Synthesis and reactions of (Z)-2-imino-5-(3,4,5-trimethoxy benzylidene)thiazolidin-4(H)one

Mahmoud, Mahmoud Refaee; Madkour, H. M. F.; El‐Bordany, Eman A.; Soliman, E. A.

doi:10.5155/eurjchem.2.4.475-479.193

Cited by 8 publications

(7 citation statements)

References 13 publications

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“…The 5-arylidene derivatives reacted with Grignard reagent via 1,4-conjugate addition to the exocyclic double bond to afford 5alkylaryl-4-thiazolidinones 224 [466e469] (Scheme 106). Such reaction has been rarely found in the current literature data [78].…”

Section: Addition Reactionsmentioning

confidence: 75%

“…Under the action of DMF/POCl 3 on 3-substituted 2-ylidene-thiazolidinones the related enamine derivatives of pyrolo[2,1-b]thiazol-3-ones 11 were synthesized (Scheme 7) [77]. The active methylene group in the 4-thiazolidinones underwent nucleophilic addition reaction with the double bond of the various arylidene malononitriles via Michael type addition reaction (ethanol medium in the presence of piperidine) to give the same 5-ene-4- For instance, reaction of a-cyano-3,4,5-trimethoxycinnamonitrile and/or ethyl-a-cyano-3,4,5-trimethoxycinnamate with 2imino-4-oxo-thiazolidine provided appropriate 5-enes' formation (instead of the expected fused heterocycles) [78,79]. It was proposed that the reactions proceeded via nucleophilic addition of the thiazolidinyl-C-5 to the b-carbon of the activated double bond of nitriles forming the 1:1 adduct followed by the elimination of malononitrile or ethylcyanoacetate.…”

Section: Modification Of the C5 Position Of The Thiazolidinone Corementioning

confidence: 99%

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

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

139

129

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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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Section: Addition Reactionsmentioning

confidence: 75%

Section: Modification Of the C5 Position Of The Thiazolidinone Corementioning

confidence: 99%

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

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

139

129

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“…Pyridopyrimidines were reported to constitute series of compounds which showed broad biological activity such as anticonvulsive, antitumor, antiasthmatic, antiallergic, antihypertensive and useful as diuretic compounds, together with many other applications [1][2][3][4][5][6][7][8][9][10] . As a continuation for our interest for the studies on synthesis of different heterocycles of expected biological activity [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] , the present investigation deals with the synthesis and chemistry of new heteroannulated pyrido [2,3-d]pyrimidine derivatives with the aim of finding new chemotherapeutic agents.…”

Section: Introductionmentioning

confidence: 99%

Heteroannulation of Pyrido[2,3-d]Pyrimidines. Synthesis and Spectral Characterization of Pyridotriazolopyrimidines, Pyridopyrimidotriazine and Pyridopyrimidotriazepine Derivatives

Mahmoud¹,

Madkour²,

Habashy³

et al. 2012

AJOC

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Number of pyridotriazolo-, pyridothiazolo-, pyridotetrazolopyrimidines and pyrido-pyrimidotriazepine derivatives were prepared using the readily obtainable starting material pyrido[2,3-d]pyrimidinthione 1 and its hydrazino derivative. The antimicrobial screening of selected synthesized compounds was done using the agar diffusion assay. The IR, 1 H NMR and mass spectra of the synthesized compounds were investigated.

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“…8,9 Among several commercially available substituted hydrazines, cyanoacetohydrazide is a versatile and convenient intermediate for the synthesis of wide variety of heterocyclic compounds. 10,11 As a continuation of our efforts [12][13][14][15][16][17][18][19][20] to identify new candidates that may be of value in designing new, potent, selective and less toxic antimicrobial agents, we report here the synthesis of some new heterocycles incorporating an indole moiety starting from cyanoacetohydrazide and isatin.…”

mentioning

confidence: 99%