Arthur J. Elliott

Borane Reduction of indoles with secondary amine substituents in a 2,3-fused side-chain

Abstract Trifluoroacetic acid treatment of the borane adducts of indoles with 2,3-fused side-chains containing secondary amines leads to the trans -indolines via intramolecular hydride transfer.

Synthesis and Biological Activity of a Novel Class of Purine Nucleoside Phosphorylase Inhibitors

Abstract Purine nucleoside phosphorylase.(PNP, EC. 2.4.2.1) functions as a salvage enzyme in the purine and is important in the T-cell portion of the immune system As such, PNP is an important therapeutic target for diseases which are T-cell mediated. The biochemical basis for using PNP inhibitors as well as the various classes of inhibitors developed has been recently reviewed. Using X-ray crystallography we have designed and synthesized a series of 7-substituted 2-amino-1,5-dihydroHpyrrolo[3,2-djpyrimidin-4-ones which are potent PNP inhibitors .2-5 The 3-(pyridinylmethyl) derivative 1 (BCX-34, peldesine, IC50 = 0.036 ± 0.003 μM) is in clinical trials for the treatment of cutaneous T-cell Ivqphoma. acute lymphoblastic leukemia and HIV infections.

A short, facile synthesis of 2-amino-1,5-dihydro-4H-pyrrolo[3,2-d]-pyrimidin-4-one (9-Deazaguanine)

Abstract 9-Deazaguanine has been synthesized in four steps in an overall isolated yield of 18% from ethyl (ethoxymethylene)cyanoacetate and diethyl aminomalonate.

Synthesis of pyrrolo[3,2-d]pyrimidines (9-deazaguanines) by reductive cyclodeamination reactions

Abstract An efficient synthesis of 9-deazaguanines by reductive cyclodeamination of 5-nitro-6-cyanomethylpyrimidine derivatives under acidic conditions is described.

trans-Reduction of 5-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole. X-Ray crystallographic study of the geometry of an intermolecular N–H ⋯ phenyl hydrogen bond

The stereochemistries of the two isomeric products (5) and (6) obtained in equal amounts from trans-reduction of 3-benzyl-5-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (3) have been determined by spectral and single-crystal X-ray analyses. Monoclinic crystals of (5) belong to space group P21/c, with a= 22.005(10), b= 10.270(5), c= 13.577(7)A, β= 106.42(1)°, Z= 8. The crystal structure was solved by direct methods, and atomic positional and thermal parameters refined by least-squares calculations to R 0.051 over 3 293 reflections measured by diffractometer. The two molecules defining the asymmetric crystal unit have identical conformations and are associated in a like manner in the solid state by N–H ⋯ N (mean N ⋯ N 3.26 A) and N–H ⋯ phenyl (mean calculated H ⋯ phenyl 2.32 A) hydrogen bonds.