525-79-1

Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H341 (97.92%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

Precautionary Statement Codes:

P203, P281, P318, P405, and P501

Hazard Classes and Categories:

Muta. 2 (97.92%)

Hazards Summary:

An irritant; [MSDSonline]

Usage

Uses

Used in Pharmaceutical Industry:
6-Furfurylaminopurine is used as a treatment for age-related photodamage of skin, as it has been shown to partially reverse the clinical signs of photodamaged skin and demonstrate a good safety profile. It also has potential in treating psoriasis and other proliferative skin disorders.
Used in Plant Growth Regulation:
6-Furfurylaminopurine is used as an auxin, plant growth regulator, and plant cell division promotor. It acts as a plant growth accelerator and is also used as a cell division factor found in various plant parts and in yeast. Additionally, it serves as a plant growth regulator to augment the growth of microbial cultures.

Originator

Senetek (UK)

Synthesis Reference(s)

The Journal of Organic Chemistry, 21, p. 1276, 1956 DOI: 10.1021/jo01117a016

Biochem/physiol Actions

FAPα has in vitro dipeptidyl peptidase activity and collagenolytic activity. It cleaves N-terminal dipeptides from polypeptides and can degrade gelatin and type I collagen. It has also been reported that FAPa has a tumor suppressor activity.

Purification Methods

It forms platelets from EtOH and sublimes at 220o, but is best done at lower temperatures in a good vacuum. It has been extracted from neutral aqueous solutions with Et2O. [Miller et al J Am Chem Soc 78 1375 1956, Bullock et al. J Am Chem Soc 78 3693 1956, Beilstein 26 III/IV 3586.]

Synthetic route

3,4-dihydro-2H-pyran (110-87-2) + 6-furfurylaminopurine (525-79-1) → 6-furfurylamino-9-(tetrahydropyran-2-yl)-9H-purine (109403-64-7)

Conditions	Yield
With formic acid In ethyl acetate at 78℃; for 3h;	80%

1-Bromo-2-chloroethane (107-04-0) + 6-furfurylaminopurine (525-79-1) → 6-furfurylamino-9-(2-chloroethyl)purine (120593-23-9)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide for 18h;	80%

ethylene dibromide (106-93-4) + 6-furfurylaminopurine (525-79-1) → 6-furfurylamino-9-(2-bromoethyl)purine (1309656-94-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;	60%

bromo-triphenyl-methane (596-43-0) + 6-furfurylaminopurine (525-79-1) → furane-2-ylmethyl-(9-trityl-9H-purine-6-yl)-amine (934244-37-8)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20 - 50℃;	53%

Upstream product

• 617-89-0 furan-2-ylmethanamine 
• 87-42-3 6-chloro-7H-purine 
• 50-66-8 6-(methylthio)-1H-purine 
• 65316-39-4 N-(7⁽⁹⁾H-purin-6-yl)-furan-2-carboxamide 
• 615-08-7 2-furoic anhydride 
• 102236-06-6 N⁴-furfuryl-pyrimidine-4,5,6-triyltriamine 
• 98-01-1 furfural 
• 66224-66-6 adenine 
• 19769-32-5 6-methylsulfonylpurine 
• 68-94-0 Allopurinol 
• 87-42-3 6-chloropurine 
• 4338-47-0 kinetin riboside 
• 1338578-79-2 C₂₃H₂₅N₅O₉ 
• 98-00-0 (2-furyl)methyl alcohol 

Downstream Products

• 124-20-9 N-(3-aminopropyl)-1,4-diaminobutane 
• 71-44-3 Spermine 
• 110-60-1 1,4-diaminobutane 
• 98-00-0 (2-furyl)methyl alcohol 
• 95121-08-7 C₅H₃N₅O₂ 
• 4338-47-0 kinetin riboside 
• 109403-64-7 6-furfurylamino-9-(tetrahydropyran-2-yl)-9H-purine 
• 934244-37-8 furane-2-ylmethyl-(9-trityl-9H-purine-6-yl)-amine 
• 617-89-0 furan-2-ylmethanamine 
• 68-94-0 hypoxanthine 
• 111853-19-1 6-furfurylamino-9-benzylpurine 

Relevant academic research and scientific papers

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

INHIBITORS OF LOW MOLECULAR WEIGHT PROTEIN TYROSINE PHOSPHATASE (LMPTP) AND USES THEREOF

Protein tyrosine phosphatases (PTPs) are key regulators of metabolism and insulin signaling. As a negative regulator of insulin signaling, the low molecular weight protein tyrosine phosphatase (LMPTP) is a target for insulin resistance and related conditions. Described herein are compounds capable of modulating the level of activity of LMPTP, compositions, and methods of using these compounds and compositions.

Synthetic method for high-purity 6-furfurylaminopurine

The invention discloses a synthetic method for high-purity 6-furfurylaminopurine. According to the synthetic method, in the existence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), furfuryl amine and 6-chloropurine are subjected to nucleophilic substitution reaction under reflux condition of hexamethyldisilazane so as to obtain a crude product of 6-furfurylaminopurine, and recrystallizing is carriedout so as to obtain 6-furfurylaminopurine, the HPLC purity is 99.5% or above, and the any individual impurity content is less than 0. 1wt%. The synthetic method has the advantages of being simple inprocess, high in yield and free of wastewater discharge.

Design, synthesis and ability of non-gold complexed substituted purine derivatives to inhibit LPS-induced inflammatory response

In order to study the anti-inflammatory activity of novel 6-substituted and 6,9-disubstituted purine derivatives, 20 compounds, L1–10 and W1–10, derived from purine and lacking a gold complex were designed, synthesized and their anti-inflammatory activity was screened. LPS-induced TNF-α, IL-1β, IL-6, PGE2, NO, COX-2 and iNOS mRNA were evaluated, and western blot and NF-κB p65 translocation assay were performed in RAW 264.7 macrophages. Furthermore, carrageenan-induced hind paw edema experiments were performed in mice. Compound L1, L4, W2, and W4 markedly exerted a dose-dependent inhibition of TNF-α, IL-1β, IL-6 and PGE2 release induced by LPS in RAW 264.7 macrophages. Moreover, these compounds strongly inhibited LPS-induced NO, COX-2 and iNOS mRNA in the same cells. Anti-inflammatory activity tests in vivo showed that L1 and L4 were more effective than Au(L3)(PPh3), a known anti-inflammatory agent, at 2–5 h, and W4 was the most effective at 3–5 h after dosing. Thus, W2, W4, and L1, L4, could effectively inhibit LPS-induced inflammatory response in vitro and in vivo suggesting a promising role as anti-inflammatory agents.

Method for synthesizing adenine and derivatives thereof

The invention discloses a method for synthesizing adenine and derivatives thereof. The method comprises the steps: firstly, subjecting diethyl malonate and dimethyl dioxirane to an oxidation reaction, so as to obtain 2-hydroxyldiethyl malonate; then, carrying out an ammonolysis reaction with ammonia water, so as to obtain 2-hydroxyl malonamide; then, carrying out a cyclization reaction with trimethyl orthoformate, so as to obtain 5-hydroxyl pyrimid-4,6-(1H,5H)-dione; then, carrying out a chlorination reaction with phosgene, so as to obtain 4,5,6-trichloropyrimidine; then, carrying out a cyclization reaction with formamidine hydrochloride, so as to obtain 4-chloro-1H-pyrazol[3, 4-d]pyrimidine; finally, carrying out an ammoniation reaction with ammonia water or an amine compound in the presence of triethylamine, thereby obtaining the adenine and derivatives thereof. According to the method, the raw materials are moderately-priced and readily available, the reaction conditions are mild, the reaction process is safe, the requirements on production equipment are low, particularly, the environmental pollution is light, and the yield is relatively high, so that the method is applicable to industrial large-scale production.

6-substituted-9H-purine derivative and preparation method and application thereof

The invention discloses a 6-substituted-9H-purine derivative and a preparation method and application thereof. The derivative has the structure shown as the formula (I). In the formula (I), R is selected from one of pyrrolidiny, furan-2-methyl, benzenesulfonyl, and substituted or unsubstituted phenyl or benzyl, wherein a substituent on phenyl or benzyl is independently selected from one or more of C1-C4 alkoxy, C1-C4 alkyl, hydroxyl, halogen and a group shown in the description, and R4 is independently selected from H or alkyl-substituted benzyl. It is shown in the experimental results that compared with 6-benzyl purine compound complex gold ions (an inhibitor 3), the 6-substituted-9H-purine derivative is higher in inhibition ratio of inflammatory factors and has better anti-inflammatory activity. The 6-substituted-9H-purine derivative has the potential as an anti-inflammatory medicine.

9-subsituted-N-(2-chlorobenzyl)purine-6-amine derivative, as well as preparation method and application thereof

The invention discloses a 9-subsituted-N-(2-chlorobenzyl)purine-6-amine derivative. The structure of the derivative is shown in a formula (I), where R is selected from a hydrogen atom, a C1-C4 alkyl group and a substituted or unsubstituted benzyl group, and a substituent on the benzyl group is one or more independently selected from halogen, -CF3, a C1-C4 alkoxy group, a C1-C4 alkyl group and a nitro group; R4 is a substituted or unsubstituted phenyl group or benzyl group, and a substituent on the phenyl group or the benzyl group is one or more of halogen and a methoxy group. Compared with a 6-benyl adenine compound complex gold ion (inhibitor 3), the 9-subsituted-N-(2-chlorobenzyl)purine-6-amine derivative is proved by testing results to have the advantages of higher inflammation factor inhibition rate, higher anti-inflammation activity and potential for use as an anti-inflammation medicament. (The formula (I) is shown in the description.).

COMPOSITIONS AND METHODS USING THE SAME FOR TREATMENT OF NEURODEGENERATIVE AND MITOCHONDRIAL DISEASE

The present disclosure is directed, in part, to compounds, or pharmaceutically acceptable salts thereof, for the treatment and/or prevention of neurodegenerative disease and/or mitchonodrial disease including Parkinson's disease and Leigh's disease.

N6-acetyl-2,3,5-tri-O-acetyladenosine; A convenient, missed out substrate for regioselective N6-alkylations

A simple and efficient route to N6-acetyl-2,3,5-tri-O- acetyladenosine (1) was developed based on selective N-deacetylation of pentaacetylated adenosine 2 with methanol at room temperature in the presence of imidazole. Preparative synthesis of 1 was elaborated utilizing a crude mixture of 2 and 1 which is produced by reaction of adenosine with acetic anhydride in pyridine at elevated temperatures. The total yield of 1 was 80-85% starting with adenosine. It was shown that 1 is a convenient substrate for selective N 6-alkylations. The study revealed the same regioselectivity in base-promoted reactions of 1 with activated alkyl halides and Mitsunobu reactions of 1 with alcohols. A series of N6-alkyladenosines 5a-f were prepared. Cytokinins 6b,d,e were prepared by enzymatic transformation of parent nucleoside derivatives 5b,d,e using a combination of nucleoside phosphorylase and alkaline phosphatase. Georg Thieme Verlag Stuttgart, New York.

The scope and mechanism of phosphonium-mediated SNAr reactions in heterocyclic amides and ureas

(Chemical Equation Presented) An efficient "one-step" synthesis of cyclic amidines and guanidines has been developed. Treatment of cyclic amides and ureas with benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), base, and nitrogen nucleophiles leads to the formation of the corresponding cyclic amidines and guanidines, typically in good to excellent yields. This method has also been used to prepare heteroaryl ethers and thioethers using phenol and thiophenol nucleophiles. Time course NMR and HPLC-MS studies have facilitated explicit characterization of the proposed intermediates (the phosphonium salt and HOBt adduct); the data reveal a stepwise reaction pathway.