21047-89-2

Usage

Uses

Used in Pharmaceutical Industry:
Propanamide, N-(6,7-dihydro-6-oxo-1H-purin-2-yl)-2-methylis used as a key intermediate in the synthesis of purine nucleosides for the pharmaceutical industry. The compound plays a vital role in the enzymic transglycosylation of purine nucleobases, which is essential for the production of various therapeutic agents, including antiviral and anticancer drugs.
Used in Research and Development:
In the field of research and development, Propanamide, N-(6,7-dihydro-6-oxo-1H-purin-2-yl)-2-methylis utilized as a valuable compound for studying the mechanisms of enzymatic transglycosylation and the synthesis of purine nucleosides. This knowledge can contribute to the development of novel drugs and therapies for various diseases, particularly those related to nucleic acid metabolism and cellular signaling pathways.
Used in Biochemical Applications:
Propanamide, N-(6,7-dihydro-6-oxo-1H-purin-2-yl)-2-methylis also employed in various biochemical applications, such as the study of enzyme kinetics, enzyme inhibition, and the development of new biocatalysts for the synthesis of purine nucleosides and their derivatives. These applications can lead to advancements in the fields of biotechnology and chemical biology, ultimately benefiting human health and well-being.

Upstream product

• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 79-30-1 isobutyryl chloride 
• 97-72-3 2-Methylpropionic anhydride 
• 1468-39-9 Isovaleric anhydride 
• 73-40-5 guanine 
• 73-40-5 guanine 

Downstream Products

• 133272-03-4 9-ethyl-6-hydroxy-2-isobutyramidopurin 
• 133294-70-9 9-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-β-D-ribofuranosyl)-6-hydroxy-2-isobutyramidopurin 
• 133272-04-5 Benzoic acid (2S,3S,4R,5R)-3-(ethoxy-hydroxy-phosphorylmethyl)-4-hydroxy-5-(6-hydroxy-2-isobutyrylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester; compound with triethyl-amine 
• 133272-05-6 C₂₆H₃₁N₅O₁₀P^(1-)*Na⁽¹⁺⁾ 
• 175915-95-4 N²-isobutyryl-9-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}guanine 
• 206055-53-0 [(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-[2-(2-methylpropanoyl-amino)-6-oxo-1H-purin-9-yl]tetrahydrofuran-2-yl]methyl acetate 
• 200562-53-4 9-[2',3'-di-O-benzoyl-5'-O-(triisopropylsilyl)-β-L-ribofuranosyl]-N³-isobutyrylguanine 
• 200562-13-6 7-[2',3'-di-O-benzoyl-5'-O-(triisopropylsilyl)-β-L-ribofuranosyl]-N³-isobutyrylguanine 
• 206055-64-3 (1S,3R,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(2-N-isobutyrylguanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 185610-53-1 N²-(isobutyryl-O⁶-diphenylcarbamoyl)guanine 
• 263254-55-3 (2-Isobutyrylamino-6-oxo-1,6-dihydropurin-9-yl)acetic acid tert-butyl ester 
• 263254-54-2 (2-Isobutyrylamino-6-oxo-1,6-dihydropurin-7-yl)acetic acid tert-butyl ester 
• 372515-42-9 N²-isobutyryl-9-(2',3',4'-tri-O-benzoyl-α-L-lyxopyranosyl)guanine 
• 372515-43-0 N²-isobutyryl-7-(2',3',4'-tri-O-benzoyl-α-L-lyxopyranosyl)guanine 

Relevant academic research and scientific papers

Observation of two N2-isobutyrylguanine tautomers by NMR spectroscopy

N2-Isobutyrylguanine was prepared by treatment of guanine with isobutyryl chloride. Two tautomers, 1,7-dihydro-2-(isobutyroyl)amino-6H-purin-6- one and 1,9-dihydro-2-(isobutyroyl)amino-6H-purin-6-one, were identified in almost 1: 1 ratio in dichloromethane-dimethyl sulfoxide (1: 1 v/v) by NMR spectroscopy. By using the selective-inversion experiments, enthalpy, entropy, and free energy for activation were determined. This work represents the first report of guanine tautomers observed directly by NMR spectroscopy. Copyright

CYCLOPENTYL NUCLEOSIDE ANALOGS AS ANTI-VIRALS

Described herein are cyclopentyl nucleoside analogs, pharmaceutical compositions that include one or more cyclopentyl nucleoside analogs and methods of using the same to treat HBV, HDV and/or HIV.

A convenient route to synthesize N2-(isobutyryl)-9-(carboxymethyl)guanine for aeg-PNA backbone

Synthesis of exclusive N2-(isobutyryl)-9-(carboxymethyl)guanine, an important moiety for peptide nucleic acid synthesis has been reported through a high-yielding reaction scheme starting from 6-chloro-2-amino purine. Crystal structures of two intermediates confirmed the formation of N9-regioisomer. This new synthetic route can potentially replace the conventional tedious method with moderate overall yield.

Chirality Dependent Potency Enhancement and Structural Impact of Glycol Nucleic Acid Modification on siRNA

Here we report the investigation of glycol nucleic acid (GNA), an acyclic nucleic acid analogue, as a modification of siRNA duplexes. We evaluated the impact of (S)- or (R)-GNA nucleotide incorporation on RNA duplex structure by determining three individu

Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides

l- And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

Biocatalytic separation of N -7/ N -9 guanine nucleosides

Vorbrueggen coupling of trimethylsilylated 2-N-isobutanoylguanine with peracetylated pentofuranose derivatives generally gives inseparable N-7/N-9 glycosyl mixtures. We have shown that the two isomers can be separated biocatalytically by Novozyme-435-mediated selective deacetylation of the 5′-O-acetyl group of peracetylated N-9 guanine nucleosides.

CYCLOPENTENOL NUCLEOSIDE COMPOUNDS, INTERMEDIATES FOR THEIR SYNTHESIS AND METHODS OF TREATING VIRAL INFECTIONS

The present invention relates to compounds according to the structure (I), Where B is formula (Ia), formula (Ib) or formula (Ic); A is H, OR2 or halogen (F, Cl, Br, I, preferably F or Br, more preferably F); A' is H, OR2 or halogen (F, Cl, Br, I, preferably F or Br, more preferably F); A" is H or OR1, with the proviso that when A' is OR , A is H; and when A is OR2 , A' is H; X is C-R3 or N; Y is C-R3 or N; preferably X or Y is N and X and Y are not both simultaneously N; R3 is H or C1-C3 alkyl; D is H or NHR2; E is absent or H; G is O or NHR2; J is N or C-R4; K is N or C-H; R4 is H, halogen (F, Cl, Br, I), CN, -C(=O)NH2, NH2, NO2, -C=C-H (cis or trans) or -C≡C-H; Ra is H or CH3; Each R1 is independently H, an acyl group, a C1 - C20 alkyl or ether group, a phosphate, diphosphate, triphosphate, phosphodiester group; Each R2 is independently H, an acyl group, a C1 - C20 alkyl or ether group; and Pharmaceutically acceptable salts, solvates or polymorphs thereof.

Synthesis of 1'-phenyl substituted nucleoside analogs

l'-Phenyl substituted ribonucleoside analogs with all four nucleobases have been synthesized by the conventional N-glycosidation method.

PNA-directed triple-helix formation by N7-xanthine

We report the first example of alkylation of underivatized xanthine with chloroacetic acid to yield a separable mixture of N7- and N 9-(methylenecarboxyl)xanthine and its conversion to a peptide nucleic acid monomer compatible with Fmoc-based oligomerization chemistry. Additionally, we have simultaneously prepared the N7- and N 9-PNA monomers of guanine by alkylation of 2-N-isobutyrylguanine which were subsequently separated. Molecular modeling of the nucleobase base triplets indicates that N7-xanthine and N7-guanine form isomorphous triplets with adenine and guanine, respectively. We also show that polyamides containing N7-xanthine are compatible with triple-helix formation. Georg Thieme Verlag Stuttgart.

Fmoc/Acyl protecting groups in the synthesis of polyamide (peptide) nucleic acid monomers

The chemical synthesis of polyamide (peptide) nucleic acid (PNA) monomers 22-25 has been accomplished using Fmoc [N-(2-aminoethyl)glycine backbone], anisoyl (adenine), 4-tert-butylbenzoyl (cytosine) and isobutyryl/ diphenylcarbamoyl (guanine) protecting-group combinations, thus allowing oligomer synthesis on both peptide and oligonucleotide synthesizers. An alternative method for the preparation of (N6-anisoyladenin-9-yl)acetic acid 7 is described using partial hydrolysis of a dianisoylated derivative. Different methods were studied for guanine alkylation including (a) Mitsunobu reaction; (b) low-temperature, sodium hydride- and (c) N, N-diisopropylethylaminemediated alkylation reactions to give preferentially N9-substituted derivatives. Empirical rules are proposed for differentiating N9/N7-substituted guanines based on their 13C NMR chemical-shift differences. The Royal Society of Chemistry 2000.