Synthesis Of Nucleosides Analogues Substituted With Oxy Amino Acetylenic Derivatives
This work describes the synthesis of 5-(5'-(4-disubstituted amino-butyn-2-yl)oxy-b-D-ribofuranose) uracil.For the synthesis of these compounds, 5-(b-D-ribofuranose) uracil wasconverted to its 5-(2',3'-O-isopropylidene-b-D-ribofuranose) uracil (1), itcontains the free hydroxyl group at...
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| Format: | Article |
| Language: | English |
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Unviversity of Technology- Iraq
2007-08-01
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| Series: | Engineering and Technology Journal |
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| Online Access: | https://etj.uotechnology.edu.iq/article_181288_57260a65551db40a85ee9c2e0dd36081.pdf |
| _version_ | 1797325111332700160 |
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| author | M. Hala |
| author_facet | M. Hala |
| author_sort | M. Hala |
| collection | DOAJ |
| description | This work describes the synthesis of 5-(5'-(4-disubstituted amino-butyn-2-yl)oxy-b-D-ribofuranose) uracil.For the synthesis of these compounds, 5-(b-D-ribofuranose) uracil wasconverted to its 5-(2',3'-O-isopropylidene-b-D-ribofuranose) uracil (1), itcontains the free hydroxyl group at C-5 for the required chemicalmodification. Accordingly (1) was prepared from 5-(b-D-ribofuranose) uraciland acetone using anhydrous ferric chloride (FeCl3) as Lewis acid catalyst.The treatment of (1) with propargyl bromide in benzene in a phase transferconditions in presence of tetrabutyl amonium bromide and 2% sodiumhydroxide solution yielded acetylenic ether derivative 5-(2',3'-Oisopropylidene-5'-(propyn-2-yl) oxy-b-D-ribofuranose) uracil (2), which wassubjected to Mannich reaction with secondary aliphatic amines andparaformaldehyde to give the acetylenic amino oxy derivatives (3a-f). Thetreatment of (3a-f) with sulfuric acid at room temperature affected selectivelythe removal of acetal group at 2',3'-position giving (4a-f) in good yield.The aim of the present work is the preparation of new carbohydratederivatives containing acetylenic amines soluble in water, which possess apossible biological activity. |
| first_indexed | 2024-03-08T06:05:19Z |
| format | Article |
| id | doaj.art-38bcb430a8aa48d48ae79ba4aa8712ca |
| institution | Directory Open Access Journal |
| issn | 1681-6900 2412-0758 |
| language | English |
| last_indexed | 2024-03-08T06:05:19Z |
| publishDate | 2007-08-01 |
| publisher | Unviversity of Technology- Iraq |
| record_format | Article |
| series | Engineering and Technology Journal |
| spelling | doaj.art-38bcb430a8aa48d48ae79ba4aa8712ca2024-02-04T17:54:42ZengUnviversity of Technology- IraqEngineering and Technology Journal1681-69002412-07582007-08-0125670271010.30684/etj.25.6.2181288Synthesis Of Nucleosides Analogues Substituted With Oxy Amino Acetylenic DerivativesM. HalaThis work describes the synthesis of 5-(5'-(4-disubstituted amino-butyn-2-yl)oxy-b-D-ribofuranose) uracil.For the synthesis of these compounds, 5-(b-D-ribofuranose) uracil wasconverted to its 5-(2',3'-O-isopropylidene-b-D-ribofuranose) uracil (1), itcontains the free hydroxyl group at C-5 for the required chemicalmodification. Accordingly (1) was prepared from 5-(b-D-ribofuranose) uraciland acetone using anhydrous ferric chloride (FeCl3) as Lewis acid catalyst.The treatment of (1) with propargyl bromide in benzene in a phase transferconditions in presence of tetrabutyl amonium bromide and 2% sodiumhydroxide solution yielded acetylenic ether derivative 5-(2',3'-Oisopropylidene-5'-(propyn-2-yl) oxy-b-D-ribofuranose) uracil (2), which wassubjected to Mannich reaction with secondary aliphatic amines andparaformaldehyde to give the acetylenic amino oxy derivatives (3a-f). Thetreatment of (3a-f) with sulfuric acid at room temperature affected selectivelythe removal of acetal group at 2',3'-position giving (4a-f) in good yield.The aim of the present work is the preparation of new carbohydratederivatives containing acetylenic amines soluble in water, which possess apossible biological activity.https://etj.uotechnology.edu.iq/article_181288_57260a65551db40a85ee9c2e0dd36081.pdfnudeosides analoguesamino acetylenic |
| spellingShingle | M. Hala Synthesis Of Nucleosides Analogues Substituted With Oxy Amino Acetylenic Derivatives Engineering and Technology Journal nudeosides analogues amino acetylenic |
| title | Synthesis Of Nucleosides Analogues Substituted With Oxy Amino Acetylenic Derivatives |
| title_full | Synthesis Of Nucleosides Analogues Substituted With Oxy Amino Acetylenic Derivatives |
| title_fullStr | Synthesis Of Nucleosides Analogues Substituted With Oxy Amino Acetylenic Derivatives |
| title_full_unstemmed | Synthesis Of Nucleosides Analogues Substituted With Oxy Amino Acetylenic Derivatives |
| title_short | Synthesis Of Nucleosides Analogues Substituted With Oxy Amino Acetylenic Derivatives |
| title_sort | synthesis of nucleosides analogues substituted with oxy amino acetylenic derivatives |
| topic | nudeosides analogues amino acetylenic |
| url | https://etj.uotechnology.edu.iq/article_181288_57260a65551db40a85ee9c2e0dd36081.pdf |
| work_keys_str_mv | AT mhala synthesisofnucleosidesanaloguessubstitutedwithoxyaminoacetylenicderivatives |