2-(4-Amino-5-iodo-7-pyrrolo[2,3-d]pyrimidinyl)-5-(hydroxymethyl)oxolane-3,4-diol

Base Information

• Chemical Name: 2-(4-Amino-5-iodo-7-pyrrolo[2,3-d]pyrimidinyl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS No.: 24386-93-4
• Molecular Formula: C11H13IN4O4
• Molecular Weight: 392.153
• Hs Code.: 29349990
• NSC Number: 113939
• Wikidata: Q27165541
• ChEMBL ID: CHEMBL63388
• Mol file: 24386-93-4.mol

Synonyms:7-Iodo-7-deaza-D-guanosine;444020-71-7;7-Deaza-7-iodoadenosine;BiomolKI_000049;BiomolKI2_000055;BMK1-F1;BSPBio_001227;KBioGR_000567;KBioSS_000567;CHEMBL63388;4-Amino-5-iodo-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine;SCHEMBL2043545;CHEBI:93817;KBio2_000567;KBio2_003135;KBio2_005703;KBio3_001013;KBio3_001014;WHSIXKUPQCKWBY-UHFFFAOYSA-N;Bio2_000444;Bio2_000924;HMS1362M09;HMS1792M09;HMS1990M09;NSC113939;AKOS030242162;CCG-100653;NSC-113939;IDI1_002199;NCGC00096117-01;NCGC00163302-01;NCGC00163302-02;NCGC00163302-03;NCGC00163302-04;FT-0620520;BRD-A18497530-001-03-8;BRD-A18497530-001-04-6;Q27165541;Z2216889315;2-(4-amino-5-iodo-7-pyrrolo[2,3-d]pyrimidinyl)-5-(hydroxymethyl)oxolane-3,4-diol;4-Amino-5-iodo-7-(b-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine;7-Iodotubercidin

Chemical Property of 2-(4-Amino-5-iodo-7-pyrrolo[2,3-d]pyrimidinyl)-5-(hydroxymethyl)oxolane-3,4-diol

Chemical Property:

• Appearance/Colour: Tan solid
• Vapor Pressure: 1.18E-20mmHg at 25°C
• Melting Point: 216-217 °C
• Refractive Index: 1.918
• Boiling Point: 701.5 °C at 760 mmHg
• PKA: 12.33±0.70(Predicted)
• Flash Point: 378 °C
• PSA: 126.65000
• Density: 2.495 g/cm³
• LogP: -0.18920
• Storage Temp.: 2-8°C
• Solubility.: 0.1 M HCl: 0.7 mg/mL
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 391.99815
• Heavy Atom Count: 20
• Complexity: 365

Purity/Quality:

98%, ^*data from raw suppliers

7-Deaza-7-iodoadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)O)N)I
• Uses: An analogue of the antibiotic tubercidin, a pyrrolo[2,3-d]pyrimidine nucleoside antibiotic. A potent inhibitor of adenosine kinase from rat or guinea pig brain. Inhibits uptake of 3H-adenosine into brain slices. A potent and competitive inhibitor of ERK2, PKA, and ADK. 5-Iodotubercidin has been used for the inhibition of retinoblastoma cells, astroglial cultures and for the inhibition of adenosine kinase in human umbilical vein endothelial cells (HUVECs).

Technology Process of 2-(4-Amino-5-iodo-7-pyrrolo[2,3-d]pyrimidinyl)-5-(hydroxymethyl)oxolane-3,4-diol

There total 2 articles about 2-(4-Amino-5-iodo-7-pyrrolo[2,3-d]pyrimidinyl)-5-(hydroxymethyl)oxolane-3,4-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.7%

4-chloro-5-iodo-7-(α-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (24386-91-2) → 5-iodotubercidin (24386-93-4)

Guidance literature:

With ammonia; In methanol; at 116 ℃; for 22h;

DOI:10.1016/S0968-0896(01)00341-8

Reference yield: 87.0%

4-chloro-5-iodo-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine (480439-89-2) → 5-iodotubercidin (24386-93-4)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; at 60 ℃; for 72h; Sealed tube;

DOI:10.1039/c4ob02081b

Reference yield: 100.0%

2-(4-{[4-methoxyphenyl]ethynyl}phenyl)-5,5-dimethyl-1,3,2-dioxaborinane + 5-iodotubercidin (24386-93-4) → 4-amino-5-(4-[{4-methoxyphenyl}ethynyl]phenyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Guidance literature:

With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; caesium carbonate; In water; acetonitrile; at 100 ℃; for 3h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c4ob02081b

upstream raw materials:

4-chloro-5-iodo-7-(α-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

4-chloro-5-iodo-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

Downstream raw materials:

4-amino-5-phenyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

4-amino-5-(4-methoxyphenyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

4-amino-5-[4-(methylthio)phenyl]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

C₁₇H₁₈N₄O₄

Refernces

• 1、 Brockway, Anthony J.,Volkov, Oleg A.,Cosner, Casey C.,MacMillan, Karen S.,Wring, Stephen A.,Richardson, Thomas E.,Peel, Michael,Phillips, Margaret A.,De Brabander, Jef K.. "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". supporting information. p. 5433 - 5440. Retrieved 2017/10/06.
• 2、 -. "COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING VIRAL INFECTION". Page/Page column 131. . Retrieved 2010/12/18.