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5987-76-8

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5987-76-8 Usage

Chemical Properties

White Solid

Uses

6-Chloro-2-iodo-9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)purine (cas# 5987-76-8) is a compound useful in organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 5987-76-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,9,8 and 7 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 5987-76:
(6*5)+(5*9)+(4*8)+(3*7)+(2*7)+(1*6)=148
148 % 10 = 8
So 5987-76-8 is a valid CAS Registry Number.
InChI:InChI=1/C16H16ClIN4O7/c1-6(23)26-4-9-11(27-7(2)24)12(28-8(3)25)15(29-9)22-5-19-10-13(17)20-16(18)21-14(10)22/h5,9,11-12,15H,4H2,1-3H3/t9-,11-,12-,15-/m1/s1

5987-76-8 Well-known Company Product Price

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  • TCI America

  • (T2691)  2',3',5'-Tri-O-acetyl-6-chloro-2-iodopurine Riboside  >97.0%(HPLC)(N)

  • 5987-76-8

  • 1g

  • 1,690.00CNY

  • Detail
  • TCI America

  • (T2691)  2',3',5'-Tri-O-acetyl-6-chloro-2-iodopurine Riboside  >97.0%(HPLC)(N)

  • 5987-76-8

  • 5g

  • 4,390.00CNY

  • Detail

5987-76-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-Chloro-2-iodo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

1.2 Other means of identification

Product number -
Other names ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(6-CHLORO-2-IODO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5987-76-8 SDS

5987-76-8Relevant articles and documents

A3 Adenosine Receptor Antagonists with Nucleoside Structures and Their Anticancer Activity

Buccioni, Michela,Dal Ben, Diego,Francucci, Beatrice,Lambertucci, Catia,Maggi, Federica,Marucci, Gabriella,Santoni, Giorgio,Spinaci, Andrea,Volpini, Rosaria

, (2022/02/10)

The overexpression of the A3 adenosine receptor (AR) in a number of cancer cell types makes it an attractive target for tumor diagnosis and therapy. Hence, in the search for new A3AR ligands, a series of novel 2,N6-disubstituted adenosines (Ados) was synthesized and tested in radioligand binding and functional assays at ARs. Derivatives bearing a 2-phenethylamino group in the N6-position were found to exert higher A3AR affinity and selectivity than the corresponding N6-(2,2-diphenylethyl) analogues. 2-Chloro-N6-phenylethylAdo (15) was found to be a potent full A3AR agonist with a Ki of 0.024 nM and an EC50 of 14 nM, in a cAMP accumulation assay. Unlike 15, the other ligands behaved as A3AR antagonists, which concentration-dependently reduced cell growth and exerted cytostatic activity on the prostate cancer cell line PC3, showing comparable and even more pronounced effects with respect to the ones elicited by the reference full agonist Cl-IB-MECA. In particular, the N6-(2,2-diphenylethyl)-2-phenylethynylAdo (12: GI50 = 14 μM, TGI = 29 μM, and LC50 = 59 μM) showed the highest activity proving to be a potential antitumor agent. The cytostatic effect of both A3AR agonist (Cl-IB-MECA) and antagonists (12 and other newly synthesized com-pounds) confirm previous observations according to which, in addition to the involvement of A3ARs, other cellular mechanisms are responsible for the anticancer effects of these ligands.

Synthesis and biological evaluation of a novel C8-pyrrolobenzodiazepine (PBD) adenosine conjugate. A study on the role of the PBD ring in the biological activity of PBD-conjugates

Bhakta, Sanjib,Brucoli, Federico,Ferguson, Lindsay,Fox, Keith R.,Wells, Geoff

supporting information, (2020/03/19)

Here we sought to evaluate the contribution of the PBD unit to the biological activity of PBD-conjugates and, to this end, an adenosine nucleoside was attached to the PBD A-ring C8 position. A convergent approach was successfully adopted for the synthesis of a novel C8-linked pyrrolo(2,1-c)(1,4)benzodiazepine(PBD)-adenosine(ADN) hybrid. The PBD and adenosine (ADN) moieties were synthesized separately and then linked through a pentynyl linker. To our knowledge, this is the first report of a PBD connected to a nucleoside. Surprisingly, the compound showed no cytotoxicity against murine cells and was inactive against Mycobacterium aurum and M. bovis strains and did not bind to guanine-containing DNA sequences, as shown by DNase I footprinting experiments. Molecular dynamics simulations revealed that the PBD-ADN conjugate was poorly accommodated in the DNA minor groove of two DNA sequences containing the AGA-PBD binding motif, with the adenosine moiety of the ligand preventing the covalent binding of the PBD unit to the guanine amino group of the DNA duplex. These interesting findings shed further light on the ability of the substituents attached at the C8 position of PBDs to affect and modulate the biological and biophysical properties of PBD hybrids.

A New Class of Fluorinated A2A Adenosine Receptor Agonist with Application to Last-Step Enzymatic [18F]Fluorination for PET Imaging

Lowe, Phillip T.,Dall'Angelo, Sergio,Mulder-Krieger, Thea,IJzerman, Adriaan P.,Zanda, Matteo,O'Hagan, David

, p. 2156 - 2164 (2017/10/07)

The A2A adenosine receptor belongs to a family of G-coupled protein receptors that have been subjected to extensive investigation over the last few decades. Due to their prominent role in the biological functions of the heart, lungs, CNS and brain, they have become a target for the treatment of illnesses ranging from cancer immunotherapy to Parkinson's disease. The imaging of such receptors by using positron emission tomography (PET) has also been of interest, potentially providing a valuable tool for analysing and diagnosing various myocardial and neurodegenerative disorders, as well as offering support to drug discovery trials. Reported herein are the design, synthesis and evaluation of two new 5′-fluorodeoxy-adenosine (FDA)-based receptor agonists (FDA-PP1 and FDA-PP2), each substituted at the C-2 position with a terminally functionalised ethynyl unit. The structures enable a synthesis of 18F-labelled analogues by direct, last-step radiosynthesis from chlorinated precursors using the fluorinase enzyme (5′-fluoro-5′-deoxyadenosine synthase), which catalyses a transhalogenation reaction. This delivers a new class of A2A adenosine receptor agonist that can be directly radiolabelled for exploration in PET studies.

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