16652-71-4

Basic information

• Product Name: L-Proline benzyl ester hydrochloride
• Synonyms: L-PYRROLIDINE-2-CARBOXYLIC ACID BENZYL ESTER HCL;L-PROLINE BENZYL ESTER;L-PROLINE BENZYL ESTER HCL;L-PROLINE BENZYL ESTER HYDROCHLORIDE SALT;L-PROLINE BENZYL ESTER MONOHYDROCHLORIDE;H-PRO-OBZL;H-PRO-OBZL HCL;PROLINE-OBZL HCL
• CAS NO: 16652-71-4
• Molecular Formula: C₁₂H₁₆NO₂*Cl
• Molecular Weight: 241.71
• EINECS: 240-700-5
• Product Categories: Amino Acid Derivatives;Amino Acids;Proline [Pro, P];Amino Acids and Derivatives;Amino Acid Benzyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acid Derivatives;Peptide Synthesis;Proline
• Mol File: 16652-71-4.mol

Chemical Properties

• Melting Point: 148-151 °C(lit.)
• Boiling Point: 309 °C at 760 mmHg
• Flash Point: 140.7 °C
• Appearance: White to pale yellow/Crystalline Powder
• Density: 1.121g/cm3
• Vapor Pressure: 0.000659mmHg at 25°C
• Refractive Index: 1.4365
• Storage Temp.: Store at RT.
• Solubility: soluble in Methanol
• Water Solubility: miscible
• Sensitive: Hygroscopic
• BRN: 3598081
• CAS DataBase Reference: L-Proline benzyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline benzyl ester hydrochloride(16652-71-4)
• EPA Substance Registry System: L-Proline benzyl ester hydrochloride(16652-71-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-22
• Safety Statements: 22-24/25-37/39-26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 16652-71-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-Proline benzyl ester hydrochloride is used as a reagent for the synthesis of goralatide analogs, which possess anti-leukemic properties. This application aids in the development of potential treatments for leukemia and other related blood disorders.

InChI:InChI=1/C12H15NO2/c14-12(11-7-4-8-13-11)15-9-10-5-2-1-3-6-10/h1-3,5-6,11,13H,4,7-9H2/p+1/t11-/m0/s1

Upstream product

• 147-85-3 L-proline 
• 100-51-6 benzyl alcohol 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 37787-77-2 Boc-L-proline benzyl ester 

Downstream Products

• 29776-70-3 N-(tert-butyloxycarbonyl)-prolyl-proline benzyl ester 
• 126255-75-2 N-(E)-crotonyl-(S)-prolinbenzylester 
• 41591-34-8 Ac-Ala-Pro-OBn 
• 68280-74-0 benzyl N⁶-((benzyloxy)carbonyl)-N²-(tert-butoxycarbonyl)-L-lysyl-L-prolinate 
• 78819-64-4 N^α-tert-butoxycarbonylvalyltyrosylproline benzyl ester 
• 141636-70-6 Boc-D-Pro-Pro-OBn 
• 87664-51-5 N-(3,4-Dimethoxybenzoyl)-2-pyrrolidincarbonsaeurebenzylester 
• 94726-50-8 N-(2-Oxo-2-phenylacetyl)prolin-benzylester 
• 88105-74-2 (S)-1-(3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 92010-25-8 1-(2-phenoxyacetyl)-L-proline benzyl ester 
• 92010-28-1 1-(2,2-dimethylpropionyl)-L-proline benzyl ester 
• 165058-72-0 (S)-1-((R)-2-tert-Butoxycarbonylamino-3-hydroxy-propionyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 57294-41-4 Z-Gly-Pro-OBzl 
• 35084-69-6 N-t-butyloxycarbonyl-L-alanyl-L-proline benzyl ester 

Relevant articles and documents

Synthesis and bioactivity of a Goralatide analog with antileukemic activity

Natural tetrapeptide Goralatide (AcSDKP) is a selective inhibitor of primitive haematopoietic cell proliferation. It is not stable in vivo and decomposes within 4.5 min when applied to live cells. In this work we developed an analog of Goralatide that exhibits cytotoxicity towards human myeloid HL-60, HEL, Nalm-6 leukemia cells, endothelial HUVEC, glioblastoma U251 and transformed kidney 293T cells. The Goralatide analog showed significant stability in organic solution with no tendency to degrade oxidatively.

PROCESS FOR MAKING BIARYL-BRIDGED CYCLIC PEPTIDES

The invention provides a method of preparing a biaryl-bridged cyclic peptide compound of Formula (I), where R1, R2, R3, R4, R5, R8, R7, R8, R9, R10, R11, R12, n and m are as defined in the specification. The biaryl-bridged cyclic peptides of Formula (I) are used in the preparation of pharmaceutically active substances, such as, for example, arylomycin and arylomycin analogues.

Design, synthesis and biological evaluation of new bivalent quinazoline analogues as IAP antagonists

We recently reported the biological evaluations of monovalent IAP antagonist 7 with good potency (MDA-MB-231, IC50 = 19 nM). In an effort to increase cellular activity and improve favorable drug-like properties, we newly designed and synthesized bivalent analogues based on quinazoline structure of 7. Optimization of cellular potency and CYP inhibition led to the identification of 27, which showed dramatic increase of over 100-fold (IC50 = 0.14 nM) and caused substantial tumor regressions in MDA-MB-231 xenograft model. These results strongly support 27 as a promising bivalent antagonist for the development of an effective anti-tumor approaches.

Synthesis and evaluation of in Vivo anti-hypothermic effect of the N- And C-terminus modified thyrotropin-releasing hormone mimetic: [(4S,5S)-(5-methyl-2-oxooxazolidine-4-yl)-carbonyl]-[3-(thiazol-4-yl)-L-alanyl]-L-prolinamide

We explored orally effective thyrotropin-releasing hormone (TRH) mimetics, which show high central nervous system effects in structure–activity relationship studies based on in vivo antagonistic activity on reserpine-induced hypothermia (anti-hypothermic effect) in mice starting from TRH. This led us to the TRH mimetic: [(4S,5S)-(5-methyl-2-oxooxazolidine-4-yl)carbonyl]-[3-(thiazol-4-yl)-L-alanyl]-L-prolinamide 1, which shows a higher anti-hypothermic effect compared with that of TRH after oral administration. We next attempted further chemical modification of the N- and C-terminus of 1 to find more orally effective TRH mimetics. As a result, we obtained several N- and C-terminus modified TRH mimetics which showed high anti-hypothermic effects.

Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions

Biaryl-bridged cyclic peptides comprise an intriguing class of structurally diverse natural products with significant biological activity. Especially noteworthy are the antibiotics arylomycin and its synthetic analogue G0775, which exhibits potent activity against Gram-negative bacteria. Herein, we present a simple, flexible, and reliable strategy based on activating-group-assisted catalytic oxidative coupling for assembling biaryl-bridged cyclic peptides from natural amino acids. The synthetic approach was utilized for preparing a number of natural and unnatural biaryl-bridged cyclic peptides, including arylomycin/G0775 and RP 66453 cyclic cores.

Amino acid benzyl ester hydrochloride salt preparation method

The present invention discloses a preparation method for amino acid benzyl ester hydrochloride. The method comprises: by taking a metal chloride as a catalyst, in a suitable solvent, firstly generating amino acid hydrochloride by amino acid and hydrogen chloride; and then, esterifying the amino acid hydrochloride with benzyl alcohol at a reflux temperature, wherein water generated is removed by azeotrope; promoting esterification reaction; after the reaction is completed, filtering a thermal reaction liquid to remove the catalyst; removing a low-boiling-point substance (solvent) under low pressure; and performing post-treatment processes such as recrystallization and the like, thereby obtaining the object product, namely amino acid benzyl ester hydrochloride. Recrystallized mother liquor is recycled for more than 5 times. The method has advantages of relatively low raw material cost, relatively high conversion rate, relatively simple post-treatment, no use of chlorinating agents such as thionyl chloride and the like, less three waste emission, and the like, and is suitable for industrial production.

QUINOLINE OR QUINAZOLINE DERIVATIVES WITH APOPTOSIS INDUCING ACTIVITY ON CELLS

Provided is a pharmaceutical composition comprising, as an active ingredient, a quinoline or quinazoline derivative of formula (I), a pharmaceutically acceptable salt, an isomer, a hydrate, and a solvate thereof, which is effective in the prevention and treatment of a cancer, inflammation, autoimmune diseases or neurodegenerative disorders which are induced by the overexpression of inhibitor of apoptosis proteins (IAPs).

Preparation and biological evaluation of key fragments and open analogs of scleritodermin A

The synthesis of key fragments of scleritodermin A, their assembly, and their biological evaluation as cytotoxic and anthelmintic were performed.Highlights of the synthetic route include formation of the a-ketoamide linkage and use of stereocontrolled reactions.Open analogs of this natural product were obtained using a convergent strategy.

A class of novel carboline intercalators: Their synthesis, in vitro anti-proliferation, in vivo anti-tumor action, and 3D QSAR analysis

Based on DOCK scores 18 N-(3-benzyloxycarbonylcarboline-1-yl)ethylamino acid benzylesters (6a-r) were synthesized as anti-tumor agents. Their IC 50 values against five human carcinoma cell lines ranged from 11.1 μM to more than 100 μM. The in vivo assay identified five derivatives of them had no anti-tumor action, the anti-tumor activity of nine derivatives of them equaled that of cytarabine, and the anti-tumor activity of three derivatives of them was higher than that of cytarabine. The UV and fluorescence spectra, as well as the relative viscosity and melting temperature measurements of calf thymus DNA (CT DNA) with and without the representative compound suggested that DNA intercalation could be their action mechanism. The 3D QSAR analysis of N-(3-benzyloxycarbonylcarboline-1-yl)ethylamino acid benzylesters (6a-r) revealed that their in vivo anti-tumor activity significantly depends on the molecular electrostatic and steric fields of the side chain of the amino acid residue.

Histone deacetylase inhibitors and process for producing the same

Compounds represented by formula (1) have strong inhibitory activity that is selective towards HDAC1 and HDAC4. Therefore, the compounds of the present invention are useful as pharmaceutical agents for treating or preventing diseases caused by HDAC1 and HDAC4.