1053266-43-5

Basic information

• Product Name: N-[(2R,3R,3aS,9aR)-2-(6-Amino-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl]-3-ethoxy-benzamide
• CAS NO: 1053266-43-5
• Molecular Weight: 656.93
• Mol File: 1053266-43-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-[(2R,3R,3aS,9aR)-2-(6-Amino-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl]-3-ethoxy-benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(2R,3R,3aS,9aR)-2-(6-Amino-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl]-3-ethoxy-benzamide(1053266-43-5)
• EPA Substance Registry System: N-[(2R,3R,3aS,9aR)-2-(6-Amino-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl]-3-ethoxy-benzamide(1053266-43-5)

Safety Data

• Hazardous Substances Data: 1053266-43-5(Hazardous Substances Data)

Upstream product

• 99-06-9 3-Carboxyphenol 
• 5432-17-7 3-ethoxybenzoic acid ethyl ester 
• 621-51-2 3-ethoxybenzoic acid 
• 160056-49-5 2'-amino-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-adenosine 

Relevant articles and documents

Synthesis and structure-activity relationships of analogs of 2'-deoxy-2'- (3-methoxybenzamido)adenosine, a selective inhibitor of trypanosognal glycosomal glyceraldehyde-3-phosphate dehydrogenase

In continuation of a project aimed at the structure-based design of drugs against sleeping sickness, analogs of 2'-deoxy-2'-(3- methoxybenzamido)adenosine (1) were synthesized and tested to establish structure-activity relationships for inhibiting glycosomal glyceraldehyde-3- phosphate dehydrogenase (GAPDH). Compound 1 was recently designed using the NAD: GAPDH complexes of the human enzyme and that of Trypanosoma brucei, the causative agent of sleeping sickness. In an effort to exploit an extra hydrophobic domain due to Val 207 of the parasite enzyme, several new 2'- amido-2'-deoxyadenosines were synthesized. Some of them displayed an interesting improvement in inhibitory activity compared to 1. Carbocyclic or acyclic analogs showed marked loss of activity, illustrating the importance of the typical (C-2'-endo) puckering of the ribose moiety. We also describe the synthesis of a pair of compounds that combine the beneficial effects of a 2- and 8-substituted adenine moiety on potency with the beneficial effect of a 2'-amide moiety on selectivity. Unfortunately, in both cases, IC50 values demonstrate the incompatibility of these combined modifications. Finally, introduction of a hydrophobic 5'-amide group on 5'-deoxyadenosine enhances the inhibition of the protozoan enzyme significantly, although the gain in selectivity is mediocre.