cas 79561-82-3, (R)-N-BOC-4-Bromophenylalanine

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Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins
Herein, we report the first Ni-catalyzed enantioselective deaminative alkylation of amino acid and peptide derivatives with unactivated olefins. Key for success was the discovery of a new sterically encumbered bis(oxazoline) ligand backbone, thus offering a de novo technology for accessing enantioenriched sp3-sp3 linkages via sp3 C-N functionalization. Our protocol is distinguished by its broad scope and generality across a wide number of counterparts, even in the context of late-stage functionalization. In addition, an enantioselective deaminative remote hydroalkylation reaction of unactivated internal olefins is within reach, thus providing a useful entry point for forging enantioenriched sp3-sp3 centers at remote sp3 C-H sites.
Cai, Yue-Ming,Martin, Ruben,Rui, Xi-Yan,Shang, Ming,Sun, Shang-Zheng,Wang, Jia-Bao,Yao, Hong-Qing,Zhang, De-Liang
supporting information
p. 1130 - 1137
(2022/02/05)

Potent Anti-SARS-CoV-2 Activity by the Natural Product Gallinamide A and Analogues via Inhibition of Cathepsin L
Cathepsin L is a key host cysteine protease utilized by coronaviruses for cell entry and is a promising drug target for novel antivirals against SARS-CoV-2. The marine natural product gallinamide A and several synthetic analogues were identified as potent inhibitors of cathepsin L with IC50 values in the picomolar range. Lead molecules possessed selectivity over other cathepsins and alternative host proteases involved in viral entry. Gallinamide A directly interacted with cathepsin L in cells and, together with two lead analogues, potently inhibited SARS-CoV-2 infection in vitro, with EC50 values in the nanomolar range. Reduced antiviral activity was observed in cells overexpressing transmembrane protease, serine 2 (TMPRSS2); however, a synergistic improvement in antiviral activity was achieved when combined with a TMPRSS2 inhibitor. These data highlight the potential of cathepsin L as a COVID-19 drug target as well as the likely need to inhibit multiple routes of viral entry to achieve efficacy.
Aggarwal, Anupriya,Ashhurst, Anneliese S.,Bedding, Max J.,Beretta, Laura,Drelich, Aleksandra,Gerwick, William H.,Hook, Vivian,Larance, Mark,Li, Linfeng,McKerrow, James H.,Meek, Thomas D.,O'Donoghue, Anthony J.,Payne, Richard J.,Pwee, Dustin,Skinner, Danielle,Stoye, Alexander,Tang, Arthur H.,Tseng, Chien-Te,Turville, Stuart,Yoon, Michael C.,Fajtová, Pavla
supporting information

(2021/11/18)

Preparation method of 2-NH-Boc-3-(3',4'-dimethyl-[1,1'-biphenyl]-4)propionic acid
The invention relates to a preparation method of 2-NH-Boc-3-(3',4'-dimethyl-[1,1'-biphenyl]-4)propionic acid, and mainly solves the technical problem of lack of industrial preparation of the 2-NH-Boc-3-(3',4'-dimethyl-[1,1'-biphenyl]-4)propionic acid at p
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Paragraph 0006-0007

(2018/05/01)

CRYSTALLINE(2S,4R)-5-(5'-CHLORO-2'-FLUORO-[1,1'-BIPHENYL]-4-YL)-2-(ETHOXYMETHYL)-4-(3-HYDROXYISOXAZOLE-5-CARBOXAMIDO)-2-METHYLPENTANOIC ACID AND USES THEREOF
In one aspect, the invention relates to a crystalline form of the structure: or a pharmaceutically acceptable salt thereof, having neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising this crys
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Page/Page column 57

(2017/09/27)

NOVEL PROCESS FOR THE PREPARATION OF SACUBITRIL AND ITS INTERMEDIATES
A process for the preparation of sacubitril and its intermediates is disclosed. By practicing the methods disclosed herein, a solid form of sacubitril may be generated. A crystalline form of sacubitril is also disclosed.
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Page/Page column 27

(2016/09/26)

(2S,4R)-5-(5'-CHLORO-2'-FLUOROBIPHENYL-4-YL)-4-(ETHOXYOXALYLAMINO)-2-HYDROXYMETHYL-2-METHYLPENTANOIC ACID
In one aspect, the invention relates to a compound of the structure: or a pharmaceutically acceptable salt thereof, and a crystalline form of this compound, having neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical
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Paragraph 0243; 0244

(2016/09/08)

Synthesis of an amidosulfonate-tagged biphenyl phosphine and its application in the Suzuki-Miyaura reaction affording biphenyl-substituted amino acids in water
An amidosulfonate-tagged phosphinobiphenyl, viz triethylammonium 2-(dicyclohexylphosphino)-4′-{[(sulfonatomethyl)amino]carbonyl}biphenyl (3), was prepared in two steps from 2-(dicyclohexylphosphino)biphenyl-4′-carboxylic acid and fully characterized including the crystal structure determination. As a highly polar phosphine ligand, compound 3 was employed in the Pd-catalyzed Suzuki-Miyaura cross-coupling of N-Boc protected 4-bromo and 4-chlorophenylalanine with aromatic boronic acids to afford the corresponding biphenyls in aqueous N,N-dimethylformamide or pure water. The coupling was demonstrated to proceed very well and without the loss of the Boc protecting group when the bromo-substituted substrate is reacted in the presence of 1 mol.% of Pd/3 catalyst in water at 40 °C. Reactions with boronic acids bearing electron-withdrawing substituents and, mainly, those with the less reactive chlorophenylalanine substrate required slightly higher reaction temperature and more catalyst to achieve similar results.
Schulz, Ji?í,Císa?ová, Ivana,?těpni?ka, Petr
p. 65 - 72
(2015/03/04)

Chemoenzymatic Synthesis of Optically Pure l- and d-Biarylalanines through Biocatalytic Asymmetric Amination and Palladium-Catalyzed Arylation
A chemoenzymatic approach was developed and optimized for the synthesis of a range of N-protected nonnatural l- and d-biarylalanine derivatives. Starting from 4-bromocinnamic acid and 4-bromophenylpyruvic acid using a phenylalanine ammonia lyase (PAL) and an evolved d-amino acid dehydrogenase (DAADH), respectively, both enantiomers of 4-bromophenylalanine were obtained and subsequently coupled with a panel of arylboronic acids to give the target compounds in high yield and optical purity under mild aqueous conditions.
Ahmed, Syed T.,Parmeggiani, Fabio,Weise, Nicholas J.,Flitsch, Sabine L.,Turner, Nicholas J.
p. 5410 - 5413
(2015/09/15)

PEPTIDYL NITRIL COMPOUNDS AS DIPEPTIDYL PEPTIDASE I INHIBITORS
The invention relates to compounds of Formula (I) and its use as a selective dipeptidyl peptidase I inhibitor, as well as pharmaceutical compositions comprising said compounds, and methods of treatment involving said compounds.
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Page/Page column 26

(2015/03/28)

NEPRILYSIN INHIBITORS
In one aspect, the invention relates to compounds having the formula I: where R1, R2a, R2b, and R3-R6 are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compound
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Paragraph 0242-0243

(2015/08/04)

5-BIPHENYL-4-HETEROARYLCARBONYLAMINO-PENTANOIC ACID DERIVATIVES AS NEPRILYSIN INHIBITORS
In one aspect, the invention relates to compounds having the formula (I): where R1, R2a, R2b, and R3-R6 are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compou
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Page/Page column 59

(2015/09/23)

NEPRILYSIN INHIBITORS
In one aspect, the invention relates to compounds having the formula: where X, Ra, Rb, R2, and R7 are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds are prodrugs
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Page/Page column 0233; 0234

(2014/03/21)

NEPRILYSIN INHIBITORS
In one aspect, the invention relates to compounds having the formula: where R1-R5 and X are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and processes and intermediates for preparing such compounds.
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Paragraph 0267

(2014/09/29)

NEPRILYSIN INHIBITORS
In one aspect, the invention relates to compounds having the formula: where R1-R6, a, b, and Z are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and processes and intermediates for preparing such compounds.
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Paragraph 0297-0298

(2013/05/09)

NEPRILYSIN INHIBITORS
In one aspect, the invention relates to compounds having the formula XII: where Ra, Rb, R2, R7, and X are as defined in the specification, or a pharmaceutically acceptable salt thereof. The compounds described herein are prodrugs of compounds having neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising these compounds; methods of using these compounds; and processes and intermediates for preparing these compounds.
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Paragraph 0229-0230

(2014/01/08)

PEPTIDYL NITRILCOMPOUNDS AS PEPTIDASE INHIBITORS
The invention relates to compounds of Formula (II) and their use in theraphy as peptidase inhibitors.
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Page/Page column 112

(2012/09/22)

NEPRILYSIN INHIBITORS
In one aspect, the invention relates to compounds having the formula: where R1-R6, a, b, and X are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and processes and intermediates for preparing such compounds.
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Page/Page column 68

(2012/06/30)

NEPRILYSIN INHIBITORS
In one aspect, the invention relates to compounds having the formula: where R1-R6, a, b, Z, and X are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and processes and intermediates for preparing such compounds.
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Page/Page column 70

(2012/09/05)

DUAL-ACTING OXAZOLE ANTIHYPERTENSIVE AGENTS
In one aspect, the invention relates to compounds having the formula: wherein: Ar, Z, R3, R4 and R5 are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds have AT1 re
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Page/Page column 23

(2011/02/18)

Discovery of pyrrolopyrimidine inhibitors of Akt
The discovery and optimization of a series of pyrrolopyrimidine based protein kinase B (Pkb/Akt) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent inhibition of all three Akt isoforms and knockdown of phospho-PRAS40 levels in LNCaP cells and tumor xenografts.
Blake, James F.,Kallan, Nicholas C.,Xiao, Dengming,Xu, Rui,Bencsik, Josef R.,Skelton, Nicholas J.,Spencer, Keith L.,Mitchell, Ian S.,Woessner, Richard D.,Gloor, Susan L.,Risom, Tyler,Gross, Stefan D.,Martinson, Matthew,Morales, Tony H.,Vigers, Guy P.A.,Brandhuber, Barbara J.
scheme or table
p. 5607 - 5612
(2010/11/17)

Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximes.
A new asymmetric synthesis of alpha-amino acids is described in which the key step is the highly diastereoselective addition of organolithium carboxyl synthons (2-furyllithium, phenyllithium, vinyllithium) to (R)- and (S)-O-(1-phenylbutyl) oximes to give hydroxylamines, with vinyllithium being the most satisfactory nucleophilic reagent. Subsequent reductive cleavage of the N-O bond in hydroxylamines, followed by N-protection, and oxidative cleavage of the carboxyl precursor gave a range of N-protected amino acids and esters. The method was exemplified by the synthesis of a range of derivatives of non-proteinogenic amino acids such as 4-bromophenylalanine, tert-leucine, norvaline, cyclohexyl- and aryl-glycines, 2-amino-8-oxodecanoic acid (Aoda) and alpha-methylvaline.
Cooper, Tracey S,Laurent, Pierre,Moody, Christopher J,Takle, Andrew K
p. 265 - 276
(2007/10/03)

NOVEL BIAROMATIC COMPOUNDS WHICH ACTIVATE PPARγ TYPE RECEPTORS, AND USE THEREOF IN COSMETIC OR PHARMACEUTICAL COMPOSITIONS
The invention relates to novel biaromatic compounds which correspond to the general formula (I), and also to a process for preparing them and to their use in pharmaceutical compositions intended for use in human or veterinary medicine (in dermatology, and also in the field of cardiovascular diseases, immune diseases and/or diseases associated with lipid metabolism), or alternatively in cosmetic compositions.
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Page 69

(2008/06/13)

Synthesis of 4-phosphono- and of 4-(phosphonomethyl)-dl-phenylalanine, two analogues of O-phosphotyrosine
:4-Phosphono-DL-phenylalanine 1 was synthetized from 4-bromo-DL-phenylalanine or from 4-(bromomethyl)-bromobenzene ; 4-(phosphonomethyl)-DL-phenylalanine 14 was prepared from methyl p-toluate. The interest of these phosphonic analogues arises from their possible interference in the metabolism of O-phosphotyrosine.
Bayle-Lacoste, Mireille,Moulines, Jean,Collignon, Noel,Boumekouez, Abdelkader,De Tinguy-Moreaud, Eliane,Neuzil, Eugene
p. 7793 - 7802
(2007/10/18)