138498-62-1

Basic information

• Product Name: N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-[1,1-dimethylethoxy-carbonylamino]-4(S)-hydroxy-6-phenyl-2(R)-(4-hydroxyphenylmethyl) hexanamide
• Synonyms: N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-[1,1-dimethylethoxy-carbonylamino]-4(S)-hydroxy-6-phenyl-2(R)-(4-hydroxyphenylmethyl) hexanamide
• CAS NO: 138498-62-1
• Molecular Weight: 560.69
• Mol File: 138498-62-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-[1,1-dimethylethoxy-carbonylamino]-4(S)-hydroxy-6-phenyl-2(R)-(4-hydroxyphenylmethyl) hexanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-[1,1-dimethylethoxy-carbonylamino]-4(S)-hydroxy-6-phenyl-2(R)-(4-hydroxyphenylmethyl) hexanamide(138498-62-1)
• EPA Substance Registry System: N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-[1,1-dimethylethoxy-carbonylamino]-4(S)-hydroxy-6-phenyl-2(R)-(4-hydroxyphenylmethyl) hexanamide(138498-62-1)

Safety Data

• Hazardous Substances Data: 138498-62-1(Hazardous Substances Data)

Upstream product

• 140468-58-2 [(R)-1-((1S,2R)-2-Hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 7480-35-5 (1S,2R)-1-amino-2-indanol 
• 7480-35-5 trans-1-aminoindan-2-ol 
• 7480-35-5 (+/-)-cis-1-amino-indan-2-ol 
• 141018-39-5 1-((3aS,8aR)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-(4-hydroxy-phenyl)-propan-1-one 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 193338-94-2 (5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one 
• 27079-92-1 4-(bromomethyl)phenol 
• 141018-44-2 [(1S,2S,4R)-1-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-hydroxy-4-(4-hydroxy-benzyl)-5-oxo-pentyl]-carbamic acid tert-butyl ester 
• 126410-44-4 L-692048 
• 142526-87-2 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-[(p-benzyloxyphenyl)methyl]-hexanoic acid 
• 140468-55-9 2-phenyl-3a,8a-dihydro-8(H)-indeno<1,2-d>oxazole 
• 140468-56-0 (L)-phenylalanine <2(R)-hydroxy-1(S)-indanyl>amide 
• 138499-15-7 [(1S,2S,4R)-1-Benzyl-5-(4-benzyloxy-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester 

Downstream Products

• 138483-63-3 L-689502 
• 138483-84-8 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-<2-(4-methylpiperazin-1-yl)ethoxy>phenyl>methyl>hexanamide 
• 138483-77-9 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-<4-<<3-(4-morpholinyl)propyl>oxy>phenyl>-2(R)-(phenylmethyl)hexanamide 
• 138484-07-8 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-<2-oxo-2-(4-morpholinyl)ethoxy>phenyl>methyl>hexanamide 
• 140468-62-8 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-(2-hydroxyethoxy)phenyl>methyl>hexanamide 
• 139934-80-8 {4-[(2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-6-phenyl-hexyl]-phenoxy}-acetic acid 
• 140468-60-6 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-<2-(4-oxo-4-morpholinyl)ethoxy>phenyl>methyl>hexanamide 
• 138483-83-7 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-<2-(1,1-dioxythiamorpholin-4-yl)ethoxy>phenyl>methyl>hexanamide 
• 138483-82-6 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-<2-(1-oxothiamorpholin-4-yl)ethoxy>phenyl>methyl>hexanamide 
• 138483-78-0 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-<2-(dimethylamino)ethoxy>phenyl>methyl>hexanamide 
• 138483-80-4 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-<2-ethoxy>phenyl>methyl>hexanamide 
• 138498-60-9 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-<2-(1-piperidinyl)ethoxy>phenyl>methyl>hexanamide 
• 138483-81-5 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-<2-(thiamorpholin-4-yl)ethoxy>phenyl>methyl>hexanamide 
• 140468-61-7 {4-[(2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-6-phenyl-hexyl]-phenoxy}-acetic acid ethyl ester 

Relevant articles and documents

HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: An investigation into the role of the P1' side chain on structure-activity

A systematic investigation was undertaken to determine the role of the P1' sidechain in a series of hydroxyethylene isostere based inhibitors of HIV-1 protease. Substitution and homologation of the benzyl P1' side chain of the Phe-Phe isostere based pseudo peptides 1 (L-682,679) and 2 (L-685,434) with various heteroalkyl groups leads to a series of extremely potent inhibitors of the enzyme. Several examples of the most potent inhibitors were very effective in an ex vivo cell based viral spread assay using human H9 T- lymphocytes and the IIIb isolate of HIV-1. Compound 19 is 120 times more potent than 1 and 16 times more potent than 2 in inhibiting the spread of infection in this assay.

Synthesis and antiviral activity of a series of HIV-1 protease inhibitors with functionality tethered to the P1 or P1'phenyl substituents: X-ray crystal structure assisted design

By tethering of a polar hydrophilic group to the P1 or P1' substituent of a Phe-based hydroxyethylene isostere, the antiviral potency of a series of HIV protease inhibitors was improved. The optimum enhancement of anti-HIV activity was observed with the 4-morpholinylethoxy substituent. The substituent effect is consistent with a model derived from inhibitor docked in the crystal structure of the native enzyme. An X-ray crystal structure of the inhibited enzyme determined to 2.25 A verifies the modeling predictions.