Bevirimat

Base Information

• Chemical Name: Bevirimat
• CAS No.: 174022-42-5
• Molecular Formula: C36H56O6
• Molecular Weight: 584.832
• European Community (EC) Number: 605-702-6
• UNII: S125DW66N8
• DSSTox Substance ID: DTXSID20169749
• Nikkaji Number: J1.169.422E
• Wikipedia: Bevirimat
• Wikidata: Q851897
• NCI Thesaurus Code: C78044
• Metabolomics Workbench ID: 63919
• ChEMBL ID: CHEMBL404519
• Mol file: 174022-42-5.mol

Synonyms:3-O-(3',3'-dimethylsuccinyl)betulinic acid;bevirimat;bevirimat dimeglumine;bevirimat dimeglumine salt;bis(1-deoxy-1-(methylamino)-D-glucitol) 3beta-(3-carboxylato-3-methylbutanoyloxy)lup-20(29)-en-28-oate;dsb-2nmg;lup-20(29)-en-28-oic acid, 3-(3-carboxy-3-methyl-1-oxobutoxy)-, (3beta)-, compd. with 1-deoxy-1-(methylamino)-D-glucitol (1:2);MPC-4326;MPC4326;PA 457;PA-103001;PA-103001-01;PA-457;PA-457 DI-NMG;PA-457N;PA103001;PA103001-01;PA103001-04;PA457

Chemical Property of Bevirimat

Chemical Property:

• Melting Point: >263°C (dec.)
• Boiling Point: 662.7±40.0 °C(Predicted)
• PKA: 4.48±0.28(Predicted)
• PSA: 100.90000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 8.14130
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Methanol (Very Slightly, Heated, Sonicated)
• XLogP3: 9.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 584.40768950
• Heavy Atom Count: 42
• Complexity: 1170

Purity/Quality:

≥98% ^*data from raw suppliers

Bevirimat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)CC(C)(C)C(=O)O)C)C(=O)O
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)CC(C)(C)C(=O)O)C)C(=O)O
• Recent ClinicalTrials: A Phase 2 Study to Assess the Pharmacokinetics of Bevirimat 100 mg Tablets Given to HIV-1 Positive Patient for 15 Days
• Description: PA-457 is an inhibitor of HIV-1 virion maturation. It inhibits the cleavage of the Gag capsid (CA) precursor CA-SP1 to the mature CA protein. PA-457 inhibits the replication of drug-sensitive and -resistant clinical isolates of HIV-1 in isolated human peripheral blood mononuclear cells (PBMCs; mean IC50s = 10.3 and 7.8 nM, respectively). In vivo, it prevents replication of HIV-1 in SCID-hu Thy/Liv mice when administered at a dose of 100 mg/kg.
• Uses: Bevirimat is a HIV-1 maturation inhibitor, targetting the Gag CA-SP1 cleavage site. HIV Inhibitor.

Technology Process of Bevirimat

There total 7 articles about Bevirimat 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: 72.0%

(3β)-3-hydroxylup-20(29)-en-28-al 3-(1-hydrogen 2,2-dimethylbutanedioate) (911140-87-9) → bevirimat (174022-42-5)

Guidance literature:

With sodium chlorite; potassium dihydrogenphosphate; In 2-methyl-but-2-ene; water; tert-butyl alcohol; at 20 ℃; for 16h; Product distribution / selectivity;

Reference yield: 71.0%

4-chloro-2,2-dimethyl-4-oxobutanoic acid (1189176-34-8) + Betulinic acid (472-15-1) → bevirimat (174022-42-5)

Guidance literature:

With pyridine; dmap; at 20 - 60 ℃; for 20h; Product distribution / selectivity;

Reference yield: 70.0%

2,2-dimethylsuccinic anhydride (17347-61-4) + Betulinic acid (472-15-1) → LH68 + bevirimat (174022-42-5)

Guidance literature:

With pyridine; dmap; Heating;

DOI:10.1016/S0968-0896(97)00158-2

upstream raw materials:

2,2-dimethylsuccinic anhydride

Betulinic acid

4-chloro-2,2-dimethyl-4-oxobutanoic acid

(3β)-3-hydroxylup-20(29)-en-28-al 3-(1-hydrogen 2,2-dimethylbutanedioate)