141018-26-0

Basic information

• Product Name: 5'-Carboxy-2-iodo-2',3'-O-isopropylidene-D-adenosine
• Synonyms: 5'-Carboxy-2-iodo-2',3'-O-isopropylidene-D-adenosine;5'-Carboxy-2-iodo-2',3'-O-isopropylideneadenosine;1-(6-AMino-2-iodo-9H-purin-9-yl)-1-deoxy-2,3-O-(1-Methylethylidene)-;(3aS,4S,6R,6aR)-6-(6-amino-2-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid
• CAS NO: 141018-26-0
• Molecular Formula: C₁₃H₁₄IN₅O₅
• Molecular Weight: 0
• Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Nucleotides;Carbohydrates & Derivatives, Nucleotides, Bases & Related Reagents
• Mol File: 141018-26-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5'-Carboxy-2-iodo-2',3'-O-isopropylidene-D-adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-Carboxy-2-iodo-2',3'-O-isopropylidene-D-adenosine(141018-26-0)
• EPA Substance Registry System: 5'-Carboxy-2-iodo-2',3'-O-isopropylidene-D-adenosine(141018-26-0)

Safety Data

• Hazardous Substances Data: 141018-26-0(Hazardous Substances Data)

Usage

Description

5'-Carboxy-2-iodo-2',3'-O-isopropylidene-D-adenosine is a chemical compound derived from adenosine, a nucleoside that plays a crucial role in cellular energy transfer and signal transduction. 5'-Carboxy-2-iodo-2',3'-O-isopropylidene-D-adenosine is characterized by the presence of a carboxylic acid group at the 5' position, an iodine atom at the 2' position, and an isopropylidene group bridging the 2' and 3' positions. It appears as an off-white powder and is used in the synthesis of various adenosine receptor agonists.

Uses

Used in Pharmaceutical Industry:
5'-Carboxy-2-iodo-2',3'-O-isopropylidene-D-adenosine is used as a key intermediate for the synthesis of 2-alkynyl-adenosine nucleosides. These nucleosides have potential applications as adenosine receptor agonists, which can modulate various physiological processes and have therapeutic potential in treating conditions such as asthma, chronic obstructive pulmonary disease (COPD), and certain cardiovascular diseases.
Additionally, due to its unique chemical structure, 5'-Carboxy-2-iodo-2',3'-O-isopropylidene-D-adenosine may also be utilized in the development of novel drug delivery systems or as a building block for the creation of new bioactive molecules with potential applications in various therapeutic areas.

Upstream product

• 141018-25-9 (3aR,4R,6R,6aR)-(6-(6-amino-2-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 35109-88-7 2-iodoadenosine 
• 118-00-3 G 
• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 5987-76-8 6-chloro-2-iodo-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine 

Downstream Products

• 141018-30-6 HE-NECA 
• 142103-07-9 2-(1-hexyn-1-yl)adenosine-5'-uronamide 
• 141018-29-3 2-iodo-5'-N-ethylcarboxamidoadenosine 
• 162936-24-5 N-ethyl-1'-deoxy-1'-(6-amino-2-iodo-9H-purin-9-yl)-2',3'-O-isopropylidene-β-D-ribofuranuronamide 

Relevant articles and documents

Synthesis, characterization and biological evaluation of purine nucleoside analogues

We present a convenient route for the synthesis of C6-amino-C5′-N-cyclopropyl carboxamido-C2-alkynylated purine nucleoside analogues 11a–g via Sonogashira coupling reaction. The nine step synthesis is easy to perform, employing commercially available reagents. Compound 9 is used as key intermediate for the synthesis of analogues 11a–g. Synthetic intermediates and final products are appropriately characterized by IR, 1H NMR, 13C NMR and Mass. The modified nucleoside analogues 11a–g is evaluated for in vitro anticancer activity against MDA-MB-231 and Caco-2 cell lines. Screening data reveals that compounds 11b and 11e displayed potent IC50 value of 7.9, 6.8 μg/mL respectively against MDA-MB-231 and of 7.5, 8.3 μg/mL respectively against Caco-2 than the standard drug doxorubicin, thus establishing the potential anti-cancer properties of these newer derivatives.

INDUCTION OF PHARMACOLOGICAL STRESS WITH ADENOSINE RECEPTOR AGONISTS

A method is provided employing A2A adenosine receptor agonists as vasodilators to detect the presence and assess the severity of coronary artery stenosis.

Nucleosides and Nucleotides. 112. 2-(1-Hexyn-1-yl)adenosine-5'-uronamides: A New Entry of Selective A2 Adenosine Receptor Agonists with Potent

Chemical modifications of the potent A2 adenosine receptor agonist 2-(1-hexyn-1-yl)adenosine (7, 2-HA) at the 5'-position have been carried out to find more potent and selective A2 agonists. these analogues were evaluated for adenosine A1 and A2 receptor binding affinity in rat brain tissues and antihypertensive effects in spontaneously hypertensive rats (SHR).Among the series of compounds, 2-(1-hexyn-1-yl)adenosine-5'-N-cyclopropyluronamide (16d) had the most potent affinity to the A2 receptor with a Ki of 2.6 nM, which is essentially the same as that of the parent agonist, 2-HA.However, the most selective agonist for the A2 receptor was 2-(1-hexyn-1-yl)adenosine-5'-N-methyluronamide (16b) with a Ki of 11 nM and a 162-fold selectivity.The N-alkyl substituents of 5'-uronamide derivatives did not seem to potentiate the A2 binding affinity but drastically reduced the A1 affinity compared with the parent 2-HA.Therefore, the A1/A2 selectivity was consequently increased.Other 5'-deoxy-5'-substituted derivatives of 2-HA such as the chloro (20), carboxamide (27, 28), sulfonamide (29), urea (30), and thiourea (22) analogues were also prepared.Among these nucleosides, no active compounds with potent or selective affinities to both receptors were found except 20.Although glycosyl conformations and sugar-puckering of these nucleosides were studied by 1H NMR spectroscopy, there were no positive correlations between active and inactive agonists. 2-(1-Hexyn-1-yl)adenosine-5'-uronamide (16a) and 16d had a potent hypotensive effect at ED30 values of 0.18 and 0.17 μg/kg, respectively, upon iv administration to anesthetized SHR.