209799-67-7

Basic information

• Product Name: Forodesine
• Synonyms: Isopamphos;4H-Pyrrolo3,2-dpyrimidin-4-one, 7-(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-pyrrolidinyl-1,5-dihydro-;Forodesine;7-[(2S,3S,4R,5R)-3,4-Dihydroxy-5-(hydroxymethyl)-2-pyrrolidinyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one;Fodosine;Immucillin-H;(1S)-1-(9-deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-iMino-D-ribitol, iMMucillin H;4H-Pyrrolo[3,2-d]pyriMidin-4-one,7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-2-pyrrolidinyl]-3,5-dihydro-
• CAS NO: 209799-67-7
• Molecular Formula: C₁₁H₁₄N₄O₄
• Molecular Weight: 266.25
• Mol File: 209799-67-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 613.5 °C at 760 mmHg
• Flash Point: 324.8 °C
• Appearance: /
• Density: 2.01
• Vapor Pressure: 6.61E-16mmHg at 25°C
• Refractive Index: 1.894
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• PKA: 13.88±0.70(Predicted)
• CAS DataBase Reference: Forodesine(CAS DataBase Reference)
• NIST Chemistry Reference: Forodesine(209799-67-7)
• EPA Substance Registry System: Forodesine(209799-67-7)

Safety Data

• Hazardous Substances Data: 209799-67-7(Hazardous Substances Data)

Usage

Description

Forodesine, also known as Fodosine, is a purine nucleoside analog and a potent inhibitor of purine nucleoside phosphorylase (PNP) with high specificity for various species, including human, mouse, rat, monkey, and dog PNP. It exhibits inhibitory effects on the proliferation of human peripheral blood lymphocytes and T cell acute lymphoblastic leukemia (T-ALL) cells. Forodesine has shown promise in prolonging survival in the hu-PBL-SCID mouse model of xenogeneic graft versus host disease (GVHD).

Uses

Used in Pharmaceutical Industry:
Forodesine is used as an inhibitor of purine nucleoside phosphorylase (PNP) for its potential therapeutic effects on T-Cell malignancies such as acute lymphoblastic leukemia (ALL) and cutaneous T-cell lymphoma (CTCL). It functions as a transition state mimic, specifically designed to inhibit bovine PNP with a 23-pM inhibitory constant.
Used in Cancer Treatment:
Forodesine is used as an anticancer agent, particularly in the treatment of T-Cell malignancies. It has demonstrated the ability to inhibit the proliferation of T cell acute lymphoblastic leukemia (T-ALL) cells and prolong survival in the hu-PBL-SCID mouse model of xenogeneic graft versus host disease (GVHD), making it a promising candidate for further research and development in cancer treatment.

InChI:InChI=1/C11H14N4O4/c16-2-5-9(17)10(18)7(15-5)4-1-12-8-6(4)13-3-14-11(8)19/h1,3,5,7,9-10,12,15-18H,2H2,(H,13,14,19)/t5-,7+,9-,10+/m1/s1

Upstream product

• 222631-13-2 (1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-(9-deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol 
• 153172-31-7 (3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole 
• 153172-33-9 (3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 
• 222631-08-5 2-((3aS,4S,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo [4,5-c]pyrrol-4-yl)acetonitrile 
• 222631-09-6 (3aR,4R,6S,6aS)-tert-butyl 4-(((tert-butyldimethylsilyl)oxy)methyl)-6-(cyanomethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate 
• 284490-14-8 (1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol 
• 222631-11-0 N-tert-butoxycarbonyl-7-O-tert-butyldimethylsilyl-2-cyano-1,2,3,6-tetradeoxy-1-N-(ethoxycarbonylmethylamino)-3,6-imino-4,5-O-isopropylidene-D-allo-hept-1-enitol 
• 284490-15-9 (3aS,4S,6R,6aR)-tert-butyl 4-(4-amino-5-(ethoxycarbonyl)-1H-pyrrol-3-yl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate 
• 222631-12-1 1-benzyl 2-ethyl 3-amino-4-((3aS,4S,6R,6aR)-5-(tert-butoxycarbonyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo [4,5-c]pyrrol-4-yl)-1H-pyrrole-1,2-dicarboxylate 
• 299916-67-9 (1S)-1-(7-N-benzyloxymethyl-9-deaza-6-O-methylhypoxanthin-9-yl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol 

Relevant articles and documents

Alternative route towards the convergent synthesis of a human purine nucleoside phosphorylase inhibitor-forodesine HCl

Forodesine HCl is being investigated as a potential target for the control of T-cell proliferation. Herein we present an alternative route for the synthesis of the target molecule with addition of lactam to the lithiated deazahypoxanthine (generated in situ). The lactam was synthesized in five steps starting from l-pyroglutamic acid.

Inhibitors of nucleoside metabolism

The present invention provides compounds having the formula: wherein A is CH or N; B is chosen from OH, NH2, NHR, H or halogen; D is chosen from OH, NH2, NHR, H, halogen or SCH3; R is an optionally substituted alkyl, aralkyl or aryl group; and X and Y are independently selected from H, OH or halogen except that when one of X and Y is hydroxy or halogen, the other is hydrogen; and Z is OH or, when X is hydroxy, Z is selected from hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted alkyl, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof; and compounds having the formula: wherein A, X, Y, Z and R are defined for compounds of formula (I) where first shown above; E is chosen from CO2H or a corresponding salt form, CO2R, CN, CONH2, CONHR or CONR2; and G is chosen from NH2, NHCOR, NHCONHR or NHCSNHR; or a tautomer thereof, or a pharmaceutically acceptable salt thereof, or an ester thereof, or a prodrug thereof. The present invention also provides the use of the above compounds as pharmaceuticals, pharmaceutical compositions containing the compounds and processes for preparing the compounds.

Inhibitors of nucleoside metabolism

The present invention provides compounds having the formula: STR1 wherein A is CH or N; B is chosen from OH, NH2, NHR, H or halogen; D is chosen from OH, NH2, NHR, H, halogen or SCH3 ; R is an optionally substituted alkyl, aralkyl or aryl group; and X and Y are independently selected from H, OH or halogen except that when one of X and Y is hydroxy or halogen, the other is hydrogen; and Z is OH or, when X is hydroxy, Z is selected from hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted alkyl, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof. The present invention also provides the use of these compounds as pharmaceuticals, pharmaceutical compositions containing the compounds and processes for preparing the compounds.