- Balancing interactions in proline-based receptors for chiral recognition of l-/d-DOPA
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Proline based receptors (1-14) attached with phenylboronic acid and benzaldehyde binding groups at the N-/C-or C-/N-termini of the proline residue were created for chiral recognition of l-/d-DOPA, in an attempt to examine if balancing the two binding even
- Guo, Lin-E.,Hong, Yuan,Jiang, Yun-Bao,Li, Zhao,Tang, Yu-Xin,Yan, Xiao-Sheng,Zhang, Shu-Ying
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Read Online
- Double-chiral binaphthalene O-N-N tridentate ligand and preparation method thereof
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The invention discloses a bis-chiral binaphthalene O-N-N tridentate ligand and a preparation method thereof. The ligand has the structural formula shown in formula (L). The preparation method comprises the following steps: (1) taking chiral 2 - methyl -2 - methoxy -binaphthalene as a raw material and replacing the reaction with an aromatic ring. As an alternative to the hydroxy protecting group, a brominated derivative (compound IV) is obtained by bromination. (2) Starting from protected chiral proline, a variety of diamine structures are obtained by conversion (Compound B). (3) Compound IV and Compound B are coupled in the presence of a catalyst in the presence of a catalyst to obtain a binaphthalene O-N-N tridentate ligand with bichirality. The ligand preparation method is simple in raw material, and has important significance for asymmetric organic synthesis.
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Paragraph 0054-0057; 0061
(2021/09/22)
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- CAL-B-mediated efficient synthesis of a set of valuable amides by direct amidation of phenoxy- and aryl-propionic acids
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An efficient, easy and sustainable amidation of a set of non-activated carboxylic acids with anilines, assisted by CAL-B, as biodegradable catalyst, is reported. The enzymatic amidation reactions are performed on set of nonsteroidal anti-inflammatory drugs (NSAIDs), phenoxypropionic acid and protected-prolines by direct condensation of one equivalent of carboxylic acids and two equivalents of anilines derivatives in heptane after 72?h of reaction at 80?°C. The obtained carboxylic amides are recovered with isolated chemical yields varied between moderate and excellent. Fourteen from them are reported for the first time, and an X-ray crystal is obtained for: N-(4-iodophenyl)-2-(4-isobutylphenyl)propanamide 1d.
- Benamara, Nourelhouda,Merabet-Khelassi, Mounia,Aribi-Zouioueche, Louisa,Riant, Olivier
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p. 4045 - 4053
(2021/04/21)
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- SAR of novel benzothiazoles targeting an allosteric pocket of DENV and ZIKV NS2B/NS3 proteases
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In recent years, dengue virus (DENV) and Zika virus (ZIKV), both mosquito-borne members of the Flaviviridae family, have emerged as intercontinental health issues since their vectors have spread from their tropical origins to temperate climate zones due to climate change and increasing globalization. DENV and ZIKV are positive-sense, single-stranded RNA viruses, whose genomes consist of three structural (capsid, membrane precursor, envelope) and seven non-structural (NS) proteins, all of which are initially expressed as a single precursor polyprotein. For virus maturation, the polyprotein processing is accomplished by host proteases and the viral NS2B/NS3 protease complex, whose inhibitors have been shown to be effective antiviral agents with loss of viral pathogenicity. In this work, we elucidate new structure–activity relationships of benzo[d]thiazole-based allosteric NS2B/NS3 inhibitors. We developed a new series of Y–shaped inhibitors, which, with its larger hydrophobic contact surface, should bind to previously unaddressed regions of the allosteric NS2B/NS3 binding pocket. By scaffold-hopping, we varied the benzo[d]thiazole core and identified benzofuran as a new lead scaffold shifting the selectivity of initially ZIKV-targeting inhibitors to higher activities towards the DENV protease. In addition, we were able to increase the ligand efficiency from 0.27 to 0.41 by subsequent inhibitor truncation and identified N-(5,6-dihydroxybenzo[d]thiazol-2-yl)-4-iodobenzamide as a novel sub-micromolar NS2B/NS3 inhibitor. Utilizing cell-based assays, we could prove the antiviral activity in cellulo. Overall, we report new series of sub-micromolar allosteric DENV and ZIKV inhibitors with good efficacy profile in terms of cytotoxicity and protease inhibition selectivity.
- Barthels, Fabian,Gellert, Andrea,Hammerschmidt, Stefan Josef,Kopp, Katja,Maus, Hannah,Millies, Benedikt,Ruggieri, Alessia,Schirmeister, Tanja
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- Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha-amino acid subunits
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A series of diamide derivatives containing α-amino acids were designed and synthesized. These compounds were evaluated for their insecticidal activities against Plutella xylostella, Mythimna separate, Myzus persicae, and Tetranychus cinnabarinus. Most of the title compounds containing an l-phenylglycine skeleton were endowed with good activities at the concentration of 500 mg·L?1. Compounds (R)-A6 showed a potential value for further optimization as an insecticidal lead with the LC50 value of 86.8 mg·L?1.
- Chen, Rui-Jia,Wang, Jun-Jie,Han, Li,Gu, Yu-Cheng,Xu, Zhi-Ping,Cheng, Jia-Gao,Shao, Xu-Sheng,Xu, Xiao-Yong,Li, Zhong
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supporting information
p. 1429 - 1436
(2021/05/06)
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- New small γ-turn type: N -primary amino terminal tripeptide organocatalyst for solvent-free asymmetric aldol reaction of various ketones with aldehydes
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New small γ-turn type N-primary amino terminal tripeptides were synthesized and their functionality as an organocatalyst was examined in the asymmetric aldol reaction of various ketones with different aromatic aldehydes under solvent-free neat conditions to afford the desired chiral anti-aldol products in good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn?:?anti/13?:?87 dr, up to 99% ee). This journal is
- Begum, Zubeda,Kwon, Eunsang,Nakano, Hiroto,Okuyama, Yuko,Seki, Chigusa,Takeshita, Mitsuhiro,Thiyagarajan, Rajkumar,Tokiwa, Michio,Tokiwa, Suguru,Uwai, Koji
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p. 38925 - 38932
(2021/12/20)
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- Chiral azo-heterocyclic carbene precursor compound with bicyclic framework and preparation method thereof
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The invention discloses a chiral azo-heterocyclic carbene precursor compound with a bicyclic framework and a preparation method thereof. A series of the chiral azo-heterocyclic carbene precursor compound with the bicyclic framework is obtained by taking c
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Paragraph 0042; 0043; 0044; 0045; 0050; 0052; 0053
(2019/01/22)
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- Modular synthesis of new bicyclic carbene precursors
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A series of new N-heterocyclic carbene (NHC) precursors, containing bicyclic pyrrolo[1,2-c]imidazole framework, were prepared from N-(tert-butoxycarbonyl)-L-proline (1-Boc-L-proline). The sequential attachment of nitrogen nucleophiles and subsequent ring
- Li, Jie,Yao, Jiaqi,He, Weiping,Yang, Fan,Liu, Xiaoming
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p. 951 - 954
(2019/11/22)
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- Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages
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The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.
- Wang, Shi-Meng,Zhao, Chuang,Zhang, Xu,Qin, Hua-Li
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supporting information
p. 4087 - 4101
(2019/04/30)
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- Synthesis and anticancer activity of conformationally constrained Smac mimetics containing pseudo β turns
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Herein, we report synthesis and in vitro anticancer activity of conformationally constrained Smac mimetics containing reverse turn inducing motifs “Ant-Pro” and “sAnt-Pro”. The synthesis of Smac analogs with diverse hydrophobic groups at the C-
- Baravkar, Sachin B.,Wagh, Mahendra A.,Paul, Debasish,Santra, Manas,Sanjayan, Gangadhar J.
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supporting information
p. 3473 - 3476
(2018/08/24)
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- Asymmetric Cα-Alkylation of Proline via Chirality Transfers of Conformationally Restricted Proline Derivative: Application to the Total Synthesis of (-)-Amathaspiramide F
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An efficient strategy for the asymmetric synthesis of Cα-tetrasubstituted proline derivatives from proline has been established. A nitrogen-fused bicyclic system was devised to control the stereodynamics of proline. Through N-quaternizations with allylic electrophiles followed by [2,3]-rearrangements, the bicyclic proline system delivered enantioenriched Cα-tetrasubstituted prolines. This strategy was applied to the concise total synthesis of (-)-amathaspiramide F.
- Cho, Hyunkyung,Shin, Jae Eui,Lee, Seokwoo,Jeon, Hongjun,Park, Soojun,Kim, Sanghee
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supporting information
p. 6121 - 6125
(2018/10/02)
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- "on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols
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The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.
- Chakraborti, Gargi,Paladhi, Sushovan,Mandal, Tirtha,Dash, Jyotirmayee
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p. 7347 - 7359
(2018/07/29)
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- Proline-Based Boronic Acid Receptors for Chiral Recognition of Glucose
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Chiral recognition remains a major challenge in the area of molecular receptor design. With this research, we set out to explore the use of proline-based receptors for chiral recognition. Importantly, the proline structure allows for the introduction of a
- Guo, Lin-E,Hong, Yuan,Zhang, Shu-Ying,Zhang, Miao,Yan, Xiao-Sheng,Cao, Jin-Lian,Li, Zhao,James, Tony D.,Jiang, Yun-Bao
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supporting information
p. 15128 - 15135
(2019/01/04)
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- A Cross-Coupling Approach to Amide Bond Formation from Esters
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A palladium-catalyzed cross-coupling between aryl esters and anilines is reported, enabling access to diverse amides. The reaction takes place via activation of the C-O bond by oxidative addition with a Pd-NHC complex, which enables the use of relatively non-nucleophilic anilines that otherwise require stoichiometric activation with strong bases in order to react. High yields of aromatic, aliphatic, and heterocyclic products are obtained. A range of activated esters are evaluated in the presence and absence of catalyst, demonstrating that the catalytic methodology substantially increases the types of electrophiles that can be utilized for amide bond formation in the absence of harsh bases.
- Ben Halima, Taoufik,Vandavasi, Jaya Kishore,Shkoor, Mohanad,Newman, Stephen G.
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p. 2176 - 2180
(2017/08/09)
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- Amine Activation: N-Arylamino Acid Amide Synthesis from Isothioureas and Amino Acids
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N-arylamino acid amides have been synthesized via a novel method based on N-arylamine activation into isothioureas followed by reaction with amino acids under iron catalysis. The activated N-arylamines are easily prepared using a three-component reaction with commercial reagents, tert-butylisocyanide and S-phenyl benzenethiosulfonate. The protocol shows a broad functional group compatibility, with respect to side chain functionality of the amino acid (e. g. aliphatic and aromatic OH, (hetero)aromatic NH, amide NH, thioether), and the chiral amino acids do not undergo epimerization. The mechanism of the new amide synthesis has been studied. (Figure presented.).
- Zhu, Yan-Ping,Mampuys, Pieter,Sergeyev, Sergey,Ballet, Steven,Maes, Bert U. W.
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p. 2481 - 2498
(2017/07/22)
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- Synthesis of Analogues of BCTC Incorporating a Pyrrolidinyl Linker and Biological Evaluation as Transient Receptor Potential Vanilloid 1 Antagonists
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A series of novel pyrrolidinyl linker TRPV1 antagonists were prepared in an effort to lower the hyperthermic side-effects of first-generation antagonist BCTC. These compounds were investigated for antagonism of hTRPV1 activation by capsaicin and acid in vitro. Preliminary results suggested the compounds 10a, 10b, 10c and 10j had favorable TRPV1 antagonism activity. In further studies in vivo, 10b, comparable to BCTC, showed potent analgesic activity in capsaicin-induced and heat-induced pain models. In addition, 10b indicated a reduced risk of body temperature elevation. All of these demonstrated that 10b can be considered as a safe candidate for the further development of analgesic drugs. A series of novel pyrrolidinyl linker TRPV1 antagonists were prepared in an effort to lower the hyperthermic side-effects of first-generation antagonist BCTC. These compounds were investigated for antagonism of hTRPV1 activation by capsaicin and acid in vitro. Preliminary results suggested the compounds 10a, 10b, 10c and 10j had favorable TRPV1 antagonism activity. In further studies in vivo, 10b, comparable to BCTC, showed potent analgesic activity in capsaicin-induced and heat-induced pain models. In addition, 10b indicated a reduced risk of body temperature elevation. All of these demonstrated that 10b can be considered as a safe candidate for the further development of analgesic drugs.
- Yan, Lin,Wang, Jingjie,Pan, Miaobo,Qiu, Qianqian,Huang, Wenlong,Qian, Hai
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p. 306 - 311
(2016/02/10)
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- The development of new amine-amide ligands for application in Cu(II)-catalyzed enantioselective Henry reactions
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A new type of chiral tertiary amine ligand was designed and derived from l-proline and (R)-BINOL. These new chiral ligands chelated with Cu(II) showed highly catalytic efficiency in enantioselective Henry reactions. Excellent yields (up to 99%) and high enantioselectivities (up to 96% ee) were achieved for aromatic, hetero-aromatic and aliphatic aldehyde substrates, without an additional base additive or the need for air or moisture exclusion.
- Ao, Chunyan,Men, Jian,Wang, Yang,Shao, Tao,Huang, Yuanyuan,Huo, Junji,Gao, Guowei
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p. 589 - 595
(2016/07/06)
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- Targeting the Src Homology 2 (SH2) Domain of Signal Transducer and Activator of Transcription 6 (STAT6) with Cell-Permeable, Phosphatase-Stable Phosphopeptide Mimics Potently Inhibits Tyr641 Phosphorylation and Transcriptional Activity
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Signal transducer and activator of transcription 6 (STAT6) transmits signals from cytokines IL-4 and IL-13 and is activated in allergic airway disease. We are developing phosphopeptide mimetics targeting the SH2 domain of STAT6 to block recruitment to phosphotyrosine residues on IL-4 or IL-13 receptors and subsequent Tyr641 phosphorylation to inhibit the expression of genes contributing to asthma. Structure-affinity relationship studies showed that phosphopeptides based on Tyr631 from IL-4Rα bind with weak affinity to STAT6, whereas replacing the pY+3 residue with simple aryl and alkyl amides resulted in affinities in the mid to low nM range. A set of phosphatase-stable, cell-permeable prodrug analogues inhibited cytokine-stimulated STAT6 phosphorylation in both Beas-2B human airway cells and primary mouse T-lymphocytes at concentrations as low as 100 nM. IL-13-stimulated expression of CCL26 (eotaxin-3) was inhibited in a dose-dependent manner, demonstrating that targeting the SH2 domain blocks both phosphorylation and transcriptional activity of STAT6.
- Mandal, Pijus K.,Morlacchi, Pietro,Knight, J. Morgan,Link, Todd M.,Lee, Gilbert R.,Nurieva, Roza,Singh, Divyendu,Dhanik, Ankur,Kavraki, Lydia,Corry, David B.,Ladbury, John E.,McMurray, John S.
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p. 8970 - 8984
(2015/12/09)
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- Synthesis and characterization of NiIIIN3S2 complexes as active site models for the oxidized form of nickel superoxide dismutase
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Nickel complexes, [Ni(H2BARTPP)](ClO 4)2 (R=Ph for 1 or iPr for 2), supported by a pentadentate ligand H2BARTPP were synthesized and oxidized to form NiIII species having a N3S2
- Chiang, Chien-Wei,Chu, Yun-Li,Chen, Hong-Ling,Kuo, Ting-Shen,Lee, Way-Zen
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p. 6283 - 6286
(2014/06/09)
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- Complementary stereochemical outcomes in proline-based self-regenerations of stereocenters
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Stereoselective alkylations of proline-based amino amides are described, where high levels of either a cis or trans configuration can be attained simply by the choice of the aminal group. Isobutryaldehyde-derived aminals provide the cis configuration, whi
- Knight, Brian J.,Stache, Erin E.,Ferreira, Eric M.
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p. 432 - 435
(2014/04/03)
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- Asymmetric lithiation trapping of N -boc heterocycles at temperatures above -78°C
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The asymmetric lithiation trapping of N-Boc heterocycles using s-BuLi/chiral diamines at temperatures up to -20°C is reported. Depending on the N-Boc heterocycle, lithiation is accomplished using s-BuLi and (-)-sparteine or the (+)-sparteine surrogate in the temperature range -50 to -20°C for short reaction times (2-20 min). Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered functionalized N-Boc heterocycles in 47-95% yield and 77:23-93:7 er. With N-Boc pyrrolidine, trapped products can be generated in ~90:10 er even at -20°C.
- Gelardi, Giacomo,Barker, Graeme,O'Brien, Peter,Blakemore, David C.
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p. 5424 - 5427
(2013/11/19)
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- Discovery and SAR studies of methionine-proline anilides as dengue virus NS2B-NS3 protease inhibitors
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A series of methionine-proline dipeptide derivatives and their analogues were designed, synthesized and assayed against the serotype 2 dengue virus NS2B-NS3 protease, and methionine-proline anilides 1 and 2 were found to be the most active DENV 2 NS2B-NS3 competitive inhibitors with Ki values of 4.9 and 10.5 μM. The structure and activity relationship and the molecular docking revealed that l-proline, l-methionine and p-nitroaniline in 1 and 2 are the important characters in blocking the active site of NS2B-NS3 protease. Our current results suggest that the title dipeptidic scaffold represents a promising structural core to discover a new class of active NS2B-NS3 competitive inhibitors.
- Zhou, Guo-Chun,Weng, Zhibing,Shao, Xiaoxia,Liu, Fang,Nie, Xin,Liu, Jinsong,Wang, Decai,Wang, Chunguang,Guo, Kai
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supporting information
p. 6549 - 6554
(2014/01/06)
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- A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant
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A simple and inexpensive proline-based organocatalyst was developed for the reduction of imines using trichlorosilane as a reductant. The reduction of N-aryl imines in the presence of 10 mol % of N-pivaloyl-l-proline anilide was carried out to give the co
- Kanemitsu, Takuya,Umehara, Atsushi,Haneji, Rieko,Nagata, Kazuhiro,Itoh, Takashi
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experimental part
p. 3893 - 3898
(2012/07/02)
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- Resolution of carboxylic acids using copper(I)-promoted removal of propargylic esters under neutral conditions
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A method for the optical resolution of carboxylic acids is described. Condensation of racemic carboxylic acids with chiral terminal propargyl alcohols gave separable diastereomeric esters. Chromatographic separation followed by heating the individual diastereomers in methanol with catalytic copper(I) halide regenerated the carboxylic acids in good yields and in enantiomeric ratios of ?94%. This method is particularly useful for the resolution of carboxylic acids that are incompatible with conventional ester hydrolysis.
- Ghosh, Partha,Aube, Jeffrey
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p. 4168 - 4172
(2011/07/30)
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- MICHAEL SYSTEMS AS TRANSGLUTAMINASE INHIBITORS
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Described herein are peptide derivatives and peptidomimetics as inhibitors for transglutaminases, methods for their preparation, pharmaceutical compositions containing said compounds as well as uses of said transglutaminase inhibitors in particular for th
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- Screening of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts for the enantioselective aldol reaction of acetone with isatin
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We have screened a range of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts incorporating N-pyridyl and N-quinolinyl groups in the synthetically useful aldol reaction of isatin with acetone. The 'reverse amide' N-pyridyl pyrrolidinylmethy
- Kinsella, Michael,Duggan, Patrick G.,Lennon, Claire M.
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p. 1423 - 1433
(2011/11/06)
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- Cross-coupling reactions of aryl halides with amines, phenols, and thiols catalyzed by an N,N′-dioxide-copper(I) catalytic system
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The coupling reactions of various N, O, and S nucleophilic reagents with aryl halides have been successfully carried out under mild conditions by using a novel chiral N,N′-dioxide-copper(I) catalytic system as the catalyst. This versatile and efficient catalyst system has been demonstrated to facilitate the cross-coupling reactions of aryl halides with amines, phenols, and thiols to afford the corresponding desired products in good to excellent yields.
- Yang, Haitao,Xi, Chao,Miao, Zhiwei,Chen, Ruyu
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supporting information; experimental part
p. 3353 - 3360
(2011/08/03)
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- Simple, inexpensive, and facile l-prolinamide used as a recyclable organocatalyst for highly efficient large-scale asymmetric direct aldol reactions
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In order to discover a simple, inexpensive, and efficient route to obtain highly enantiomerically enriched anti-aldol products for applications in industry, a series of prolinamides 1-5 with different carbocyclic rings have been synthesized from achiral c
- Xu, Jiangwei,Fu, Xiangkai,Wu, Chuanlong,Hu, Xiaoyan
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experimental part
p. 840 - 850
(2011/08/21)
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- Chemoselective peptidomimetic ligation using thioacid peptides and aziridine templates
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Chemoselective peptidomimetic ligation has been made possible using thioacid peptides and NH aziridine-terminated amino acids and peptides. In the course of this reaction, a reduced amide bond is incorporated into the backbone of a peptide. This process e
- Assem, Naila,Natarajan, Aditya,Yudin, Andrei K.
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supporting information; experimental part
p. 10986 - 10987
(2010/09/16)
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- Highly diastereo- And enantioselective aldol reactions in common organic solvents using N-arylprolinamides as organocatalysts with enhanced acidity
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A broad set of N-arylprolinamides 1-8 with increasing NH acidity and steric crowding has been synthesized and its catalytic activity explored for enantioselective aldol reactions. In DMF containing 10 mol-% of TFA, all arylamides are found to catalyze the reaction between cyclohexanone and a variety of electrophilic aldehydes leading to aldols in excess of 90% yield and >95 % enantioselectivity. The per-fluorophenyl catalyst 8 is found to perform best with a broad substrate scope as compared to all other N-arylamides 1-7. It is shown that 8 can indeed be employed in highly nonpolar as well as polar solvents including brine to afford high yields of aldols with excellent diastereo- as well as enantio-selectivity. The results observed for 8 are amongst the best reported so far for prolinamides that do not contain additional stereogenic center(s) and hydrogen-bonding site(s). The molecular structures of 7 and 8, determined by X-ray crystallography and presumed to reflect the most stable conformations, reveal a notable difference in the conformations of the N-aryl rings; the aryl ring exhibits tendency to lie coplanar with the amide functionality in the case of 7, while the per- fluorophenyl ring twists almost orthogonally with respect to the plane of the amide of functionality in 8. The superior performance of the latter is attributed to, in addition to the enhanced NH acidity, the tendency of the perfluorophenyl ring to lie orthogonally to the amide group, which may facilitate a stronger binding of the electrophilic aldehyde via hydrogen bonding in the transition state.
- Moorthy, Jarugu Narasimha,Saha, Satajit
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experimental part
p. 739 - 748
(2009/07/19)
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- Oxazoline-substituted prolinamide-based organocatalysts for the direct intermolecular aldol reaction between cyclohexanone and aromatic aldehydes
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Oxazoline-substituted prolinamides catalyse the direct asymmetric aldol reaction between cyclohexanone and a range of aldehydes to give excellent conversions and enantioselectivities up to 84% under optimum conditions. Reactions were highly substrate-spec
- Doherty, Simon,Knight, Julian G.,McRae, Amy,Harrington, Ross W.,Clegg, William
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experimental part
p. 1759 - 1766
(2009/04/06)
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- Proline bis-amides as potent dual orexin receptor antagonists
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A series of OX2R/OX1R dual orexin antagonists was prepared based on a proline bis-amide identified as a screening lead. Through a combination of classical and library synthesis, potency enhancing replacements for both amide portions
- Bergman, Jeffrey M.,Roecker, Anthony J.,Mercer, Swati P.,Bednar, Rodney A.,Reiss, Duane R.,Ransom, Richard W.,Meacham Harrell,Pettibone, Douglas J.,Lemaire, Wei,Murphy, Kathy L.,Li, Chunze,Prueksaritanont, Thomayant,Winrow, Christopher J.,Renger, John J.,Koblan, Kenneth S.,Hartman, George D.,Coleman, Paul J.
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p. 1425 - 1430
(2008/12/21)
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- An N,N′-dioxide/In(OTf)3 catalyst for the asymmetric hetero-Diels-Alder reaction between Danishefsky's dienes and aldehydes: Application in the total synthesis of triketide
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(Chemical Equation Presented) In-teresting catalyst: An asymmetric hetero Diels-Alder reaction between Danishefsky's dienes and various aldehydes using an N,N′-dioxide/In(OTf)3 complex affords highly substituted chiral dihydropyranones with up
- Yu, Zhipeng,Liu, Xiaohua,Dong, Zhenhua,Xie, Mingsheng,Feng, Xiaoming
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p. 1308 - 1311
(2008/12/22)
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- Enantiomerically pure cyclopalladated diazaphospholidine
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Enantiomerically pure (S)-2-(anilinomethyl)pyrrolidine (S)-2 was obtained from (S)-proline using a modified four-step procedure in a total yield of 56%. Diamine (S)-2 was converted to diazaphospholidine (S)-1 using oTolP(NMe2)2
- Dunina, Valery V.,Gorunova, Olga N.,Stepanova, Valeriya A.,Zykov, Pavel A.,Livantsov, Michail V.,Grishin, Yuri K.,Churakov, Andrey V.,Kuz'mina, Lyudmila G.
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p. 2011 - 2015
(2008/02/11)
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- Asymmetric intramolecular Michael reaction catalyzed by proline-derived small anilides
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Simple proline-derived anilide-catalyzed asymmetric intramolecular Michael reaction was described. Chiral cyclic ketoaldehydes were obtained from acyclic formyl enones in excellent yields with good stereoselectivity. The reaction proceeded in exceptionall
- Kikuchi, Makoto,Inagaki, Tomohiko,Nishiyama, Hisao
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p. 1075 - 1078
(2008/02/13)
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- Chiral bisformamides as effective organocatalysts for the asymmetric one-pot, three-component strecker reaction
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(Chemical Equation Presented) C2-symmetric chiral bisformamides have been shown to catalyze the asymmetric one-pot, three-component Strecker reaction, which produced the α-amino nitriles in excellent yields (up to 99%) with good enantioselectiv
- Wen, Yuehong,Xiong, Yan,Chang, Lu,Huang, Jinglun,Liu, Xiaohua,Feng, Xiaoming
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p. 7715 - 7719
(2008/02/12)
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- Prolinamides derived from aminophenols as organocatalysts for asymmetric direct aldol reactions
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N-(2-Hydroxyphenyl)-prolinamides were synthesized with the aim to introduce an additional hydrogen bonding site to the prolinamide structure. These compounds were evaluated as organocatalysts for asymmetric aldol reactions between aromatic aldehydes and c
- Sathapornvajana, Sornpranart,Vilaivan, Tirayut
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p. 10253 - 10259
(2008/02/13)
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- Asymmetric cyanosilylation of aldehydes catalyzed by novel organocatalysts
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A novel proline-based N,N′-dioxide, which is easily prepared from inexpensive chemicals, serves as an effective catalyst for enantioselective cyanosilylation of aldehydes in up to 73% ee. Georg Thieme Verlag Stuttgart.
- Wen, Yuehong,Huang, Xiao,Huang, Jinglun,Xiong, Yan,Qin, Bo,Feng, Xiaoming
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p. 2445 - 2448
(2007/10/03)
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- L-prolinethioamides - Efficient organocatalysts for the direct asymmetric aldol reaction
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A series of novel L-proline derived thioamides has been synthesised. They have been evaluated as organocatalysts in the direct asymmetric aldol reaction for the first time. Thioamides exhibit catalytic ability higher than proline itself and the model aldol reaction of 4-cyanobenzaldehyde with acetone proceeds well in the presence of 5 mol % of catalyst (ee up to 100%). Other aromatic aldehydes gave aldol products with high ees and moderate yields. Small changes in the catalyst's structure [e.g., N-Bn versus N-CH(CH3)Ph] as well as the addition of an acid have a profound effect on their activity. The unexpected formation of the catalyst-derived cyclic adducts was observed and their reactivity was established giving valuable insight into the course of the reaction.
- Gryko, Dorota,Lipinski, Radoslaw
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p. 1948 - 1952
(2007/10/03)
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- HYDROXAMIC ACID DERIVATIVES
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Novel hydroxamic acid derivatives, e.g., of formula (I), wherein R1, R2, R3 and R4 are as defined, are found to be useful as pharmaceuticals, e.g., for the suppression of TNF release and the treatment of autoimm
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Page/Page column 27
(2008/06/13)
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- Potent and selective nonpeptide inhibitors of caspases 3 and 7
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5-Dialkylaminosulfonylisatins have been identified as potent, nonpeptide inhibitors of caspases 3 and 7. The most active compound within this series (34) inhibited caspases 3 and 7 in the 2-6 nM range and exhibited approximately 1000-fold selectivity for caspases 3 and 7 versus a panel of five other caspases (1, 2, 4, 6, and 8) and was at least 20-fold more selective versus caspase 9. Sequence alignments of the active site residues of the caspases strongly suggest that the basis of this selectivity is due to binding in the S2 subsite comprised of residues Tyr204, Trp206, and Phe256 which are unique to caspases 3 and 7. These compounds inhibit apoptosis in three cell-based models: human Jurkat T cells, human chondrocytes, and mouse bone marrow neutrophils.
- Lee,Long,Murray,Adams,Nuttall,Nadeau,Kikly,Winkler,Sung,Ryan,Levy,Keller,DeWolf Jr.
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p. 2015 - 2026
(2007/10/03)
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