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

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

Used in Ophthalmology:
IB-MECA is used as a measurement tool for intraocular pressure and corneal thickness in rabbits. This application is particularly relevant for studying the effects of various treatments and conditions on eye health and for developing new therapies for ocular disorders.
Used in Pharmaceutical Research:
IB-MECA, due to its adenosine derivative nature, may have potential applications in the development of drugs targeting adenosine receptors. These receptors are involved in various physiological processes, including cardiovascular function, immune response, and neuroprotection. As a result, IB-MECA could be used as a starting point for designing new drugs with specific therapeutic effects in these areas.
Used in Chemical Synthesis:
The unique structure of IB-MECA may also make it a valuable compound for use in chemical synthesis, particularly in the development of new adenosine receptor agonists or antagonists. Its 3-iodobenzyl group and N-ethylcarboxamido substitution could provide novel opportunities for chemical modification and the creation of new compounds with specific biological activities.

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

• 35788-27-3 5'-N-methylcarboxamidoadenosine 
• 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 
• 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

PROCESS FOR THE SYNTHESIS OF IB-MECA

The present disclosure provides a method for the synthesis of IB-MECA. More specifically, the present disclosure provides a simple and high yield method for Good Manufacturing Production (GMP) of IB-MECA. The method involves the reaction of 6-halopurine-9

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.

Structure-Activity Relationships of N6-Benzyladenosine-5'-uronamides as A3-Selective Adenosine Agonists

Adenosine analogues modified at the 5'-position as uronamides and/or as N6-benzyl derivatives were synthesized.These derivatives were examined for affinity in radioligand binding assays at the newly discovered rat brain A3 adenosine receptor and at rat brain A1 and A2a receptors. 5'-Uronamide substituents favored A3 selectivity in the order N-methyl > N-ethyl ca. unsubstituted carboxamide > N-cyclopropyl. 5'-(N-Methylcarboxamido)-N6-benzyladenosine was 37-56-fold more selective for A3 receptors.Potency at A3 receptors was enhanced upon substitution of the benzyl substituent with nitro and other groups. 5'-N-Methyluronamides and N6-(3-substitutedbenzyl)adenosines are optimal for potency and selectivity at A3 receptors.A series of 3-(halobenzyl)-5'-N-ethyluronamide derivatives showed the order of potency at A1 and A2a receptors of I ca.Br > Cl > F.At A3 receptors the 3-F derivative was weaker than the other halo derivatives. 5'-N-Methyl-N6-(3-iodobenzyl)adenosine displayed a Ki value of 1.1 nM at A3 receptors and selectivity versus A1 and A2a receptors of 50-fold.A series of methoxybenzyl derivatives showed that a 4-methoxy group best favored A3 selectivity.A 4-sulfobenzyl derivative was a specific ligand at A3 receptors of moderate potency.An aryl amino derivative was prepared as a probe for radioiodination and receptor cross-linking.