152918-18-8

Basic information

• Product Name: IB-MECA
• Synonyms: 1-DEOXY-1-[6-[[(3-IODOPHENYL)METHYL]AMINO]-9H-PURIN-9-YL]-N-METHYL-BETA-D-RIBOFURANURON-AMIDE;IB-MECA;N6-(3-IODOBENZYL)ADO-5'N-METHYLURONAMIDE;n(6)-(3-iodobenzyl)-5’-n-methylcarboxamidoadenosine;IB-MECA SELECTIVE A3 ADENOSIN;1-deoxy-1-[6-[((3-iodophenyl)methyl)amino]-9h-purin-9-yl]-n-methyl-β-d-ribofuranuronamide;N6-(3-Iodobenzyl)adenosine-5μ-N-methyluronamide, 1-Deoxy-1-[6-[((3-Iodophenyl)methyl)amino]-9H-purin-9-yl]-N-methyl-β-D-ribofuranuronamide;b-D-RibofuranuronaMide, 1-deoxy-1-[6-[[(3-iodophenyl)Methyl]aMino]-9H-purin-9-yl]-N-Methyl-
• CAS NO: 152918-18-8
• Molecular Formula: C₁₈H₁₉IN₆O₄
• Molecular Weight: 510.29
• Mol File: 152918-18-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/solid
• Density: 1.98g/cm³
• Refractive Index: 1.808
• Storage Temp.: 2-8°C
• Solubility: hot ethanol: >10 mg/mL
• PKA: 12.72±0.70(Predicted)
• CAS DataBase Reference: IB-MECA(CAS DataBase Reference)
• NIST Chemistry Reference: IB-MECA(152918-18-8)
• EPA Substance Registry System: IB-MECA(152918-18-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 152918-18-8(Hazardous Substances Data)

Usage

Uses

IB-MECA has been used for intraocular pressure and corneal thickness measurements in rabbits.

Definition

ChEBI: A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and one of the hydrogens of the exocyclic amino function is substituted by a 3-iodobenzyl group.

Biological Activity

Potent and selective A 3 adenosine receptor agonist (K i values are 1.1, 54 and 56 nM for A 3 , A 1 and A 2A receptors respectively). Cardioprotective, reduces infarct size upon reperfusion in rats.

Biochem/physiol Actions

Selective A3 adenosine receptor agonist.

InChI:InChI=1/C18H19IN6O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-3-2-4-10(19)5-9/h2-5,7-8,12-14,18,26-27H,6H2,1H3,(H,20,28)(H,21,22,23)/t12?,13-,14-,18+/m0/s1

Upstream product

• 120355-42-2 (3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 
• 39824-26-5 6-chloro-9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine 
• 2004-06-0 6-Chloropurine riboside 
• 152918-47-3 2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide 
• 104940-65-0 1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride 
• 3718-88-5 3-iodobenzylamine hydrochloride 
• 35788-27-3 5'-N-methylcarboxamidoadenosine 
• 696-41-3 m-iodobenzaldehyde 
• 152918-48-4 IB-MECA acetonide 

Downstream Products

• 163042-96-4 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide 

Relevant articles and documents

Novel Adenine Derivatives and the Use Thereof

The present invention relates to a novel adenine derivative and a pharmaceutical use thereof and, more specifically, to a novel adenine derivative having a structure of chemical formula 1 or a pharmaceutically acceptable salt thereof, and to a composition containing the same for preventing or treating degenerative brain disease. The novel adenine derivative and the pharmaceutically acceptable salt thereof according to the present invention are adenosine A3 receptor agonists, and have an action of inhibiting the migration (or infiltration) of inflammatory cells (microglia, macrophages, neutrophils, etc.), to disease areas and the activities thereof. In addition, the adenine derivative according to the present invention was verified to suppress and treat brain injury more remarkably when compared with the known adenosine A3 receptor agonists in a cerebral ischemia experimental model, exhibit a significant effect by drug administration 10 hours after cerebral infarction, and allow long-term survival in spite of brain injury due to cerebral ischemia, and thus can be useful as an agent for treating and preventing degenerative brain disease including stroke.(AA,BB,CC,DD) Chemical formula 5COPYRIGHT KIPO 2015

A novel and facile reaction to N6-alkylated adenosine via benzotriazole as a synthetic auxiliary

The reaction of benzotriazole with aliphatic, aromatic or heteroaromatic aldehyde and adenosine leads to a benzotriazole adduct which is reduced with sodium borohydride to the corresponding N6-alkylated adenosine derivatives. This procedure is also utilized in a new route to N6-(3- iodobenzyl)adenosine-5'-N-methyluronamide (IB-MECA) which is considered an important adenosine agonist at A3 adenosine receptors.