2,5-Methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one,2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-

Names

[ Name ]:
2,5-Methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one,2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-

[Synonym ]:
2,3'-Anhydro-D-thymidine
Anhydrothymidine
2,3'-O-Cyclothymidine
5-methyl-2'-deoxy-2,3'-anhydrouridine
threo-2,3'-anhydro-thymidine
O2,3'-Cyclothymidine

Biological Activity

[Description]:

2,3’-Anhydrothymidine; 2’-Deoxy-3’,2-anhydro-5-methyluridine is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

[References]

[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88.

Chemical & Physical Properties

[ Density]:
1.72g/cm3

[ Boiling Point ]:
381.8ºC at 760mmHg

[ Melting Point ]:
246-247ºC

[ Molecular Formula ]:
C₁₀H₁₂N₂O₄

[ Molecular Weight ]:
224.21

[ Flash Point ]:
184.7ºC

[ Exact Mass ]:
208.08500

[ PSA ]:
64.35000

[ Vapour Pressure ]:
2.12E-07mmHg at 25°C

[ Index of Refraction ]:
1.735

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Articles

[3'-(Tetrazol-2''-yl-3'-deoxythymidine and its 5''-substituted form: synthesis and conformation in the crystalline state. Substrate properties of 3'-(tetrazol-2''-yl)-3'-deoxythymidine-5'-triphosphate in relation to DNA polymerases].

Bioorg. Khim. 21 , 49-54, (1995)

5''-Derivatives of 3'-(tetrazole-2''-yl)-3'-deoxythymidines were synthesized by interaction of 5'-benzoyl-2',3'-anhydrothymidine with tetrazole or its 5-derivatives followed by debenzoylation. Structu...

Study on disulfur-backboned nucleic acids: part 3. Efficient synthesis of 3',5'-dithio-2'-deoxyuridine and deoxycytidine.

Nucleosides Nucleotides Nucleic Acids 27 , 1272-1281, (2008)

A general method is described for synthesizing 3',5'-dithio-2'-deoxypyrimidine nucleosides 6 and 13 from normal 2'-deoxynucleosides. 2,3'-Anhydronucleosides 2 and 9 are applied as intermediates in the...