362-74-3

Basic information

• Product Name: N-(9-beta-D-Ribofuranosyl-9H-furin-6-yl)-butyramide cyclic 3',5'-(hydrogen phosphate) 2'-butyrate
• Synonyms: BUCLADESINE;n-6,o-2'-dibutyryl adenosine cyclic 3':5'-monophosphate;n-(9-beta-d-ribofuranosyl-9h-furin-6-yl)-butyramide cyclic 3',5'-(hydrogen phosphate) 2'-butyrate;3',5'-Cyclic AMP dibutyrate;Cyclic AMP dibutyrate;Dibutyryl 3',5'-Cyclic AMP;Dibutyryl cyclic 3',5'-AMP;N-(9-beta-D-Ribofura
• CAS NO: 362-74-3
• Molecular Formula: C₁₈H₂₄N₅O₈P
• Molecular Weight: 469.389
• EINECS: 206-649-8
• Mol File: 362-74-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.72 g/cm³
• Refractive Index: 1.717
• Storage Temp.: -20°C Freezer
• Solubility: DMSO; Methano
• PKA: 0.82±0.60(Predicted)
• CAS DataBase Reference: N-(9-beta-D-Ribofuranosyl-9H-furin-6-yl)-butyramide cyclic 3',5'-(hydrogen phosphate) 2'-butyrate(CAS DataBase Reference)
• NIST Chemistry Reference: N-(9-beta-D-Ribofuranosyl-9H-furin-6-yl)-butyramide cyclic 3',5'-(hydrogen phosphate) 2'-butyrate(362-74-3)
• EPA Substance Registry System: N-(9-beta-D-Ribofuranosyl-9H-furin-6-yl)-butyramide cyclic 3',5'-(hydrogen phosphate) 2'-butyrate(362-74-3)

Safety Data

• Hazardous Substances Data: 362-74-3(Hazardous Substances Data)

Usage

Description

Bucladesine is a cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed)

Uses

Bucladesine is a cell permeable cAMP analog. The compound is used in a wide variety of research applications because it mimics cAMP and can induce normal physiological responses when added to cells in experimental conditions. cAMP is only able to elicit minimal responses in these situations. The neurite outgrowth instigated by bucladesine in cell cultures has been shown to be enhanced by nardosinone.

Definition

ChEBI: Bucladesine is a 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP. It has a role as an agonist, a vasodilator agent and a cardiotonic drug. It is a butyrate ester, a 3',5'-cyclic purine nucleotide and a member of butanamides. It is functionally related to a 3',5'-cyclic AMP.

InChI:InChI=1/C18H24N5O8P/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24)/t10-,14-,15-,18?/m1/s1

Upstream product

• 106-31-0 butanoic acid anhydride 
• 60-92-4 cAMP 

Relevant articles and documents

Preparation method of dibutyryl adenosine cyclophosphate compound and metal salt thereof

The invention discloses a preparation method of a dibutyryl adenosine cyclophosphate compound and a metal salt thereof. The preparation method of the dibutyryl adenosine cyclophosphate compound comprises the following steps that in an aprotic solvent, in the presence of organic alkali, adenosine cyclophosphate shown in the formula I and n-butyric anhydride are subjected to an acylation reaction shown in the specification to obtain the dibutyryl adenosine cyclophosphate compound, wherein anions of the dibutyryl adenosine cyclophosphate compound are shown in the formula II, wherein cations of the dibutyryl adenosine cyclophosphate compound are H and/or cations formed by the organic alkali and H , and the volume-to-mass ratio of the aprotic solvent to adenosine cyclophosphate as shownin the formula I is (2-40): 1ml/g. Compared with the traditional process, the method for preparing the dibutyryl adenosine cyclophosphate compound has the advantages that single quaternary ammonium salt preparation is omitted, the solvent consumption is low, and the production period is shortened. The liquid phase content of the final product is higher than 99%, the preparation process is simplified, and the method is suitable for industrial production.