reaction of cyanoacetyl hydrazide with cyclopentanone: synthesis of coumarin, pyridine and thiazole derivatives

This work concerns with studying the reaction of cyanoacetyl hydrazide with cyclopentanone to give the hydrazide-hydrazone derivative 3. The reactivity of compound 3 towards different chemical reagents was studied to give coumarin, pyridine and thiazole derivatives. The antimicrobial evaluation of the synthesized products was studied where most of them showed interesting activities

Antitumor activity of some new 1,3,8-trisubstituted purine-2,6-diones and 1,3,6-trisubstitutedthiazolo[2,3-f] purine-2,4-diones

New l,3,8-trisubsttiuted purine-2,6-diones and 1,3,6-trisubstituted thiazolo[2,3-f] purine-2,4-diones were designed and synthesized as potential antitumor agents. The cytotoxic effects of the tested compounds were assessed against two human malignant-cell lines: T-cell leukemia derived SKW-3 and breast cancer -derived MDA-MB-231 using the methyl thiazolyl tetrazolium [MTT-dye] reduction assay, after 72 h exposure. The data -were fitted to sigmoidal concentration response curves and the corresponding 1C 50 values were calculated using commercially available software [GraphPad Prizm]. Compound AH-206 was the most potent cytotoxic agent among the newly synthesized compounds, with 1C 50 value of 17.3 micro M. Prominent activity was also encountered with compounds AH-201, AH-205, AH-208, AH-214 and AH-217, all having 1C[50] values below 100 micro M

Use of ethyl beta-[4-hydroxyphenyl]-alpha-cyanoacrylate in the synthesis of carbazone, thiazol and imidazolidin-2-thione derivatives

Condensation of ethyl beta-[4-hydroxyphenyl]-alpha-cyanoacrylate with thiosemicarbazide gave the 4-hydroxybenzaldehyde thiosemicarbazone [3]. Treatment of 3 with acetic anhydride, 4-substituted phenacyl bromide and ethyl chloroacetate yielded the corresponding N-acetyl derivative [4], thiazol derivative [5] and 3-substituted 4-oxo-imidazolidin-2-thione [6]. Compound 6 reacted with benzyl chloride, methyl acrylate, phenyl- diazonium chloride and hydrazine hydrate to give 1-substituted imidazo-lidine-2-thione derivatives [7,8,9] and 1,2-bis [4-hydroxy-benzal-dehyde] hydrazone [10]. Treatment of 6 with acetic anhydride and 4-hydroxybenzaldehyde afforded the corresponding N-acetyl derivatives [11] and 5-substitued-imidazolidin-2-thione [12]. The mass spectral fragmentation patterns of some compounds are described

Synthesis and mass spectral fragmentation patterns of some thiazole and 2-thioxo-imidazolidin-4-one derivatives

2-[[5-ARYL-THIAZOL-2-YL]-hydrazonomethyl-phenols [2a, b] and 3-[[2-hydroxybenzylidiene]-amino]-2-thioxo-imidazolidin-4-one [3] were prepared via cyclization of salicylaldehydethiosemicarbazone [1] with omega [small latter]-bromomethyl aryl ketones and ethyl chloroacetate in presence of fused sodium acetate. Reaction of 3 with hydrazine hydrate, acetic anhydride, benzaldehyde, ethyl iodide, methyl acrylate and diazonium chloride yielded the corresponding salicylaldazine [4], 1-acetyl-3-[[2-acetoxybenzylidene]-amino]-2-thioxoimidazolidin-4-one [5], 3-[[2-hydroxybenzylidene]-amino]-5-benzylidene-2-thioxo-imidazolidin-4-one [6], 1-substituted-3-[[2-hydroxybenzylidene]-amino]-2-thioxo-imidazolidin-4-ones [8 and 9] and 3-[[5-phenylazo-2-hydroxybenzylidene]-amino]-2-thioxo-imidazolidin-l-one [10]. The mass spectral fragmentation patterns of the compounds are described

Analgesic activity of new synthetic thiazolidine-4-ones derivatives.

Ten new synthetic thiazolidine-4-ones derivatives (5 chlorothiazolidine-4-ones, 3 methoxythiazolidine-4-ones and 2 hydoxythiazolidine-4-ones) having different substituents at R1, R2 and R3 were evaluated for their analgesic activity using different animal models and their structure activity relationship was also elucidated. Chlorothiazolidine-4-ones and methoxythiazolidine-4-ones exhibited analgesic activity in tail flick test, tail immersion test and acetic acid writhing test. C-III (chloride substituents at R1 and R2) produced higher latencies than any other compounds in tail flick test and C-I (no substituents at R1 and R2) was not effective in acetic acid writhing test. Hydroxythiazolidine-4-ones did not show analgesic activity in any of the animal models used. In conclusion, the character of substituents at R3 of thiazolidine moiety position may have an effect on the analgesic activity of thiazolidine-4-ones and either chloride or methoxy substitution may be necessary to produce analgesic activity. Two chloride substituents in a compound may increase the central analgesic activity of the compound.

Synthesis of some parabanic acid and thiazoline derivatives coumarines with expected pharmacological activity part II

New parabanic acids and thiazolines derived from different coumarinyloxyacetic acid hydrazides have been prepared and subjected to preliminary pharmacological screening. Some of the tested compounds showed anticonvulsant activity

Synthesis and antischistosomal activity of some new thiazolidinones and 1,3,4-thiadiazoline

In this study, new series of thiazolidinones 3a-e was synthesized by the cyclocondensation of the Schiff bases 2a-e with mercaptoacetic acid. The thiadiazole 5 was obtained by refluxing 4 with carbondisulfide. The antischistosomal activity was determined for the new representative compounds

Synthesis of certain benzothiazole derivatives to be evaluated as anthelmintics

New derivatives of 6-nitro-2-substituted acetamidobenzothiazole [2a, 3a-e], 3-substituted 2-iminothiazolidin-4-one [4a-e] and 5-arylidene-2-iminothiazolidin-4-one [5a-j] were prepared. The testing for the anthelminitic activity of two of the newly prepared compounds using the earthworm method showed that they produce a promising effect. The detailed synthesis, spectroscopic and biological data are reported

Synthesis, estrogen receptor binding affinity and biological evaluation of some 2-thiazolylestrone and estratrieno [17,16-d] thiazole derivatives

Two series of 2-thiazolyestrone and estratrieno [17,16-d] thiazole derivatives have been designed and synthesized to study the effect of such heterocyclic rings, as modifications of estrone, on the receptor biding affinity, uterotrophic and antiimplantation activities. The key step in the synthesis involved regioselective 16-alpha bromination of 2-acetylestrone with cupric bromide avoiding 2-acetyl bromination. The other key intermediate 2-bromoacetylestrone was prepared by combined Friedel-Crafts reaction and Fries rearrangement of estrone with bromoacetyl chloride and aluminium chloride. The tested products were found to be relatively weak competitors at 0C for estrogen receptor. Uterotrophic and postcoital antifertility assays indicated variable effects relative to estradiol. Some products, particularly compounds IX and XI-XIII, induced significant increase [75-90%] in the rat uterine weight while compounds III, XI and XII displayed notable antiimplantation activity of 69-88% relative to that of estradiol. 2[2-p-chloroanilinothiazol-4-yl] estrone [XIII] had a significant agonist activity eliciting the highest uterotrophic activity [90%] while exhibiting a weak antiimplantation activity [32%]. The p-bromo XII and the p-tolyl XIV derivative imparted strong uterotrophic and antiimplantation activities

Enaminonitrile in heterocyclic synthesis: synthesis of thiazolo [4,5-b] pyridine and thiazolo [4,5-d] pyrimidine derivatives

Ammoniumn- phenyldithiocarbamate reacted with bromomalononitrile and alpha chloroacetylacetone to afford thiazole derivatives 3a, b. Compound 3a reacted with benzylidenemalononitrile, malononitrile, phenylisothiocyanate, benzoylisothiocyanate, trichloroacetonitrile, formamide, carbon disulphide and triethylorthoformate to afford thiazolo [4,5-b] pyridine derivatives 6,9 and thiazolo [4,5-d] pyrimidine derivatives 13, 16, 18, 19, 20 and 21. Most of the synthesized products show high fungicidal and bactericidal activities

Synthesis of thiosemicarbazones, thiazolines and thiazolidinones derived from Theophylline as potential anticancer agents

A series of novel thiosemicarbazone derivatives of theophylline was Synthesized, then cyclized to the corresponding thiazoline and thiazolidinone derivatives with the aim of obtaining new anticancer agents with diminished toxicity

Synthesis and reaction of 5- [6,6-dimethyl-1-4-oxo4, 5,6,7-teteahydroindol-2-yl] -1,3-diarylpyrazolines

A number of 3-[6,6-dimethyl-4-oxo-4,5,6,7-tetrahydroindol-2-yl]-1- aryl-2-propen-1-ones II-V have been prepared and transformed into the corresponding arylhydrazones VI-XI. The latter compounds were cyclized to the pyrazolines XII-XX, which were oxidized the corresponding pyrazoles XXI-XXIV. The spectral properties of the prepared compounds were discussed

Synthesis of some new pyridyl beta-lactam and thiazolidine derivatives

In search for new Beta-Lactam derivatives of modified antibiotic activity we have investigated the incorporation of pyridyl nucleus onto the Beta-Lactam moiety. Several pyridyl derivatives are known to exhibit interesting pharmacological properties as anti-inflammatory agents potentiators of adrenaline, ganglionic blockers, antiphlogistics, and postemergence agents on broad leaved plants. Thus 2-aminopyridine I was treated with aromatic aldehydes in absolute ethanol in presence of piperidine as a basic catalyst to afford Schiff bases II. Treatment of II with an acid chloride and tertiary amino would yield the desired Beta-lactam. The low yield of II in this case may be due to tautomerisation of 2-aminopyridine I/a to the mine form I/b. The presence of an electron withdrawing group would decrease such tautomerisation, and would facilitate condensation with aromatic aldehydes. Therefore nitration of 2-aminopyridine was carried out to afford a mixture of 3-and 5-nitro derivatives III and IV respectively. Interaction of IV and aromatic aldehydes afforded V[a] [R=H] in 37 percent yield. Higher yield was obtained when IV was allowed to react with 4-nitrobenzaldehyde. Treatment of V with chloroacetyl chloride and triethylamine afforded the corresponding Beta-lactam VI[6. The IR spectra of compounds VI showed a well definite absorption band at 1760-1720 cm[-1] [the C=O stretching of monocyclic Beta-latam]. The cycloaddition reactions of thioglycolic acid with the azomethine group in V was also investigated using a water separator system for about five days giving of the cyclic 4-thiazolidinone compounds VII but in low yields. The IR spectra of VII showed a definite absorption band at 1680 -1645 cm[-1] [C=O group]