A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives

Kokovina, Tatiana S.; Gadomsky, S. Ya.; Terentiev, Alexei A.; Sanina, Nataliya A.

doi:10.3390/molecules26175159

Cited by 13 publications

(7 citation statements)

References 24 publications

(29 reference statements)

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“…Polyphosphate ester (PPE) is a known mild reagent for cyclo-dehydration reactions [21,22], and it can be used even without additional protection of the phenol groups [21]. Here we report for the first time the usage of PPE as the dehydration additive for imidization reaction.…”

Section: Resultsmentioning

confidence: 99%

A Reaction of N-substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids

Tretyakov¹,

Gadomsky²,

Terentiev³

2023

Preprint

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We describe a new reaction for the synthesis of compounds with a hydroxylamide group (hydroxamic acids) which are widely known for their biological activity (histone deacetylase inhibitors, matrix metalloproteinases inhibitors and others). The reaction involves the interaction between N-substituted succinimides and hydroxylamine in aqueous solution. A novel two step approach to the synthesis of hydroxamic acids was developed based on the new reaction. The first stage is the synthesis of N-substituted succinimide via the reaction of aromatic amine or carboxylic acid hydrazide with succinic anhydride. The second step involves the imide ring opening reaction in the presence of hydroxylamine. For the both stages, universal synthetic methods have been developed that exclude additional purification stages for the target compounds. Sixteen hydroxamic acids were synthesized using the developed approach. Most of the compounds were obtained for the first time.

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Section: Resultsmentioning

confidence: 99%

A Reaction of N-substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids

Tretyakov¹,

Gadomsky²,

Terentiev³

2023

Preprint

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“…Kokovina et al [11] developed a new method for synthesis of 1,3,4-thiadiazol-2-amine derivatives in a one-pot manner using the reaction between a thiosemicarbazide and carboxylic acid without toxic additives such as POCl 3 or SOCl 2 . The reaction was investigated in the presence of polyphosphate ester (PPE).…”

Section: Rcho + Nhmentioning

confidence: 99%

Synthesis of 1,3,4-thiadiazole Derivative Using Appropriate Reaction Conditions

Kadu¹,

Masand²

2022

IJRASET

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Five membered heterocyclic rings possessing a mixture of different heteroatoms like S, N, O, etc. not only possess interesting chemical properties but also have a myriad number of biological activities. Of these, 1,3,4-thiadiazole moiety and its derivatives have gained a deep interest in recent year due to their crucial role in wide variety of drugs, dyes, and other substances of high interests. The present work is focussed on the different methods of their synthesis. The review highlights the key features of their synthesis

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“…High morbidity and mortality rates characterize the disease; after cardiovascular disease, it is the second leading cause of death in many countries. In order to reduce cancer death rates worldwide, chemotherapy is currently the main treatment modality for cancer, whether used alone or combined with surgery and radiotherapy [ 1 ].…”

Section: Introductionmentioning

confidence: 99%

An Understanding of Mechanism-Based Approaches for 1,3,4-Oxadiazole Scaffolds as Cytotoxic Agents and Enzyme Inhibitors

et al. 2023

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The world’s health system is plagued by cancer and a worldwide effort is underway to find new drugs to treat cancer. There has been a significant improvement in understanding the pathogenesis of cancer, but it remains one of the leading causes of death. The imperative 1,3,4-oxadiazole scaffold possesses a wide variety of biological activities, particularly for cancer treatment. In the development of novel 1,3,4-oxadiazole-based drugs, structural modifications are important to ensure high cytotoxicity towards malignant cells. These structural modification strategies have shown promising results when combined with outstanding oxadiazole scaffolds, which selectively interact with nucleic acids, enzymes, and globular proteins. A variety of mechanisms, such as the inhibition of growth factors, enzymes, and kinases, contribute to their antiproliferative effects. The activity of different 1,3,4-oxadiazole conjugates were tested on the different cell lines of different types of cancer. It is demonstrated that 1,3,4-oxadiazole hybridization with other anticancer pharmacophores have different mechanisms of action by targeting various enzymes (thymidylate synthase, HDAC, topoisomerase II, telomerase, thymidine phosphorylase) and many of the proteins that contribute to cancer cell proliferation. The focus of this review is to highlight the anticancer potential, molecular docking, and SAR studies of 1,3,4-oxadiazole derivatives by inhibiting specific cancer biological targets, such as inhibiting telomerase activity, HDAC, thymidylate synthase, and the thymidine phosphorylase enzyme. The purpose of this review is to summarize recent developments and discoveries in the field of anticancer drugs using 1,3,4-oxadiazoles.

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A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives

Cited by 13 publications

References 24 publications

A Reaction of N-substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids

A Reaction of N-substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids

Synthesis of 1,3,4-thiadiazole Derivative Using Appropriate Reaction Conditions

An Understanding of Mechanism-Based Approaches for 1,3,4-Oxadiazole Scaffolds as Cytotoxic Agents and Enzyme Inhibitors

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