144164-11-4

Basic information

• Product Name: (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane
• Synonyms: 2S,3S,5S-5-AMINO-2-[N-[[(5-THIAZOLYL)METHOXY]CARBONYL]AMINO]-1,6-DIPHENYL-3-HYDROXYHEXANE;RIT-X;Thiazol-5-ylMethyl ((2S,3S,5S)-5-aMino-3-hydroxy-1,6-diphenylhexan-2-yl)carbaMate;1,3-Thiazol-5-ylMethyl N-[(1S,2S,4S)-4-aMino-1-benzyl-2-hydroxy-5-phenylpentyl]car baMate;144164-11-4;(5-amino-3-hydroxy-1,6-diphenylhexan-2-yl)carbamic acid;Carbamic acid,N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-,5-thiazolylmethyl ester;(2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane###144164-11-4
• CAS NO: 144164-11-4
• Molecular Formula: C₂₃H₂₇N₃O₃S
• Molecular Weight: 425.54378
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Intermediates
• Mol File: 144164-11-4.mol

Chemical Properties

• Boiling Point: 656.1 °C at 760 mmHg
• Flash Point: 350.6 °C
• Appearance: Light yellow oil
• Density: 1.251 g/cm³
• Vapor Pressure: 4.17E-18mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 11.48±0.46(Predicted)
• CAS DataBase Reference: (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane(144164-11-4)
• EPA Substance Registry System: (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane(144164-11-4)

Safety Data

• Hazardous Substances Data: 144164-11-4(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Oil

Uses

An intermediate in the synthesis of Ritonavir.

InChI:InChI=1/C23H27N3O3S/c24-19(11-17-7-3-1-4-8-17)13-22(27)21(12-18-9-5-2-6-10-18)26-23(28)29-15-20-14-25-16-30-20/h1-10,14,16,19,21-22,27H,11-13,15,24H2,(H,26,28)/t19-,21-,22-/m0/s1

Upstream product

• 144163-97-3 ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate 
• 165315-39-9 (4S,6S,1'S)-6-(1-amino-2-phenylethyl)-4-benzyl-2-phenyl-3-aza-2-bora-1-oxacyclohexane 
• 144163-44-0 (2S,3S,5S)-3-hydroxy-2,5-bisamino-1,6-diphenylhexane 
• 162849-95-8 (2S,3S,5S)-5-(t-butyloxycarbonylamino)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane 
• 98-80-6 phenylboronic acid 
• 155213-67-5 ritonavir 
• 144163-85-9 (2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 

Downstream Products

• 155213-67-5 ritonavir 
• 192725-21-6 (2S,3S,5S)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-5-((2S-(1-imidazolidin-2-onyl)-3-methyl-butanoyl)-amino)-3-hydroxy-1,6-diphenylhexane 
• 192725-22-7 (2S,3S,5S)-2-(N-((5-Thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-5-(2S-(1-imidazolidin-2-onyl)-3,3-dimethyl butanoyl)amino-1,6-diphenylhexane 
• 1217720-20-1 C₃₇H₄₂⁽²⁾H₆N₆O₅S₂ 

Relevant articles and documents

IBodies: Modular synthetic antibody mimetics based on hydrophilic polymers decorated with functional moieties

Antibodies are indispensable tools for biomedicine and anticancer therapy. Nevertheless, their use is compromised by high production costs, limited stability, and difficulty of chemical modification. The design and preparation of synthetic polymer conjugates capable of replacing antibodies in biomedical applications such as ELISA, flow cytometry, immunocytochemistry, and immunoprecipitation is reported. The conjugates, named "iBodies", consist of an HPMA copolymer decorated with low-molecular-weight compounds that function as targeting ligands, affinity anchors, and imaging probes. We prepared specific conjugates targeting several proteins with known ligands and used these iBodies for enzyme inhibition, protein isolation, immobilization, quantification, and live-cell imaging. Our data indicate that this highly modular and versatile polymer system can be used to produce inexpensive and stable antibody substitutes directed toward virtually any protein of interest with a known ligand.

A method of preparing anti HIV drug ritonavir

The invention discloses a method for preparing anti-HIV medicine ritonavir and belongs to the technical field of medicines. In conditions of proper temperature, taking weak base as acid-binding agent and certain organic solvent, N-[N(-methyl-N-[(2-isopropyl-4-thiazolyl) methyl] amino-carbonyl]-L-valine and thionyl chloride are reacted to produice N(-[N-methyl-N-[(2-isopropyl-4-thiazolyl) methyl] amino-carbonyl]-L-valine acyl chloride, which is not required to be purified and can be directly subjected to amide reaction with (2s, 3s, 5s)-5-amino-2-((i)N(/i)-((5-thiazolyl)-methoxycarbonyl group) amino)-1, 6-diphenyl-3-hydroxy hexane at a room temperature, so as to obtain ritonavir; the mole ratio of the N-[N-methyl-N-[(2-isopropyl-4-thiazolyl) methyl] amino-carbonyl]-L-valine to thionyl chloride is 1:1 to 1:8; the mole ratio of the N-[N-methyl-N-[(2-isopropyl-4-thiazolyl) methyl] amino-carbonyl]-L-valine acyl chloride to weak base is 1:1 to 1:15. The method has the advantages that the price of thionyl chloride is low, the material cost is reduced, the production pollution is low, the pollution can be changed into soluble effluent brine, the method is simple to operate, the product yield is high, and the method is easy for separation and purification, and is applicable to industrial production.

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METHOD OF DETECTION OF ANALYTE ACTIVE FORMS AND DETERMINATION OF THE ABILITY OF SUBSTANCES TO BIND INTO ANALYTE ACTIVE SITES

The invention provides a method for detection of active form of analytes in a sample and/or for determination of ability of tested substances to bind to the active site of these analytes, comprising the following steps: a) analyte or group of analytes from the sample is immobilized on the surface of a solid carrier either by non-specific non-covalent adsorption or by covalent binding of surface functional groups of the analyte and corresponding functional groups of the solid carrier, or preferably via a binding molecule which is bound to the surface of the solid carrier before immobilization of the analyte or group of analytes and is capable of selectively binding the analyte or group of analytes contained in the sample during incubation of the solid carrier with the sample; b) analyte or group of analytes is incubated with a detection probe which binds selectively to the analyte or group of analytes via a compound for selective binding to the analyte active site; whereas the probe consists of a low molecular compound for selective binding to the analyte active site; an oligonucleotide tag, optionally with a covalently attached fluorophore, biotin or a chemical group, and a chemical linker covalently linking the compound for selective binding to the analyte active site and the oligonucleotide tag; c) then the solid carrier is washed to remove unbound detection probe; and subsequently, the amount of bound detection probe is determined, whereas this amount is directly proportional to the amount of the analyte or group of analytes in the sample. The described method has broad application in medicine. Given the exceptional sensitivity of only a few dozen molecules, it provides the ability to determine the protein markers in blood in a concentration yet undetectable.

MACROMOLECULAR CONJUGATES FOR VISUALIZATION AND SEPARATION OF PROTEINS AND CELLS

The present invention describes macromolecular water-soluble conjugates based on synthetic copolymers to which at least one affinity tag, at least one imaging probe and at least one targeting ligand are bound via covalent bonds. The macromolecular conjugate may be used in identification, visualization, quantification or isolation of proteins and/or cells.

CYTOCHROME P450 OXIDASE INHIBITORS AND USES THEREOF

The present invention features compounds of formula I or pharmaceutically acceptable salts, solvates or prodrugs thereof, and methods of using the same to inhibit the metabolizing activities of CYP enzymes. The present invention also features methods of using these compounds, salts, solvates or prodrugs to improve the pharmacokinetics of drugs that are metabolized by CYP enzymes.

A PROCESS FOR THE SYNTHESIS OF 2-AMINO-5-PROTECTED AMINO-3-HYDROXY-1, 6-DIPHENYLHEXANE OR A SALT THEREOF - AN INTERMEDIATE FOR ANTIVIRAL DRUGS

The present invention relates to an improved process for preparing 2-amino-5-protected-amino-3-hydroxy-1,6-diphenylhexane compounds or acid addition salts thereof, which can be useful intermediates for preparing compounds with antiviral activity. The present invention further provides a process for preparing HIV protease inhibitors, lopinavir and ritonavir.

ACID ADDITION SALT OF 2-ISOPROPYL-4-(((N-METHYL)AMINO)METHYL)THIAZOLE AND ITS?USE IN THE PREPARATION OF RITONAVIR

The present invention relates to a novel acid addition salt of 2-Isopropyl-4-(((N-methyl)amino)methyl)thiazole of Formula (I) which is a useful intermediate for preparing HIV protease inhibitors. The present invention further provides a process for preparing ritonavir, a HIV protease inhibitor, using the compound of Formula (I).

RITONAVIR ANALOGOUS COMPOUND USEFUL AS RETROVIRAL PROTEASE INHIBITOR, PREPARATION OF THE RITONAVIR ANALOGOUS COMPOUND AND PHARMACEUTICAL COMPOSITION FOR THE RITONAVIR ANALOGOUS COMPOUND.

The present invention describes a new one ritonavir analogous compound that presents significantly superior activity in inhibition of HIV protease. There are also described the usage of the ritonavir analogous compound of the present invention or salt, ester or prodrug thereof as well as the usage of the compound and its pharmaceutical compositions in medicine, particularly, in the treatment of HIV infection, by itself or in combination with others anti-HIV drugs.

Retroviral protease inhibiting compounds

A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.