114978-80-2

Usage

Uses

Used in Pharmaceutical Industry:
(2Z)-4-(6-amino-9H-purin-9-yl)but-2-en-1-ol is used as a pharmaceutical compound for its potential role in drug development. Its unique structure and presence in nucleic acids suggest that it may have therapeutic applications, although further research is needed to fully understand its properties and potential uses.
Used in Drug Development:
(2Z)-4-(6-amino-9H-purin-9-yl)but-2-en-1-ol is used as a starting material or intermediate in the synthesis of other purine-based drugs. Its structural features may allow for the development of new drugs with novel mechanisms of action, potentially leading to more effective treatments for various diseases and conditions.
Used in Research:
(2Z)-4-(6-amino-9H-purin-9-yl)but-2-en-1-ol is used as a research tool to study the structure and function of purine derivatives in biological systems. Understanding the role of (2Z)-4-(6-amino-9H-purin-9-yl)but-2-en-1-ol in nucleic acids and other biological processes can provide valuable insights into the development of new drugs and therapies.

Upstream product

• 114978-79-9 4-(6-Amino-purin-9-yl)-but-2-yn-1-ol 
• 131656-26-3 (Z)-N⁹-(4-chloro-2-buten-1-yl)adenine 
• 66224-66-6 adenine 
• 114978-78-8 9-<1-(benzoyloxy)but-2-yn-1-yl>adenine 
• 18055-47-5 N-Benzoyl-N,9-bis(trimethylsilyl)adenin 
• 164211-99-8 9-[(2'Z)-4'-hydroxy-2'-buten-1'-yl]-N⁶-benzoyladenine 
• 116664-17-6 9-<(Z)-4-(benzyloxy)but-2-en-1-yl>adenine 

Downstream Products

• 164212-01-5 N⁶-benzoyl-9-<(Z)-4-<(ethylphosphonyl)methoxy>but-2-en-1-yl>adenine 
• 164211-99-8 9-[(2'Z)-4'-hydroxy-2'-buten-1'-yl]-N⁶-benzoyladenine 

Relevant academic research and scientific papers

An expeditious and efficient procedure for the synthesis of unsaturated acyclonucleosides of Z configuration related to D4T

Enantiopure 2,5-dihydrofuran derivatives were prepared from (S)-glycidol through a new reaction sequence involving epoxide opening with a vinylcuprate, selenium-induced cyclization to give exclusively the 5-endo product, and regioselective selenoxide elimination. Unsaturated acyclonucleosides of Z configuration were obtained in a straight-forward manner by treating 2,5-dihydrofuran with iodotrimethylsilane in the presence of silylated purinic or pyrimidinic bases. This synthetic process involves opening of the dihydrofuran ring by trimethylsilyl iodide and substitution of iodine by the nucleic base in a single reaction step.

Novel open-chain nucleotides imitating 2',3'-dideoxy-2',3'- didehydronucleotides: Synthesis and substrate properties toward DNA polymerases

A new series of acyclic nucleotide diphosphates was synthesized and evaluated as potential inbibitors of HIV reverse transcriptases.

Novel acyclic nucleotides and nucleoside 5'-triphosphates imitating 2',3'- dideoxy-2',3'-didehydronucleotides: Synthesis and biological properties

A series of pyrophosphoryl (Z)-(phosphonomethoxy)but-2-enyl derivatives of pyrimidines and purines 9a-d and the corresponding phosphonates 10a-d were synthesized. The prepared compounds contain the phosphonate group as an α- phosphate mimic as well as an

Unsaturated and Carbocyclic Nucleoside Analogues: Synthesis, Antitumor, and Antiviral Activity

A series of unsaturated analogues of nucleosides were prepared and their cytotoxic, antitumor, and antiviral activities were investigated.Alkylation of cytosine with (E)-1,4-dichloro-2-butene gave chloro derivative 2f, which was hydrolyzed to alcohol 2h.Cytosine, adenine, 2-amino-6-chloropurine, thymine, and (Z)-1,4-dichloro-2-butyne gave compounds 4c-f, which, after hydrolysis, afforded alcohols 4a, 4b, 4g, and 4h.Alkenes 4d and 4e were cyclized to heterocycles 12 and 13.Alkylation of 2,6-diaminopurine with 1,4-dichloro-2-butene led to chloro derivative 6a, which was hydrolyzed to alcohol 6b.Allenic isomerization of 6b gave compound 5c.Chloro derivatives 2e-g, 4c-f, 5d, and 6c-e as well as pyrimidine oxacyclopentenes 9c and 9d are slow-acting inhibitors of murine leukemia L1210 of IC50 10-100 μM.The most active were analogues 4c, 4d, 4e, and 6e (IC50 10-20 μM).The corresponding hydroxy derivatives were less active of inactive.Inhibition of macromolecular synthesis with compounds 4c, 4d, 6e, 9c, and 9d follows the order: DNA > RNA >/ protein.Cytotoxic effects of 4c, 6e, and 9d are not reversed with any of the four basic ribonucleosides or 2'-deoxyribonucleosides.Inhibitory activity of cytosine derivative 9c is reversed with uridine and 2'-deoxyuridine but not with the corresponding cytosine nucleosides.Zone assays in several tumor cell lines show that active compounds are cytotoxic agents with little selectivity for tumor cells.Analogue 6c showed 16.7percent ILS in leukemia P388/o implanted ip in mice at 510 and 1020 mg/kg, respectively.Cytallene (5b) and 6'β-hydroxyaristeromycin (10) exhibited significant activity against Friend and Rauscher murine leukemia viruses.The rest of the hydroxy derivatives, with the exception of 4a, were moderately effective or inactive as antiviral agents.None of the chloro derivatives or oxacyclopentenes exhibited an antiviral effect at noncytotoxic concentrations.Z-Olefin 4b and 2-aminoadenallene (5c) are substrates for adenosine deaminase.

Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase

A series of 9-(hydroxyalkenyl)purines (adenines and 3-deazaadenines), which are analogues of neplanocin A, were synthesized. The analogues were tested as inhibitors of bovine liver and murine L929 cell S-adenosylhomocysteine (AdoHcy) hydrolase (EC 3.3.1.1) and as inhibitors of vaccinia virus replication in murine L929 cells. Compounds 1b, 2a, 2b, 4a, 4b, 7, 9a, and 9b showed the best inhibitory effects toward bovine liver AdoHcy hydrolase, with compound 4b being the most potent. The compounds that were shown to be the most potent inhibitors of the bovine liver AdoHcy hydrolase all contained an allylic hydroxyl group in the cis position to the adenine or the 3-deazaadenine rings. It was concluded that the cis arrangement of the allylic hydroxyl groups in these acyclic compounds represented the minimum structural requirement of the trihydroxycyclopentenyl ring of neplanocin A to show inhibitory effects against AdoHcy hydrolase. The antiviral effects of these acyclic analogues were significantly less than neplanocin A; however, there appears to be a correlation between the antiviral activity and the inhibition of AdoHcy hydrolase for compounds 2a, 2b, 4a, 4b, and 7. Analogue 4b, which exhibited the best antiviral activity (IC50=70 μM) in this acyclic series, is substantially less potent than neplanocin A (IC50=0.08 μM) as an antiviral agent.

Synthesis and antiherpetic activity of (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds

A series of analogues of acyclovir and ganciclovir were prepared in which conformational constrainst were imposed by incorporation of a cyclopropane ring or unsaturation into the side chain. In addition, several related base-modified compounds were synthesized. These acyclonucleosides were evaluated for enzymatic phosphorylation and DNA polymerase inhibition in a staggered assay and for inhibitory activity against herpes simplex virus types 1 and 2 in vitro. Certain of the guanine or 8-azaguanine derivatives were good substrates for the viral thymidine kinase and were further converted to triphosphate, but none was a potent inhibitor of the viral DNA polymerase. Nevertheless, one member of this group, (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine (3a), displayed significant antiherpetic activity in vitro, superior to that of the corresponding cis olefin 4a. Another group, typified by (±)-9-[[(E)-2-(hydroxymethyl)cyclopropyl]methyl]adenine (17b), possessed modest antiviral activity despite an apparent inability to be enzymatically phosphorylated. The relationship of side-chain conformation and flexibility to biological activity in this series is discussed.