20419-68-5

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine is used as an intermediate in the synthesis of 2,8-Dihydroxyadenine (D450105), a derivative of adenine. 2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine is relevant in the study and treatment of 2,8-Dihydroxyadenine Urolithiasis, a condition characterized by the accumulation of 2,8-dihydroxyadenine in the body, leading to the formation of kidney stones.
In the synthesis process, 2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine plays a crucial role as a building block for the development of potential therapeutic agents targeting adenine derivatives and related metabolic disorders.

InChI:InChI=1/C10H10Cl2N4O/c11-8-7-9(15-10(12)14-8)16(5-13-7)6-3-1-2-4-17-6/h5-6H,1-4H2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 5451-40-1 2,6 dichloropurine 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 5451-40-1 2,6-dichloro-7H-purine 
• 142-68-7 TETRAHYDROPYRANE 
• 5451-40-1 2,6-dichloropurine 
• 3174-74-1 dihydropyran 
• 69-89-6 xanthine 

Downstream Products

• 95758-01-3 2-chloro-6-(4-phenylpiperazino)-8-(2-tetrahydropyranyl)-9H-purine 
• 77111-77-4 2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine 
• 95757-99-6 2-chloro-6-(3,4-dimethoxyphenethylamino)-8-(2-tetrahydropyranyl)-9H-purine 
• 917235-39-3 6-(benzoyloxymethyl)-2-chloro-9-(tetrahydropyran-2-yl)purine 
• 917235-43-9 2,6-bis(benzoyloxymethyl)-9-(tetrahydropyran-2-yl)purine 
• 889673-54-5 2,6-bis(4-methoxyphenyl)-9-(tetrahydropyran-2-yl)-9H-purine 
• 889673-50-1 2-chloro-6-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 
• 889673-51-2 2,6-diphenyl-9-(tetrahydropyran-2-yl)-9H-purine 
• 57476-37-6 2,6-dichloro-8-methyl-9H-purine 
• 838821-29-7 2,8-dimethyl-6-phenyl-9-(tetrahydropyran-2-yl)purine 
• 838821-30-0 6,8-dimethyl-2-phenyl-9-(tetrahydropyran-2-yl)purine 
• 838821-28-6 2-chloro-8-methyl-6-phenyl-9-(tetrahydropyran-2-yl)purine 
• 838821-26-4 2,8-dichloro-6-phenyl-9-(tetrahydropyran-2-yl)purine 
• 838821-31-1 8-methyl-2,6-diphenyl-9-(tetrahydropyran-2-yl)purine 

Relevant academic research and scientific papers

Scaffold hopping of the SYK inhibitor entospletinib leads to broader targeting of the BCR signalosome

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Development of a Commercial Manufacturing Route to 2-Fluoroadenine, the Key Unnatural Nucleobase of Islatravir

We report the practical synthesis of a key fragment of islatravir (MK-8591), a novel nucleoside reverse transcriptase translocation inhibitor (NRTTI) currently under investigation for treatment and pre-exposure prophylaxis (PrEP) against HIV infection. The fragment, the unnatural nucleobase 2-fluoroadenine, is incorporated into MK-8591 via a biocatalytic aldol-glycosylation cascade, which imposes stringent requirements for its synthesis and isolation. Presented herein is the development work leading to a practical, scalable route from guanine, featuring a dual fluorination approach to a novel 9-THP-2,6-difluoropurine intermediate that enables a mild, highly selective, direct amination. This one-pot fluorination/amination sequence utilizes a direct isolation to deliver high purity 9-THP-2-fluoroadenine, which features ideal properties with respect to reactivity, solubility, and crystallinity. An acid-catalyzed liberation of 2-fluoroadenine in aqueous buffer delivers the appropriate purity profile to facilitate the enzymatic cascade to access MK-8591.

Copper-catalyzed N-alkoxyalkylation of nucleobases involving direct functionalization of sp3 CeH bonds adjacent to oxygen atoms

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Structure-activity relationship studies of QS11, a small molecule Wnt synergistic agonist

Both the Wnt/β-catenin signaling pathway and small GTPases of the ADP-ribosylation factors (ARF) family play important roles in regulating cell development, homeostasis and fate. The previous report of QS11, a small molecule Wnt synergist that binds to AR

L-ProT catalyzed highly regioselective N-alkoxyalkylation of purine rings with vinyl ethers

An efficient and regioselective synthesis of N-9 alkoxyalkylated purine nucleoside derivatives was achieved via the N-alkoxyalkylation of purine rings with vinyl ethers catalyzed by l-ProT. The advantages of this protocol include good to excellent yield,

N-9 Alkylation of purines via light-promoted and metal-free radical relay

A metal-free and light-promoted approach to the synthesis of N-9 alkylated purine nucleoside derivatives, via a CF3 radical triggered radical relay pathway, has been developed. Purine nucleoside derivatives were prepared regioselectively in good to high yields. Photosensitizers and metals are free in this transformation. Visible light or even sunlight can be used as the source of light for the reactions.

Synthesis and photophysical properties of 2-azolyl-6-piperidinylpurines

[Figure not available: see fulltext.] A synthesis of novel fluorescent 2-azolyl-6-piperidinylpurine derivatives was designed. Azolyl substituent at purine C-2 atom was introduced via nucleophilic aromatic substitution or in the case of tetrazolyl and 1,2,3-triazolyl substituents via a ring formation on a preinstalled amine or azide moiety, respectively. The obtained purine intermediates were functionalized at N-9 position using Mitsunobu reaction conditions to achieve amorphous compounds, which form thin-layer films of good quality. The synthesized push-pull systems exhibited fluorescence with emission in range of 360–400 nm and quantum yields up to 66% in CH2Cl2 solution and up to 45% in the thin-layer film.

Purine-aminomethyl-pyridone derivative, preparation method and applications thereof

The invention relates to a purine-aminomethyl-pyridone derivative, a preparation method and applications thereof, and belongs to the field of medicines, and provides a compound represented by a formula I or a pharmaceutically acceptable salt thereof. According to the invention, the pharmacodynamic experiment results prove that the purine-aminomethyl-pyridone derivative can significantly inhibit the proliferation of multiple tumor cells such as colorectal cancer, breast cancer, liver cancer, lung cancer and the like, and has broad-spectrum antitumor effect, and the IC50 values of part of the compounds can reach the nano-mole level wide and are equivalent to the effect of the anti-cancer drug doxorubicin, so that the new choice is provided for development and application of antitumor drugs.

Design, synthesis and biological evaluation of a novel tubulin inhibitor SKLB0565 targeting the colchicine binding site

A series of 3-(((9H-purin-6-yl) amino) methyl) pyridin-2(1H)-one derivatives were designed, synthesized and confirmed as tubulin polymerization inhibitors. All compounds were evaluated for their anti-proliferative activities on three colorectal carcinoma (CRC) cell lines. Among these compounds, SKLB0565 displayed noteworthy potency against eight CRC cell lines with IC50 values ranging from 0.012 μM and 0.081 μM. Besides, SKLB0565 inhibited tubulin polymerization, caused G2/M phase cell cycle arrest, depolarized mitochondria and induced cell apoptosis in CRC cells. Furthermore, SKLB0565 suppressed cell migration and disrupted the capillary tube formation of human umbilical vein endothelial cells (HUVECs). Our data clarified that SKLB0565 is a promising anti-tubulin agent for CRC therapy which is worthy of further evaluation.

PROCESS FOR THE PREPARATION OF 2-FLUOROADENINE

The present invention provides processes for the preparation of 2-fluoroadenine, as well as certain intermediates useful in the preparation of 2'-deoxy-4'-C-ethynyl-2-fluoroadenosine (EFdA): EFdA.