2'-Deoxycoformycin

Base Information

• Chemical Name: 2'-Deoxycoformycin
• CAS No.: 53910-25-1
• Molecular Formula: C11H16N4O4
• Molecular Weight: 268.272
• Hs Code.: 2934999090
• European Community (EC) Number: 637-271-5
• DSSTox Substance ID: DTXSID00860661
• Wikipedia: Pentostatin
• Wikidata: Q104999421
• Mol file: 53910-25-1.mol

Synonyms:2' Deoxycoformycin;2'-Deoxycoformycin;CI 825;CI-825;CI825;Co-vidarabine;Deoxycoformycin;Imidazo(4,5-d)(1,3)diazepin-8-ol, 3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydro-, (R)-;Nipent;NSC 218321;NSC-218321;NSC218321;Pentostatin

Chemical Property of 2'-Deoxycoformycin

Chemical Property:

• Appearance/Colour: White crystals
• Vapor Pressure: 1.43E-17mmHg at 25°C
• Melting Point: 220 ºC
• Refractive Index: 1.793
• Boiling Point: 646 ºC at 760 mmHg
• PKA: 5.2(at 25℃)
• Flash Point: 344.5 ºC
• PSA: 112.13000
• Density: 1.81 g/cm³
• LogP: -1.41540
• Storage Temp.: Store at +4°C
• Solubility.: H2O: soluble10mg/mL, clear
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 268.11715500
• Heavy Atom Count: 19
• Complexity: 356

Purity/Quality:

99.5% ^*data from raw suppliers

Pentostatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC3=C2NC=NCC3O)CO)O
• Recent ClinicalTrials: DCF Combined With Camrelizumab in the Treatment of Esophageal Cancer
• Description: Pentostatin, an adenosine deaminase inhibitor, is an orphan drug introduced for the treatment of hairy cell leukemia. The agent is considered a significant advance over alpha-interferon, the only other drug available for this indication. The majority of patients treated with pentostatin have been reported to remain in remission for at least four years. It is also under investigation for the treatment of other kinds of leukemia and in transplant rejection. Because of their antitumor activity via inhibition of DNA synthesis, purine nucleoside derivatives resistant to deamination have been developed for the treatment of various leukemias. Pentostatin is a purine nucleoside analog that irreversibly inhibits adenosine deaminase (Ki = 0.9 pM) and thus interrupts DNA synthesis in dividing cells. Pentostatin has been reported to display strong efficacy in the clinical treatment of hairy cell leukemia as well as relapsed chronic lymphocytic leukemia.
• Uses: Pentostatin is a potent antitumour antibiotic isolated from a Streptomyces species. Pentostatin is a potent inhibitor of adenine deaminase and has been used therapeutically as an antitumour agent. Pentostatin is a potent antitumor antibiotic isolated from a Streptomyces species. Pentostatin is a potent inhibitor of adenine deaminase and has been used therapeutically as an antitumor agent. An adenosine deaminase inhibitor used as an anti-cancer therapeutic drug. Shown to be effective in the treatment of hairy cell leukemia as well as having use in the treatment of other types of cancer such as chronic lymphocytic leukemia.
• Indications: Pentostatin (Nipent, deoxycoformycin) is a purine isolated from fermentation cultures of the microbe Streptomyces antibioticus. Its mechanism of action involves inhibition of the enzyme adenosine deaminase, which plays an important role in purine salvage pathways and DNA synthesis.The resulting accumulation of deoxyadenosine triphosphate (dATP) is highly toxic to lymphocytes. Pentostatin is effective in the therapy of hairy cell leukemia, producing remissions in 80 to 90% of patients and complete remissions in more than 50%. The major toxic effects of the drug include myelosuppression, nausea, and skin rashes.
• Clinical Use: Pentostatin is a ring-expanded purine ribonucleoside that inhibits adenosine deaminase and is used in the treatment of hairy cell leukemia. The elevated levels of deoxyadenosine triphosphate that result from inhibition of this degradative enzyme inhibit the action of ribonucleotide reductase (the enzyme that converts ribose diphosphate to deoxyribose diphosphate), thus halting DNA synthesis within the tumor cell.
• Drug interactions: Potentially hazardous interactions with other drugs Antipsychotics: avoid with clozapine (increased risk of agranulocytosis). Cytotoxics: increased risk of toxicity with high-dose cyclophosphamide - avoid; increased pulmonary toxicity with fludarabine (unacceptably high incidence of fatalities).

Technology Process of 2'-Deoxycoformycin

There total 14 articles about 2'-Deoxycoformycin 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: 83.0%

3-(2-deoxy-β-D-erythro-pentofuranosyl)-6,7-dihydroimidazo<4,5-d><1,3>diazepin-8(3H)-one (69196-03-8) → 2'-deoxycoformycin (53910-25-1)

Guidance literature:

With Noyori's catalyst; formic acid; triethylamine; at 40 ℃; for 24h; stereoselective reaction; Inert atmosphere;

Reference yield:

3-(2-deoxy-3,5-di-O-p-chlorobenzoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol → (S)-pentostatin (69196-04-9) + 2'-deoxycoformycin (53910-25-1)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 24h;

Reference yield:

3-(2-deoxy-β-D-erythro-pentofuranosyl)-6,7-dihydroimidazo<4,5-d><1,3>diazepin-8(3H)-one (69196-03-8) → (S)-pentostatin (69196-04-9) + 2'-deoxycoformycin (53910-25-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; at 20 ℃; for 1h;

upstream raw materials:

3-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)-6,7-dihydroimidazo<4,5-d><1,3>diazepin-8(3H)-one

2-deoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentofuranosyl chloride

2-amino-1-(5-amino-1H-imidazol-4-yl)ethanone dihydrochloride

2-amino-1-[5-amino-1-(phenylmethyl)-1H-imidazol-4-yl]ethanone dihydrochloride

Downstream raw materials:

phenol

Refernces

• 1、 -. "Concatamers for Immunemodulation". . . Retrieved 2012/04/23.
• 2、 -. "Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same". . . Retrieved 2010/05/13.