their in-vitro anti-cancer and antimicrobial activities. Among all synthesized compounds, the hydrazono based coumarin benzene sulfonamide scaffold(31) showed the best activity against MCF-7 with an IC 50 value of 1.08 µg/mL when compared with the reference drug MTX (methotrexate) which had an IC 50 value of 12.3 µg/mL.…”

mentioning

confidence: 99%

Coumarin sulfonamide derivatives: An emerging class of therapeutic agents

Irfan

Rubab

Rehman

et al. 2020

Heterocyclic Communications

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Coumarin sulfonamide is a heterocyclic pharmacophore and an important structural motif which is a core and integral part of different therapeutic scaffolds and analogues. Coumarin sulfonamides are privileged and pivotal templates which have a broad spectrum of applications in the fields of medicine, pharmacology and pharmaceutics. Coumarin sulfonamide exhibited versatile and myriad biomedical activities such as anti-bacterial, antiviral, antifungal, anti-inflammatory and anti-cancer. This review article focuses on the structural features of coumarin sulfonamide derivatives in the treatment of different lethal diseases on the basis of structure-activity relationships (SAR). The plethora of research cited in this review article summarizes and discusses the various substitutions around the coumarin sulfonamide nucleus which have provided a wide spectrum of biological activities and therapeutic potential that has proved attractive to many researchers looking to exploit the coumarin sulfonamide skeleton for drug discovery and the development of novel therapeutic agents.

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Section: Pyrazoline-based Coumarin Sulfonamide Hybrids As Anticancer ...mentioning

confidence: 99%

“…Debbabi and coworkers reported the series of substituted cyanoacetohydrazonoethyl methyl-based benzenesulfonamide derivatives (Scheme 19) and evaluated for anticancer and antimicrobial therapeutic potential. The different coumarin-based benzenesulfonamides scaffolds 112 and 114 were achieved in dioxane under refluxing conditions via the reaction of cyanoacetyl containing hydrazonoethyl methyl-based benzenesulfonamide 110 with salicyldehyde 111 and 2-hydroxy naphthalene-1-carbaldehyde 113, respectively (Scheme 19) [82]. The series of all newly synthesized cyanoacetohydrazonoethyl-N-ethyl-N-methyl benzenesulfonamide derivatives were evaluated for anti-cancer therapeutic potential against the MCF cell line.…”

Section: Coumarin-6-sulfonamide Derivatives As Anticancer Agentsmentioning

confidence: 99%

“…The coumarin moiety containing a benzenesulfonamide 112 scaffold (Figure 20) displayed significant and remarkably high anticancer activity against the MCF-7 cell line, with the IC50 value 1.08 µg/mL (Table 18) among all synthesized scaffolds. The MTX (methotrexate) was used as a standard compound with an IC50 value of 12.3 µg/mL (Table 18) against MCF-7 [82]. Debbabi and coworkers reported the series of substituted cyanoacetohydrazonoethyl methyl-based benzenesulfonamide derivatives (Scheme 19) and evaluated for anticancer and antimicrobial therapeutic potential.…”

Section: Coumarin-6-sulfonamide Derivatives As Anticancer Agentsmentioning

confidence: 99%

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An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents

et al. 2022

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Coumarin is an important six-membered aromatic heterocyclic pharmacophore, widely distributed in natural products and synthetic molecules. The versatile and unique features of coumarin nucleus, in combination with privileged sulfonamide moiety, have enhanced the broad spectrum of biological activities. The research and development of coumarin, sulfonamide-based pharmacology, and medicinal chemistry have become active topics, and attracted the attention of medicinal chemists, pharmacists, and synthetic chemists. Coumarin sulfonamide compounds and analogs as clinical drugs have been used to cure various diseases with high therapeutic potency, which have shown their enormous development value. The diversified and wide array of biological activities such as anticancer, antibacterial, anti-fungal, antioxidant and anti-viral, etc. were displayed by diversified coumarin sulfonamides. The present systematic and comprehensive review in the current developments of synthesis and the medicinal chemistry of coumarin sulfonamide-based scaffolds give a whole range of therapeutics, especially in the field of oncology and carbonic anhydrase inhibitors. In the present review, various synthetic approaches, strategies, and methodologies involving effect of catalysts, the change of substrates, and the employment of various synthetic reaction conditions to obtain high yields is cited.

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Study of reactivity of cyanoacetohydrazonoethyl-N-ethyl-N-methyl benzenesulfonamide: preparation of novel anticancer and antimicrobial active heterocyclic benzenesulfonamide derivatives and their molecular docking against dihydrofolate reductase

Cited by 13 publications

References 42 publications

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

Coumarin sulfonamide derivatives: An emerging class of therapeutic agents

An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents

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