Farouk M. E. Abdel-Megeid

Synthesis and antiviral evaluation of some new pyrazole and fused pyrazolopyrimidine derivatives

Some novel substituted pyrazole and pyrazolo[3,4-d]pyrimidine derivatives 2, 4, 8, and 9 were synthesized. Also, some acyclic S-nucleosides of pyrazolo[3,4-d]pyrimidine derivatives 10-13 were prepared via reaction of pyrazolo[3,4-d]pyrimidine-4(3H)-thione derivative 9 with some acyclic sugars. Moreover, the N-nucleoside derivative 14 was prepared via reaction of compound 8 with glucosamine hydrochloride. The antiviral evaluation of some selected new products showed that they have promising antiviral activity against hepatitis-A virus (HAV) and herpes simplex virus type-1 (HSV-1).

Synthesis and anti-HSV-1 evaluation of some pyrazoles and fused pyrazolopyrimidines

5-Amino-1-substituted-1H-pyrazole-4-carbonitrile derivative 1 was used as a precursor for preparation of some novel substituted pyrazole and pyrazolo[3,4-d]pyrimidine derivatives 2-10. Furthermore, the preparation of sugar hydrazone derivatives 11a,b, 12a,b and their annelated C-nucleosides 13a,b was described. Some of the prepared products revealed promising antiviral activity against herpes simplex virus type-1 (HSV-1) in comparison to Acyclovir as a control.

Synthesis, Reactions, and Antimicrobial Activity of Some Fused Thieno[2,3-d]pyrimidine Derivatives

Some new indeno[1′,2′ :4,5]thieno[2,3-d]pyrimidines were prepared from the reaction of 2-aminoindeno[2,1-b]thiophene-3-carbonitrile ( 1 ) with different reagents. Also, some indeno[1′,2′ :4,5]thieno[3,2-e]tetrazolo[1,5-c]pyrimidines and indeno[1′,2′ :4,5]thieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidines and their isomeric [1,2,4]triazolo[1,5-c]pyrimidines were prepared. The antimicrobial evaluation of some prepared products showed that many of them revealed promising antimicrobial activity.

Synthesis And Antimicrobial Activity Of Some Cyclic And Acyclic Nucleosides Of Thieno[2,3-d]Pyrimidines

The reaction of compounds 1, 2, 3, 4, or 13 with 2-chloroethyl methyl ether or 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide, afforded some acyclic and cyclic nucleosides of thieno[2,3-d]pyrimidine derivatives. Furthermore, cyclic C-nucleosides 24 and 25 were prepared from the reaction of 20, 21 or from 26, 27 with D-glucose. The antimicrobial evaluation of some prepared products showed promising antimicrobial activity.

Preparation and some reactions ofD-glucosyl derivatives of 2-thioxo-1,3,4-oxadiazoles and 2-thioxo-1,3,4-thiadiazoles and their 2-oxo analogues

Abstract 2-Thioxo-1,3,4-oxadiazoles (1a,b) and 2-thioxo-1,3,4-thiadiazoles (1c,d) reacted with tetra- O -acetyl-α- D -glucopyranosyl bromide in the presence of potassium hydroxide to yield thioglucosides (2a–d , respectively, in good yield) and N -glucosyl derivatives (3a–d , respectively, in poor yield). Oxidation of 2a–d with potassium permanganate yielded the corresponding sulphones (4a–d) , whereas 3a–d yielded the corresponding 2-oxo derivatives (5a–d) . The acetates 2a–d , 3a–d , and 5a–d were deacetylated with ammonia to give the parent D -glucosyl derivatives. The products were characterized by u.v. and i.r. spectroscopy.

Synthesis and Antitumor Evaluation of Some Newly Synthesized Pyrazolopyrimidine and Pyrazolotriazolopyrimidine Derivatives

A series of novel pyrazolo[3,4-d]pyrimidine 2b, 3, 5b, pyrazolotetrazolopyrimidine 4, and pyrazolotriazolopyrimidine derivatives 6a,b–10a,b have been synthesized and characterized by elemental analysis and spectroscopic data. Furthermore, the cytotoxicity and in vivo antitumor evaluation of some prepared compounds have been assessed, and derivatives 1a and 6b revealed promising activity in comparison to that of Cisplatin. Supplemental materials are available for this article. Go to the publishers online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Anticancer Evaluation of Tris(triazolyl)triazine Derivatives Generated via Click Chemistry

Click chemistry has been utilised for the preparation of new tris(triazolyl)triazines containing aliphatic and polar side chains through coupling of 2,4,6-triethynyl-[1,3,5]triazines, which possess free terminal alkyne moieties with substituted aromatic azides. The cytotoxic activity and in vitro anticancer potential of the newly synthesised compounds have been evaluated against seven human cancer cell lines including liver HepG2, breast MCF-7, lung A549, acute myeloid leukemia HL-60, colon HCT116, and prostate PC3 cancer cell lines in addition to human normal melanocyte, HFB4. The results revealed that all the compounds did not exhibit any activity against A549, HL-60, and PC3. However compound G2 was effective against MCF-7 and HepG2 cancer cell lines. On the other hand, compound G1a exhibited higher potency against MCF-7 and HepG2 cells with no toxicity on normal cells in comparison with the standard drug doxorubicin.

Synthesis and Characterization of New 3″,5″-DIARYL-3″H-Dispiropyran/Thiopyran[4,2′-Chroman-3′,2″-[1,3,4-Thiadiazol]-4′-One Derivatives and Related Compounds as Anticancer and Antiviral Agents

GRAPHICAL ABSTRACT Abstract A series of 3″,5″-diaryl-3″H-dispiropyran/thiopyran[4,2′-chroman-3′,2″-[1,3,4-thiadiazol]-4′-ones 5a-n were synthesized from the reaction of trispiro[tetrahydropyran(tetrahydrothiopyran)-4,5′-2H-chromeno-[3,4-e][1,3,4]oxadithiin-2′,3″-chroman-2″4′″-tetrahydropyran-(tetrahydrothiopyran)]-4″-ones 3a,b with nitrilimines (generated in situ via triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides). A single crystal diffraction of compound 5a adds support for the established structure. The results of the anticancer evaluation against human breast adenocarcinoma MCF-7 cell line through inhibiting of human tyrosine kinase showed that most of the tested compounds possess antiproliferative activity as potent to moderate growth inhibitory activity, especially compounds 3b, 5a, 5c, 5e, 5g, and 5k. Also, the prepared compounds were tested against rotavirus Wa strain and adenovirus type 7 and the results showed that two compounds (5e,n) were active.

Three-component Reaction of Cycloheptanone, 6-Amino-1,3-Dimethyluracil and Aromatic Aldehydes; X-Ray Structure, and Anti-inflammatory Evaluation of the Products

1,3-Dimethyl-5-aryl-1,6,7,8,9,10-hexahydrocyclohepta[5,6]pyrido[2,3-d]pyrimidine-2,4-diones 4a, b (the linear regioisomers) and the Schiff bases, 6-N-benzylidenamino-1,3-dimethyluracil derivatives 5a, b, were isolated from a three-component reaction of cycloheptanone, 6-amino-1,3- dimethyluracil, and 4-chloro- or 4-bromobenzaldehyde. Surprisingly, 1,3-dimethyl-10-aryl-1,5,6,7, 8,9-hexahydrocyclohepta[4,5]pyrido-[2,3-d]pyrimidine-2,4-diones 6f, g (the angular regioisomers which are described for the first time in the literature under the given reaction conditions) and the Schiff bases, 6-N-benzylidenamino-1,3-dimethyluracil derivatives 5f, g, were isolated and characterized from the reaction with 4-methoxybenzaldehyde and 4-cyanobenzaldehyde. However, the three-component reaction of 6-amino-1,3-dimethyluracil, cycloheptanone, and 2-methoxybenzaldehyde afforded 1,3-dimethylbenzo[4,5]pyrido[3,2-d]pyrimidine-3,4-dione (7). Single crystal X-ray diffraction and 13C NMR studies of 4a and 6f provided support for the established structures. Some of the new products were tested for antiinflammatory activity comparable to indomethacin.