ABSTRACT
A convenient method for preparation of cyclic and acyclic nucleosides was achieved by alkylation of 6-(2,4-dichlorophenoxymethyl) pyrimidine-2,4-dione (1) with a variety of acyclic and cyclic activated sugar analogues, namely (2-acetoxyethoxy)methyl acetate (3), 2-(acetoxymethoxy)propane-1,3-diyl dibenzoate (4), benzyloxymethyl acetate (5), 2-acetoxy-5-(benzoyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate (12), 5-chloro-2-((4-chlorobenzoyloxy)methyl) tetrahydrofuran-3-yl 4-chlorobenzoate (13) and 2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate (14), respectively. Deprotection of the synthesized nucleosides was achieved by using methanolic ammonia. The structures of the newly synthesized nucleoside analogues were fully characterized by analytical methods (mass spectrometry, 1H NMR, 13C NMR, and elemental analysis).
Subject(s)
Acids, Acyclic/chemistry , Antiviral Agents/chemical synthesis , Pyrimidine Nucleosides/chemical synthesis , Alkylation , Ammonia/chemistry , Catalysis , Molecular Structure , Oxidation-Reduction , Structure-Activity RelationshipABSTRACT
Some new 1,3,4-triazolo-, 1,3,4-oxadiazolo-, 1,3,4-thiadiazol-, and pyrazolo-3,4-dimethylphenyl-1(2H)-oxo-phthalazine derivatives were synthesized and identified by IR, (1)H NMR, MS and elemental analysis. Most of the newly synthesized products were tested for their anti-inflammatory activities. Among them, compounds 11, 17b, 20, 21 and 22 are active compare to the activity of indomethacin.
Subject(s)
Anti-Inflammatory Agents/chemical synthesis , Anti-Inflammatory Agents/pharmacology , Phthalazines/chemical synthesis , Phthalazines/pharmacology , Anti-Inflammatory Agents/chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Phthalazines/chemistry , Spectrophotometry, InfraredABSTRACT
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.
Subject(s)
Antiviral Agents/chemical synthesis , Antiviral Agents/pharmacology , Herpesvirus 1, Human/drug effects , Pyrazoles/chemical synthesis , Pyrazoles/pharmacology , Pyrimidines/chemical synthesis , Pyrimidines/pharmacology , Animals , Antiviral Agents/chemistry , Cell Line , Humans , Pyrazoles/chemistry , Pyrimidines/chemistryABSTRACT
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).
Subject(s)
Antiviral Agents/chemical synthesis , Antiviral Agents/pharmacology , Pyrazoles/chemistry , Pyrazoles/pharmacology , Hepatitis A virus/drug effects , Hepatitis A virus/growth & development , Herpesvirus 1, Human/drug effects , Herpesvirus 1, Human/growth & development , Molecular Structure , Structure-Activity Relationship , Viral Plaque Assay , Virus Replication/drug effectsABSTRACT
Some chromeno[4,3-b]quinolines 4a-i were obtained from beta-chloro carboxyaldehydes 3a-c with different aniline derivatives namely, aniline, 4-fluoroaniline, and 2-aminophenol. Surprisingly, 3a-c reacted with 2-aminothiophenol and afforded the chromeno[3,4-c]quinoline derivatives 5a-c. Single-crystal X-ray diffraction studies of 4e and 5b provided good support for the established structure. Compounds 4b and 5b showed significant anti-inflammatory and ulcerogenic score activities compared to that of indomethacin.
Subject(s)
Anti-Inflammatory Agents/chemical synthesis , Quinolines/chemical synthesis , Animals , Crystallography, X-Ray , Female , Male , Mice , Quinolines/chemistry , Quinolines/pharmacology , Rats , Rats, Wistar , Stomach Ulcer/chemically induced , Structure-Activity RelationshipABSTRACT
The reaction of compounds 1, 2, 3, 4, or 13 with 2-chloroethyl methyl ether or 2,3,4,6-tetra-O-acetyl-alpha-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.
Subject(s)
Anti-Infective Agents/chemical synthesis , Nucleosides/chemical synthesis , Pyrimidines/chemical synthesis , Anti-Infective Agents/pharmacology , Bacteria/growth & development , Candida albicans/growth & development , Microbial Sensitivity Tests , Nucleosides/pharmacology , Pyrimidines/pharmacologyABSTRACT
Some new aldazino 4, pyrazolo 5, thieno 8, and thiooxopyrimidino chromenes 10 were prepared via reaction of the corresponding beta-chlorocarboxaldehyde 3 with hydrazine hydrate, mercaptoacetic acid, and thiourea, respectively. Wherever, 4-chlorochromene derivatives 2 along with 4-chlorochromen-3-carboxaldehyde derivatives 3 were prepared from the corresponding ketone 1 with Vilsmeier-Haack reagent. Some of the new products showed good anti-inflammatory, analgesic, anticonvulsant, and antiparkinsonian activities comparable to indomethacin, diclofenace, carbamazepine, and benztropine.