69427-81-2

Usage

Usage

Chemotherapy agent for T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma

Mechanism of Action

Interferes with DNA synthesis and repair in cancer cells, leading to cell death

Prodrug Nature

Inactive until metabolized in the body into its active form

Administration

Intravenous

Efficacy

Promising results observed in patients unresponsive to other chemotherapy forms

Common Side Effects

Nausea, vomiting, bone marrow suppression

Patient Tolerance

Generally well-tolerated

InChI:InChI=1/C10H14N6O4/c11-4-6(18)3(1-17)20-9(4)16-2-13-5-7(16)14-10(12)15-8(5)19/h2-4,6,9,17-18H,1,11H2,(H3,12,14,15,19)/t3-,4+,6-,9?/m1/s1

Upstream product

• 87791-88-6 3′,5′-(1,1,3,3-tetraisopropyl-1,3-disiloxan-1,3-yl)-9-(β-D-ribofuranosyl)purin-2,6-diamine 
• 193885-49-3 2,6-diamino-9-(2-amino-2-deoxy-β-D-arabinofuranosyl)purine 
• 2096-10-8 adenosine-2-amine 
• 193885-48-2 2,6-diamino-9-[2-O-trifluoromethanesulfonyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanyl)-β-D-ribofuranosyl]purine 
• 193885-46-0 2,6-diamino-9-(2-azido-2-deoxy-β-D-arabinofuranosyl)purine 

Relevant academic research and scientific papers

Synthesis of sugar-modified 2,6-diaminopurine and guanine nucleosides from guanosine via transformations of 2-aminoadenosine and enzymatic deamination with adenosine deaminase

Treatment of 2,6-diaminopurine riboside (2-aminoadenosine) with α- acetoxyisobutyryl bromide in acetonitrile gave mixtures of the trans 2',3'- bromohydrin acetates 2. Treatment of 2 with zinc-copper couple effected reductive elimination, and deprotection gave 2,6-diamino-9-(2,3-dideoxy-β- D-erythro-pent-2-enofuranosyl)purine (3a). Treatment of 2 with Dowex 1 x 2 (OH-) resin in methanol gave the 2',3-anhydro derivative 4. Stannyl radical- mediated hydrogenolysis of 2 and deprotection gave the 2'-deoxy 6a and 3'- deoxy 7a nucleosides. Treatment of the 3',5'-O-(tetraisopropyldisiloxanyl) derivative (5a) with trifluoromethanesulfonyl chloride - 4- (dimethylamino)pyridine gave 2'-triflate 5c. Displacement with lithium azide -dimethylformamide and deprotection gave the arabino 2'-azido derivative 8a, which was reduced to give 2,6-diamino-9 (2-amino-2-deoxy-β-D- arabinofuranosyl)purine (8b). Sugar-modified 2,6-diaminopurine nucleosides were treated with adenosine deaminase to give the corresponding guanine analogues. Treatment of 2,6-diaminopurine riboside (2-aminoadenosine) with α-acetoxyisobutyryl bromide in acetonitrile gave mixtures of the trans 2',3'-bromohydrin acetates 2. Treatment of 2 with zinc-copper couple effected reductive elimination, and deprotection gave 2,6-diamino-9-(2,3-dideoxy-β-D-erythro-pent-2-enofuranosyl) purine (3a). Treatment of 2 with Dowex 1 × 2 (OH-) resin in methanol gave the 2',3'-anhydro derivative 4. Stannyl radical-mediated hydrogenolysis of 2 and deprotection gave the 2'-deoxy 6a and 3'-deoxy 7a nucleosides. Treatment of the 3',5'-O-(tetraisopropyldisiloxanyl) derivative (5a) with trifluoromethanesulfonyl chloride - 4-(dimethylamino)pyridine gave 2'-triflate 5c. Displacement with lithium azide - dimethylformamide and deprotection gave the arabino 2'-azido derivative 8a, which was reduced to give 2,6-diamino-9-(2-amino-2-deoxy-β-D-arabinofuranosyl)purine (8b). Sugar-modified 2,6-diaminopurine nucleosides were treated with adenosine deaminase to give the corresponding guanine analogues.