78571-81-0Relevant articles and documents
PROCESS FOR SYNTHESIS OF SYN AZIDO EPOXIDE AND ITS USE AS INTERMEDIATE FOR THE SYNTHESIS OF AMPRENAVIR and SAQUINAVIR
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Paragraph 0077, (2015/02/18)
Disclosed herein is a novel route of synthesis of syn azide epoxide of formula 5, which is used as a common intermediate for asymmetric synthesis of HIV protease inhibitors such as Amprenavir, Fosamprenavir, Saquinavir and formal synthesis of Darunavir an
Dynamic kinetic asymmetric transformations of β-stereogenic α-ketoesters by direct aldolization
Corbett, Michael T.,Johnson, Jeffrey S.
, p. 255 - 259 (2014/01/17)
Dynamic kinetic asymmetric transformations (DyKAT) of racemic β-bromo-α-keto esters by direct aldolization of nitromethane and acetone provide access to fully substituted α-glycolic acid derivatives bearing a β-stereocenter. The aldol adducts are obtained
Enantioselective synthesis of HIV protease inhibitor amprenavir via Co-catalyzed HKR of 2-(1-azido-2-phenylethyl)oxirane
Gadakh, Sunita K.,Santhosh Reddy,Sudalai, Arumugam
experimental part, p. 898 - 903 (2012/09/22)
A short and efficient enantioselective synthesis of the HIV protease inhibitor amprenavir 1 (99% ee) as well as a formal synthesis of saquinavir 3 have been achieved in high enantiomeric purity starting from commercially available materials. Our strategy mainly comprises a Co-catalyzed two-stereocentred hydrolytic kinetic resolution (HKR) of racemic 2-(1-azido-2-phenylethyl)oxirane as the chirality inducing step. Also presented is a concise synthesis of (S)-3-hydroxytetrahydrofuran 4, the key structural feature, in high enantiomeric purity (98% ee).
Stereoselective synthesis of alpinoid-C and its analogues and study of their cytotoxic activity against cancer cell lines
Purushotham Reddy,Chinnababu,Shekhar,Kumar Reddy,Bhanuprakash,Velatoor,Venkateswara Rao,Venkateswarlu
, p. 4182 - 4184 (2012/07/03)
A simple, highly efficient and stereoselective synthetic route has been developed for synthesis of alpinoid-C (1) and its analogues (2, 3 and 4) from commercially available starting materials by using Wittig olefination, Sharpless asymmetric epoxidation,
FITNESS ASSAY AND ASSOCIATED METHODS
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Page/Page column 16, (2010/11/30)
The present invention provides an assay for determining the biochemical fitness of a biochemical species in a mutant replicating biological entity relative to its predecessor. The present invention further provides a continuous fluorogenic assay for measuring the anti-HIV protease activity of protease inhibitor. The present invention also provides a method of administering a therapeutic compound that reduces the chances of the emergence of drug resistance in therapy. The present invention also provides a compound of formula (I) or a pharmaceutically acceptable salt, a prodrug, a composition, or an ester thereof, wherein A is a group of formulas (A), (B), (C) or (D); R1, R2, R3, R5 or R6 is H, or an optionally substituted and/or heteroatom-bearing alkyl, alkenyl, alkynyl, or cyclic group; Y and/or Z are CH2, O, S, SO, SO2, amino, amides, carbamates, ureas, or thiocarbonyl derivatives thereof, optionally substituted with an alkyl, alkenyl, or alkynyl group; n is from 1 to 5; X is a bond, an optionally substituted methylene or ethylene, an amino, O or S; Q is C(O), C(S), or SO2; m is from 0 to 6; R4 is OH, ═O (keto), NH2, or alkylamino, including esters, amides, and salts thereof; and W is C(O), C(S), S(O), or SO2. Optionally, R5 and R6, together with the N—W bond of formula (I), comprise a macrocyclic ring.
Synthesis and evaluation of novel pyrazolidinone analogs of PGE2 as EP2 and EP4 receptors agonists
Zhao, Zhong,Araldi, Gian Luca,Xiao, Yufang,Reddy, Adulla P.,Liao, Yihua,Karra, Srinivasa,Brugger, Nadia,Fischer, David,Palmer, Elizabeth
, p. 6572 - 6575 (2008/09/16)
Replacement of the hydroxy cyclopentanone ring in PGE2 with chemically more stable heterocyclic rings and substitution of the unsaturated α-alkenyl chain with a metabolically more stable phenethyl chain led to the development of potent and selective analogs of PGE2. Compound 10f showed the highest potency and selectivity for EP4 the receptor.
Enantiodivergent, catalytic asymmetric synthesis of γ-amino vinyl sulfones
Pico, Anna,Moyano, Albert,Pericas, Miquel A.
, p. 5075 - 5083 (2007/10/03)
A set of diversely substituted N-Boc-γ-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of α-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given γ-amino vinyl sulfone can be obtained with equal ease.
First one-pot copper-catalyzed synthesis of α-hydroxy-β-amino acids in water. A new protocol for preparation of optically active norstatines
Fringuelli, Francesco,Pizzo, Ferdinando,Rucci, Mauro,Vaccaro, Luigi
, p. 7041 - 7045 (2007/10/03)
α-Hydroxy-β-amino acids were synthesized with excellent yields for the first time in water and by a simple procedure based on a copper catalytic cycle, which included the recovery and reuse of the catalyst and is possible to realize by using only water as reaction medium.
Base promoted isomerization of aziridinyl ethers: a new access to alpha- and beta-amino acids.
Mordini, Alessandro,Sbaragli, Laura,Valacchi, Michela,Russo, Francesco,Reginato, Gianna
, p. 778 - 779 (2007/10/03)
Aziridinyl ethers are selectively and easily converted to either amino vinyl ethers or alkoxy allylamines by treatment with mixed metal bases (superbases).
Base-promoted elaboration of aziridines
Mordini, Alessandro,Russo, Francesco,Valacchi, Michela,Zani, Lorenzo,Degl'Innocenti, Alessandro,Reginato, Gianna
, p. 7153 - 7163 (2007/10/03)
The base-promoted isomerization of aziridines to allyl amines is still an almost unknown reaction. However, the use of superbasic reagents has shown to be able to promote a regio- and stereoselective conversion of monocyclic and bicyclic sulfonyl aziridin
