Corrigendum to “Investigation of 3-sulfamoyl coumarins against cancer-related IX and XII isoforms of human carbonic anhydrase as well as cancer cells leads to the discovery of 2-oxo-2H-benzo[h]chromene-3-sulfonamide – A new caspase-activating proapoptotic agent” [J. Med. Chem. 222 (2021) 113589]

Dar’in, Dmitry; Kantin, Grigory; Kalinin, Stanislav; Sharonova, Tatiana; Bunev, Alexander S.; Ostapenko, Gennady I.; Nocentini, Alessio; Sharoyko, Vladimir V.; Supuran, Claudiu T.; Krasavin, Mikhail

doi:10.1016/j.ejmech.2021.113788

Cited by 2 publications

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“…Dar'in et al [78] : A series of 17 compounds of triaryl substituted coumarin‐sulfonamide were designed and synthesized in Scheme 18; further the liberated products were tested for their in vitro inhibition of four different isoenzymes of includes h CA‐1, II and two transmembrane tumor‐associated h CA‐XI, XII. The desired coumarin congeners 107a–q were synthesized by stirring the reaction mixture of corresponding substituted salicylaldehyde 105a–q and ethyl sulfomoyl acetate 106 in butanol solution in closed vessels for about 2–4 h; then the obtained precipitate was collected and washed with ether.…”

Section: Synthetic Strategy Of Coumaryl‐sulfonamide Congenersmentioning

confidence: 99%

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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: Synthetic Strategy Of Coumaryl‐sulfonamide Congenersmentioning

confidence: 99%

“…Among them, the compound 107q had shown concentration‐dependent apoptosis‐inducing activity associated with caspase 3/7 activation in respective cancer cell lines and it may lead to being a potent candidate for anticancer agent. [ 78 ]…”

Section: Synthetic Strategy Of Coumaryl‐sulfonamide Congenersmentioning

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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“…[9,10] After Supuran and coworkers reported coumarins as novel suicidal inhibitors of CA, especially CAs IX and XII, [11,12] several groups including ours have worked on the development of selective and potent inhibitors of both these isoforms. [13][14][15][16][17] The five-membered heterocycle, 1,3-thiazole as well as its derivatives have also shown a multitude of biological profiles like antitumor activity, anti-inflammatory activity, anticonvulsant activity, antibacterial activity, and antifungal activity. [18] Several hCAs, including hCAs IX and XII, have also been found to be effectively inhibited by compounds incorporating the 1,3-thiazole moiety.…”

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Synthesis and biological evaluation of coumarin‐thiazole hybrids as selective carbonic anhydrase IX and XII inhibitors

Thacker

Newaskar

Angeli

et al. 2022

Archiv der Pharmazie

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A series of coumarin‐linked thiazoles (6a–p) was synthesized and the synthesized compounds were evaluated against human carbonic anhydrases (hCAs) IX and XII, which have been implicated in cancer. All the compounds exhibited selective inhibition of both isoforms. The designed compounds inhibited hCA IX in a moderate nanomolar to submicromolar range. The hCA XII was inhibited in a low to moderate nanomolar range. Compound 6o exhibited the best inhibition of hCA XII with a Ki value of 91.1 nM. The hydrolyzed form of compound 6o also exhibited favorable interactions as well as good docking scores with both the isoforms. Hence, this compound can be taken as a template for the design of selective and potent hCA XII inhibitors.

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Cited by 2 publications

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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

Synthesis and biological evaluation of coumarin‐thiazole hybrids as selective carbonic anhydrase IX and XII inhibitors

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