34245-49-3

Upstream product

• 24514-56-5 9-((3aR,4R,6S,6aS)-6-(chloromethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine 
• 74-89-5 methylamine 
• 68179-90-8 ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl methanesulfonate 
• 1194995-79-3 5'-deoxy-5'-N-methyl-N-o-nitrobenzenesulfonylamino-2',3'-O,O-(1-methylethylidene)adenosine 
• 362-75-4 2',3'-isopropylidene adenosine 
• 5605-63-0 ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate 

Downstream Products

• 478161-08-9 4-({[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-methyl-amino}-methyl)-benzonitrile 
• 478161-09-0 2-({[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-methyl-amino}-methyl)-benzonitrile 
• 111770-79-7 5'-[N-[(3S)-3-amino-3-carboxypropyl]-N-methylamino]-5'-deoxyadenosine 
• 1129995-73-8 5'-deoxy-5'-N-methyl-N-[4-{(S)-2-(N-tert-butoxycarbonyl)amino-butyric acid}] benzyl ester-2',3'-O,O-(1-methylethylidene)adenosine 
• 1381764-18-6 1-(4-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)butan-2-yl)-3-(4-(tert-butyl)phenyl)urea 
• 1381764-07-3 benzyl (4-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)-2-methylbutan-2-yl)carbamate 
• 1381764-14-2 N-(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)-3-(3-(4-(tert-butyl)phenyl)ureido)-N-methylpropanamide 
• 1381761-95-0 benzyl((R)-1-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)-4-methylpentan-3-yl)carbamate 
• 1381761-93-8 1-((S)-1-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)pentan-3-yl)-3-(4-(tert-butyl)phenyl)urea 
• 1381761-82-5 1-((R)-1-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)pentan-3-yl)-3-(4-(tert-butyl)phenyl)urea 
• 1381761-77-8 1-[(1S)-3-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methyl-amino]-1-methyl-propyl]-3-(4-tert-butylphenyl)urea 
• 1381761-59-6 C₂₆H₃₅N₇O₅ 
• 1381761-62-1 C₃₀H₄₄N₈O₄ 
• 1381761-85-8 1-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)methyl)(2,2,2-trifluoroethyl)amino)propyl)-3-(4-(tert-butyl)phenyl)urea 

Relevant academic research and scientific papers

Synthesis and evaluation of analogs of 5′-(((Z)-4-amino-2-butenyl)methylamino)-5′-deoxyadenosine (MDL 73811, or AbeAdo) – An inhibitor of S-adenosylmethionine decarboxylase with antitrypanosomal activity

We describe our efforts to improve the pharmacokinetic properties of a mechanism-based suicide inhibitor of the polyamine biosynthetic enzyme S-adenosylmethionine decarboxylase (AdoMetDC), essential for the survival of the eukaryotic parasite Trypanosoma brucei responsible for Human African Trypanosomiasis (HAT). The lead compound, 5′-(((Z)-4-amino-2-butenyl)methylamino)-5′-deoxyadenosine (1, also known as MDL 73811, or AbeAdo), has curative efficacy at a low dosage in a hemolymphatic model of HAT but displayed no demonstrable effect in a mouse model of the CNS stage of HAT due to poor blood–brain barrier permeation. Therefore, we prepared and evaluated an extensive set of analogs with modifications in the aminobutenyl side chain, the 5′-amine, the ribose, and the purine fragments. Although we gained valuable structure–activity insights from this comprehensive dataset, we did not gain traction on improving the prospects for CNS penetration while retaining the potent antiparasitic activity and metabolic stability of the lead compound 1.

Improved Synthesis of MDL 73811 - A Potent AdoMetDC Inhibitor and Anti-Trypanosomal Compound

An improved synthesis of MDL 73811 - a potent AdoMetDC (S-adenosylmethionine decarboxylase) inhibitor and anti-trypanosomal compound with in vivo activity - has been completed in four steps from commercially available 2′,3′-O-isopropylideneadenosine. Util

An acyl-SAM analog as an affinity ligand for identifying quorum sensing signal synthases

N-Acylhomoserine lactones (AHLs) are quorum sensing signals produced by Gram-negative bacteria. We here report the affinity purification of AHL synthases using beads conjugated with an enzyme inhibitor, which was designed based on the catalytic intermediate acyl-SAM. the Partner Organisations 2014.

IMMUNOASSAY OF S-ADENOSYLMETHIONINE USING ANALOGS THEREOF AND PERSONALIZED THERAPEUTICS

A method of detecting the presence or absence of a disease in a patient wherein said disease is accompanied by deficient levels of S-adenosylmethionine comprising: identifying a patient that is suspected of having said disease or is at risk of having said

Identification of stable S-adenosylmethionine (SAM) analogues derivatised with bioorthogonal tags: Effect of ligands on the affinity of the E. coli methionine repressor, MetJ, for its operator DNA

The efficient synthesis of a range of stable SAM mimetics, and their ability to promote the binding of the E. coli methionine repressor (MetJ) to its operator DNA, is described.

New insights into the design of inhibitors of human S-adenosylmethionine decarboxylase: studies of adenine C8 substitution in structural analogues of S-adenosylmethionine

S-Adenosylmethionine decarboxylase (AdoMetDC) is a critical enzyme in the polyamine biosynthetic pathway and depends on a pyruvoyl group for the decarboxylation process. The crystal structures of the enzyme with various inhibitors at the active site have shown that the adenine base of the ligands adopts an unusual syn conformation when bound to the enzyme. To determine whether compounds that favor the syn conformation in solution would be more potent AdoMetDC inhibitors, several series of AdoMet substrate analogues with a variety of substituents at the 8-position of adenine were synthesized and analyzed for their ability to inhibit hAdoMetDC. The biochemical analysis indicated that an 8-methyl substituent resulted in more potent inhibitors, yet most other 8-substitutions provided no benefit over the parent compound. To understand these results, we used computational modeling and X-ray crystallography to study C8-substituted adenine analogues bound in the active site.

Synthesis and evaluation of analogues of 5′-([(Z)-4-amino-2-butenyl]methylamino)-5′-deoxyadenosine as inhibitors of tumor cell growth, trypanosomal growth, and HIV-1 infectivity

A well-defined series of 5′-([(Z)-4-amino-2-butenyl]methylamino)-5′-deoxyadenosine analogues was designed and synthesized in order to further ascertain the optimal structural requirements for S-adenosylmethionine decarboxylase inhibition and potentially t

The Synthesis of the N-Methyl Analogue of S-Adenosylmethionine; N.M.R. Observation of Diastereomers

The N-methyl analogue (1; X =N-Me) of S-adenosylmethionine has been synthesized; the intermediates and the end-product are racemic at the amino acid α-carbon, and show diastereomeric splitting in their 13C n.m.r. spectra.