399024-19-2

Upstream product

• 362505-25-7 1-[5-O-Benzoyl-3-azido-2,3-dideoxy-α,β-D-erythro-pentofuranosyl]-thymine 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 25442-42-6 5'-O-trityl-2,3'-anhydrothymidine 
• 123533-06-2 3'-azido-3'-deoxy-5'-O-thexyldimethylsilylthymidine 
• 136011-36-4 1-(3-azido-2,3-dideoxy-β-D-ribo-hexofuranosyl)thymine 
• 108441-68-5 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-4-methoxy-5-methyl-2(1H)-pyrimidinone 
• 162332-45-8 C₁₀H₁₂N₅O₇P^(2-) 
• 151029-28-6 5',5'-Di-O-(3'-azido-2',3'-dideoxythymidinyl) H-phosphonate diester 
• 166318-76-9 1-Hydroxy-1-phenylmethylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester 
• 166318-75-8 1-Hydroxy-1-(4-methylphenyl)methylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester 
• 166318-77-0 1-Hydroxy-1-(4-chlorophenyl)methylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester 
• 166318-74-7 1-Hydroxy-1-(4-methoxyphenyl)methylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester 
• 166318-78-1 1-Hydroxy-1-(4-cyanophenyl)methylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester 
• 164652-13-5 1-Hydroxy-1-(2-nitrophenyl)methylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester 

Downstream Products

• 151239-37-1 3'-azido-3'-deoxythymidine-5'-O-(dibenzyl phosphate) 
• 151239-29-1 3'-Azido-3'-deoxythymidin-5'-yl bis(4-acetoxybenzyl) phosphate 
• 151239-32-6 3'-Azido-3'-deoxythymidin-5'-yl bis(4-pivaloyloxybenzyl) phosphate 
• 92586-35-1 Zidovudine triphosphate 
• 141171-21-3 3'-azido-3'-deoxythymidine 5'-<β,γ-imido>triphosphate 
• 171284-23-4 4-acetyloxybenzyl bis(3'-azido-3'-deoxythymidin-5-yl) phosphate 
• 171284-24-5 4-butanoyloxybenzyl bis(3'-azido-3'-deoxythymidin-5-yl) phosphate 
• 90053-16-0 3'-amino-3'-deoxythymidine-5'-triphosphate 

Relevant academic research and scientific papers

Synthesis and anti-HIV activity of triazolo-fused 3′,5′-cyclic nucleoside analogues derived from an intramolecular Huisgen 1,3-dipolar cycloaddition

Triazolo-fused 3′,5′-cyclic nucleoside analogues were synthesized by an intramolecular 1,3-dipolar cycloaddition of nucleoside-derived azido-alkynes in a regio- and stereospecific manner. The thymine nucleoside base in these target compounds was transform

Synthesis method of (1 beta, 2 alpha, 4 beta) halogenated nucleoside compound

The invention provides a synthesis method of a (1 beta, 2 alpha, 4 beta) halogenated nucleoside compound, and belongs to the field of organic synthesis. The synthesis method comprises the following steps of dissolving a compound 1 and a chiral phosphoric acid small-molecule catalyst in a solvent to obtain a mixed solution, adding an additive and a halogen source into the mixed solution, and carrying out an olefin asymmetric halogen cyclization reaction to prepare the (1 beta, 2 alpha, 4 beta) halogenated nucleoside compound as shown in a formula I. The synthesis method is simple and convenient in process, suitable for various reaction substrates and wide in application; and the synthesis method has high stereoselectivity on the beta-nucleoside compound and low cost, and the obtained beta-nucleoside compound has the advantages of high yield, high purity and very excellent effect. Meanwhile, the synthesis method is environment-friendly due to no use of a metal catalyst and the like. The synthesis method disclosed by the invention solves the technical problem of preparing the (1 beta, 4 beta) nucleoside compound in the prior art, can be used for efficiently preparing the (1 beta, 4 beta) nucleoside compound, and has a good application prospect.

Modular click chemistry libraries for functional screens using a diazotizing reagent

Click chemistry is a concept in which modular synthesis is used to rapidly find new molecules with desirable properties1. Copper(i)-catalysed azide–alkyne cycloaddition (CuAAC) triazole annulation and sulfur(vi) fluoride exchange (SuFEx) catalysis are widely regarded as click reactions2–4, providing rapid access to their products in yields approaching 100% while being largely orthogonal to other reactions. However, in the case of CuAAC reactions, the availability of azide reagents is limited owing to their potential toxicity and the risk of explosion involved in their preparation. Here we report another reaction to add to the click reaction family: the formation of azides from primary amines, one of the most abundant functional groups5. The reaction uses just one equivalent of a simple diazotizing species, fluorosulfuryl azide6–11 (FSO2N3), and enables the preparation of over 1,200 azides on 96-well plates in a safe and practical manner. This reliable transformation is a powerful tool for the CuAAC triazole annulation, the most widely used click reaction at present. This method greatly expands the number of accessible azides and 1,2,3-triazoles and, given the ubiquity of the CuAAC reaction, it should find application in organic synthesis, medicinal chemistry, chemical biology and materials science.

A preparation method of zidovudine

The invention relates to a preparation method of zidovudine. The method is a one kettle way, has characteristics of not separating intermediate products prepared in the separation and purification steps and continuously carrying out three-step reactions to directly prepare a reaction liquid containing zidovudine, and has advantages as follows: raw materials for reactions are cheap and easily available; there is no need to separate and purify reaction intermediate products; reactions are continuous; reaction operation steps are few; preparation period is short; preparation is simple; there are few three wastes (waste gas, waste water and industrial residue) and wastes are easy to recover and process; cost is low; reaction yield of zidovudine reaches up to more than 72%; and the method is easy for industrial production.

Antimalarial naphthoquinones. Synthesis via click chemistry, in vitro activity, docking to PfDHODH and SAR of lapachol-based compounds

Lapachol is an abundant prenyl naphthoquinone occurring in Brazilian Bignoniaceae that was clinically used, in former times, as an antimalarial drug, despite its moderate effect. Aiming to search for potentially better antimalarials, a series of 1,2,3-triazole derivatives was synthesized by chemical modification of lapachol. Alkylation of the hydroxyl group gave its propargyl ether which, via copper-catalyzed cycloaddition (CuAAC) click chemistry with different organic azides, afforded 17 naphthoquinonolyl triazole derivatives. All the synthetic compounds were evaluated for their in vitro activity against chloroquine resistant Plasmodium falciparum (W2) and for cytotoxicity to HepG2 cells. Compounds containing the naphthoquinolyl triazole moieties showed higher antimalarial activity than lapachol (IC50 123.5 μM) and selectivity index (SI) values in the range of 4.5–197.7. Molecular docking simulations of lapachol, atovaquone and all the newly synthesized compounds were carried out for interactions with PfDHODH, a mitochondrial enzyme of the parasite respiratory chain that is essential for de novo pyrimidine biosynthesis. Docking of the naphthoquinonolyl triazole derivatives to PfDHODH yielded scores between ?9.375 and ?14.55 units, compared to ?9.137 for lapachol and ?12.95 for atovaquone and disclosed the derivative 17 as a lead compound. Therefore, the study results show the enhancement of DHODH binding affinity correlated with improvement of SI values and in vitro activities of the lapachol derivatives.

Methyl ketone derivative, and preparation method and applications thereof

The invention discloses a methyl ketone derivative, and a preparation method and applications thereof. The preparation method comprises following steps: a ketone derivative and an organic peroxide are dissolved in a solvent, and reaction is carried out at 80 to 130 DEG C so as to obtain methyl pyrimidone and a methyl pyrimidone derivative. According to the preparation method, the ketone derivative is taken as a starting material; the raw materials are easily and widely available; products of different kinds can be obtained via the preparation method, and can be used directly or used in other further reaction. No metal is involved, so that the preparation method is suitable to be applied in pharmaceutical preparation technology. The preparation method is short in route, mild in reaction conditions, simple in reaction operation and postprocessing process, and high in yield, and is suitable for large-scale production.

Zidovudine derivative with antimicrobial activity and preparation method and application thereof

The invention discloses a zidovudine derivative with the antimicrobial activity and a preparation method and application thereof, and belongs to the technical filed of synthesis of drugs with antimicrobial activity. The zidovudine derivative with the antimicrobial activity is technologically characterized in that the structural formula of the zidovudine derivative with the antimicrobial activity is shown in the specification, wherein R in the structural formula is C1-4 alkyl or halogen atoms. The invention further discloses a specific synthesis process of the zidovudine derivative with the antimicrobial activity and the application of the zidovudine derivative with the antimicrobial activity in antibacterial drug preparation. According to the zidovudine derivative with the antimicrobial activity, zidovudine molecules contain azide groups and are subjected to the click reaction with aniline polyacetylenes with different substituent groups, so that the zidovudine derivative is obtained; and gram-positive bacterium-staphylococcus aureus and Gram-negative bacterium-escherichia coli and fungus-Candida albicans are selected to be used for measuring the in-vitro antimicrobial activity of the synthesized zidovudine derivative, and the result shows that the zidovudine derivative has good antimicrobial activity.

Method for synthesizing zidovudine-1,2,3-triazole compound

The invention discloses a method for synthesizing a zidovudine-1,2,3-triazole compound, belonging to the technical field of antibacterial active medicines. According to the technical scheme of the invention, the specific route of the method for synthesizing the zidovudine-1,2,3-triazole compound is as shown in the specification. According to the method, on the basis that zidovudine molecules comprise azide groups, click reaction can be performed to enable zidovudine to react with aniline allylene compounds with different substituent groups so as to obtain the zidovudine-1,2,3-triazole compound, moreover gram-positive bacterium-staphylococcus aureus, gram-negative bacterium-escherichia coli and fungus-candida albicans are selected to perform in-vitro antibacterial activity testing on the zidovudine-1,2,3-triazole compound, and the results show that the compound has relatively good antibacterial activity.

Intermediate preparation zidovudines and method

Disclosed is a method for preparing zidovudine (B). The method comprises the following steps: 1) 2'-halothymidine (A) is used as the raw material to obtain a compound of formula (I) by protecting the hydroxyl group thereof in the 5'-position; 2) the compound of formula (I) is subjected to the acylation of the hydroxyl group in the 3'-position to obtain a compound of formula (VI); 3) the compound of formula (VI) is dehalogenated to obtain a compound of formula (111); 4) the compound of formula (III) is subjected to an elimination reaction to obtain a compound of formula (IV); 5) the compound of formula (IV) is subjected to an azidation reaction to obtain a compound of formula (V); and 6) the compound of formula (V) is deprotected to obtain zidovudine (B); the specific reaction formula being shown in (C)below. In the formulae: X is a halogen, P1 is a protecting group for hydroxyl; and P2 is C1-C4 alkylsulfonyl, fluoro-C1-C4 alkylsulfonyl, arylsulfonyl or -CS-R, wherein R is C1-C4 alkyl.

BIOCATALYTIC PRODUCTION OF NUCLEOSIDE ANALOGUES AS ACTIVE PHARMACEUTICAL INGREDIENTS

A biocatalytic process for producing active pharmaceutical ingredients (APIs) or intermediates thereof, wherein those APIs or their intermediates are nucleoside analogues (NAs) of formula I and wherein said NAs are active as pharmaceutically relevant antivirals and anticancer medicaments, intermediates or prodrugs thereof.