1-[3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide

Base Information

• Chemical Name: 1-[3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide
• CAS No.: 50924-49-7
• Molecular Formula: C9H13N3O6
• Molecular Weight: 259.219
• Hs Code.: 29349990
• NSC Number: 289637
• DSSTox Substance ID: DTXSID30860619
• Wikidata: Q105035788
• Metabolomics Workbench ID: 100528
• ChEMBL ID: CHEMBL165000
• Mol file: 50924-49-7.mol

Synonyms:NSC289637;NSC 289637;HE 69;5-hydroxy-1-pentofuranosyl-1h-imidazole-4-carboxamide;SCHEMBL7119;CHEMBL165000;DTXSID30860619;HMS3372M17;HMS3869H13;AKOS015895934;1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide;NCI60_002375;FT-0630635;FT-0652030

Chemical Property of 1-[3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 5.2E-24mmHg at 25°C
• Melting Point: >200 °C
• Refractive Index: 1.794
• Boiling Point: 755.9 °C at 760 mmHg
• PKA: 6.75(at 25℃)
• Flash Point: 410.9 °C
• PSA: 151.06000
• Density: 2.06 g/cm³
• LogP: -2.00060
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Water (Slightly)
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 259.08043514
• Heavy Atom Count: 18
• Complexity: 329

Purity/Quality:

99%min ^*data from raw suppliers

Mizoribine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 46-60-61-36/37/38
• Safety Statements: 53-22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C(N1C2C(C(C(O2)CO)O)O)O)C(=O)N
• Description: Mizoribine is an orally active immunosuppressant isolated from Eupenicillium brefeldianum. It is reported to inhibit both cell-mediated and antibody mediated immune responses. Mizoribine is approved for use in the prevention of rejection of kidney transplants. Mizoribine is an imidazole nucleoside with immunosuppressive properties. It inhibits T cell proliferation in response to various mitogenic stimuli by 10-100% when used at concentrations ranging from 1 to 50 μg/mL. Mizoribine inhibits proliferation of stimulated T cells (IC50 = 5 μg/ml), which can be reversed by guanosine. It also inhibits guanine nucleotide formation in T cells, reducing GTP pools by 40-60% when used at a concentration of 5 μg/ml. Mizoribine inhibits replication of hepatitis C virus (HCV) RNA in vitro (IC50 = 100 μM). It suppresses glomerulosclerosis, urinary albumin excretion, interstitial fibrotic lesions, and macrophage infiltration into glomeruli and the interstitium in a rat model of type 2 diabetes when used at doses of 5 or 10 mg/kg. Mizoribine also reduces MCP-1, osteopontin (OPN), and TGF-β1 mRNA expression in the kidney in the same model. Formulations containing mizoribine have been used for the prevention of rejection after renal transplantation as well as in the treatment of lupus nephritis, rheumatoid arthritis, and primary nephritic syndrome.
• Uses: Mizoribine has been used in topical treatment to evaluate its effect on ocular surface damage of dry eye in B6 mice subjected to desiccating stress (DS). It has also been used as an inosine monophosphate dehydrogenase (IMPDH) inhibitor to test its in vivo efficacy. Nucleoside antibiotic with cytotoxic and immunosuppressive activity

Technology Process of 1-[3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide

There total 11 articles about 1-[3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide 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: 82.0%

bredinin 2',3',5'-tri-O-acetate (55726-67-5) → Mizoribine<*> (50924-49-7)

Guidance literature:

With ammonia; In methanol; for 5.5h; Ambient temperature;

DOI:10.1248/cpb.34.3653

Reference yield: 61.0%

Acetic acid (3aR,4R,6R,6aR)-6-(4-carbamoyl-5-hydroxy-imidazol-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (168906-86-3) → mizoribine (50924-49-7)

Guidance literature:

With water; trifluoroacetic acid; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2011.09.085

Reference yield: 56.0%

Acetic acid (3aR,4R,6R,6aR)-6-(4-carbamoyl-5-hydroxy-imidazol-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (168906-86-3) → Mizoribine<*> (50924-49-7)

Guidance literature:

With trifluoroacetic acid; In water; for 0.0333333h; Ambient temperature;

DOI:10.1080/15257779508012385

upstream raw materials:

bredinin 2',3',5'-tri-O-acetate

4-carbamoyl-3-(4-nitrobenzyl)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazolium-5-olate

2-amino-N-(β-D-ribofuranosyl)malondiamide

orthoformic acid triethyl ester

Downstream raw materials:

mizoribine 5'-monophosphate

N-{5-O-[3-(Benzyloxycarbonylamino)propylcarbamoyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-3-(tert-butoxycarbonylamino)malonamide

choline

Hexadecanoic acid (S)-2-{[(2R,3S,4R,5R)-5-(4-carbamoyl-5-hydroxy-imidazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester

Refernces

• 1、 Fukukawa,Shuto,Hirano,Ueda. "Synthesis of bredinin from 5-aminoimidazole-4-carboxamide-ribofuranoside (AICA riboside)". . p. 1644 - 1646. Retrieved 1984.
• 2、 -. "Process for producing mizoribine by Eupenicillium javanicum". . . Retrieved 2008/06/13.