203259-85-2Relevant articles and documents
AMP deaminase inhibitors. 2. Initial discovery of a non-nucleotide transition-state inhibitor series
Bookser, Brett C.,Kasibhatla, Srinivas Rao,Appleman, James R.,Erion, Mark D.
, p. 1495 - 1507 (2007/10/03)
A series of N3-substituted coformycin aglycon analogues are described that inhibit adenosine 5'-monophosphate deaminase (AMPDA) or adenosine deaminase (ADA). The key steps involved in the preparation of these compounds are (1) treating the sodium salt of 6,7-dihydroimidazo[4,5-d][1,3]diazepin- 8(3H)-one (4) with an alkyl bromide or an alkyl mesylate to generate the N3- alkylated compound 5 and (2) reducing 5 with NaBH4. Selective inhibition of AMPDA was realized when the N3-substituent contained a carboxylic acid moiety. For example, compound 7b which has a hexanoic acid side chain inhibited AMPDA with a K(i) = 4.2 μM and ADA with a K(i) = 280 μM. Substitution of large lipophilic groups α to the carboxylate provided a moderate potency increase with maintained selectivity as exemplified by the α-benzyl analogue 7j (AMPDA K(i) = 0.41 μM and ADA K(i) > 1000 μM). These compounds, as well as others described in this series of papers, are the first compounds suitable for testing whether selective inhibition of AMPDA can protect tissue from ischemic damage by increasing local adenosine concentrations at the site of injury and/or by minimizing adenylate loss.
Exploring functional and molecular diversity with polymer-bound p-alkoxybenzyl ethers - Scope and applicaitons of preparatively useful organic reactions
Hanessian, Stephen,Xie, Fang
, p. 737 - 740 (2007/10/03)
Alcohols immobilized as p-alkoxybenzyl ethers on Wang resins have been subjected to a variety of chemical transformations based on existing functionality (enolate chemistry, carbonyl group reactivity, Mitsunobu inversion, ozonolysis, Heck reactions, etc.), in an effort to test the suitability of this novel resin-bound ether linkage. The modified substrate was released from the resin by mild acid treatment.
