A Concise Approach to N-Substituted Rhodanines through a Base-Assisted One-Pot Coupling and Cyclization Process

Liang, Yongxi; Tang, Mingkai; Huo, Zhipeng; Zhang, Chenchen

doi:10.3390/molecules25051138

Cited by 5 publications

(5 citation statements)

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“…This type of compounds, when interacting with carbon disulfide 2, forms carbamine salts 3. The resulting compounds, when interacting with chloroacetic acid and their derivatives, cyclize into the target compounds [1][2][3]23 Alternative method for converting aminogroup into rhodanine cycle 5 includs the reaction of aminocompounds with acid 4. [1][2][3] Rhodanine derivatives 5 are also formed by the raction of isothiocyanates 6 with mercaptoacetic acid 7.…”

Section: Methods Of Construction Of the Rhodanine (2-thioxothiazolidi...mentioning

confidence: 99%

“…The methylene group in rhodanine derivatives 10 is highly active and, upon interaction with furfural and its substituted derivatives 11 in the presence of basic catalysis, easily forms the target (5E)-3-R 1 -5-[(5-R-furan-2-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-ones 12 (Scheme 3). [1][2][3][23][24][25][26] The geometric placement of substituents at the 5-th position of the rhodanine ring of the above compounds has not been studied separately. However, by analogy with other 5-arylidenerhodanines, it can be argued that this is the Z-configuration 1-3 .…”

Section: Methods Of Construction Of the Rhodanine (2-thioxothiazolidi...mentioning

confidence: 99%

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Synthesis and biological activity of rhodanine-furan conjugates: A review

Matiichuk,

Drapak,

Darmograi

et al. 2024

10.5267/j.ccl

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Rhodanines are recognized as privileged heterocycles in medicinal chemistry. The main achievements include the development of drug-like molecules with numerous biological activities as well as approved drugs. The Furan nucleus is considered one of the promising heterocyclic cores in medicinal chemistry that showed numerous ranges of activity. The combination of several heterocycles in a one molecule commonly provides much more interest in the enhanced activity profile of its analogs than their parent separate constituents. Such conjugates are promising objects for modern medicinal chemistry. In this review paper recent advances in the synthesis and biological activities rhodanine-furan conjugates which its application in the different field of drug discovery.

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Section: Methods Of Construction Of the Rhodanine (2-thioxothiazolidi...mentioning

confidence: 99%

Section: Methods Of Construction Of the Rhodanine (2-thioxothiazolidi...mentioning

confidence: 99%

Synthesis and biological activity of rhodanine-furan conjugates: A review

Matiichuk,

Drapak,

Darmograi

et al. 2024

10.5267/j.ccl

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“…The proposed reaction mechanism for this process is depicted in [Figure 3]. [31] In scheme 7, Kumar et al demonstrated an effective and stereospecific procedure for the conversion of free amino group (9) to the equivalent (±)-2-thioxo-thiazolidine-4ones. The synthetic strategy involves the conversion of amino acid to ammonium salt which, in turn, reacts with carbon disulfide (2) to form dithiocarbomates (10).…”

Section: Methods For the Synthesis Of Rhodanine Corementioning

confidence: 99%

Synthetic strategy of 2-thioxo-4-thiazolidinone with core chemistry and biological importance

Chaurasiya¹,

Chawla²

2022

Pharmaspire

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Due to the vast range of biological actions that rhodanine and its derivatives exhibit, they are recognized as privileged structures in pharmacological research. However, the rhodanine skeleton synthesis process has certain limitations. However, the rhodanine ring’s reactivity enabled the creation of various arylidenes at position 5 and carboxylic acids at position 3, respectively. The principal pathways of heterocycle alteration are determined by the most reactive sites in 4-thiazolidinone, which are 3 and 5. In a review paper, the chemistry of 4-thiazolidinones was discussed, in particular the rhodanine ring and several methods for its reactions, including ring modification. The study deals with thioureas and thioglycolic acid react in a single step, catalyzed by protic acid, resulting in the direct preparation of N-aryl rhodanines as well as the rhodanine skeleton, offering a novel method for the synthesis of rhodanine and its derivatives. The presented approach is simple, effective, atom-efficient, and practical in high yields.

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“…All the other solvents were investigated, and MeCN was used as the most selective one (yield 94%, Scheme 6, Figure 3a). The proposed reaction mechanism for this process is depicted in Figure 3b (Liang et al, 2020).…”

Section: Synthesis Of Rhodanine From Carbamatementioning

confidence: 99%

Rhodanine derivatives: An insight into the synthetic and medicinal perspectives as antimicrobial and antiviral agents

et al. 2022

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Rhodanine or 2-Thioxothiazolidin-4-one is a privileged heterocyclic compound offering a wide opportunity for structural modification, lead development, and modification. It is one of the highly decorated scaffolds in the drug discovery process. Rhodanine derivatives possess a plethora of biological activities due to their ability to interact with a diverse range of protein targets, which provide tremendous opportunities to discover new drugs with different modes of action. The most common strategy for developing novel rhodanine derivatives is the introduction of structurally diverse substituents at the C-5 or N-3, or both positions. Since the inception of Epralestat into the market in 1992, the exploration of rhodanine-3acetic acids has led to the development of novel leads against different biological targets such as MRSA, HHV-6, Mycobacterial tuberculosis, dengue, etc. In the current pandemic era, some rhodanine compounds have been explored against SARS-CoV-2. In recent years, rhodanine and its derivatives have witnessed significant progress in developing new drug leads as potential antimicrobial and antiviral agents. Different synthetic methodologies and recent developments in the medicinal chemistry of rhodanine derivatives, including biological activities, their mechanistic aspects, structure-activity relationships, and in silico findings, have been compiled in the present review. This article will benefit the scientific community and offer perspectives on how these scaffolds as privileged structures might be exploited in the future for rational design and discovery of rhodaninebased bio-active molecules.

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A Concise Approach to N-Substituted Rhodanines through a Base-Assisted One-Pot Coupling and Cyclization Process

Cited by 5 publications

References 50 publications

Synthesis and biological activity of rhodanine-furan conjugates: A review

Synthesis and biological activity of rhodanine-furan conjugates: A review

Synthetic strategy of 2-thioxo-4-thiazolidinone with core chemistry and biological importance

Rhodanine derivatives: An insight into the synthetic and medicinal perspectives as antimicrobial and antiviral agents

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