Design,synthesis and immunomodulating activity of C-pseudonucleosides containing thiazolidin-4-one and phenyl connected by acetamide bond

Several novel C-pseudonucleosides containing thiazolidin-4-one and phenyl connected by acetamide bond were rationally designed and easily synthesized at room temperature by using the unprotected sugar aldehyde as the starting material. The effects of the compounds on Con A-induced T cell proliferation were evaluated at five concentrations of 5, 10, 25, 50, and 100 mmol/L Interestingly, compounds 7a and 8a (n = 2, R = H) exhibited immunostimulating activities, while compounds 5a, 6a (n = 1, R = H) and 7b, 8b (n = 2,R = CH₃) showed immunosuppressive activities. Another two compounds 5b and 6b (n = 1,R = CH3) had no immunomodulating activities. These initial biological results suggested that subtle structural changes to the phenyl and acetamide bond of C-pseudonucleosides could have a significant effect on T cell proliferation bias, although it was difficult to formulate a rigorous structureactivity relationship based on the observed activities.     

Synthesis and spectroscopic investigation of some arylazo derivatives of thiazolidin-4-one

The reaction of 2-phenylimino- and 2-(p-tolylimino)thiazolidin-4-ones with benzene-, p-nitrobenzene, p-sulfamoylbenzene-, and p-toluenediazonium chlorides in glacial acetic acid in the presence of anhydrous sodium acetate (pH of the medium 4.5–5.0) has been studied. A spectroscopic investigation in the IR and UV regions has shown that the 5-(p-nitrophenylazo) derivatives of thiazolidin-4-one exist in the azo tautomeric form; the 5-phenylazo and p-tolylazo derivatives of thiazolidin-4-one are mixtures of the azo and hydrazone tautomers.     

An efficient synthesis of new thiazolidin-4-one fused s-triazines as potential antimicrobial and anticancer agents

As a part of our endeavor toward the synthesis of new heterocyclic bioactive agents, two series of thiazolidin-4-one fused s-triazines were synthesized by applying an efficient palladium catalyzed C–C Suzuki coupling using catalyst system Pd(OAC)₂, Xphos and K₃PO₄ as a base in toluene solvent. Moreover, the synthesized analogs were further screened for their in vitro antimicrobial as well as anticancer efficacy against prostate cancer PC3 cells. Some compounds displayed remarkable antimicrobial activity and noticeable anticancer activity. It was observed that, both benzonitrile and nicotinonitrile are essential to increase the different pharmacological activities. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and MS analysis.     

Synthesis, antibacterial and antifungal activity of some derivatives of 2-phenyl-chromen-4-one

Some derivatives of 2-phenyl-chromen-4-one (flavone ring) have been synthesized and tested for antibacterial and antifungal activities along with their chalcone precursors against four human pathogenic bacteria and five plant mould fungi. The structures of the synthesized compounds were elucidated by UV, IR and¹H NMR spectroscopic techniques, and elemental analysis. The antibacterial and antifungal screens of the synthesized compounds were performed in vitro by the filter paper disc diffusion method and the poisoned food technique.     

Synthesis and anti-inflammatory activity of some benzofuran and benzopyran-4-one derivatives

New series of furosalicylic acids 3a-c, furosalicylanilides 6a-n, furobenzoxazines 8a-f, 1-benzofuran-3-arylprop-2-en-1-ones 12a,b, 6-(aryl-3-oxoprop-1-enyl)-4H-chromen-4-ones 16a-c and 6-[6-aryl-2-thioxo-2,5-dihydropyrimidin-4-yl]-4H-chromen-4-ones 17a-c were synthesized. Anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema model in rats and prostaglandin E(2) (PGE(2)) synthesis inhibition activity. Some of the tested compounds revealed comparable activity with less ulcerogenic effect than Diclofenac at a dose 100 mg/kg. All the synthesized compounds were docked on the active site of cyclooxygenase-2 (COX-2) enzyme and most of them showed good interactions with the amino acids of the active site comparable to the interactions exhibited by Diclofenac.     

Expeditive synthesis of homochiral fused tri- and tetrazoles-piperazines from β-amino alcohols

N-Cyanomethyl and N-propargyl β-amino alcohols are chlorinated with SOCl₂ and treated with NaN₃ in DMSO. A substitution/cycloaddition process affords in good yields, with high diastereoselectivity and a regioselectivity depending on the substitution pattern of the starting amino alcohol, fused tri- and tetrazoles-piperazines. These heterocycles were further lithiated with n-BuLi at the benzylic position and reacted diastereoselectively with a range of electrophiles.     

Synthesis and anticonvulsant activity of some quinazolin-4-(3H)-one derivatives

A number of 3-substituted-2-(substituted-phenoxymethyl) quinazolin-4(3H)-one derivatives 4a,b, 5a-c, 6, 7a-f, 8a-e and 9a,b have been synthesized. Their structures have been elucidated on the basis of elemental analyses and spectroscopic studies (IR, 1H-NMR, MS). A preliminary evaluation of the anticonvulsant activity of the prepared compounds has indicated that compounds 4b, 7b-f, 8a and 9b exhibit significant anticonvulsant activity, while compounds 6, 8b and 8d show mild to moderate activity.     

Synthesis and antioxidant properties of some new thiazolyl coumarin derivatives

ABSTRACT

A three-component one-pot synthesis of new thiazolyl coumarin derivatives was carried out by condensing 3-acetyl-4-hydroxycoumarin, arylaldehydes, thiourea and ammonium acetate at reflux in DMC. The optimization details of the developed novel protocol are recorded. In addition, we have also synthesized these compounds via another second route in two steps. High atom-economy, excellent yields, simple procedure, and mild reaction conditions are the important features of this one-pot protocol. The chemical structures of the newly synthesized compounds were elucidated by using analytical (IR, ¹H NMR, ¹³C NMR). Further, all the compounds were screened for their antioxidant activities.     

Synthesis of some new 4-oxo-thiazolidines,tetrazole and triazole derived from 2-SH-benzothiazole and antimicrobial screening of some synthesized

A new heterocyclic derivative of 2-mercaptobenzothiazole (MBT) comprising 4-oxothiazolidines, tetrazole and triazole, through the reaction of (MBT) with hydrazine hydrate obtained 2-hydrazobenothiazol (1), which was condensed with various aromatic aldehydes. Azomethine derivatives (2a–c) are converted into a number of 4-oxothiazolidines (3a–c) and tetrazole derivatives (4a–c), through the reaction of azomethine derivatives (2a–c) with mercaptoacetic acid and sodium azide, respectively. Also the reaction of compound (1) with triethylorthoformate and nitrous acid to produce the corresponding (triazole and tetrazole) benzothiazole (5,6) was reported.Triazole moieties reported condensation (MBT) with ethylbromo acetate and potassium hydroxide by the fusion method and resulted in ester-2-mercaptobenzothiazole (7), which was treated with hydrazine hydrate to give a hydrazine derivative (8), then converting these compounds (8) to phenyl semicarbazide (9) and phenyl thiosemicarbazide (10) derivatives. Cyclization compounds (9,10) in alkaline media (4 N·NaOH) gave triazoles compounds (11,12). Furthermore the compound (8) was converted to the dithiocarbazate salt (13) which was then cyclized with hydrazine hydrate to give substituted triazole (14). The prepared compounds were identified by spectral methods (FTIR, ¹H NMR, ¹³C NMR) and some of its physical properties were measured and furthermore the effects of the preparing compounds on some strains of bacteria were studied.     

Synthesis and structure of 4-arylspirodihydro-pyranochromen-2-one derivatives

Syntheses are reported for sulfur-and nitrogen-containing derivatives of 4-arylspiro-2-benzopyranones modified at the exocyclic oxygen atom. The structure of these products was demonstrated by correlational NMR spectroscopy. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 518–527, April, 2007.     

Synthesis of 2-thioxo-1,3-thiazolidin-4-one derivatives

A series of new 2-thioxo-1,3-thiazolidin-4-one derivatives containing arylidene, arylazo, and aminomethylene fragments in position 5 of the rhodanine cycle was synthesized. Dedicated to Academician V. A. Tartakovsky on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1564–1569, August, 2007.     

Structure and temperature controlled synthesis of novel thiazolidin-4-one derivatives bearing an azasugar

Novel thiazolidin-4-one linked pseudo-aza-disaccharides and thiazolidin-4-ones containing C-pseudo-aza-nucleosides were synthesized via a one-pot three component reaction. The former was synthesized stereoselectively by the tandem Staudinger/aza-Wittig/cyclization reaction of azasugar aldehyde 1, an azidosugar, and mercaptoacetic acid. The reaction was structure and temperature controlled, and could be performed stereospecifically under 40 °C. It was the first report of a stereospecific synthesis of thiazolidin-4-one linked derivatives. However, these derivatives were synthesized with low stereoselectivity by involving the condensation reaction of azasugar aldehyde 1, aniline, and mercaptoacetic acid.     

Synthesis of some novel 5-substituted benzamido-6-arylamino-pyrazolo[3,4-D]pyrimidin-4-one derivatives for herbicidal activity

Abstract

Sixteen novel 3-methylthio-5-substituted benzamido-6-arylamino-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4 (5H)-one derivatives (4a–p) were successfully synthesized from iminophosphoranes, aryl isocyanate, and substituted benzoylhydrazine. The structures of the title compounds were elucidated by FT-IR, ¹H NMR, ¹³C NMR, and HRMS. Herbicidal activity of the compounds 4a–p against Brassica napus (rape), Echinochloa crusgalli (barnyard grass), Cucumis sativus (cucumber), and Triticum aestivum (wheat) were determined. The results showed that 5-(2-chlorobenzamido)-6-phenylamino-3-methylthio-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4 (5H)-one (4c) displayed remarkable inhibition activity against the stalk and root of rape with 100% inhibition rate at the dosages of 10?mg/L and 100?mg/L, and 5-(4-nitrobenzamido)-6-phenylamino-3-methylthio-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4 (5H) -one (4d) exhibited excellent activity against the stalk and root of barnyard grass with 100% inhibition rate at the same dosages.     

Synthesis of some novel 2-thioxoimidazolidin-4-one substituted glycosyl hydrazone derivatives

Russian Journal of General Chemistry - A series of novel 2-thioxoimidazolidine glycosides were prepared via reaction of the key intermediate...     

Synthesis and antioxidant activities of flavonoids derivatives, troxerutin and 3’, 4’, 7-triacetoxyethoxyquercetin

Syntheses of two very important derivatives of quercetin,troxerutin and 3’,4’,7-triacetoxyethoxyquercetin were described.The latter was synthesized by highly selective esterification reaction in first time.The compounds were characterized by NMR,IR and Mass spectroscopy.Additionally,the antioxidant activities of the compounds were tested by means of improved pyrogallol autoxidation method.This was the first in using this method to test the antioxidant activities of these two compounds in vitro.The optimum system of pyorgallol autoxidation spectrophotometry was investigated and established according to the reaction rules.The assay indicated that these compounds showed noticeable antioxidant activities,and compound 2 was much more effective as a free radical scavenger than the compound 1 vitamin C was used as a reference material.     

Synthesis of 3-methyl-substituted pyrazolotriazolopyrimidin-4-one and pyrazolothiazolopyrimidin-4-one derivatives

As a part of a research on anti-inflammatory analgesic compounds 3-methyl substituted pyrazolotria-zolopyrimidin-4-one and pyrazolothiazolopyrimidin-4-one derivatives were prepared by previously reported procedures. None of the compounds showed improved activity when compared with the previously reported unsubstituted analogs.     

Synthesis of some 5H-benzo[a]phenothiazin-5-one derivatives

Several substituted 6-anilino-5H-benzo[a]phenothiazin-5-one derivatives were prepared by condensation of substituted 1,4-naphthoquinones with 2-aminobenzenethiol in pyridine. The reduction and acetylation of the resulting compounds were also investigated.

---

Synthese einiger 5H-Benzo[a]phenothiazin-5-on-Derivate

Zusammenfassung Es wurden mittels Kondensation substituierter 1,4-Naphthochinone mit 2-Aminothiophenol in Pyridin einige substituierte 6-Anilino-5H-benzo[a]phenothiazin-5-one dargestellt. Die Reduktion und Acetylierung der resultierenden Verbindungen wurde ebenfalls untersucht.