- "one-Pot" Aminolysis/Thiol-Maleimide End-Group Functionalization of RAFT Polymers: Identifying and Preventing Michael Addition Side Reactions
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We show that many of the nucleophiles (catalysts, reducing agents, amines, thiols) present during "one-pot" aminolysis/thiol-maleimide end-group functionalization of RAFT polymers can promote side reactions that substantially reduce polymer end-group functionalization efficiencies. The nucleophilic catalyst 1,8-diazabicyclo[5.4.0]undec-7-ene and the reducing agent tributylphosphine were shown to initiate anionic polymerization of N-methylmaleimide (NMM) in both polar and nonpolar solvents whereas hexylamine-initiated polymerization of NMM occurred only in high-polarity solvents. Furthermore, triethylamine-catalyzed Michael reactions of the representative thiol ethyl 2-mercaptopropionate (E2MP) and NMM in polar solvents resulted in anionic maleimide polymerization when [NMM]0 > [E2MP]0. Base-catalyzed enolate formation on the α-carbon of thiol-maleimide adducts was also shown as an alternative initiation pathway for maleimide polymerization in polar solvents. Ultimately, optimal "one-pot" reaction conditions were identified allowing for up to 99% maleimide end-group functionalization of dithiobenzoate-terminated poly(N,N-dimethylacrylamide). Much of the work described herein can also be used to ensure near-quantitative conversion of small molecule thiol-maleimide reactions while preventing previously unforeseen side reactions.
- Abel, Brooks A.,McCormick, Charles L.
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- Triethylamine-catalyzed synthesis of oxazepine from maleamic acids
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2-Thioxo-1,3-oxazepine-4,7-dione compounds were obtained via triethylamine-catalyzed condensation of maleamic acids with thiophosgene under anhydrous conditions. This method features relatively a simple methodology, use of inexpensive reagents, convenient operating conditions and high yields.
- Badru, Rahul,Singh, Baldev
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- Dichloro Butenediamides as Irreversible Site-Selective Protein Conjugation Reagent
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We describe maleic-acid derivatives as robust cysteine-selective reagents for protein labelling with comparable kinetics and superior stability relative to maleimides. Diamide and amido-ester derivatives proved to be efficient protein-labelling species with a common mechanism in which a spontaneous cyclization occurs upon addition to cysteine. Introduction of chlorine atoms in their structures triggers ring hydrolysis or further conjugation with adjacent residues, which results in conjugates that are completely resistant to retro-Michael reactions in the presence of biological thiols and human plasma. By controlling the microenvironment of the reactive site, we can control selectivity towards the hydrolytic pathway, forming homogeneous conjugates. The method is applicable to several scaffolds and enables conjugation of different payloads. The synthetic accessibility of these reagents and the mild conditions required for fast and complete conjugation together with the superior stability of the conjugates make this strategy an important alternative to maleimides in bioconjugation.
- Abegg, Daniel,Adibekian, Alexander,Afonso, Cláudia F.,Bernardes, Gon?alo J. L.,Corzana, Francisco,Laserna, Victor,Martin, Esther M.,Ravn, Peter
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supporting information
p. 23750 - 23755
(2021/10/01)
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- Thermally Sensitive Protecting Groups for Cysteine, and Manufacture and Use Thereof
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In a preferred embodiment, there is provided a protecting group for protecting the thiol side chain of a cysteine residue, the protecting group comprising a Diels-Alder cycloadduct of a furan and a maleimide, and optionally, a linker interposed between the thiol side chain and the Diels-Alder cycloadduct.
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Paragraph 0085
(2021/02/12)
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- Synthesis and biological evaluation of novel benzylidene-succinimide derivatives as noncytotoxic antiangiogenic inhibitors with anticolorectal cancer activity in vivo
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A novel series of benzylidene-succinimide derivatives were synthesized, characterized and evaluated for their cytotoxicities against HCT116, and SW480 cancer cells and NCM460 normal human cells. Their antiangiogenic capabilities were evaluated using a chick chorioallantoic membrane (CAM) assay. The compound, XCF-37b, was selected as the most potent antiangiogenic inhibitor with noncytotoxicity to evaluate the pharmacological effects on human umbilical vein endothelial cells (HUVECs) and cancer cells in vivo and in vitro. The results showed that XCF-37b inhibited HT29-cell colon tumor growth in vivo, without showing cytotoxicity against the five other cancer cell lines in vitro. Experiments confirmed that XCF-37b had obvious antiangiogenic activity by HUVEC migration and invasion and rat aortic ring angiogenesis ex vivo. Mechanism studies showed that XCF-37b inhibited the AKT/mTOR and VEGFR2 signaling pathways, as evidenced by decreased expressions of phosphor-AKT (p-AKT), p-mTOR, p-VEGFR2 (Tyr175), p-Src (Tyr416), p-FAK (Tyr925), and p-Erk1/2 (Thr202/Tyr204). Moreover, XCF-37b significantly decreased the protein expressions of matrix metalloproteinase-2 (MMP-2), MMP-9 and hypoxia-inducible factor-1α (HIF-1α). XCF-37b generally regulated angiogenic inhibition through several regulatory pathways, without significantly interfering with colorectal cancer cell growth.
- Luo, Kaixiu,Bao, Yafeng,Liu, Feifei,Xiao, Chuanfan,Li, Ke,Zhang, Conghai,Huang, Rong,Lin, Jun,Zhang, Jihong,Jin, Yi
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p. 805 - 827
(2019/07/10)
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- 1, 3-Dipolar cycloaddition reactions: Synthesis of 5-benzyl-1-(2',4'- dibromophenyl)-3-(4''-substituted phenyl)-3a,4,6,6a-tetrahydro-1H, 5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives
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1,3-Dipolar cycloaddition of nitrilimines 3 with N-benzyl maleimide 4 has provided 5-benzyl-1-(2',4'-dibromophenyl)-3-(4''-substituted phenyl)-3a,4,6,6a-tetrahydro-1H,5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives 5 in excellent yield as the only isomer through a concerted pathway. Indian Academy of Sciences.
- Kaur, Manpreet,Singh, Baldev,Singh, Baljit
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p. 1529 - 1534
(2014/04/03)
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- Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds
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The synthesis, in vitro evaluation and SAR studies of 67 maleimides and derivatives acting as antifungal agents are reported. A detailed SAR study supported by theoretical calculations led us to determine that: an intact maleimido ring appears to be necessary for a strong antifungal activity, dissimilarly affected by the substituents in positions 2 and 3. The best activities were shown by 2,3-nonsubstituted followed by 2,3 dichloro- and 2-methyl-substituted maleimides. They all were fungicide rather than fungistatic enhancing the importance of their antifungal activity. 2,3-Dimethyl and 2,3-diphenyl-maleimides possessed marginal or null activity. The presence of a flexible connecting chain in N-phenylalkyl maleimides appears not to be essential for antifungal activity, although its length shows a correlation with the antifungal behavior, displaying maleimides with alkyl chains of n = 3 and n = 4 the best antifungal activities in most fungi. Different substituents on the benzene ring did not have a clear influence on the activity. Values of chemical potential properties as well as of energy do not sufficiently discriminate between active and inactive compounds. Nevertheless, it was found that, although log P alone is not strong enough to properly predict the antifungal activity, the comparison of its values for compounds within the same sub-type, showed an enhancement of antifungal activity along with an increment of lipophilicity. In addition, the LUMO's electronic clouds of the highly active compounds showed to be concentrated on the imido ring, indicating that their carbon atoms are potential sites for nucleophilic attack. Same results were obtained from MEPs. Most of the active compounds did not show cytotoxic activity against human cancer cell lines and no one possessed hemolytic activity, indicating that their activity is selective to pathogenic fungi and that they are not toxic at MIC concentrations.
- Sortino,Garibotto,Cechinel Filho,Gupta,Enriz,Zacchino
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experimental part
p. 2823 - 2834
(2011/06/21)
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- Terification of maleamic acids without double bond isomerization
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Activation of the carboxylic acid group of a maleamic acid by treatment with an arenesulfonyl chloride followed by addition of an alcohol affords a fumaramate or a maleamate, depending on the reaction conditions. The E isomer is obtained when the acid is treated with nearly equimolar amounts of 2,4,6-triisopropylbenzenesulfonyl chloride and an alcohol in pyridine. Replacement of pyridine by 2-picoline and use of a larger excess of activating agent (mesitylenesulfonyl chloride) and alcohol affords the Z isomer. In both cases, high diastereomeric excesses and yields are achieved.
- Sanchez, Albert,Pedroso, Enrique,Grandas, Anna
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experimental part
p. 2600 - 2606
(2010/09/07)
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- Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2
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A practical method for the multigram scale selective cis-dihydroxylation of electron deficient alkenes such as diethyl fumarate and N-alkyl and N-aryl-maleimides using H2O2 is described. High turnovers (>1000) can be achieved with this efficient manganese based catalyst system, prepared in situ from a manganese salt, pyridine-2-carboxylic acid, a ketone and a base, under ambient conditions. Under optimized conditions, for diethyl fumarate at least 1000 turnovers could be achieved with only 1.5 equiv. of H2O2 with d/l-diethyl tartrate (cis-diol product) as the sole product. For electron rich alkenes, such as cis-cyclooctene, this catalyst provides for efficient epoxidation.
- Saisaha, Pattama,Pijper, Dirk,Van Summeren, Ruben P.,Hoen, Rob,Smit, Christian,De Boer, Johannes W.,Hage, Ronald,Alsters, Paul L.,Feringa, Ben L.,Browne, Wesley R.
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supporting information; experimental part
p. 4444 - 4450
(2010/11/05)
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- Synthesis of an amino moiety in trovafloxacin by using an in-expensive amidine base, N, N-diethylacetamidine
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The simple and in-expensive amidine base, N.N-diethylacetamidine, has been prepared and utilized in the construction of bicyclic hetero compound, 4 and employed for further reduction of amidic carbonyl groups of 4 by using NaBH 4I2-THF condition which is an efficient and commercially viable method to prepare 5 towards the synthesis of amino moiety I, in Trovafloxacin 2 an antibacterial agent.
- Madhusudhan,Balraju,Rajesh,Narayana, B. Venkata,Reddy
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experimental part
p. 569 - 573
(2009/12/06)
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- Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors
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The endocannabinoid 2-arachidonoylglycerol (2-AG) plays a major role in many physiological processes, and its action is quickly terminated via enzymatic hydrolysis catalyzed by monoglyceride lipase (MGL). Regulating its endogenous level could offer therapeutic opportunities; however, few selective MGL inhibitors have been described so far. Here, we describe the synthesis of N-substituted maleimides and their pharmacological evaluation on the recombinant human fatty acid amide hydrolase (FAAH) and on the purified human MGL. A few N-arylmaleimides were previously described (Saario, S. M.; Salo, O. M.; Nevalainen, T.; Poso, A.; Laitinen, J. T.; Jarvinen, T.; Niemi, R. Characterization of the Sulfhydryl-Sensitive Site in the Enzyme Responsible for Hydrolysis of 2-Arachidonoylglycerol in Rat Cerebellar Membranes. Chem. Biol. 2005, 12, 649-656) as MGL inhibitors, and along these lines, we present a new set of maleimide derivatives that showed low micromolar IC50 and high selectivity toward MGL vs FAAH. Then, structure-activity relationships have been investigated and, for instance, 1-biphenyl-4-ylmethylmaleimide inhibits MGL with an IC50 value of 790 nM. Furthermore, rapid dilution experiments reveal that these compounds act as irreversible inhibitors. In conclusion, N-substituted maleimides constitute a promising class of potent and selective MGL inhibitors.
- Matuszak, Nicolas,Muccioli, Giulio G.,Labar, Geoffray,Lambert, Didier M.
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experimental part
p. 7410 - 7420
(2010/04/30)
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- N-Phenyl and N-phenylalkyl-maleimides acting against Candida spp.: Time-to-kill, stability, interaction with maleamic acids
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N-Phenyl and N-phenylalkyl maleimides (alkyl chain = (CH2)n; n = 0-4) and their respective open derivatives (maleamic acids) were evaluated against Candida spp. with the microbroth dilution method following the guidelines of CLSI (formely NCCLS). MIC values of maleimides without pre-incubation and submitted to different pre-incubation times into the growth media, time-to-kill studies as well as a time-dependent UV-spectroscopy study of the maleimides in water, led to determine that maleimides display antifungal activities with their intact maleimide ring, being in addition their activities not dependent on the length of the alkyl chain. They are not only fungistatic but fungicidal with very low MICs and MFCs, displaying strong fungicide activities not only against standardized but also clinical isolates of Candida albicans and non-albicans Candida spp.
- Sortino, Maximiliano,Cechinel Filho, Valdir,Correa, Rogerio,Zacchino, Susana
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p. 560 - 568
(2008/09/18)
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- Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide
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A series of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide have been synthesized by condensation of substituted amines with maleic anhydride (MA) followed by cyclization with o-aminothiophenol (o-ATP). All the compounds have been screened for their antifungal activity against Tricophyton rubrum, Epidermophyton floccosum and Malassazia furfur. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 7a-z have been established on the basis of elemental analysis and spectral data.
- Gupta,Wagh
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p. 697 - 702
(2007/10/03)
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- In vitro antifungal properties, structure-activity relationships and studies on the mode of action of N-phenyl, N-aryl, N-phenylalkyl maleimides and related compounds
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The synthesis, in vitro antifungal evaluation and structure-activity relationship studies of 14 compounds of the N-phenyl-, N-aryl-, N-phenylalkyl- maleimide and 3,4-dichloromaleimide series are reported. The compounds were evaluated against a panel of standardized yeasts and filamentous fungi as well as clinical isolates of Candida albicans. The activities of N-phenylalkyl-3,4- dichloromaleimide derivatives but not those of N-phenylalkyl-maleimide derivatives showed to be dependent on the length of the alkyl chain. N-Phenylpropyl-3,4-dichloromaleimide showed the broadest spectrum of action and lower minimal inhibitory concentrations (MIC) in all of the fungi tested. The nitrogen-carbon distance between the two rings seems to play an important role in the antifungal behavior of these compounds. The most active structure showed inhibited (1,3)β-D-glucan and chitin synthases, enzymes that catalyze the synthesis of the major fungal cell-wall polymers. ECV · Editio Cantor Verlag, Aulendorf (Germany).
- Lopez, Silvia N.,Castelli, Maria V.,De Campos, Fatima,Correa, Rogerio,Cechinel Filho, Valdir,Yunes, Rosendo A.,Zamora, Miguel A.,Enriz, Ricardo D.,Ribas, Juan C.,Furlan, Ricardo L. E.,Zacchino, Susana A.
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p. 123 - 132
(2007/10/03)
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- Rational Design of an Indolebutanoic Acid Derivative as a Novel Aldose Reductase Inhibitor Based on Docking and 3D QSAR Studies of Phenethylamine Derivatives
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A series of 45 phenethylamine derivatives were synthesized and evaluated for their inhibitory activity against pig kidney aldose reductase (ALR2, EC 1.1.1.21). Their IC50 values ranged from 400 μM to 24 μM. The binding modes of compounds at the active site of ALR2 were examined using flexible docking. The results indicated that phenethylamine derivatives nicely fit into the active pocket of ALR2 by forming various hydrogen bonding and hydrophobic interactions. 3D-QSAR analysis was also conducted using FlexX-docked alignment of the compounds. The best prediction was obtained by CoMSIA combined with hydrophobic and hydrogen bond donor/acceptor field (q 2 = 0.557, r2 = 0.934). A new derivative, 4-oxo-4-(4-hydroxyindole)butanoic acid, was designed, taking into account the CoMSIA field and the binding mode derived by FlexX docking. This rationally designed compound exhibits an ALR2 inhibition with an IC50 value of 7.4 μM, which compares favorably to that of a well-known ALR2 inhibitor, tolrestat (IC50 = 16 μM) and represents a potency approximately 240-fold higher than that of an original phenethylamine lead compound, YUA001.
- Sun, Won Suck,Park, Yoon Sun,Yoo, Jakyung,Park, Ki Duk,Kim, Sung Han,Kim, Jung-Han,Park, Hyun-Ju
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p. 5619 - 5627
(2007/10/03)
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- First triphenylphosphine promoted reduction of maleimides to succinimides
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Triphenylphosphine (TPP) in refluxing methanol effectively reduces maleimides 1a-g to the corresponding succinimides 2a-g in good yields. It was observed that some maleimides obtained from aromatic halogen compounds 1h-j were transformed into the corresponding succinamic acid methyl esters 3a-c by this reaction.
- Pal, Bikash,Pradhan, Prasun K.,Jaisankar, Parasuraman,Giri, Venkatachalam S.
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p. 1549 - 1552
(2007/10/03)
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- Synthesis and antimicrobial activities of N-substituted imides
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In the field of our research programs concerning novel antimicrobial agents, a series of N-substituted imides was synthesized. These compounds were obtained by cyclization of amido-acids in acetic anhydride/sodium acetate or hexamethyldisilazane/zinc bromide for the hydroxy-aromatic derivatives. The hydroxy-alkyl maleimides were directly prepared by condensation of the corresponding amino-alcohol with maleic anhydride in boiling toluene. Most of N-substituted maleimides showed an interesting antimicrobial activity towards bacteria from the ATCC collection (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) but the MIC values for P. aeruginosa were always high (128 μg/ml). The imides with alkyl substituents showed higher activities than aromatic analogues with MIC values in the range of 8-32 μg/ml. Comparatively, succinimides were practically inactive.
- Zentz, Frederic,Valla, Alain,Le Guillou, Regis,Labia, Roger,Mathot, Anne-Gabrielle,Sirot, Danielle
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p. 421 - 426
(2007/10/03)
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- Non-hydroxylic clathrate hosts of [4 + 2]π cycloadducts of phencyclone and N-arylmaleimides: Recognition of aromatic guests
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A series of non-hydroxylic crystalline host compounds, [4 + 2]π cycloadducts of phencyclone and N-arylmaleimides having a bicyclo[2.2.1]heptene-7-one system, was synthesized and their inclusion behavior investigated. X-Ray crystal analyses of the inclusion compounds of the N-(1-naphthyl) derivative with butan-2-one, the N-(m-tolyl) derivative with p-xylene, together with the guest-free host and the N-(p-tolyl) derivative with m-xylene indicate that the "space" surrounded by the phenanthrene ring, two phenyl rings and bridge carbonyl of the 1,3-diphenyl-1,3-dihydrocyclopenta[l]phenanthren-2-one moiety plays an important role, not only in the formation of inclusion complexes with the aromatic guests but also in host-host interactions. In every case, the N-aryl succinimide assists complex formation with the guests, in which the weak lattice forces due to C-H ... π and C-H ... O interactions are operative. Methyl-substituted benzenes are effectively recognized by the C-H ... π interactions between the guest molecules and the phenanthrene ring of the hosts.
- Yoshitake, Yasuyuki,Misaka, Junichi,Setoguchi, Koji,Abe, Masaki,Kawaji, Tomohiro,Eto, Masashi,Harano, Kazunobu
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p. 1611 - 1619
(2007/10/03)
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- Click Chemistry: Diverse Chemical Function from a Few Good Reactions
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Examination of nature's favorite molecules reveals a striking preference for making carbon-heteroatom bonds over carbon-carbon bonds - surely no surprise given that carbon dioxide is nature's starting material and that most reactions are performed in water. Nucleic acids, proteins, and polysaccharides are condensation polymers of small subunits stitched together by carbon-heteroatom bonds. Even the 35 or so building blocks from which these crucial molecules are made each contain, at most, six contiguous C-C bonds, except for the three aromatic amino acids. Taking our cue from nature's approach, we address here the development of a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links (C-X-C), an approach we call "click chemistry". Click chemistry is at once defined, enabled, and constrained by a handful of nearly perfect "spring-loaded" reactions. The stringent criteria for a process to earn click chemistry status are described along with examples of the molecular frameworks that are easily made using this spartan, but powerful, synthetic strategy.
- Kolb, Hartmuth C.,Finn,Sharpless, K. Barry
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p. 2004 - 2021
(2007/10/03)
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- Asymmetric cycloaddition of anthrone with n-substituted maleimides with C2-chiral pyrrolidines
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Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral N-substituted maleimides was carried out in the presence of C2-chiral pyrrolidines in almost quantitative yields. Chiral, non-racemic [4+2] adducts up to 61% ee were produced with achiral N-methyl and N-benzylmaleimide using the chiral catalysts. De's of the adducts up to 38% were observed in the cases of chiral N-substituted maleimides and achiral pyrrolidine, in which the absolute configuration Of the major product was established by X-ray analysis. The combination of chiral maleimides and chiral catalysts afforded the adducts having up to 80% de.
- Tokioka, Kyohei,Masuda, Satoshi,Fujii, Tomomi,Hata, Yasuo,Yamamoto, Yukio
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p. 101 - 107
(2007/10/03)
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- Synthesis of new succinimides and sulphonated derivatives with analgesic action in mice
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Recently, we have investigated the chemistry and biology of cyclic imides and have used phyllanthimide to obtain several analogues such as maleimides, succinimides and related compounds, which have demonstrated analgesic activity, amongst other properties. The work presented here describes the synthesis of new succinimides and their sulphonated derivatives. These substances were confirmed as having analgesic activity through abdominal constriction tests in mice. The results showed that some of the compounds, given intraperitoneally at a dose of 10 mg kg-1, were more effective than aspirin and paracetamol.
- Correa,Cechinel Filho,Rosa,Isolani Pereira,Schlemper,Nunes
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- An Approach to the 3,8-Diazabicyclooctane Moiety of Naphthyridinomycin and Quinocarcin via 1,3-Dipolar Cycloaddition of Photochemically Generated Azomethine Ylides.
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An attractive strategy for construction of the 3,8-diazabicyclooctane moiety of targets 1 and 2 involving the 1,3-dipolar cycloaddition of photochemical generated azomethine ylides is presented.
- Garner, Philip,Sunitha, K.,Shanthilal, T.
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p. 3525 - 3528
(2007/10/02)
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- Synthesis of N-Aryl/heteroaryl/-substituted-methyl-&α-(p-substituted anilino)succinimides as Antituberculosis Agents
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A series of N-Aryl/heteroaryl/substituted-methyl-α-(p-substituted anilino)succinimides (II) have been prepared and screened in vitro against H37Rv strain of Mycobacterium tuberculosis.Some of these compounds exhibit activity upto 0.39 μg/ml concentration.
- Rangnekar, V. M.,Bhamaria, R. P.,Khadse, B. G.
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p. 342 - 344
(2007/10/02)
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- Synthesis of N-Aryl/substituted-methyl/heteroaryl-&α-pyrrolidino/piperidino Succinimides as Antituberculosis Agents
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A series of N-Aryl/substituted-methyl/heteroaryl-α-pyrrolidino- and piperidino-succinimides (II) have been prepared and screened in vitro against H37Rv strain of Mycobacterium tuberculosis.Some of these compounds exhibit activity upto 1.56 μg/ml concentration.
- Rangnekar, V. M.,Lokhande, S. R.,Bhamaria, R. P.,Khadse, B. G.
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p. 1070 - 1071
(2007/10/02)
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- Antitumor chemotherapy. XIV. Cytotoxic activity of compounds possessing an ethylenic double bond substituted at the α and β positions with an electron attracting group
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The authors have previously shown that molecules possessing an ethylene double bond, activated by one or 2 electron attracting substituents, show a cytotoxic activity which must be connected with the addition of a cellular nucleophil to their double bond. This correlation has been extended to N alkylmaleinimides and different compounds with paraquinonine structure. The compounds examined possess a distinct cytotoxic antitumor activity which is, however, inferior to that of α nitro stilbenes and β nitro styrenes, the simplified analogs of aristolochic acid.
- Dore Ch.,Viel
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