152918-18-8 Usage
Description
IB-MECA, or 3-Iodobenzyl-5'-N-ethylcarboxamidoadenosine, is a derivative of adenosine with a 5'-hydroxymethyl group replaced by N-ethylcarboxamido and one of the hydrogens of the exocyclic amino function substituted by a 3-iodobenzyl group. It is a compound with potential applications in various fields due to its unique chemical structure.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 152918-18-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,2,9,1 and 8 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 152918-18:
(8*1)+(7*5)+(6*2)+(5*9)+(4*1)+(3*8)+(2*1)+(1*8)=138
138 % 10 = 8
So 152918-18-8 is a valid CAS Registry Number.
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
152918-18-8Relevant articles and documents
Novel Adenine Derivatives and the Use Thereof
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Paragraph 0221; 0222; 0247; 0248, (2017/01/02)
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
Afify, Hanan M. N. M.,Pedersen, Erik B.,Zahran, Magdy A.
, p. 339 - 341 (2007/10/03)
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.