140468-58-2

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 7480-35-5 (1S,2R)-1-amino-2-indanol 
• 18942-49-9 Boc-D-Phe-OH 
• 7480-35-5 (+/-)-cis-1-amino-indan-2-ol 
• 140468-55-9 2-phenyl-3a,8a-dihydro-8(H)-indeno<1,2-d>oxazole 
• 7480-35-5 trans-1-aminoindan-2-ol 

Downstream Products

• 142694-73-3 N-<1-phenyl-2(S)-<(tert-butoxycarbonyl)amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide 
• 142580-67-4 {(1S,2S)-1-Benzyl-2-hydroxy-3-[(S)-1-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethylamino]-propyl}-carbamic acid tert-butyl ester 
• 142580-74-3 N-<1-phenyl-2(S)-<amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide 
• 142580-72-1 N-<1-phenyl-2(S)-amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide 
• 142580-73-2 N-<1-phenyl-2(S)-(N-L-asparaginylamino)-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide 
• 142580-71-0 N-<1-phenyl-2(S)-amino-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide 
• 160002-09-5 (4S,5S)-4-Benzyl-7-[(S)-1-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethyl]-2-oxo-1-oxa-3,7-diaza-spiro[4.4]nonane-3-carboxylic acid tert-butyl ester 
• 160080-47-7 (4S,5R)-4-Benzyl-7-[(S)-1-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethyl]-2-oxo-1-oxa-3,7-diaza-spiro[4.4]nonane-3-carboxylic acid tert-butyl ester 
• 140468-56-0 (L)-phenylalanine <2(R)-hydroxy-1(S)-indanyl>amide 
• 142694-72-2 {(1S,2R)-1-Benzyl-2-hydroxy-3-[(R)-1-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethylamino]-propyl}-carbamic acid tert-butyl ester 
• 142694-71-1 {(1S,2S)-1-Benzyl-2-hydroxy-3-[(R)-1-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethylamino]-propyl}-carbamic acid tert-butyl ester 
• 142580-61-8 (D)-phenylalanine <2(R)-hydroxy-1(S)-indanyl>amide 
• 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 
• 138483-79-1 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-<<4-<2-(1-pyrrolidinyl)ethoxy>phenyl>methyl>hexanamide 

Relevant academic research and scientific papers

α-Substituted norstatines as the transition-state mimic in inhibitors of multiple digestive vacuole malaria aspartic proteases

The impact of moving the P1 side-chain from the β-position to the α-position in norstatine-containing plasmepsin inhibitors was investigated, generating two new classes of tertiary alcohol-comprising α-benzylnorstatines and α-phenylnorstatines. Twelve α-s

A convergent synthesis of novel conformationally restricted HIV-1 protease inhibitors

Conformationally restricted HIV-1 protease inhibitors containing the transition state hydroxyl group in pyrrolidine or piperidine ring systems were synthesized stereoselectively utilizing the inherent stereochemistry of an amino acid derivative. A converg

A Series of Potent HIV-1 Protease Inhibitors Containing a Hydroxyethyl Secondary Amine Transition State Isostere: Synthesis, Enzyme Inhibition, and Antiviral Activity

A series of HIV-1 protease inhibitors containing a novel hydroxyethyl secondary amine transition state isostere has been synthesized.The compounds exhibit a strong preference for the (R) stereochemistry at the transition state hydroxyl group.Molecular modeling studies with the prototype compound 11 have provided important insights into the structural requirements for good inhibitor-active site binding interaction.N-Terminal extension of 11 into the P2-P3 region led to the discovery of 19, the most potent enzyme inhibitor in the series (IC50 = 5.4 nM). 19 was shown to have potent antiviral activity in cultured MT-4 human T-lymphoid cells.Comparison of analogs of 19 with analogs of 1 (Ro31-8959) demonstrates that considerably different structure-activity relationships exist between these two subclasses of hydroxyethylamine HIV-protease inhibitors.

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.