- SuFExable Isocyanides for Ugi Reaction: Synthesis of Sulfonyl Fluoro Peptides
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Herein, the sulfonyl fluoro isocyanides were first developed as a new type of SuFExable synthon, and they are used as building blocks in the Ugi reaction (U-4CR). The Ugi reaction was established and the substrate scope was investigated, and various sulfonyl fluoro α-amino amides and peptides could be reached in a one-step synthesis. Therefore, this protocol opens a new vision for SuFExable building blocks and click chemistry, and it also provides a distinct approach to sulfonyl fluoro peptides.
- Xu, Shuheng,Cui, Sunliang
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supporting information
p. 5197 - 5202
(2021/07/20)
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- Sulfono-γ-AA modified peptides that inhibit HIV-1 fusion
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The utilization of bioactive peptides in the development of highly selective and potent pharmacological agents for the disruption of protein-protein interactions is appealing for drug discovery. It is known that HIV-1 entry into a host cell is through a f
- Bolarinwa, Olapeju,Zhang, Meng,Mulry, Erin,Lu, Min,Cai, Jianfeng
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supporting information
p. 7878 - 7882
(2018/11/21)
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- Preparation method of taurylamine hydrochloride
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The invention discloses a preparation method of taurylamine hydrochloride. The preparation method comprises the following steps: by using taurine as an initial raw material, sequentially carrying out amino protecting reaction, chlorination reaction, ammonolysis reaction and deprotection-salification to obtain the taurylamine hydrochloride. The amino protecting group adopted by the amino protecting reaction is benzyl chloroformate, and the amino protecting group is carried out at 5-15 DEG C in the presence of sodium hydroxide and water. The chlorination reagent adopted by the chlorination reaction is thionyl chloride, and the chlorination reaction temperature is 60-70 DEG C. The ammonolysis reaction is carried out in tetrahydrofuran under the action of stronger ammonia water, and the ammonolysis reaction temperature is 5-15 DEG C. The total yield of the four-step reaction can reach 80% or above, the product purity can reach 99% or above, and thus, the method is suitable for industrialized mass production.
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- Tert -Butyl Hypochlorite Mediated Oxidative Chlorination of S -Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides
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Under neutral conditions, a variety of S-alkylisothiourea salts were smoothly converted into the corresponding sulfonyl chlorides through tert-butyl chlorite mediated oxidative chlorination in good to excellent yields after simple purification. In addition to the environmental and procedural advantages of this method, the neutral conditions potentially make it applicable to substrates that bear acid-sensitive functional groups. For example, the Cbz-protected 2-aminoethanesulfonyl chloride could be synthesized in moderate to good yields under the current neutral conditions, and the acid-sensitive Cbz-protecting group was not affected.
- Qiu, Kui,Wang, Rennan
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p. 3186 - 3190
(2015/10/19)
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- Synthesis of taurine-containing peptides, sulfonopeptides, and N - And O -conjugates
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Taurine-containing water-soluble peptidomimetics were designed and synthesized. N-terminal taurine acylations allowed synthesis of a number of taurine-containing peptides. N-protection of taurine with Cbz and SO 2-activation with benzotriazole followed by coupling with various amino esters, dipeptides and nucleophiles provided taurine N- and O-conjugates and sulfonopeptides.
- Vertesaljai, Peter,Biswas, Suvendu,Lebedyeva, Iryna,Broggi, Evan,Asiri, Abdullah M.,Katritzky, Alan R.
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p. 2688 - 2693
(2014/04/17)
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- An efficient and facile synthesis of N-Cbz-β-aminoalkanesulfonamides
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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
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p. 2548 - 2553
(2013/06/27)
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- 4-(SUBSTITUTED ANILINO)QUINAZOLINE DERIVATIVES AS TYROSINE KINASE INHIBITORS
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The present invention relates to 4-(substituted anilino)-quinazoline derivatives as tyrosine kinase inhibitors. Specifically, compounds of formula I, or pharmaceutically acceptable salts or solvates thereof are disclosed, in which each substitutent in formula I is defined in the description. Preparation method of the compounds of formula I, pharmaceutical compositons and pharmaceutical uses thereof are also disclosed. The compounds of formula I are effective tyrosine kinase inhibitors.
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Page/Page column 14
(2012/08/14)
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- 4-(Substituted Anilino)-Quinazoline Derivatives Useful as Tyrosine Kinase Inhibitors
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The present invention relates to 4-(substituted anilino)-quinazoline derivatives as tyrosine kinase inhibitors. Specifically, compounds of formula I, or pharmaceutically acceptable salts or solvates thereof are disclosed, in which each substitutent in formula I is defined in the description. Preparation method of the compounds of formula I, pharmaceutical compositions and pharmaceutical uses thereof are also disclosed. The compounds of formula I are effective tyrosine kinase inhibitors.
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Page/Page column 10
(2012/08/28)
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- Facile synthesis of hybrid sulfonophosphinodipeptides composing of taurines and 1-aminoalkylphosphinic acids
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Both sulfonopeptides and phosphonopeptides are important analogs of naturally occurring peptides and have been widely used as enzyme inhibitors and haptens for producing catalytic antibodies due to their tetrahedrally structural features. A series of hybr
- Meng, Fanhua,He, Fengdan,Song, Xiuqing,Zhang, Leilei,Hu, Wenxiang,Liu, Gang,Xu, Jiaxi
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p. 423 - 429
(2012/07/28)
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- A simple large-scale synthesis of Cbz-protected taurylsulfonyl azide
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A simple and efficient method for the large-scale synthesis of Cbz-taurylsulfonyl azide is described. This sulfonyl azide is accessible from taurine using three or four synthetic steps. Georg Thieme Verlag Stuttgart - New York.
- Brouwer, Arwin J.,Liskamp, Rob M. J.
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experimental part
p. 2228 - 2230
(2011/11/12)
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- Synthesis of β-aminoethanesulfonyl fluorides or 2-substituted taurine sulfonyl fluorides as potential protease inhibitors
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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.
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body text
p. 3391 - 3393
(2009/09/05)
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- First and convergent synthesis of hybrid sulfonophosphinopeptides
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Figure Presented Hybrid sulfonophosphinopeptides were first and convergently synthesized in satisfactory to good yields via the Mannich-type reaction of N-protected 2-aminoalkanesulfonamides, aromatic aldehydes, and aryldichlorophosphines and subsequent aminolysis with amino esters.
- He, Fengdan,Meng, Fanhua,Song, Xiuqing,Hu, Wenxiang,Xu, Jiaxi
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supporting information; experimental part
p. 3922 - 3925
(2009/12/05)
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- α-Peptide/β-sulfonamidopeptide hybrids: Analogs of the chemotactic agent for-Met-Leu-Phe-OMe
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In order to gain information on the activity shown by α-peptide/ β-sulfonamidopeptide hybrid analogs of the potent chemotactic agent fMLF-OMe, a structure-activity study is reported on N-Boc- and N-formyl tripeptide models containing an aminoalkanesulfoni
- Giordano, Cesare,Lucente, Gino,Masi, Annalisa,Paradisi, Mario Paglialunga,Sansone, Anna,Spisani, Susanna
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p. 2642 - 2652
(2007/10/03)
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- Probing the structural requirements of peptoids that inhibit HDM2-p53 interactions
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Many cellular processes are controlled by protein-protein interactions, and selective inhibition of these interactions could lead to the development of new therapies for several diseases. In the area of cancer, overexpression of the protein, human double minute 2 (HDM2), which binds to and inactivates the protein p53, has been linked to tumor aggressiveness and drug resistance. In general, inhibition of protein-protein interactions with synthetic molecules is challenging and currently remains a largely uncharted area for drug development. One strategy to create inhibitors of protein-protein interactions is to recreate the three-dimensional arrangement of side chains that are involved in the binding of one protein to another, using a nonnatural scaffold as the attachment point for the side chains. In this study, we used oligomeric peptoids as the scaffold to begin to develop a general strategy in which we could rationally design synthetic molecules that can be optimized for inhibition of protein-protein interactions. Structural information on the HDM2-p53 complex was used to design our first class of peptoid inhibitors, and we provide here, in detail, the strategy to modify peptoids with the appropriate side chains that are effective inhibitors of HDM2-p53 binding. While we initially tried to develop rigid, helical peptoids as HDM2 binders, the best inhibitors were surprisingly peptoids that lacked any helix-promoting groups. These results indicate that starting with rigid peptoid scaffolds may not always be optimal to develop new inhibitors.
- Hara, Toshiaki,Durell, Stewart R.,Myers, Michael C.,Appella, Daniel H.
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p. 1995 - 2004
(2007/10/03)
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- Synthesis and applications of β-aminoethanesulfonyl azides
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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.
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p. 455 - 460
(2007/10/03)
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- Synthesis of N-phthalimido β-aminoethanesulfonyl chlorides: The use of thionyl chloride for a simple and efficient synthesis of new peptidosulfonamide building blocks
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N-Phthalimido β-aminoethanesulfonyl chlorides, new building blocks for the synthesis of peptidosulfonamide peptidomimetics, were prepared in a straightforward manner from amino acids. In the crucial synthetic step, sulfonic acids or their sodium salts were converted into the corresponding sulfonyl chlorides using an excess of refluxing thionyl chloride or thionyl chloride/DMF. This simple and effective chlorinating method is also applicable to β-aminoethane sulfonic acids and their sodium salts with other N-protecting groups.
- Humljan, Jan,Gobec, Stanislav
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p. 4069 - 4072
(2007/10/03)
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- Aza- and polyaza-naphthalenyl carboxamides useful as HIV integrase inhibitors
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Aza- and polyaza-naphthalenyl carboxamide derivatives including certain quinoline carboxamide and naphthyridine carboxamide derivatives are described. These compounds are inhibitors of HIV integrase and inhibitors of HIV replication, and are useful in the
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- Targeted multivalent macromolecules
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Targeted therapeutic agents, comprising a linking carrier, a therapeutic entity associated with the linking carrier, and at least one targeting entity are provided, as well as methods for their preparation and use.
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- Targeted multivalent macromolecules
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Targeted macromolecules comprising a linking carrier and more than one targeting entity are provided, as well as methods for their preparation and use.
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- N - ( 2 - aryl - propionyl ) - sulfonamides and pharmaceutical preparations containing them
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The compounds of formula 1, wherein R and R2 are as defined in the disclosure, are useful in the prevention and treatment of tissue damage due to exacerbated recruitment of polymorphonuclear neutrophils (PMN leukocytes) at the inflammatory sites.
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- Synthesis of RGD analogs as potential vectors for targeted drug delivery
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RGD analogs bind to integrin receptors with high affinity and therefore have the potential to be used as vectors for the targeted delivery of pharmaceutical agents to designated sites. Critical to this application is the ability to synthesize RGD analogs
- Jiang, Ji,Wang, Wei,Sane, David C.,Wang, Binghe
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p. 357 - 379
(2007/10/03)
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- Amino acid derivatives with anticonvulsant activity
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A series of benzylamides of N-alkylated, N-acylated or free nine cyclic and one linear amino acids as potential anticonvulsants have been synthesized. The structures of the obtained compounds were designed on the basis of the previously determined structure and physicochemical properties/anticvonvulsant activity relationship of the formerly synthesized compounds of this type. The obtained compounds were evaluated in mice after intraperitoneal (ip) administration, by maximal electroshock seizure test (MES test), subcutaneous (sc) pentylenetetrazol test (sc PTZ test) and by the rotarod neurotoxicity test (Tox test). The results were the basis for their classification into one of three classes of the Anticonvulsant Screening Project (ASP) of the Antiepileptic Drug Development Program (ADDP) of the NIH. Three selected compounds were tested quantitatively in rats after oral administration. The MES ED50, sc PTZ ED50, Tox TD50 were determined and their protective index (PI) values were calculated. Anticonvulsant activity of the most promising compound (15) was examined in different seizure models. The respective ED50 and PI values of this compound were as follows: against bicuculline, 73 and 1.4; against PTZ, 47 and 2.2; against strychnine, 73 and 1.4; against pilocarpine 156, and 0.7; against kainic acid (2-carboxy-4-isopropenyl-3-pyrrolidineacetic acid), 39 and 2.6; against AMPA (α-amino-3-hydroxy-5methyl-4-isoxazolepropionic acid), 10 and 10.3 and against NMDA (N-methyl-D-Aspartic acid), 114 and 0.9.
- Paruszewski,Strupinska,Stables,Swiader,Czuczwar,Kleinrok,Turski
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p. 629 - 631
(2007/10/03)
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- An efficient synthesis of N-protected β-aminoethanesulfonyl chlorides: Versatile building blocks for the synthesis of oligopeptidosulfonamides
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A very efficient method for the synthesis of β-aminoethanesulfonyl chlorides is described. These aliphatic functionalized sulfonyl chlorides are accessible starting from a variety of protected amino acids, including those having functionalized side chains
- Brouwer,Monnee,Liskamp
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p. 1579 - 1584
(2007/10/03)
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- Sulfonopeptide inhibitors of leukocyte adhesion
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The amino acid sequence L-D-T-S-L has been shown to be a significant recognition motif involved in the interaction of integrin α4β7, with its endothelial ligand, MAdCAM-1. Based on the known active peptide, a series of sulfonamide peptidomimetics was synthesized. Sulfonopeptide 2, Ac-L-ΨD-V-NH2, was shown to inhibit leukocyte adhesion.
- Carson, Kenneth G.,Schwender, Charles F.,Shroff, Hitesh N.,Cochran, Nancy A.,Gallant, Debra L.,Briskin, Michael J.
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p. 711 - 714
(2007/10/03)
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- Synthesis of β-aminosulfonopeptides activated through selective N-nitration of a taurine amide unit
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β-Sulfonopeptides bearing a taurine in place of a penultimate amino acid unit were designed and synthesized as inhibitors of D-alanyl-D-alanine transpeptidase; N-nitration of the sulfonamide bond in the presence of multiple carboxamide groups was selectively accomplished through use of NO2BF4.
- Paik, Seunguk,White, Emil H.
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p. 4663 - 4666
(2007/10/03)
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- Design and synthesis of a bifunctional label for selection of β-lactamase displayed on filamentous bacteriophage by catalytic activity
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A bifunctional activity label 1c has been constructed for the selection of active β-lactamases displayed on filamentous bacteriophage. It features an original 6-sulfonylamido-penam sulfone moiety, as β-lactamase suicide-inhibitor, and a biotinyl residue, for separation by affinity chromatography, connected through a linker including a cleavable disulfide bond. The inhibitor 28 resulted from coupling of methoxymethyl 6-aminopenicillinate 8 with N-protected (aminoethoxy)ethoxyethanesulfonyl chloride 23, followed by oxidation into the corresponding sulfone 25, and usual deprotections. The biotinyl ester 32 reacted with 3-(2-aminoethyldithio)propanoic acid 31 as linker, to give 33 which was further activated as pentafluorophenol ester 34b. Final coupling of the building blocks 28 and 34b gave the target label 1c.
- Marchand-Brynaert, Jacqueline,Bouchet, Michele,Touillaux, Roland,Beauve, Cecile,Fastrez, Jacques
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p. 5591 - 5606
(2007/10/03)
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