5105-78-2

Basic information

• Product Name: Z-GAMMA-ABU-OH
• Synonyms: GAMMA-N-CARBOBENZOXY-4-AMINO-N-BUTYRIC ACID;4-BENZYLOXYCARBONYLAMINO-BUTYRIC ACID;N-GAMMA-CARBOBENZOXY-GAMMA-AMINOBUTYRIC ACID;N-GAMMA-CBZ-GAMMA-AMINOBUTYRIC ACID;N-GAMMA-CARBOBENZOXY-4-AMINOBUTANOIC ACID;N-CBZ-4-AMINOBUTYRIC ACID;N-CARBOBENZOXY-4-AMINOBUTYRIC ACID;N-CARBOBENZOXY-4-AMINO-N-BUTYRIC ACID
• CAS NO: 5105-78-2
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.25
• EINECS: 1533716-785-6
• Product Categories: Unusual Amino Acids;Aliphatics;Amino Acids & Derivatives
• Mol File: 5105-78-2.mol

Chemical Properties

• Melting Point: 64°C
• Boiling Point: 454.9°Cat760mmHg
• Flash Point: 228.9°C
• Appearance: /Solid
• Density: 1.215g/cm³
• Vapor Pressure: 4.57E-09mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: Store at RT.
• Solubility: Dichloromethane, Ethyl Acetate
• PKA: 4.70±0.10(Predicted)
• CAS DataBase Reference: Z-GAMMA-ABU-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-GAMMA-ABU-OH(5105-78-2)
• EPA Substance Registry System: Z-GAMMA-ABU-OH(5105-78-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: ES8137200
• HazardClass: IRRITANT
• Hazardous Substances Data: 5105-78-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Z-GAMMA-ABU-OH is used as an antineoplastic agent for its potential to inhibit the growth and progression of cancer cells. Its mechanism of action may involve targeting specific signaling pathways or cellular processes that contribute to tumor development and maintenance.
Used in Neurological Applications:
Z-GAMMA-ABU-OH is used as an anticonvulsant agent for its ability to suppress electrically induced seizures. This property makes it a promising candidate for the development of treatments for epilepsy and other neurological disorders characterized by abnormal electrical activity in the brain.

InChI:InChI=1/C12H15NO4/c14-11(15)7-4-8-13-12(16)17-9-10-5-2-1-3-6-10/h1-3,5-6H,4,7-9H2,(H,13,16)(H,14,15)

Upstream product

• 501-53-1 benzyl chloroformate 
• 56-12-2 4-amino-n-butyric acid 
• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 
• 1245613-12-0 4-benzyloxycarbonylaminobutyric acid propyl ester 
• 1245613-13-1 4-benzyloxycarbonylaminobutyric acid butyl ester 
• 1245613-15-3 4-benzyloxycarbonylaminobutyric acid pentyl ester 
• 1245613-16-4 4-benzyloxycarbonylaminobutyric acid hexyl ester 
• 1245613-17-5 4-benzyloxycarbonylaminobutyric acid 2-methoxyethyl ester 
• 1020167-32-1 N-benzyloxycarbonyl-γ-aminobutyric acid (6-methoxy-2-oxo-2H-benzo[f]benzopyran-4-yl)methyl ester 
• 1333386-45-0 N-(benzyloxycarbonyl)-L-γ-aminobutyric acid (6-methoxy-2-oxo-2H-benzo[h]benzopyran-4-yl)methyl ester 
• 104-57-4 benzyl formate 
• 869541-05-9 γ-(benzyloxycarbonylamino)butanoic acid benzyl ester 
• 108-55-4 glutaric anhydride, 
• 100-51-6 benzyl alcohol 

Downstream Products

• 66051-53-4 Z-N-γ-Aminobutyryl-β-alaninamid 
• 66592-94-7 4-Benzyloxycarbonylamino-butyric acid tert-butoxycarbonylmethyl ester 
• 58773-38-9 2-(4-Aminobutyryl)-1-methylhydrazinessigsaeure 
• 5105-79-3 4-(((benzyloxy)carbonyl)amino)butyric acid tert-butyl ester 
• 28493-86-9 4-nitrophenyl 4-{[(benzyloxy)carbonyl]amino}butanoate 
• 117290-27-4 [4-(Octane-1-sulfonylamino)-4-oxo-butyl]-carbamic acid benzyl ester 
• 95015-71-7 benzyl 3-(phenethylcarbamoyl)propylcarbamate 
• 93767-93-2 N,N'-Bis-(N-carbobenzoxy-γ-aminobutyryl)-diaza-18-crown-6 
• 118970-66-4 3-[4-[4-[4-(benzyloxycarbonylamino)butylamido]-1-methylpyrrole-2-carbonylamino]-1-methylpyrrole-2-carbonylamino]dimethylaminopropane 
• 118970-69-7 [3-(5-{5-[5-(3-Dimethylamino-propylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-ylcarbamoyl}-1-methyl-1H-pyrrol-3-ylcarbamoyl)-propyl]-carbamic acid benzyl ester 
• 98008-66-3 4-{[(benzyloxy)carbonyl](methyl)amino}butanoic acid 
• 64187-40-2 4-Benzyloxycarbonylamino-butyric acid cyanomethyl ester 
• 64187-39-9 4-Benzyloxycarbonylamino-butyric acid prop-2-ynyl ester 
• 164466-93-7 methyl 4-(acetylamino)-3-<<4-butanoyl>amino>benzoate 

Relevant articles and documents

Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part I: Synthesis of the C1-C13 Subunit

Amphidinolide N, the structure of which has been recently revised, is a 26-membered macrolide featuring allyl epoxide and tetrahydropyran moieties with 13 chiral centers. Due to its challenging structure and extraordinary potent cytotoxicity, amphidinolide N is a highly attractive target of total synthesis. During our total synthesis studies of the 7,10-epimer of the proposed structure of amphidinolide N, we have synthesized the C1-C13 subunit enantio- and diastereoselectively. Key reactions include an l-proline catalyzed enantioselective intramolecular aldol reaction, Evans aldol reaction, Sharpless asymmetric epoxidation and Tamao-Fleming oxidation. To aid late-stage manipulations, we also developed the 4-(N-benzyloxycarbonyl-N-methylamino)butyryl group as a novel ester protective group for the C9 alcohol.

CONJUGATES OF A CELL-BINDING MOLECULE WITH CAMPTOTHECIN ANALOGS

Provided are conjugates of camptothecin analogs with a cell-binding molecule of formula (I), wherein R1, R2, R3, R4, R5, X, L, n, m, T and ----- are defined herein. It also provides methods of making the conjugates of camptothecin analogs to a cell-binding agent, as well as methods of using the conjugates in targeted treatment of cancer, infection, and immunological disorders.

Abolishing Dopamine D2long/D3Receptor Affinity of Subtype-Selective Carbamoylguanidine-Type Histamine H2Receptor Agonists

3-(2-Amino-4-methylthiazol-5-yl)propyl-substituted carbamoylguanidines are potent, subtype-selective histamine H2receptor (H2R) agonists, but their applicability as pharmacological tools to elucidate the largely unknown H2R functions in the central nervous system (CNS) is compromised by their concomitant high affinity toward dopamine D2-like receptors (especially to the D3R). To improve the selectivity, a series of novel carbamoylguanidine-type ligands containing various heterocycles, spacers, and side residues were rationally designed, synthesized, and tested in binding and/or functional assays at H1-4and D2long/3receptors. This study revealed a couple of selective candidates (among others31and47), and the most promising ones were screened at several off-target receptors, showing good selectivities. Docking studies suggest that the amino acid residues (3.28, 3.32, E2.49, E2.51, 5.42, and 7.35) are responsible for the different affinities at the H2- and D2long/3-receptors. These results provide a solid base for the exploration of the H2R functions in the brain in further studies.

MACROCYCLIC COMPOUNDS USEFUL AS CHITINASE INHIBITORS

The present invention relates to macrocyclic compounds of formula (I) and their use as chitinase inhibitors as well as to pharmaceutical compositions and methods of preparation thereof. The compounds can in particular be used in the treatment, prevention and/or amelioration of asthma.

CROSS-LINKED PYRROLOBENZODIAZEPINE DIMER (PBD) DERIVATIVE AND ITS CONJUGATES

A novel cross-linked cytotoxic agents, pyrrolobenzo-diazepine dimer (PBD) derivatives, and their conjugates to a cell-binding molecule, a method for preparation of the conjugates and the therapeutic use of the conjugates.

CONJUGATION LINKERS CONTAINING 2,3-DIAMINOSUCCINYL GROUP

Provided is a conjugate of a cytotoxic drug/molecule to a cell-binding molecule with a bis-linker (adual-linker) containing a 2, 3-diaminosuccinyl group. It also relates to preparation of the conjugate of a cytotoxic drug/molecule to a cell-binding molecule with the bis-linker, particularly when the drug having functional groups of amino, hydroxyl, diamino, amino-hydroxyl, dihydroxyl, carboxyl, hydrazine, aldehyde and thiol for conjugation with the bis-linker in a specific manner, as well as the therapeutic use of the conjugates.

A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS

The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS

The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

CONJUGATION OF A CYTOTOXIC DRUG WITH BIS-LINKAGE

What provided is the conjugation of cytotoxic to a cell-binding molecule with a bis-linker(dual-linker) as shown in Formula (I). It provides bis-linkage methods of making a conjugate of a cytotoxic drug molecule to a cell-binding agent in a specific manner. It also relates to application of the conjugates for the treatment of a cancer, or an autoimmune disease, or an infectious disease.

Selective Synthesis of (+)-Dysoline

Dysoline, a novel chromone alkaloid isolated from Dysoxylum binectariferum, was reported to have selective cytotoxicity for HT1080 fibrosarcoma cells (IC50 of 0.21 μM). Given the scarcity of natural material, a concise synthesis of (+)-dysoline was developed, allowing for further biological evaluation. An enantioselective nucleophile-catalyzed aldol lactonization formed the piperidine ring with control of relative and absolute stereochemistry. Construction of the C6-chromone core with complete regioselectivity was achieved using a Danheiser benzannulation.