192725-49-8

Basic information

• Product Name: N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide
• Synonyms: N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide;N-((2S,3S,5S)-5-Amino-3-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide
• CAS NO: 192725-49-8
• Molecular Formula: C₂₈H₃₄N₂O₃
• Molecular Weight: 446.58116
• Product Categories: Aromatics;Chiral Reagents;Intermediates
• Mol File: 192725-49-8.mol

Chemical Properties

• Melting Point: 124-126°C
• Appearance: Off-white solid
• Storage Temp.: Refrigerator
• CAS DataBase Reference: N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide(192725-49-8)
• EPA Substance Registry System: N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide(192725-49-8)

Safety Data

• Hazardous Substances Data: 192725-49-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide is used as a key intermediate in organic synthesis for the development of new compounds with potential applications in various industries. Its unique structure and functional groups make it a valuable building block for creating novel molecules with specific properties and functions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide is used as a starting material for the synthesis of new drug candidates. Its versatile chemical properties allow for the development of compounds with potential therapeutic applications, such as in the treatment of various diseases and medical conditions.
Used in Chemical Research:
N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide is also utilized in chemical research for studying the properties and behavior of complex organic molecules. Its unique structure provides researchers with valuable insights into the synthesis, reactivity, and potential applications of similar compounds in various fields.

Upstream product

• 162849-93-6 (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 
• 13335-71-2 2-(2,6-dimethylphenoxy)acetic acid 
• 75-09-2 dichloromethane 
• 192725-45-4 (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 
• 156732-13-7 (5S)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene 
• 156732-15-9 (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane 
• 144163-85-9 (2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 

Downstream Products

• 192725-39-6 4-Oxo-ABT-378 
• 192725-17-0 lopinavir 
• 1255196-41-8 C₇₄H₉₆N₆O₁₅ 
• 221553-72-6 (S)-N-{(1S,3S,4S)-1-Benzyl-4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-5-phenyl-pentyl}-2-(4-hydroxy-2-oxo-tetrahydro-pyrimidin-1-yl)-3-methyl-butyramide 

Relevant articles and documents

Novel crystal form of lopinavir and preparation method thereof

The invention discloses a novel crystal form of lopinavir and a preparation method thereof, belonging to the technical field of medicine crystal forms. According to the invention, lopinavir is prepared, and the novel crystal form of lopinavir is cultured; a real stereo structure of four chiral centers in a lopinavir molecule can be seen from an obtained single crystal structure; crystal data is recorded by a crystal database, namely CCDC 1969375, of the British Cambridge University for the first time; and compared with other detection methods reported at present, an X-ray single crystal diffraction method is the most direct and intuitive method for determining the absolute configuration and space structure of lopinavir.

Preparation method of lopinavir

The invention provides a preparation method represented by formula (I) shown in the specification, and particularly provides a preparation method of (2S)-N-{(1S, 3S, 4S)-1-benzyl-4-[2-(2, 6-dimethylphenoxy)acetamido]-3-hydroxy-5-phenylamyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1-yl)butyramide. The novel method is provided for preparing lopinavir.

Synthesis of novel heterocyclic sulfonamides as protease inhibitors of HIV-1

Background: HIV-1 protease is a prime target for drug therapy due to its integral role in HIV viral replication. Several protease inhibitors such as lopinavir and tipranavir were shown to possess potent inhibitory activities against the HIV virus. Due to the high mutation rate of HIV, resistance remains a major problem in the treatment of this virus and design and synthesis of new protease inhibitors is an area of continued interest in new drug discovery research. Methods: Utilizing the key fragments of structures of both peptide-based and non-peptide-based protease inhibitors lopinavir and tipranavir, we explored designing some new compounds. Results: Six new protease inhibitors were designed and synthesized based on the key structural fragments in lopinavir and tipranavir. The designed new compounds contain heterocyclic groups such as thiophene, isoxazole, and imidazole groups, and the best compound exhibited 0.6 nm of the protease inhibitory activity. Conclusion: We have prepared some novel heterocyclic sulfonamides utilizing a key fragment based approach by recombining structural fragments of the potent protease inhibitors lopinavir and tipranavir. Some of these newly designed compounds showed good to excellent HIV-1 protease inhibitory activity, which indicated that this method would be useful for the discovery of new drug lead compounds that target HIV.

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.

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.

Novel Lopinavir analogues incorporating non-Aromatic P-1 side chains - Synthesis and structure-activity relationships

The HIV protease inhibitor Lopinavir has a pseudosymmetric core unit incorporating benzyl groups at both P-1, P-1′ positions. A series of analogues incorporating non-aromatic side chains at the P-1 position were synthesized and the structure-activity relationships explored.

Synthesis and antiviral activities of the major metabolites of the HIV protease inhibitor ABT-378 (Lopinavir)

The HIV protease inhibitor ABT-378 (Lopinavir) is metabolized rapidly and extensively by CYP-3A4 catalyzed oxidation. Three of the major metabolites identified were synthesized and their antiviral (HIV) activities determined.

RETROVIRAL PROTEASE INHIBITING COMPOUNDS

A compound of the formula: STR1 is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.