144348-08-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(Cyclohexylmethylidenehydrazino)adenosine is used as a diagnostic agent for the detection and evaluation of coronary heart disease. As an adenosine A2A agonist, it plays a crucial role in the diagnosis process by interacting with specific receptors in the heart, providing valuable information about the condition and helping healthcare professionals make informed decisions regarding treatment options.
Used in Diagnostic Applications:
In the field of cardiology, 2-(cyclohexylmethylidenehydrazino)adenosine is utilized as a diagnostic tool for coronary heart disease. Its agonistic properties towards the adenosine A2A receptors allow for the assessment of blood flow and the identification of any blockages or narrowing in the coronary arteries. This information is vital for determining the severity of the condition and the most appropriate course of treatment.

InChI:InChI=1/C17H25N7O4/c18-14-11-15(22-17(21-14)23-20-6-9-4-2-1-3-5-9)24(8-19-11)16-13(27)12(26)10(7-25)28-16/h6,8-10,12-13,16,25-27H,1-5,7H2,(H3,18,21,22,23)/b20-6+/t10-,12-,13-,16-/m1/s1

Upstream product

• 15763-11-8 2-hydrazinoadenosine 
• 2043-61-0 cyclohexanecarbaldehyde 
• 146-77-0 2-Chloroadenosine 
• 3056-18-6 (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 
• 118-00-3 G 
• 79999-39-6 2',3',5'-tri-O-acetyl-2-chloroadenosine 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of 2-hydrazinyladenosine derivatives as A2A adenosine receptor ligands

A series of 2-hydrazinyladenosine derivatives was synthesized and investigated in radioligand binding studies for their affinity at the adenosine receptor subtypes with the goal to obtain potent and A2AAR selective agonists and to explore the structure-activity relationships of this class of compounds at A2AAR. Modifications included introduction of a second sugar moiety at position 2 of adenosine to form new bis-sugar nucleosides and/or modifications of the 2-position linker in different ways. The performed modifications were found to produce compounds with relatively high A 2AAR affinity and very high selectivity toward A2AAR. The most potent bis-sugar nucleoside was obtained with the D-galactose derivative 16 which exhibited a Ki value of 329 nM at A2AAR with marked selectivity against the other AR subtypes. In another set of compounds, compound 3 was modified via replacement of its cyclic structure with mono- and disubstituted phenyl moieties and the resulting hydrazones 10-14 were found to have low nanomolar affinity for A2AAR. In addition to 3, compounds 10, 11 and 13 have been identified as the most potent compounds in the present series with Ki values of 16.1, 24.4, and 12.0 nM, respectively, at rat A2AAR. Species differences were tested and found to exist in different rates. Functional properties of the most potent compounds 10, 11, 13 and 16 were assessed showing that the compounds acted as agonists at A 2AAR.

2-hydrazoadenosines and their utility for the treatmeat of vascular conditions

The present invention discloses a compound of the formula: STR1 where R1 is hydrogen or the group STR2 where R3 and R4 are the same or different and are hydrogen, C1 to C12 linear or branched alkyl, C3 to C7 cycloalkyl, C6 to C10 aryl unsubstituted or substituted with C1 to C6 linear or branched alkyl, C1 to C6 linear or branched alkoxy, nitro, amino, amino substituted with at least one C1 to C6 linear or branched alkyl or phenyl, C2 to C10 aralkyl, C4 to C8 heteroaryl wherein said heteroatom is nitrogen, phosphorous, sulfur or oxygen, and R2 is hydrogen, or taken together with R5, forms a chemical bond, and R is a monosaccharide radical selected from the group consisting essentially of glucose, fructose, ribose, 2-deoxyribose, mannose, galactose, xylose and arabinose.

2-(N'-alkylidenehydrazino)adenosines: Potent and selective coronary vasodilators

The reaction of aliphatic aldehydes and ketones with 2-hydrazinoadenosine under relatively mild conditions (at room temperature or in refluxing methanol) formed 2-(N'-alkylidenehydrazino)-adenosines, 5-22, in good yields. Two kinds of adenosine receptors regulate cardiac and coronary physiology. In supraventricular tissues an A1AR coupled to muscarinic K channels mediates the negative chronotropic, dromotropic, and inotropic actions of adenosine, and an inhibitory A1AR coupled to adenylate cyclase mediates the 'antiadrenergic' action of adenosine. One or more kinds of A2 receptors mediate coronary vasodilation. Bioassays employing a guinea pig heart Langendorff preparation showed that 5-22 weakly retard impulse conduction through the AV node (negative dromotropic effect), but several analogues were very active coronary vasodilators. The coronary vasoactivity of the (n- alkylidene- and of the (isoalkylidenehydrazino)adenosines paralleled the length of the alkyl chain, the EC50s of the most active n-pentylidene (8) and isopentylidene (18) congeners being 1 nM. The EC50s of the cyclohexylmethylene (9), cyclohexylethylidene (10), and cyclohex-3- enylmethylene (12), analogues were likewise 50s of the negative dromotropic effects of 8, 9, and 18 by 5-28-fold and the EC50s of coronary vasodilation of 22-90-fold. Catalytic reduction of 9 increased the hydrophobicity and changed the UV spectrum, suggesting reduction of the -CH=N- bond. The product darkened on exposure to air and so was not characterized further. A new method for preparing 2',3',5'-tri-O- acetyl-2,6-dichloropurine riboside, a precursor in the synthesis of 2- hydrazinoadenosine, consists of the addition of tert-butyl nitrite to a mixture of 2',3',5'-tri-O-acetyl-6-chloroguanosine and CuCl in CHCl3 saturated with Cl2.