Thiazolothiadiazoles and Thiazolooxadiazoles: Synthesis and Biological Applications

Abdel‐Wahab, Bakr F.; Shaaban, Saad

doi:10.1055/s-0033-1338627

Cited by 34 publications

(6 citation statements)

References 16 publications

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“…The porphyrin mode(s) of action, their cytotoxicity are due to caspase 3/7 activation and subsequent induction of apoptosis. Additionally, different phenotypical changes were observed and these included endoplasmic reticulum, actin cytoskeleton, and cellular morphology alterations as well as cell cycle arrest and various biochemical changes (e.g., ROS and GSH levels) …”

Section: Resultsmentioning

confidence: 99%

Efficient synthesis of meso‐substituted porphyrins and molecular docking as potential new antioxidant and cytotoxicity agents

Abu‐Melha

2019

Archiv der Pharmazie

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An improved methodology is reported for the synthesis of new series of mesotetrakis-[aryl]-21H,23H-porphyrin derivatives 2a-h and was considered as a model to study their antioxidant and cytotoxic activities. The structures of the novel compounds were determined in 1 H and 13 C NMR, UV-Vis, and elemental analyses. Among the derivatives, compounds 2c, 2d, and 2h showed strongest radical-scavenging activity.Moreover, according to our results, compounds 2c, 2d, 2g, and 2h have very strong activity against the HepG2 hepatoma cell line, with IC 50 values from 9 to 25 μg/mL.Molecular docking was performed to investigate the binding between the most active porphyrin derivatives 2c, 2d, 2g, 2h and the two molecular targets Bcl-2 and caspase-3.Compounds 2c and 2d seem to have better affinities to both proteins than 2g and 2h.

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Section: Resultsmentioning

confidence: 99%

Efficient synthesis of meso‐substituted porphyrins and molecular docking as potential new antioxidant and cytotoxicity agents

Abu‐Melha

2019

Archiv der Pharmazie

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“…The fused-heterocyclic thiazolothiadiazoles were widely used as scaffolds for active agents in medicine and agricultural chemistry, [70] exhibiting a range of biological activities, such as antihypertensive, antiallergic, anti-inflammatory, and so on. [71] In 2023, Singh and co-workers synthesized functionalized thiazolothiadiazoles 51 via the cascade heteroannulation of thioamides 50 with diazomethyl-substituted iodine(III) compounds 3 (Scheme 17). [72] This synthesis method was achieved by constructing the C(sp 2 )À S bond through the nucleophilic pathway.…”

Section: C(sp 2 )à S Bond-forming Reactionsmentioning

confidence: 99%

Synthesis of Hypervalent Iodine Diazo Compounds and Their Application in Organic Synthesis

Zhang,

Wan

2023

Chemistry A European J

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Hypervalent iodine diazo reagents with electron‐withdrawing groups (EWG) connected to diazo methyl center were a type of donor‐acceptor diazo compounds with potential reaction abilities similar to ordinary diazo compounds. Although several hypervalent iodine diazo reagents were synthesized and used in the nucleophilic substitution reactions as early as 1994, the synthesis and application of new iodine(III) diazo reagents have only been reported to a certain extent in recent years. In the presence of rhodium catalyst, photocatalyst, or nucleophiles, hypervalent iodine diazo reagents can be converted into rhodium‐carbenes, diazomethyl radicals, ester radicals or nucleophilic intermediates, which can be used as key intermediates for the formation of chemical bonds. The aim of this review is to give an overview of hypervalent iodine diazo compounds in organic synthesis.

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“…Furthermore, the advancement of the reaction was only depicted on the basis of various catalysts explored, neglecting its synthetic applications, scopes and secondary transformations. With this in mind and our interest in MCRs and drug discovery [18][19][20][21][22][23], we herein summarize the efforts of the chemical community in the progress and applications of GBBR since 1998. This review will cover the biological profiles, synthetic scopes and respective proposed mode(s) of action of GBBR products.…”

Section: Introductionmentioning

confidence: 99%

“…The component variations, postmodifications and secondary transformations will also be discussed. For general information about MCRs, IMCRs and their applications in the synthesis of biologically relevant heterocycles, the reader is directed towards more comprehensive reviews and monographs [13,18,19,[22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37]. …”

Section: Introductionmentioning

confidence: 99%

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

2015

Self Cite

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The Groebke-Blackburn-Bienaymé reaction (GBBR) is used for the one-pot synthesis of therapeutically relevant fused imidazoles bridgehead nitrogen heterocyclic compounds from readily available aldehyde, isocyanide and amidine building blocks. The reaction is driven by a wide range of catalysts and can be performed either under solvent or solvent-free conditions, or under microwave irradiation as heat source. The GBBR products can be used for the synthesis of a variety of more complex scaffolds via postmodification reactions. These include cyclization and nucleophilic substitution as well as further MCRs. The GBBR reaction has seen diverse applications in combinatorial and medicinal chemistry and its products are of great use in drug discovery. In this review, we summarize the efforts of the chemistry community in the progress and applications of GBBR since 1998. This review also includes some biological profiles and synthetic scopes of GBBR products. The component variations, postmodifications and secondary transformations will also be discussed throughout this review.

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Thiazolothiadiazoles and Thiazolooxadiazoles: Synthesis and Biological Applications

Cited by 34 publications

References 16 publications

Efficient synthesis of meso‐substituted porphyrins and molecular docking as potential new antioxidant and cytotoxicity agents

Efficient synthesis of meso‐substituted porphyrins and molecular docking as potential new antioxidant and cytotoxicity agents

Synthesis of Hypervalent Iodine Diazo Compounds and Their Application in Organic Synthesis

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

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