Quinonaphthothiazines, syntheses, structures and anticancer activities

Jeleń, Małgorzata; Pluta, Krystian; Suwińska, Kinga; Morak‐Młodawska, Beata; Latocha, Małgorzata; Shkurenko, Aleksander

doi:10.1016/j.molstruc.2015.06.046

Cited by 11 publications

(3 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Amongst all the prepared molecules, compound 232 and 233 displayed promising anticancer potential on all the three tumor cell lines and were comparable with that of the reference drug cisplatin (Table 13). Whereas, compound 234 showed higher potency towards the SNB‐19 cells (IC 50 : 8.82 µg/ml) 265 …”

Section: Introductionmentioning

confidence: 94%

“…Whereas, compound 234 showed higher potency towards the SNB-19 cells (IC 50 : 8.82 µg/ml). 265 T A B L E Jelen et al, 266 in 2016, synthesized propargylated quinobenzothiazines and assessed them for their biological potency as prospective antiproliferative, anti-inflammatory, and anticancer agents. Most of the derivatives when tested showed promising antiproliferative activity with low cytotoxicity and TNF-α inhibition.…”

Section: Phenothiazine and Azaphenothiazinementioning

confidence: 99%

See 1 more Smart Citation

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Laxmikeshav

Kumari

Shankaraiah

2021

Medicinal Research Reviews

View full text Add to dashboard Cite

This review article proposes a comprehensive report of the design strategies engaged in the development of various sulfur-bearing cytotoxic agents. The outcomes of various studies depict that the sulfur heterocyclic framework is a fundamental structure in diverse synthetic analogs representing a myriad scope of therapeutic activities. A number of five-, six-and seven-membered sulfur-containing heterocyclic scaffolds, such as thiazoles, thiadiazoles, thiazolidinediones, thiophenes, thiopyrans, benzothiazoles, benzothiophenes, thienopyrimidines, simple and modified phenothiazines, and thiazepines have been discussed. The subsequent studies of the derivatives unveiled their cytotoxic effects through multiple mechanisms (viz. inhibition of tyrosine kinases, topoisomerase I and II, tubulin, COX, DNA synthesis, and PI3K/Akt and Raf/MEK/ERK signaling pathways), and several others. Thus, our concise illustration explains the design strategy and anticancer potential of these five-and six-membered sulfur-containing heterocyclic molecules along with a brief outline on seven-membered sulfur heterocycles. The thorough assessment of antiproliferative activities with the reference drug allows a proficient assessment of the structure-activity relationships (SARs) of the diversely synthesized molecules of the series.

show abstract

Section: Introductionmentioning

confidence: 94%

Section: Phenothiazine and Azaphenothiazinementioning

confidence: 99%

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Laxmikeshav

Kumari

Shankaraiah

2021

Medicinal Research Reviews

View full text Add to dashboard Cite

show abstract

“…About 40 types of azaphenothiazines are known as monoaza-, diaza-, triaza-, and tetraazaphenothiazines and their monobenzo-and dibenzo derivatives 16 . Some of these azaphenothiazines being pyridobenzothiazines [17][18][19][20][21] , pyrimidobenzothiazines 22,23 , pyrazinobenzothiazines 24,25 , dipyridothiazines [26][27][28][29][30] , quinobenzothiazines [31][32][33][34][35][36] , quinobenzothiazinium salts [37][38][39] , diquinothiazines 26,27 , and quinonaphthothiazines 36,40 exhibited promising anticancer, antibacterial, antiviral, immunosuppressive, antioxidative anti-inflammatory, and enzyme inhibiting activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel propargylquinobenzothiazines and their derivatives as potential antiproliferative, anti-inflammatory, and anticancer agents

Jeleń

Pluta

Zimecki

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

Azaphenothiazines containing the quinoline ring, 8-10-substituted 6H-quinobenzothiazines and 6H-diquinothiazine were transformed into new 6-propargyl and 6-dialkylaminobutynyl derivatives containing the triple bond. Most of them displayed strong antiproliferative actions against human peripheral blood mononuclear cells (PBMC) stimulated with phytohemagglutinin A (PHA), strongly suppressed lipopolysaccharide (LPS)-induced TNF-a production by whole blood human cell cultures, and exhibited low cytotoxicity. Three propargylquinobenzothiazines with the bromine, trifluoromethyl, and methylthio groups at position 9 and propargyldiquinothiazine exhibited comparable actions to cisplatin against the L-1210 and SW-948 tumor lines. 6-Propargyl-9-trifluoromethylquinobenzothiazine was shown to block caspase 3 expression and inhibit expression of caspase 8 and 9 in Jurkat cells indicating its possible mechanism of action. These derivatives could be promising, potential therapeutics for treatment of neoplastic diseases and autoimmune disorders.

show abstract

Copper‐Catalyzed C‐4 Carboxylation of 1‐Naphthylamide Derivatives with CBr₄/MeOH

et al. 2019

View full text Add to dashboard Cite

A simple and practical copper catalyzed C-4 carboxylation reaction of 1-naphthylamide derivatives using carbon tetra bromide and methanol is reported here. Picolinamide and its derivatives are used as a bidentate directing group for the distal C4-H functionalization. Various substituted naphthylamide derivatives, and anilides are employed for the carboxylation and proceeds in good yields under mild condition. From the outcome of experimental results, it is proposed that C4-H carboxylation reaction of 1-naphthylamides might proceed through a single electron transfer (SET) pathway.

show abstract

Quinonaphthothiazines, syntheses, structures and anticancer activities

Cited by 11 publications

References 28 publications

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Synthesis and biological evaluation of novel propargylquinobenzothiazines and their derivatives as potential antiproliferative, anti-inflammatory, and anticancer agents

Copper‐Catalyzed C‐4 Carboxylation of 1‐Naphthylamide Derivatives with CBr₄/MeOH

Contact Info

Product

Resources

About

Quinonaphthothiazines, syntheses, structures and anticancer activities

Cited by 11 publications

References 28 publications

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Synthesis and biological evaluation of novel propargylquinobenzothiazines and their derivatives as potential antiproliferative, anti-inflammatory, and anticancer agents

Copper‐Catalyzed C‐4 Carboxylation of 1‐Naphthylamide Derivatives with CBr4/MeOH

Contact Info

Product

Resources

About

Copper‐Catalyzed C‐4 Carboxylation of 1‐Naphthylamide Derivatives with CBr₄/MeOH