ChemInform Abstract: STUDIES IN THE SYNTHESIS OF THIAZOLIDINONES PART 2, 5‐BENZAL DERIVATIVES OF 2‐(SUBSTITUTED BENZOTHIAZOLE‐2′‐YL‐IMINO)‐4‐THIAZOLIDINONES AND THEIR BROMINATED PRODUCTS

Dhal, P. N.; Achary, T. E.; Nayak, A.

doi:10.1002/chin.197529258

Cited by 2 publications

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“…2-Chloro- N -(thiazole/benzo[ d ]thiazol-2-yl/benzo[ d ]isothiazol-3-yl)acetamides efficiently reacted with ammonium thiocyanate in refluxing ethanol to produce 2-(thiazol-2-ylimino)thiazolidin-4-ones or 2-(heteroarylimino)thiazolidin-4-ones. ,, …”

Section: Resultsmentioning

confidence: 99%

“…The first step of the synthetic procedure was carried out by reaction of appropriate amines with chloroacetyl chloride in DMF at room temperature for 2 h or by heating in dry benzene for 3 h. 29,30 2-Chloro-N-(thiazole/benzo[d]thiazol-2-yl/benzo[d]isothiazol-3-yl)acetamides efficiently reacted with ammonium thiocyanate in refluxing ethanol to produce 2-(thiazol-2-ylimino)thiazolidin-4-ones or 2-(heteroarylimino)thiazolidin-4-ones. 28,31,32 The final compounds were obtained by refluxing the previous products with commercially available aromatic aldehydes and anhydrous sodium acetate in glacial acetic acid (Scheme 1). The mechanism suggested for the formation of all synthesized compounds is described in our previous publications.…”

Section: Resultsmentioning

confidence: 99%

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2-Thiazolylimino/Heteroarylimino-5-arylidene-4-thiazolidinones as New Agents with SHP-2 Inhibitory Action

et al. 2008

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SHP-2, a nonreceptor protein tyrosine phosphatase encoded by the PTPN11 gene, mediates cell signaling by growth factors and cytokines via the RAS/MAP kinase pathway. Somatic mutations in PTPN11 gene account for approximately 18% of juvenile myelomonocytic leukemia (JMML) patients. Moreover, SHP-2 mutations leading to continuously active enzyme were found in more than 50% of Noonan syndrome patients and are considered to be responsible for the high tendency of these patients to juvenile leukemias and other cancer types. Recently SHP-2 became a new drug target, but till now little has been done in this field. In the present study, 17 2-thiazolylimino/heteroarylimino-5-arylidene-4-thiazolidinones divided into three series of derivatives bearing thiazole-, benzo[d]thiazole-, and benzo[d]isothizole rings were tested for SHP-2 inhibitory activity. Most of the compounds were good SHP-2 inhibitors. Benzo[d]thiazole derivatives exhibited the best inhibitory action. Docking studies revealed that hydrophobic interactions and hydrogen bond formation stabilize enzyme-inhibitor complex.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

2-Thiazolylimino/Heteroarylimino-5-arylidene-4-thiazolidinones as New Agents with SHP-2 Inhibitory Action

et al. 2008

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“…Similar heterocycles based on the same starting compound (5ylidene-3-phenyl-cyclohexane(1 0 -2)thiazolidin-4-one) are described in the reaction with the difunctional nucleophiles (thiourea, hydrazine hydrate derivatives, malononitrile and ethylcyanoacetate) that yielded thiazolo [4,5-d] The bromination of the double bond is the efficient approach to the synthesis of compounds 223 with high antimicrobial activity [464,465] (Scheme 105).…”

Section: Addition Reactionsmentioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

133

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The presented review is an attempt to summarize a huge volume of data on 5-ene-4-thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-thiazolidinone modification.

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ChemInform Abstract: STUDIES IN THE SYNTHESIS OF THIAZOLIDINONES PART 2, 5‐BENZAL DERIVATIVES OF 2‐(SUBSTITUTED BENZOTHIAZOLE‐2′‐YL‐IMINO)‐4‐THIAZOLIDINONES AND THEIR BROMINATED PRODUCTS

Cited by 2 publications

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2-Thiazolylimino/Heteroarylimino-5-arylidene-4-thiazolidinones as New Agents with SHP-2 Inhibitory Action

2-Thiazolylimino/Heteroarylimino-5-arylidene-4-thiazolidinones as New Agents with SHP-2 Inhibitory Action

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

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