7-Deazadenosine

Base Information

• Chemical Name: 7-Deazadenosine
• CAS No.: 69-33-0
• Molecular Formula: C11H14 N4 O4
• Molecular Weight: 266.257
• Hs Code.: 29419090
• NSC Number: 56408
• DSSTox Substance ID: DTXSID60861614
• Wikidata: Q105026690
• Mol file: 69-33-0.mol

Synonyms:7-Deazadenosine;NSC56408;2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol;4-Amino-7.beta.-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine;7.beta.-D-Ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-4-amine;(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol;NSC-56408;TBC;7-pentofuranosyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine;7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 7-.beta.-D-ribofuranosyl-;SCHEMBL1652797;SCHEMBL20418952;SCHEMBL23982115;DTXSID60861614;(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol;HDZZVAMISRMYHH-UHFFFAOYSA-N;7H-Pyrrolo(2, 4-amino-7.beta.-D-ribofuranosyl-;WLN: T56 BN GN INJ FZ I- BT5OTJ CQ DQ E1Q;4-Amino-7-(.beta.-D-ribofuranosyl)-pyrrolo(2,3-d)pyrimidine;4-Amino-7-.beta.-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine;7-.beta.-D-ribofuranosyl-7H-pyrrolo-[2,3-d]pyrimidin-4-amine;7H-Pyrrolo(2,3-d)pyrimidine, 4-amino-7.beta.-D-ribofuranosyl-;(2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol

Chemical Property of 7-Deazadenosine

Chemical Property:

• Vapor Pressure: 1.02E-17mmHg at 25°C
• Melting Point: 247-248 °C (decomp)(Solv: water (7732-18-5))
• Refractive Index: 1.8340 (estimate)
• Boiling Point: 648.8 °C at 760 mmHg
• PKA: 12.44±0.70(Predicted)
• Flash Point: 346.2 °C
• PSA: 126.65000
• Density: 1.9 g/cm³
• LogP: -0.79380
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Soluble in DMSO
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 266.10150494
• Heavy Atom Count: 19
• Complexity: 334

Purity/Quality:

98%min ^*data from raw suppliers

7-Deazaadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 28
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN(C2=NC=NC(=C21)N)C3C(C(C(O3)CO)O)O
• Recent EU Clinical Trials: A phase 1/2a, first-in-human, open-label, multicenter, dose escalation study of MP0533 in patients with relapsed/refractory (R/R) acute myeloid leukemia (AML) or myelodysplastic syndrome (MDS)
• General Description: Tubercidin is a nucleoside antibiotic analog known for its antimicrobial and antineoplastic properties, structurally related to adenosine but featuring a 7-deazapurine core. It has demonstrated activity against bacteria, viruses, and certain cancers, and its synthetic isosteres, such as those derived from pyrrolo[2,1-f][1,2,4]triazine C-nucleosides, are being explored to enhance or modify its biological effects.

Technology Process of 7-Deazadenosine

There total 20 articles about 7-Deazadenosine 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: 88.0%

→ tubercidin (69-33-0)

Guidance literature:

Reference yield: 85.0%

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate (29914-75-8) → tubercidin (69-33-0)

Guidance literature:

With ammonia; In methanol; at 130 ℃; for 16h;

DOI:10.1021/acs.joc.8b00343

Reference yield: 82.0%

4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine (16754-80-6) → tubercidin (69-33-0)

Guidance literature:

With ammonia; In methanol; at 50 ℃; for 24h;

DOI:10.1002/hlca.19880710623

upstream raw materials:

7-[3,5-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

4-Amino-2-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin

4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine

4-(methylsulfonyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine

Downstream raw materials:

N⁴-(Δ²-Isopentenyl)tubercidin

N⁴,N⁴,2',3',5'-O-Pentabenzoyltubercidin

4-<<(dimethylamino)methylidene>amino>-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine

7-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-amine

Refernces

Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin

10.1016/S0008-6215(01)00017-9

The research involves the synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides, which are isosteres of nucleoside antibiotics such as sangivamycin, tubercidin, and toyocamycin. These compounds have shown potential in combating bacteria, viruses, and cutaneous neoplasms. The study aimed to develop a general synthetic method for these C-nucleosides, starting from an intermediate, 6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3(2H,6H)one. The study successfully synthesized the target C-nucleosides and is currently examining their biological activities.