Neplanocin A

Base Information

• Chemical Name: Neplanocin A
• CAS No.: 72877-50-0
• Molecular Formula: C11H13 N5 O3
• Molecular Weight: 263.256
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30993658
• Nikkaji Number: J53.047F
• Pharos Ligand ID: QLPST2GPDLWD
• Metabolomics Workbench ID: 106208
• ChEMBL ID: CHEMBL8771
• Mol file: 72877-50-0.mol

Synonyms:halo-neplanocin A;neplanocin A;neplanocin A, hydrochloride, (1S-(1alpha,2alpha,5beta))

Chemical Property of Neplanocin A

Chemical Property:

• Vapor Pressure: 7.18E-17mmHg at 25°C
• Melting Point: 214-216 °C (decomp)
• Boiling Point: 632.6°C at 760 mmHg
• PKA: 13.43±0.70(Predicted)
• Flash Point: 336.4°C
• PSA: 130.31000
• Density: 1.91g/cm³
• LogP: -0.81510
• XLogP3: -2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 263.10183929
• Heavy Atom Count: 19
• Complexity: 379

Purity/Quality:

97% ^*data from raw suppliers

(?)-Neplanocin A ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(C(C1N2C=NC3=C(N=CN=C32)N)O)O)CO
• Isomeric SMILES: C1=C([C@H]([C@H]([C@@H]1N2C=NC3=C(N=CN=C32)N)O)O)CO
• Description: S-Adenosylhomocysteine (SAH) hydrolase catalyzes the reversible hydrolysis of SAH to adenosine and homocysteine. The inhibition of SAH hydrolase causes the intracellular accumulation of SAH, elevating the ratio of SAH to S-adenosylmethionine (SAM) and inhibiting SAM-dependent methyltransferase. (?)-Neplanocin A potently and irreversibly inactivates SAH hydrolase (Ki = 8.39 nM). It has antitumor activity against mouse leukemia L1210 cells and broad-spectrum antiviral activity. Neplanocin A is more potent against vesicular stomatitis than the reversible SAH hydrolase inhibitor 3-deazaneplanocin (ID50 = 0.07 and 0.3 μg/ml, respectively).

Technology Process of Neplanocin A

There total 112 articles about Neplanocin A 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: 99.0%

(1R,4R,5S)-9-[3-(tert-butyldiphenylsilyloxymethyl)-4,5-isopropylidenedioxy-2-cyclopenten-1-yl]-N6,N6-bis(tert-butoxycarbonyl)adenine (952418-11-0) → neplanocin A (72877-50-0,156407-85-1)

Guidance literature:

With methanol; trifluoroacetic acid; In 1,2-dichloro-ethane; at 20 ℃;

DOI:10.1016/j.tet.2007.06.100

Reference yield: 99.0%

(1R,4R,5S)-9-[3-(tert-butyldiphenylsilyloxymethyl)-4,5-isopropylidenedioxy-2-cyclopenten-1-yl]adenine (952418-12-1) → neplanocin A (72877-50-0,156407-85-1)

Guidance literature:

With methanol; trifluoroacetic acid; In 1,2-dichloro-ethane; at 20 ℃;

DOI:10.1016/j.tet.2007.06.100

Reference yield: 95.0%

(3'R,4'S,5'R)-3'-(6-aminopurin-9-yl)-1'-hydroxymethyl-4',5'-O-isopropylidene-cyclopent-1'-en-4',5'-diol (79386-50-8) → neplanocin A (72877-50-0,156407-85-1)

Guidance literature:

With hydrogenchloride; In methanol; for 18h;

DOI:10.1016/S0040-4039(00)95558-8

upstream raw materials:

9-<(1R,2S,3R)-4-<((methoxymethyl)oxy)methyl>-2,3-<(dimethylmethylene)dioxy>-4-cyclopenten-1-ylk>adenine

9-<(1'R,4'R,5'S)-3-(tert-butoxymethyl)-4,5-(cyclohexylidenedioxy)-2-cyclopenten-1-yl>adenine

(3'R,4'S,5'R)-3'-(6-aminopurin-9-yl)-1'-hydroxymethyl-4',5'-O-isopropylidene-cyclopent-1'-en-4',5'-diol

(-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine

Downstream raw materials:

choline

Octadecanoic acid (S)-2-{[(3R,4S,5R)-3-(6-amino-purin-9-yl)-4,5-dihydroxy-cyclopent-1-enylmethoxy]-hydroxy-phosphoryloxy}-1-octadecanoyloxymethyl-ethyl ester

N⁶-benzoyl-9-<(1R,2S,3R)-2,3-dihydroxy-4-(hydroxymethyl)-4-cyclopenten-1-yl>adenine

C₂₇H₂₅N₅O₅