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Novel sulfonamide-based carbamates as selective inhibitors of bche
A series of 14 target benzyl [2-(arylsulfamoyl)-1-substituted-ethyl]carbamates was prepared by multi-step synthesis and characterized. All the final compounds were tested for their abil-ity to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase
?těpánková, ?árka,Enriz, Ricardo D.,Garro, Adriana D.,Ho?ek, Jan,Imramovsky, Ale?,Jampílek, Josef,Jendrzejewska, Izabela,Magar, Pratibha,Parravicini, Oscar,Pauk, Karel,Svr?ková, Katarina
(2021/09/04)

Mild, Rapid, and Chemoselective Procedure for the Introduction of the 9-Phenyl-9-fluorenyl Protecting Group into Amines, Acids, Alcohols, Sulfonamides, Amides, and Thiols
The 9-phenyl-9-fluorenyl (PhF) group has been used as an Nα protecting group of amino acids and their derivatives mainly as a result of its ability to prevent racemization. However, installing this group using the standard protocol, which employs 9-bromo-9-phenylfluorene/K3PO4/Pb(NO3)2, often takes days and yields can be variable. Here, we demonstrate that the PhF group can be introduced into the amino group of Weinreb's amides and methyl esters of amino acids, as well as into alcohols and carboxylic acids, rapidly and in excellent yields, using 9-chloro-9-phenylfluorene (PhFCl)/N-methylmorpholine (NMM)/AgNO3. Nα-PhF-protected amino acids can be prepared from unprotected α-amino acids, rapidly and often in near quantitative yields, by treatment with N,O-bis(trimethylsilyl)acetamide (BSA) and then PhFCl/NMM/AgNO3. Primary alcohols can be protected with the PhF group in the presence of secondary alcohols in moderate yield. Using PhFCl/AgNO3, a primary alcohol can be protected in good yield in the presence of a primary ammonium salt or a carboxylic acid. Primary sulfonamides and amides can be protected in moderate to good yields using phenylfluorenyl alcohol (PhFOH)/BF3·OEt2/K3PO4, while thiols can be protected in good to excellent yield using PhFOH/BF3·OEt2 even in the presence of a carboxylic acid or primary ammonium group.
Soley, Jacob,Taylor, Scott D.
(2020/02/04)

O-Alkyl S-(Pyridin-2-yl)carbonothiolates: Operationally Simple and Highly Nitrogen-Selective Reagents for Alkoxy Carbonylation of Amino Groups
Amino groups are selectively protected in good yields by reaction with O-Alkyl S-(pyridin-2-yl)carbonothiolates in an appropriate solvent at room temperature in air. Even glucosamine, which contains multiple hydroxyl groups, is selectively N-protected in methanol.
Hashimoto, Yoshimitsu,Morita, Nobuyoshi,Suzuki, Tomoyuki,Tamura, Osamu,Tanaka, Kosaku
p. 899 - 902
(2020/05/28)

Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates
A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols; fortunately, we were not concerned about both these factors as precursor-azides were prepared easily by standard protocols, and the present protocol can pave the way for accessing title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy eliminates the need for the use of amines to obtain title compounds and thus, this method is step-economical; additional advantages include retention of chirality, convenient handling and easy purification. A few hitherto unreported compounds were also prepared, and all final compounds were completely characterized by IR, mass, optical rotation, and 1H and 13C NMR studies.
Santhosh,Durgamma,Shekharappa,Sureshbabu, Vommina V.
p. 4874 - 4880
(2018/07/15)

Regioselective Fluorination of α-Hydroxy-β-aminophosphonates by Using PyFluor
We report a simple protocol for the synthesis of α-fluoro-β-aminophosphonates by the regioselective fluorination of α-hydroxy-β-aminophosphonates under mild conditions. The fluorination reactions were mediated by the PyFluor reagent and occurred with the retention of configuration. The main products of this reaction were a series of α-fluoro-β-aminophosphonates, which can be used as precursors in the preparation of medicinally important compounds (e.g., dipeptide analogues).
Ka?mierczak, Marcin,Kubicki, Maciej,Koroniak, Henryk
p. 3844 - 3852
(2018/07/31)

PROTEASOME INHIBITOR COMPRISING A SIGNAL-EMITTING MOIETY
The present invention relates to compounds such as peptides which act as proteasome inhibitors. The compounds are covalently linked with a signal emitting compound or a precursor thereof, via an ester such as a sulfonic ester group for imaging of the inhibition of the proteasome. The compound is for use in the quantification of proteasomal inhibition, diagnosis and/or prevention and/or treatment of autoimmune diseases, cancer, neurodegenerative diseases, viral infections and/or diseases associated with inflammation. The invention further relates to methods to produce the compounds.
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(2017/03/14)

A Simple, efficient, Catalyst-Free and Solvent-Less Microwave-Assisted process for N-Cbz Protection of Several amines
A simple, green and chemo-selective method for the N-benzyloxycarbonylation of amines, β-amino alcohols, α-amino esters and sulfonamides has been developed under microwave irradiation. Good to excellent yields of the N-benzyloxy-carbamates compounds were obtained in short times without any side products.
Aouf, Zineb,Mansouri, Rachida,Lakrout, Salah,Berredjem, Malika,Aouf, Nour-Eddine
p. 151 - 156
(2017/08/02)

Metastin derivatives and use thereof
The invention provides stable metastin derivatives having excellent biological activities (a cancer metastasis suppressing activity, a cancer growth suppressing activity, etc.). By modifying the constituent amino acids of metastin with specific modifying groups, metastin derivatives having more improved blood stability, etc. than native metastin and showing excellent cancer metastasis suppressing activity or cancer growth suppressing activity have been found. Furthermore, it has been found that these metastin derivatives exhibit effects of suppressing gonadotropic hormone secretion, suppressing sex hormone secretion, etc., which are wholly different from the effects heretofore known.
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(2016/08/23)

Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
p. 10145 - 10149
(2016/08/16)

A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H
N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.
Ivkovic, Jakov,Lembacher-Fadum, Christian,Breinbauer, Rolf
supporting information
p. 10456 - 10460
(2015/11/10)

Substrate derived peptidic α-ketoamides as inhibitors of the malarial protease PfSUB1
Peptidic α-ketoamides have been developed as inhibitors of the malarial protease PfSUB1. The design of inhibitors was based on the best known endogenous PfSUB1 substrate sequence, leading to compounds with low micromolar to submicromolar inhibitory activity. SAR studies were performed indicating the requirement of an aspartate mimicking the P1′ substituent and optimal P1-P4length of the non-prime part. The importance of each of the P1-P4amino acid side chains was investigated, revealing crucial interactions and size limitations.
Kher, Samir S.,Penzo, Maria,Fulle, Simone,Finn, Paul W.,Blackman, Michael J.,Jirgensons, Aigars
supporting information
p. 4486 - 4489
(2015/02/19)

Solvent-free reduction of carboxylic acids to alcohols with NaBH4 promoted by 2,4,6-trichloro-1,3,5-triazine and PPh3 in the presence of K2CO3
A simple, rapid, and eco-friendly method for NaBH4 reduction of carboxylic acids to alcohols under solvent-free conditions was developed using a combination of 2,4,6-trichloro-1,3,5-triazine (TCT) with a catalytic amount of triphenylphosphine as an acid activator. With the 1 : 0.2 : 1.5 : 2 mole ratio of TCT : PPh3 : K2CO3 : NaBH4, carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids (Fmoc, Z) could readily undergo reduction to give the corresponding alcohols in good to excellent yields within 10 min.
Jaita, Subin,Kaewkum, Pantitra,Duangkamol, Chuthamat,Phakhodee, Wong,Pattarawarapan, Mookda
p. 46947 - 46950
(2014/12/10)

Synthesis of Nα-Z protected amino alkyl triazole acids and their application to neo-glycopeptides synthesis
The synthesis of triazole linked glycopeptides employing 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) mediated coupling of Z-protected triazole acids with glycosyl amines and amino acid esters is described. The coupling proceeded smoothly at room temperat
Madhu, Chilakapati,Panguluri, Nageswara Rao,Sureshbabu, Vommina V.
p. 858 - 864
(2014/08/05)

Hydrodehalogenation of alkyl iodides with base-mediated hydrogenation and catalytic transfer hydrogenation: Application to the asymmetric synthesis of N-protected α-methylamines
We report a very mild synthesis of N-protected α-methylamines from the corresponding amino acids. Carboxyl groups of amino acids are reduced to iodomethyl groups via hydroxymethyl intermediates. Reductive deiodination to methyl groups is achieved by hydrogenation or catalytic transfer hydrogenation under alkaline conditions. Basic hydrodehalogenation is selective for the iodomethyl group over hydrogenolysis-labile protecting groups, such as benzyloxycarbonyl, benzyl ester, benzyl ether, and 9-fluorenyloxymethyl, thus allowing the conversion of virtually any protected amino acid into the corresponding N-protected α-methylamine.
Mandal, Pijus K.,Birtwistle, J. Sanderson,McMurray, John S.
p. 8422 - 8427
(2015/03/18)

Selective inhibition of the immunoproteasome by ligand-induced crosslinking of the active site
The concept of proteasome inhibition ranks among the latest achievements in the treatment of blood cancer and represents a promising strategy for modulating autoimmune diseases. In this study, we describe peptidic sulfonyl fluoride inhibitors that selecti
Dubiella, Christian,Cui, Haissi,Gersch, Malte,Brouwer, Arwin J.,Sieber, Stephan A.,Krüger, Achim,Liskamp, Rob M. J.,Groll, Michael
supporting information
p. 11969 - 11973
(2015/03/04)

A mild multistep conversion of n-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction
Current methods of homologation of α-amino acids to β-amino acids have limitations. To overcome these shortfalls the Nef reaction has been utilized in the multistep synthesis of β3-amino acids from α-amino acids. In this approach, N-protected a
Sleebs, Brad E.,Nguyen, Nghi H.,Hughes, Andrew B.
p. 747 - 751
(2013/05/08)

Modular, gold-catalyzed approach to the synthesis of lead-like piperazine scaffolds
Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.
James, Thomas,Simpson, Iain,Grant, J. Andrew,Sridharan, Visuvanathar,Nelson, Adam
supporting information
p. 6094 - 6097
(2014/01/06)

An expedient route for the reduction of carboxylic acids to alcohols employing 1-propanephosphonic acid cyclic anhydride as acid activator
A simple and efficient method for the synthesis of alcohols from the corresponding carboxylic acids is described. Activation of carboxylic acid with 1-propane phosphonic acid cyclic anhydride (T3P) and subsequent reduction of the intermediate phosphonic anhydride with NaBH4 yield the alcohol in excellent yields with good purity in less duration. Reduction of several alkyl/aryl carboxylic acids and Nα-protected amino acids/peptide acids as well as Nβ-protected amino acids was successfully carried out to obtain corresponding alcohols in good yields and the products characterized. The procedure is mild, safe, simple and the isolation of the products is easy.
Nagendra,Madhu,Vishwanatha,Sureshbabu, Vommina V.
experimental part
p. 5059 - 5063
(2012/09/22)

Resolution and absolute configuration of some a-aminoacetals: En route to enantiopure N-protected a-aminoaldehydes
The first successful resolution of rac-a-aminoacetals via diastereoisomeric salt formation with optically pure N-protected aminoacids is reported. The absolute configuration assignment of a-aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving N-protection and a new efficient hydrolysis step followed by a reduction of the resulting N-protected a-aminoaldehyde intermediates. A racemization method of optically enriched a-aminoacetals is exemplified to allow valorisation of both enantiomers. Springer-Verlag 2011.
Albalat-Serradeil, Muriel,Primazot, Geraldine,Wilhelm, Didier,Vallejos, Jean-Claude,Vanthuyne, Nicolas,Roussel, Christian
p. 687 - 696
(2012/09/22)

An efficient and facile synthesis of N-Cbz-β-aminoalkanesulfonamides
An efficient method for the synthesis of N-Cbz-β- aminoalkanesulfonamides was described. N-Cbz-β-aminoalkanesulfona-mides were readily prepared in good yields from a variety of amino alcohols, including optically active ones, via N-Cbz protection with ben
Meng, Fanhua,Chen, Ning,Xu, Jiaxi
p. 2548 - 2553
(2013/06/27)

Synthesis and biological evaluation of novel irreversible serine protease inhibitors using amino acid based sulfonyl fluorides as an electrophilic trap
We have designed and synthesized novel irreversible serine protease inhibitors containing aliphatic sulfonyl fluorides as an electrophilic trap. These substituted taurine sulfonyl fluorides derived from taurine or protected amino acids were conveniently s
Brouwer, Arwin J.,Ceylan, Tarik,Jonker, Anika M.,Linden, Tima Van Der,Liskamp, Rob M.J.
p. 2397 - 2406
(2011/05/12)

Synthesis of the orthogonally protected amino alcohol Phaol and analogs
The development of a multigram synthesis of the orthogonally protected amino acid-derived Phaol [2-{[(2S)-2-amino-3-phenylpropyl]amino}ethanol] is described. The goal of this work is to synthesize an orthogonally protected Phaol in a multigram scale up to
Nelissen, Jo,Nuyts, Koen,Dehaen, Wim,De Borggraeve, Wim M.
p. 527 - 532
(2012/05/04)

IMPROVED AMINOHYDROXYLATION OF ALKENES
The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.
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(2012/01/06)

Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction
Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.
Harris, Lawrence,Mee, Simon P. H.,Furneaux, Richard H.,Gainsford, Graeme J.,Luxenburger, Andreas
p. 358 - 372
(2011/04/17)

Addition of allylzinc to a-amino acid-derived imines: Synthesis of diamino alcohols by Hydroboration
Imines obtained by condensation of Z-pro- tected or Boc-protected α-amino aldehydes with α-amino tert-butyl esters or with O-silyl-protected amino alcohols were reacted with preformed allyl zinc yielding homoal- lylamines with yields around 50% and selectivities ranging from 50:50 to 90:10. Hydroboration of the terminal double bond furnished diamino alcohols with yields up to 97%. The configuration of the substrates was determined by X-ray-crystallographic analysis of a hydroboration product and comparison of physical data. Springer-Verlag 2010.
Virlouvet, Mickael,Goesmann, Helmut,Feldmann, Claus,Podlech, Joachim
scheme or table
p. 177 - 198
(2010/08/05)

Simple and efficient synthesis of Fmoc/Boc/Cbz-protected-β-amino alcohols and peptidyl alcohols employing Boc2O
An efficient method for the activation of Fmoc/Boc/Cbz-protected amino acids using Boc2O and the reduction of the in situ generated carbonic-carbonic anhydride to their corresponding 1β-amino alcohols using sodium borohydride has been described. The method is simple, rapid and free from racemization. Besides, the protocol is also extended for the conversion of N-urethane protected peptide acids to their corresponding alcohols. Copyright
Lalithamba,Sureshbabu, Vommina V.
experimental part
p. 1372 - 1378
(2011/01/13)

Carbamate derivatives of felbamate as potential anticonvulsant agents
Several monocarbamate compounds derived from felbamate were synthesized and 11 target compounds (1, 4, and 6-14) were initially evaluated in mice MES and PTZ models in our laboratory. Carbamate compounds with varying substituents on the oxygen (1-4) gave anticonvulsant activity with a wide range of ED 50 in MES test from 300 mg/kg (4) and compounds with different groups on the nitrogen (5-14) also were quite active in the range of 15 mg/kg (14) to 170.5 mg/kg (6). This suggested that the spatial limitation in the MES model seemed flexible especially on the nitrogen end. All tested compounds showed some activity against mice scPTZ test, but none had the ED50 value 50 mg/kg. Ten selected compounds (1 and 6-14) for subsequent pharmacological evaluation in NIH all gave positive mice MES activity except 8 and 9, which were unexpectedly active in rats after further evaluations. Among the compounds, 1, 8, and 9 advanced to the quantitative study and 1 and 9 provided the highest PI values, 15 and 21, respectively, in the rat oral MES test.
Kung, Ching-Hsin,Kwon, Chul-Hoon
experimental part
p. 498 - 513
(2011/03/19)

A simple synthesis of N β-Fmoc/Z-amino alkyl thiols and their use in the synthesis of N β-Fmoc/Z-amino alkyl sulfonic acids
A simple and efficient protocol for the synthesis of Nβ- Fmoc/Z-amino alkyl thiols is described. The approach uses sodium pyrosulfite-mediated hydrolysis of isothiouronium salts resulting from the reaction between N-protected aminoalkyl iodides and thiourea. N-Protected taurines were prepared through performic acid oxidation of the thiols and the products were further utilized for the synthesis of dipeptidosulfonamides. Georg Thieme Verlag Stuttgart - New York.
Sureshbabu,Vishwanatha,Vasantha
body text
p. 1037 - 1042
(2010/07/06)

Expedient solid-phase synthesis of both symmetric and asymmetric diol libraries targeting aspartic proteases
C2-symmetric diols have been shown to be highly potent against HIV-1 protease (PR). However, gaining access to these compounds has been hampered by the need of multistep solution-phase reactions which are often tedious and inefficient. In this Letter, we have disclosed a solid-phase strategy for rapid preparation of small molecule-based, symmetric and asymmetric diols as potential HIV-1 protease inhibitors. Upon biological screening, we found one of them, SYM-5, to be a potent and selective inhibitor (Ki = 400 nM) against HIV-1 protease.
Shi, Haibin,Liu, Kai,Leong, Wendy W.Y.,Yao, Shao Q.
supporting information; experimental part
p. 3945 - 3948
(2010/03/30)

Synthesis of β-aminoethanesulfonyl fluorides or 2-substituted taurine sulfonyl fluorides as potential protease inhibitors
Substituted taurine sulfonyl fluorides derived from taurine or protected amino acids are conveniently synthesized from β-aminoethanesulfonyl chlorides using KF/18-crown-6 or from β-aminoethanesulfonates using DAST.
Brouwer, Arwin J.,Ceylan, Tarik,Linden, Tima van der,Liskamp, Rob M.J.
scheme or table
p. 3391 - 3393
(2009/09/05)

Dihydroxyacetone phosphate aldolase catalyzed synthesis of structurally diverse polyhydroxylated pyrrolidine derivatives and evaluation of their glycosidase inhibitory properties
The chemoenzymatic synthesis of a collection of pyrrolidine-type iminosugars generated by the aldol addition of dihydroxyacetone phosphate (DHAP) to C-α-substituted N-Cbz-2-aminoaldehydes derivatives, catalyzed by DHAP aldolases is reported. L-Fuculose-1-phosphate aldolase (FucA) and L-rhamnulose-1-phosphate aldolase (RhuA) from E. coli were used as biocatalysts to generate configurational diversity on the iminosugars. Alkyl linear substitutions at C-α were well tolerated by FucA catalyst (i.e., 40-70% conversions to aldol adduct), whereas no product was observed with C-α-alkyl branched substitutions, except for dimethyl and benzyl substitutions (20%). RhuA was the most versatile biocatalyst: C-α-alkyl linear groups gave the highest conversions to aldol adducts (60-99%), while the C-α-alkyl branched ones gave moderate to good conversions (50-80%), with the exception of dimethyl and benzyl substituents (20%). FucA was the most stereoselective biocatalyst (90-100% anti (3R,4R) adduct). RhuA was highly stereoselective with (S)-N-Cbz-2-aminoaldehydes (90-100% syn (i.e., 3R,4S) adduct), whereas those with R configuration gave mixtures of antilsyn adducts. For iPr and iBu substituents, RhuA furnished the anti adduct (i.e., FucA stereochemistry) with high stereoselectivity. Molecular models of aldol products with iPr and iBu sub-stituents and as complexes with the RhuA active site suggest that the and adducts could be kinetically preferred, while the syn adducts would be the equilibrium products. The polyhydroxylated pyrrolidines generated were tested as inhibitors against seven glycosidases. Among them, good inhibitors of a-L-fucosidase (IC50 = 1-20 μM), moderate of α-L-rhamnosidase (IC50=7-150 μM), and weak of α-D-mannosidase (IC50 = 80-400 μM) were identified. The apparent inhibition constant values (Ki) were calculated for the most relevant inhibitors and computational docking studies were performed to understand both their binding capacity and the mode of interaction with the glycosidases.
Calveras, Jordi,Egido-Gabas, Meritxell,Gomez, Livia,Casas, Josefina,Parella, Teodor,Joglar, Jesus,Bujons, Jordi,Clapes, Pere
experimental part
p. 7310 - 7328
(2010/03/24)

Simple and rapid synthesis of Nα-urethane protected β-amino alcohols and peptide alcohols employing HATU
The activation of the Nα--urcihanc protected (Fmoc-/Boc-/Z-/Bsmoc) α-amino acids employing l-[bis(dimethylamino)- methylene]-lH-l,2,3-triazolo-[4,5-6]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the in situ generated -OAt ester with NaBH 4 results in the corresponding ss-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent HATU for practical synthesis of ss-amino alcohols. The protocol is general for all common N-protecting groups including the highly base sensitive Bsmoc group. The protocol has also been successfully extended for the synthesis of peptide alcohols.
Surcshbabu, Vommina V.,Sudarshan,Chennakrishnareddy
experimental part
p. 574 - 579
(2009/12/06)

Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step
Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected β3-amino nitriles into their corresponding N-protected β3-amino acids. The biotransformations were obtained in different proportions depending on the nitrilase involved. The best hydrolysis results were achieved for the N-Cbz-β3-amino nitrile from l-alanine using the NIT-107, in a phosphate buffer at 0.05 M. However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide β3-amino nitriles. Two simple and efficient procedures to prepare the β3-amino nitriles from their analogous α-amino acids are described. Thirty four new substances were synthesized and characterized over the course of this work.
Veitia, Maite Sylla-Iyarreta,Brun, Pierre Louis,Jorda, Pierre,Falguieres, Annie,Ferroud, Clotilde
experimental part
p. 2077 - 2089
(2010/03/04)

Synthesis of novel amino-acid-derived sulfinamides and their evaluation as ligands for the enantioselective transfer hydrogenation of ketones
Novel chiral mono-sulfinyl diamines bearing a stereogenic sulfur atom were prepared in moderate to good yields starting from amino acids by means of a reductive amination of the corresponding amino aldehydes. Their potential as ligands for asymmetric catalysis was evaluated in the metal-catalyzed enantioselective transfer hydrogenation of alkyl-aryl ketones. The catalysts were generated in situ from sulfinamides 1a-i and arene complexes of rhodium and ruthenium, and the catalytic reductions led to the formation of chiral alcohols with up to 91% ee. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Zani, Lorenzo,Eriksson, Lars,Adolfsson, Hans
scheme or table
p. 4655 - 4664
(2009/04/11)

COMPOUNDS AND COMPOSITIONS AS CHANNEL ACTIVATING PROTEASE INHIBITORS
The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating channel activating proteases, and methods for using such compounds to treat, ameliorate or prevent a condition associated with a channel activating protease, including but not limited to prostasin, PRSS22, TMPRSS11 (e.g., TMPRSS11B, TMPRSS11E), TMPRSS2, TMPRSS3, TMPRSS4 (MTSP-2), matriptase (MTSP-1), CAP2, CAP3, trypsin, cathepsin A, or neutrophil elastase.
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(2008/12/08)

Truly catalytic and chemoselective cleavage of benzylidene acetal with phosphomolybdic acid supported on silica gel
Phosphomolybdic acid supported on silica gel provides a truly catalytic method for the chemoselective cleavage of benzylidene acetals having sensitive functional groups under mild conditions. It is easy to perform on large scale owing to minimal catalyst loading (0.5 mol-%). Several sensitive functional groups such as TBDPS ether, -OMs, -OAc, allyl ether, N-Boc, N-Fmoc and N-Cbz are stable under the reaction conditions. In addition, benzylidene acetal is selectively cleaved in the presence of isopropylidene ketal. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Kumar, Ponminor Senthil,Kumar, Gaddale Devanna Kishore,Baskaran, Sundarababu
supporting information; scheme or table
p. 6063 - 6067
(2009/05/27)

Synthesis of 2,6-disubstituted piperazines by a diastereoselective palladium-catalyzed hydroamination reaction
(Chemical Equation Presented) A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic disp
Cochran, Brian M.,Michael, Forrest E.
p. 329 - 332
(2008/09/19)

Synthesis of N-urethane protected β-amino alcohols employing N-(protected-α-aminoacyl)benzotriazoles
A simple and racemisation-free synthesis of N-urethane protected α-amino/peptidyl alcohols by the reduction of the corresponding easily accessible N-acylbenzotriazoles is described. The method is practical, straightforward, fast and efficient for the synt
Sureshbabu, Vommina V.,Sudarshan,Muralidhar,Narendra
p. 683 - 685
(2008/09/20)

Reduction of pentafluorophenyl esters to the corresponding primary alcohols using sodium borohydride
Primary alcohols and chiral N-protected 2-amino alcohols can be obtained in high yields from the reaction of pentafluorophenyl esters of the corresponding carboxylic acids with sodium borohydride in THF under mild conditions. This reductive method is rapid and compatible with various functional groups as well as with the most common N-protective groups Z, Boc and Fmoc.
Papavassilopoulou, Eleni,Christofis, Petros,Terzoglou, Despina,Moutevelis-Minakakis, Panagiota
p. 8323 - 8325
(2008/04/13)

Synthesis and applications of β-aminoethanesulfonyl azides
A very efficient method for the synthesis of β-aminoethanesulfonyl azides is descibed. These aliphatic sulfonyl azides are accessible starting from a variety of protected amino acids, including those having functionalized side chains. Furthermore, these s
Brouwer, Arwin J.,Merkx, Remco,Dabrowska, Katarzyna,Rijkers, Dirk T. S.,Liskamp, Rob M. J.
p. 455 - 460
(2007/10/03)

Procedure for the oxidation of β-amino alcohols to α-amino aldehydes
A novel procedure for the mild oxidation of β-amino alcohols to α-amino aldehydes using commercially available manganese(IV) oxide is reported. There are several important advantages of the new method, such as high enantiopurity of the reaction and the absence of either over-oxidation or any reaction by-products during the process. A number of N-protected L-α-amino aldehydes was obtained. All new compounds were characterized by their NMR spectra and optical rotation data. Georg Thieme Verlag Stuttgart.
Sergeev, Maxim E.,Pronin, Victor B.,Voyushina, Tatiana L.
p. 2802 - 2804
(2007/10/03)

Phosphate/sulfate ester compounds and pharmaceutical composition for inhibiting protein interacting NIMA (PIN1)
Phosphate/sulfate ester compounds that modulate and/or inhibit the activity of protein interacting NIMA (PIN1), and to pharmaceutical compositions containing such compounds are described. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating disorders characterized by hypertension, inappropriate cell proliferation, infectious diseases, and neurodegenerative brain disorders, by administering effective amounts of such compounds.
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Page/Page column 31

(2010/02/14)

New pyrrole-based amino acids for the synthesis of peptidomimetic constrained scaffolds
A new family of pyrrole-based amino acids have been prepared through the microwave assisted Paal-Knorr reaction of 1-4 ketoesters derived from the corresponding β-ketoester with a functional homologation. The carboxylic group is located in position 3 of the pyrrole, whereas the amino group, protected with the Cbz moiety, is present on the side chain in positions 1 or 2. These compounds were used to prepare constrained oligopeptides.
Alongi, Maddalena,Minetto, Giacomo,Taddei, Maurizio
p. 7069 - 7072
(2007/10/03)

A facile, catalytic, and environmentally benign method for selective deprotection of teri-butyldimethylsilyl ether mediated by phosphomolybdic acid supported on silica gel
An environmentally benign PMA supported on SiO2 is found to be an efficient catalyst for the chemoselective deprotection of TBDMS ethers under very mild conditions. Various labile functional groups such as isopropylidene acetal, OTBDPS, OTHP, Oallyl, OBn, alkene, alkyne, OAc, OBz, N-Boc, N-Cbz, N-Fmoc, mesylate, and azide are found to be stable under the reaction conditions. This "truly catalytic" heterogeneous reaction does not require aqueous workup, and the supported catalyst and the solvent can be readily recovered and recycled.
Kishore Kumar,Baskaran, Sundarababu
p. 4520 - 4523
(2007/10/03)

New Odorless Protocols for the Synthesis of Aldehydes and Ketones from Thiol Esters
Dodecanethiol esters derived from odorless dodecanethiol proved to be suitable substrates for Pd-catalyzed reduction with triethylsilane, coupling with organozinc reagents, and coupling with terminal acetylenes.
Miyazaki, Tohru,Han-Ya, Yuki,Tokuyama, Hidetoshi,Fukuyama, Tohru
p. 477 - 480
(2007/10/03)

Inhibition of α-chymotrypsin with thiol-bearing substrate analogues in the presence of zinc ion
We have demonstrated that thiol-bearing analogues of α-chymotrysin (α-CT) substrates such as (S)-(1-benzyl-2-thiolethyl)-carbamic acid, benzyl ester (3) inhibits α-CT, a prototypical serine protease, in the presence of Zn(II) ion. They constitute a novel class of small molecule inhibitors for α-CT believed to inhibit the enzyme by forming a ternary complex consisting of α-CT, Zn(II) ion, and the inhibitor.
Han, Min Su,Oh, Dong Ju,Kim, Dong H.
p. 701 - 705
(2007/10/03)

PHOSPHATE/SULFATE ESTER COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR INHIBITING PROTEIN INTERACTING NIMA (PIN1)
Phosphate/sulfate ester compounds that modulate and/or inhibit the activity of protein interacting NIMA (PIN1), and to pharmaceutical compositions containing such compounds are described. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating disorders characterized by hypertension, inappropriate cell proliferation, infectious diseases, and neurodegenerative brain disorders, by administering effective amounts of such compounds.
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Page 45

(2010/02/08)

HYDROXYMORPHOLINONE DERIVATIVE AND MEDICINAL USE THEREOF
A compound represented by the following formula (I) wherein R1 and R2 are each a lower alkyl group optionally having substituents, which has a calpain inhibitory activity, or a salt thereof is provided.
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Page 14

(2010/02/09)

A mild, efficient, and inexpensive protocol for the selective deprotection of TBDMS ethers using KHSO4
Potassium hydrogensulfate in 30% aq. methanol deprotects a variety of tert-butyldimethylsilyl ethers at room temperature in excellent yields.
Arumugam, Pandurangan,Karthikeyan, Ganesan,Perumal, Paramasivan T.
p. 1146 - 1147
(2007/10/03)

IgE antibody production inhibitors and autoimmune diseases inhibitors
The present invention relates to an IgE antibody production inhibitor and an autoimmune disease suppressant containing a heterocyclic amide compound represented by the following general formula (1) or a pharmaceutically acceptable salt thereof as an activ
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(2008/06/13)