152918-27-9

Basic information

• Product Name: I-AB-MECA
• Synonyms: I-AB-MECA REFERENCE STANDARD FO;1-[6-[[(4-amino-3-iodophenyl)methyl]amino]-9h-purin-9-yl]-1-deoxy-n-methyl-β-d-ribofuranuronamide;3-Iodo-4-aminobenzyl-5μ-N-methylcarboxamidoadenosine, 1-[6-[[(4-Amino-3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide, N6-(4-Amino-3-iodobenzyl)-5μ-N-methylcarbamoyladenosine;3-Iodo-4-aminobenzyl-5′-N-methylcarboxamidoadenosine;N6-(4-Amino-3-iodobenzyl)-5′-N-methylcarbamoyladenosine
• CAS NO: 152918-27-9
• Molecular Formula: C18H20IN7O4
• Molecular Weight: 525.301
• Mol File: 152918-27-9.mol
• Article Data: 1

Chemical Properties

• Appearance: off-white/solid
• Density: 2.066g/cm³
• Refractive Index: 1.842
• Storage Temp.: −20°C
• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2 mg/mL
• PKA: 12.72±0.70(Predicted)
• CAS DataBase Reference: I-AB-MECA(CAS DataBase Reference)
• NIST Chemistry Reference: I-AB-MECA(152918-27-9)
• EPA Substance Registry System: I-AB-MECA(152918-27-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 152918-27-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H20IN7O4/c1-21-17(29)14-12(27)13(28)18(30-14)26-7-25-11-15(23-6-24-16(11)26)22-5-8-2-3-10(20)9(19)4-8/h2-4,6-7,12-14,18,27-28H,5,20H2,1H3,(H,21,29)(H,22,23,24)/t12-,13+,14-,18+/m0/s1

Upstream product

• 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 
• 1053726-11-6 (3aS,4S,6R,6aR)-6-[6-(4-Amino-3-iodo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide 

Relevant articles and documents

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.