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ChemicalBook >  Product Catalog >  Analytical Chemistry >  Standard >  Pharmaceutical Impurity Reference Standards >  (1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL

(1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL

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(1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL Basic information

Product Name:
(1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL
Synonyms:
  • 5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL
  • NEAMINE
  • U-5214
  • 2-deoxy-4-o-(2,6-diamino-2,6-dideoxy-alpha-d-glucopyranosyl)-d-streptamin
  • (1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL
  • 5-amino-2-(aminomethyl)-6-(4,6-diamino-2,3-dihydroxycyclohexyl)oxyoxane-3,4-diol
  • dekamycinv
  • neamin
CAS:
3947-65-7
MF:
C12H26N4O6
MW:
322.36
Product Categories:
  • Intermediates
Mol File:
3947-65-7.mol
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(1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL Chemical Properties

Melting point:
225.5°C (rough estimate)
Boiling point:
460.98°C (rough estimate)
alpha 
D25+112.8° (c = 1)
Density 
1.1885 (rough estimate)
refractive index 
1.6120 (estimate)
storage temp. 
Hygroscopic, Refrigerator, Under inert atmosphere
solubility 
Aqueous Acid (Slightly), Methanol (Slightly, Heated), Water (Slightly)
pka
13.24±0.70(Predicted)
form 
Solid
color 
White to Pale Yellow
Stability:
Hygroscopic
InChI
InChI=1/C12H26N4O6/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20/h3-12,17-20H,1-2,13-16H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/s3
InChIKey
SYJXFKPQNSDJLI-CLPOQDAFNA-N
SMILES
[C@@H]1(O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@H](O)[C@@H](CN)O1 |&1:0,2,3,6,8,10,12,14,16,18,r|
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(1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL Usage And Synthesis

Uses

Neamine is normally found as a core structure of aminoglycoside antibiotics. It is used in the synthesis of disaccharide neamine derivatives as antibacterial agents.

Definition

ChEBI: 2-Deoxy-D-streptamine glycosylated at the 4-oxygen with a 6-amino-alpha-D-glucosaminyl group.

in vivo

Neamine (30-60 mg/kg; subcutaneous injection; daily; for 14 days; male Balb/c nude mice) has anti-tumor effects on AsPC-1 xenograft models. Neamine reduces the expression levels of ANG, Ki-67 and CD31 in tumor xenografts[1].

Animal Model:Male Balb/c nude mice (4 weeks old) injected with AsPC-1 cells[1]
Dosage:30 mg/kg, 60 mg/kg
Administration:Subcutaneous injection; daily; for 14 days
Result:Had anti-tumor effects on AsPC-1 xenograft models.

IC 50

Aminoglycoside

(1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOLSupplier

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