2365-40-4

Basic information

• Product Name: N6-(delta 2-Isopentenyl)-adenine
• Synonyms: 6-(GAMMA,GAMMA-DIMETHYLALLYLAMINO)-PURINE;6-(3,3-DIMETHYLALLYLAMINO)PURINE;2IP;N6-[2-ISOPENTENYL]ADENINE;N6-(DELTA2-ISOPENTENYL)ADENINE;TRIACANTHINE;2-iP N6-(2-Isopentenyl)adenine;6-(gamma,gamma-dimethylallylamino)*purine commerc
• CAS NO: 2365-40-4
• Molecular Formula: C₁₀H₁₃N₅
• Molecular Weight: 203.24
• EINECS: 1312995-182-4
• Product Categories: Plantgrowth
• Mol File: 2365-40-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 218-220 °C
• Boiling Point: 477.144 °C at 760 mmHg
• Flash Point: 242.368 °C
• Appearance: /
• Density: 1.267 g/cm³
• Vapor Pressure: 0.000352mmHg at 25°C
• Refractive Index: 1.659
• Storage Temp.: −20°C
• Solubility: DMF (Slightly), Methanol (Slightly)
• PKA: 9.36±0.20(Predicted)
• CAS DataBase Reference: N6-(delta 2-Isopentenyl)-adenine(CAS DataBase Reference)
• NIST Chemistry Reference: N6-(delta 2-Isopentenyl)-adenine(2365-40-4)
• EPA Substance Registry System: N6-(delta 2-Isopentenyl)-adenine(2365-40-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2365-40-4(Hazardous Substances Data)

Usage

Description

N6-(delta 2-Isopentenyl)-adenine, also known as 6-(γ,γ-Dimethylallylamino)purine (2iP), is a purine alkaloid first isolated from the leaves of Gleditsia triacanthus L. It has been found in other plants such as Chidlowia sanguinea and Holarhena floribunda. The free alkaloid forms colorless crystals and can yield crystalline salts and derivatives. It is a 6-isopentenylaminopurine with the isopentenyl double bond located between the 2 and 3 positions of the isopentenyl group.

Uses

1. Used in Biological Studies:
N6-(delta 2-Isopentenyl)-adenine is used as a cytokinin in the study of cytokinins-stimulated expression of stress-related proteins and transcripts in Arabidopsis thaliana with isopentenyltransferase overexpression.
2. Used in Plant Tissue Culture:
N6-(delta 2-Isopentenyl)-adenine is used as a bacteria-derived riboside cytokinin for growing plant tissues such as tobacco and soybean callus. It is a precursor of the cytokinin Zeatin and has been used in Schenk and Hildebrandt medium to support in vitro propagation of microshoot cultures from shoot tips of Genista plants.
3. Used in Pharmaceutical Applications:
Although not explicitly mentioned in the provided materials, N6-(delta 2-Isopentenyl)-adenine, due to its role as a cytokinin, may have potential applications in the pharmaceutical industry for the development of drugs targeting plant growth and development-related processes.

Biochem/physiol Actions

6-(γ,γ-Dimethylallylamino)purine (2iP) is a bacteria-derived riboside cytokinin used to grow plant tissues such as tobacco and soybean callus. 2iP is a precursor of the cytokinin Zeatin. 2iP is used in Schenk and Hildebrandt medium to support in vitro propagation of microshoot cultures from shoot tips of Genista plants.

References

Belikov, Ban'kowsky, Tsarev.,J. Gen. Chern., USSR, 24,919 (1954) Janot, Cave, Goutarel., Bull. Soc. Chirn. Fr., 896 (1959) Monseur, Adriaens.,J. Pharrn. Belg., 279 (1960) Leonard, Deyrup., J. Arner. Chern. Soc., 84, 2148 (1962) Leonard, Laursen.,J. Org. Chern., 27, 1778 (1962) Belikov., Ref. Zh. Khirn., 13Zh608 (1970)

InChI:InChI=1/C10H13N5/c1-7(2)3-4-11-9-8-10(13-5-12-8)15-6-14-9/h3,5-6,8H,4H2,1-2H3,(H,11,12,13,14,15)

Upstream product

• 86386-73-4 fluconazole 
• 13822-06-5 3,3-dimethylallylamine 
• 87-42-3 6-chloropurine 
• 7387-58-8 6-N-2',3',5'-tri-O-tetraacetyladenosine 
• 870-63-3 prenyl bromide 
• 1338578-80-5 N⁶-acetyl-N⁶-isopentenyl-2',3',5'-tri-O-acetyladenosine 
• 29911-54-4 (2-chloro-7⁽⁹⁾H-purin-6-yl)-(3-methyl-but-2-enyl)-amine 
• 5451-40-1 2,6 dichloropurine 
• 26728-58-5 (3-methyl-2-butenyl)amine hydrochloride 
• 556-82-1 3-methyl-2-buten-1-ol 
• 7724-76-7 6-N-(2-isopentenyl)adenosine 
• 56329-06-7 trans-zeatin O-β-D-glucopyranoside 

Downstream Products

• 1351394-25-6 6-[(3-methylbut-2-en-1-yl)amino]-9-(4-chlorobutyl)purine 
• 1351394-26-7 6-[(3-methylbut-2-en-1-yl)amino]-9-(3-cyanopropyl)-9H-purine 
• 1351394-27-8 6-[(3-methylbut-2-en-1-yl)amino]-9-(4-ethoxy-4-oxobutyl)purine 
• 1351394-21-2 6-[(3-methylbut-2-en-1-yl)amino]-9-(acetoxy)purine 
• 1351394-28-9 6-[(3-methylbut-2-en-1-yl)amino]-9-(3-carboxypropyl)purine 
• 1351394-29-0 6-[(3-methylbut-2-en-1-yl)amino]-9-(2-aminoethyl)purine 
• 1351394-24-5 6-[(3-methylbut-2-en-1-yl)amino]-9-(2-azidoethyl)-9H-purine 
• 1351394-23-4 6-[(3-methylbut-2-en-1-yl)amino]-9-(2-chloroethyl)-9H-purine 
• 1351394-22-3 6-[(3-methylbut-2-en-1-yl)amino]-9-(2-bromoethyl)-9H-purine 
• 7724-76-7 6-N-(2-isopentenyl)adenosine 
• 62061-49-8 3<(3S)-3-Amino-3-carboxypropyl>-6-(3-methyl-2-butenylamino)-3H-purine 
• 6025-53-2 trans-zeatin 9-β-D-ribofuranoside 
• 13822-06-5 3,3-dimethylallylamine 
• 68-94-0 hypoxanthine 

Relevant articles and documents

THE SYNTHESIS OF COMPOUNDS POSSESSING KINETIN ACTIVITY. THE USE OF A

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CYTOKININS IN IMMATURE SEEDS OF DOLICHOS LABLAB

Key Word Index - Dolichos lablab; Leguminoasae; cytokins; trans-zeatin; ribosyl-trans-zeatin; ribosyl-cis-zeatin; glucosyl-trans-zeatin; glucosyl ribosyl-trans-zeatin. Five cytokinins, trans-zeatin, 9-β-D-ribofuranosyl-trans-zeatin, 9-β-D-ribofuranosyl-cis-zeatin, 6-(trans-4-O-β-D-glucopyranosyl-3-methyl-2-butenylamino)purine and 6-(trans-4-O-β-D-glucopyranosyl-3-methyl-2-butenylamino)-9-β-D-ribofuranosylpurine were identified from immature seeds of Dolichos lablab.

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.

Chemical modification of the plant isoprenoid cytokinin N6-isopentenyladenosine yields a selective inhibitor of human enterovirus 71 replication

In this study, we demonstrate that N6-isopentenyladenosine, which essentially is a plant cytokinin-like compound, exerts a potent and selective antiviral effect on the replication of human enterovirus 71 with an EC50 of 1.0 ± 0.2 mM and a selectivity index (SI) of 5.7. The synthesis of analogs with modification of the N6-position did not result in a lower EC50 value. However, in particular with the synthesis of N6-(5-hexene-2-yne-1-yl)adenosine (EC50 = 4.3 ± 1.5 mM), the selectivity index was significantly increased: because of a reduction in the adverse effect of this compound on the host cells, an SI 101 could be calculated. With this study, we for the first time provide proof that a compound class that is based on the plant cytokinin skeleton offers an interesting starting point for the development of novel antivirals against mammalian viruses, in the present context in particular against enterovirus 71.