13089-45-7

Basic information

• Product Name: 8-broMo-2',3'-O-(1-Methylethylidene)adenosine
• Synonyms: 8-broMo-2',3'-O-(1-Methylethylidene)adenosine
• CAS NO: 13089-45-7
• Molecular Formula: C₁₃H₁₆BrN₅O₄
• Molecular Weight: 386.20124
• Mol File: 13089-45-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 615.1°C at 760 mmHg
• Flash Point: 325.8°C
• Appearance: /
• Density: 2.11g/cm³
• Vapor Pressure: 5.48E-16mmHg at 25°C
• Refractive Index: 1.828
• CAS DataBase Reference: 8-broMo-2',3'-O-(1-Methylethylidene)adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-broMo-2',3'-O-(1-Methylethylidene)adenosine(13089-45-7)
• EPA Substance Registry System: 8-broMo-2',3'-O-(1-Methylethylidene)adenosine(13089-45-7)

Safety Data

• Hazardous Substances Data: 13089-45-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H16BrN5O4/c1-13(2)22-7-5(3-20)21-11(8(7)23-13)19-10-6(18-12(19)14)9(15)16-4-17-10/h4-5,7-8,11,20H,3H2,1-2H3,(H2,15,16,17)

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 2946-39-6 8-bromoadenosine 
• 77-76-9 2,2-dimethoxy-propane 
• 58-61-7 adenosine 
• 56676-90-5 2',3'-O-isopropylidene-1,N⁶-ethenoadenosine 
• 67-64-1 acetone 
• 362-75-4 2',3'-isopropylidene adenosine 

Downstream Products

• 13089-46-8 5'-O-acetyl-8-bromo-2',3'-O-(1-methylethylidene)adenosine 
• 1309803-44-8 (3aR,4R,6R,6aR)-{6-[6-amino-8-(benzylmethylamino)purin-9-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}methanol 
• 1309803-40-4 9-{(3aR,4R,6R,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-N₈-methyl-9H-purine-6,8-diamine 
• 1309803-41-5 C₂₁H₃₂N₆O₄ 
• 1309803-45-9 C₂₁H₃₂N₆O₄ 
• 1309803-31-3 (2R,3R,4S,5R)-2-(6-amino-8-methylaminopurin-9-yl)-5-benzyloxymethyltetrahydrofuran-3,4-diol 
• 1309803-32-4 (2R,3R,4S,5R)-2-(6-amino-8-methylaminopurin-9-yl)-5-cyclohexylmethoxymethyltetrahydrofuran-3,4-diol 
• 1186091-87-1 8-phenyl-2′,3′-O-isopropylideneadenosine 
• 1018828-71-1 8-Phenyl-AMP 
• 73340-78-0 8-Phenyladenosine 
• 3868-33-5 8-aminoadenosine 
• 1356152-03-8 N1-(5-O-phosphoryl-β-D-ribofuranosyl)-5'-O-(phenylthio)phosphoryl-8-bromoinosine 
• 1356152-02-7 N1-(5-O-phosphoryl-β-D-ribofuranosyl)-5'-O-di(phenylthio)phosphoryl-8-bromoinosine 
• 1356152-01-6 N1-[2,3-O-isopropylidene-5-O-di(tert-butyl)phosphoryl-β-D-ribofuranosyl]-5'-O-di(phenylthio)phosphoryl-2',3'-O-isopropylidene-8-bromoinosine 

Relevant articles and documents

Nucleosides VI: A novel and convenient synthesis of purine S- cyclonucleosides via mitsunobu reaction

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Structure-activity relationship of adenosine 5′-diphosphoribose at the transient receptor potential melastatin 2 (TRPM2) channel: Rational design of antagonists

Adenosine 5′-diphosphoribose (ADPR) activates TRPM2, a Ca 2+, Na+, and K+ permeable cation channel. Activation is induced by ADPR binding to the cytosolic C-terminal NudT9-homology domain. To generate the first structure-activity relationship, systematically modified ADPR analogues were designed, synthesized, and evaluated as antagonists using patch-clamp experiments in HEK293 cells overexpressing human TRPM2. Compounds with a purine C8 substituent show antagonist activity, and an 8-phenyl substitution (8-Ph-ADPR, 5) is very effective. Modification of the terminal ribose results in a weak antagonist, whereas its removal abolishes activity. An antagonist based upon a hybrid structure, 8-phenyl-2′-deoxy-ADPR (86, IC50 = 3 μM), is more potent than 8-Ph-ADPR (5). Initial bioisosteric replacement of the pyrophosphate linkage abolishes activity, but replacement of the pyrophosphate and the terminal ribose by a sulfamate-based group leads to a weak antagonist, a lead to more drug-like analogues. 8-Ph-ADPR (5) inhibits Ca2+ signalling and chemotaxis in human neutrophils, illustrating the potential for pharmacological intervention at TRPM2.

Inhibition of siderophore biosynthesis in Mycobacterium tuberculosis with nucleoside bisubstrate analogues: Structure-activity relationships of the nucleobase domain of 5′-O-[N-(salicyl)sulfamoyl]adenosine

5′-O-[N-(salicyl)sulfamoyl]adenosine (Sal-AMS) is a prototype for a new class of antitubercular agents that inhibit the aryl acid adenylating enzyme (AAAE) known as MbtA involved in biosynthesis of the mycobactins. Herein, we report the structure-based design, synthesis, biochemical, and biological evaluation of a comprehensive and systematic series of analogues, exploring the structure-activity relationship of the purine nucleobase domain of Sal-AMS. Significantly, 2-phenyl-Sal-AMS derivative 26 exhibited exceptionally potent antitubercular activity with an MIC99 under iron-deficient conditions of 0.049 μM while the N-6-cyclopropyl-Sal-AMS 16 led to improved potency and to a 64-enhancement in activity under iron-deficient conditions relative to iron-replete conditions, a phenotype concordant with the designed mechanism of action. The most potent MbtA inhibitors disclosed here display in vitro antitubercular activity superior to most current first line TB drugs, and these compounds are also expected to be useful against a wide range of pathogens that require aryl-capped siderphores for virulence.