Bestatin hydrochloride

Base Information

• Chemical Name: Bestatin hydrochloride
• CAS No.: 65391-42-6
• Molecular Formula: C₁₆H₂₄N₂O₄*ClH
• Molecular Weight: 344.838
• Hs Code.: 29242995
• European Community (EC) Number: 613-790-2
• UNII: BY7Y2JX7NQ
• ChEMBL ID: CHEMBL538595
• Mol file: 65391-42-6.mol

Synonyms:Bestatin hydrochloride;65391-42-6;Ubenimex hydrochloride;Bestatin (hydrochloride);Ubenimex HCl;BESTATIN HCL;(-)-Bestatin hydrochloride;N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine hydrochloride;(S)-2-((2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoic acid hydrochloride;65391-42-6 (HCl);((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)-L-leucine hydrochloride;(2S)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid;hydrochloride;SR-01000075724;NCGC00093685-01;MFCD00058004;Bestatin monohydrochloride;Bestatin hydrochloride- Bio-X;CHEMBL538595;SCHEMBL3880484;HY-B0134A;CHEBI:180575;Tox21_500214;AKOS030526173;CCG-207863;CS-1911;LP00214;Bestatin hydrochloride, >=98% (HPLC);NCGC00260899-01;AS-57675;BB164242;B4000;EU-0100214;B 8385;B-2270;H11007;M01391;A914271;SR-01000075724-1;SR-01000075724-2;SR-01000075724-6;Bestatin, [(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine hydrochloride;L-LEUCINE, N-((2S,3R)-3-AMINO-2-HYDROXY-1-OXO-4-PHENYLBUTYL)-, MONOHYDROCHLORIDE;(2S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid hydrochloride;L-LEUCINE, N-((2S,3R)-3-AMINO-2-HYDROXY-1-OXO-4-PHENYLBUTYL)-, HYDROCHLORIDE (1:1)

Chemical Property of Bestatin hydrochloride

Chemical Property:

• Vapor Pressure: 1.06E-12mmHg at 25°C
• Melting Point: 216-218 °C
• Boiling Point: 604.7 °C at 760 mmHg
• Flash Point: 319.5 °C
• PSA: 112.65000
• LogP: 2.42600
• Storage Temp.: −20°C
• Solubility.: H2O: 25 mg/mL, clear, colorless
• Water Solubility.: Soluble in water (4 mg/ml, warm), DMSO (>25 mg/ml), methanol, acetic acid, dimethyl formamide, and 100% ethanol.
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 344.1502850
• Heavy Atom Count: 23
• Complexity: 367

Purity/Quality:

99.5% ^*data from raw suppliers

Bestatin Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)NC(=O)C(C(CC1=CC=CC=C1)N)O.Cl
• Isomeric SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O.Cl
• Description: Bestatin HCl (65391-42-6) inhibits leucine aminopeptidase and aminopeptidases B and N. Inhibits leukotriene A4 hydrolase. Displays immunostimulant activity via activation of macrophages and T lymphocytes. Displays antitumor activity.
• Uses: Bestatin Hydrochloride is an inhibitor of aminopeptidases, LAP3, and leukotriene A4 hydrolase. It is the salt form of Bestatin (B319500). competitive aminopeptidase B inhibitor Bestatin is an inhibitor of amino peptidases and a potent, irreversible inhibitor of LTA4 hydrolase. It inhibits the amino peptidase activity of LTA4 hydrolase with a Ki value of 201 nM. It offers promise as a novel analgesic because it protects endogenous opioid peptides against degradation. It does not inhibit carboxypeptidases. Bestatin has been used as a protease inhibitor for the purification of his-tagged Tau protein.

Technology Process of Bestatin hydrochloride

There total 31 articles about Bestatin hydrochloride 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: 100.0%

(S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid methyl ester (145872-16-8) → Bestatin hydrochloride (65391-42-6,100992-60-7)

Guidance literature:

With hydrogenchloride; sodium hydroxide; 1) EtOH, reflux;

DOI:10.1016/S0040-4039(00)61780-X

Reference yield: 90.1%

benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate (60016-66-2) → Bestatin hydrochloride (65391-42-6,100992-60-7)

Guidance literature:

With hydrogen; palladium; In methanol; water; at 25 ℃; for 4h; under 2574.28 Torr;

DOI:10.1271/bbb.63.1304

Reference yield: 86.0%

methyl (2S)-2-(((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)amino)-4-methylpentanoate (65322-89-6) → Bestatin hydrochloride (65391-42-6,100992-60-7)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 16h;

DOI:10.1021/jo0358269

upstream raw materials:

(S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid methyl ester

benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate

2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid benzyl ester

methyl (2S)-2-(((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)amino)-4-methylpentanoate

Refernces

• 1、 Kudyba, Iwona,Raczko, Jerzy,Jurczak, Janusz. "Asymmetric Nitroaldol Reaction. Synthesis of Taxotere Side Chain and (-)-Bestatin Using (1R)-8-Phenylmenthyl Glyoxylate". . p. 2844 - 2850. Retrieved 2007/10/03.
• 2、 Kudyba, Iwona,Raczko, Jerzy,Jurczak, Janusz. "Synthesis of (-)-bestatin and the Taxotere side-chain via nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate". . p. 8685 - 8687. Retrieved 2007/10/03.