- Human serum albumin binding assay based on displacement of a non selective fluorescent inhibitor
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In this paper, we describe a fluorescent antibacterial analog, 6, with utility as a competition probe to determine affinities of other antibacterial analogs for human serum albumin (HSA). Analog 6 bound to HSA with an affinity of 400 ± 100 nM and the fluorescence was environmentally sensitive. With 370 nm excitation, environmental sensitivity was indicated by a quenching of the 530 nm emission when the probe bound to HSA. Displacement of dansylsarcosine from HSA by 6 indicated it competed with compounds that bound at site II (ibuprofen binding site) on HSA. Analog 6 also shifted the NMR peaks of an HSA bound oleic acid molecule that itself was affected by compounds that bound at site II. In addition to binding at site II, 6 interacted at site I (warfarin binding site) as indicated by displacement of dansylamide and the shifting of NMR peaks of an HSA bound oleic acid molecule affected by warfarin site binding. Additional evidence for multiple site interaction was discovered when a percentage of 6 could be displaced by either ibuprofen or phenylbutazone. A competition assay was established using 6 to determine relative affinities of other antibacterial inhibitors for HSA.
- Thorarensen, Atli,Sarver, Ronald W.,Tian, Fang,Ho, Andrea,Romero, Donna L.,Marotti, Keith R.
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Read Online
- Chirality in the absence of rigid stereogenic elements: The design of configurationally stable C3-symmetric propellers
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Residual stereoisomerism is a form of stereoisomerism scarcely considered so far for applicative purposes, though extremely interesting, since the production of stereoisomers does not involve classical rigid stereogenie elements. In three-bladed propeller
- Benincori, Tiziana,Marchesi, Andrea,Pilati, Tullio,Ponti, Alessandro,Rizzo, Simona,Sannicolo, Francesco
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Read Online
- Palladium-catalyzed acylation of a 1,2-disubstituted 3-indolylzine chloride
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3-Acylindoles were prepared by palladium catalyzed coupling of an acid sensitive 1,2-disubstituted 3-indolylzinc chloride with a number of acid chlorides to give the corresponding ketones in 33-74% yields.
- Faul, Margaret M.,Winneroski, Leonard L.
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Read Online
- Palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-, benzothiophene- and indole-based substrates by dimethyl malonate anion
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The palladium-catalyzed benzylic-like nucleophilic substitution of acetates derived from benzofuran, benzothiophene and indole was investigated. The asymmetric substitution on racemic 1-(2-benzofuryl) ethyl acetate gave disappointing results, but the subs
- Primault, Ga?lle,Legros, Jean-Yves,Fiaud, Jean-Claude
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Read Online
- Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides
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New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2)∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H?Zn?Cl)2 is the key species for the production of amines.
- Ong, Derek Yiren,Yen, Zhihao,Yoshii, Asami,Revillo Imbernon, Julia,Takita, Ryo,Chiba, Shunsuke
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supporting information
p. 4992 - 4997
(2019/03/13)
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- Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones
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A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series of tetrahydro-β-carbolinones in good yields under mild conditions. Gram-sca
- Zhang, Kaifan,Xu, Xiaoying,Zheng, Jiuan,Yao, Hequan,Huang, Yue,Lin, Aijun
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p. 2596 - 2599
(2017/05/24)
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- Fluorination-Oxidation of 2-Hydroxymethylindole Using Selectfluor
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An unexpected fluorination-oxidation of 2-hydroxymethylindole using selectfluor under mild condi-tions without a catalyst is described. This new chemistry allows for efficient and rapid synthesis of various 3-fluoroindole-2-aldehydes and novel quaternary
- Jiang, Xiaojian,Zhang, Feng,Yang, Junjie,Yu, Pei,Yi, Peng,Sun, Yewei,Wang, Yuqiang
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supporting information
p. 853 - 858
(2017/03/11)
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- Rh(II)-catalyzed intramolecular annulation of N-sulfonyl 1,2,3-triazoles with indole derivatives: A new method for synthesis pyranoindoles
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A direct and highly stereoselective approach for the synthesis of Z-alkenyl-pyranoindoles had been developed by utilizing Rh(II)-catalyzed intramolecular cyclization of N-sulfonyl-1,2,3-triazoles with indole derivatives. A variety of pyranoindoles were obtained in 44-93% yields. Moreover, a more convenient synthesis of pyranoindoles starting from terminal alkyne was realized via a Cu-Rh sequentially catalyzed one-pot cascade reaction.
- Xie, Hui,Yang, Jian-Xin,Bora, Pranjal Protim,Kang, Qiang
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supporting information
p. 3014 - 3021
(2016/05/19)
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- Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines
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An efficient zinc(II)-catalyzed alkyne oxidation/C￡H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described.
- Li, Long,Zhou, Bo,Wang, Yong-Heng,Shu, Chao,Pan, Yi-Fei,Lu, Xin,Ye, Long-Wu
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supporting information
p. 8245 - 8249
(2015/07/07)
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- KAHA ligations that form aspartyl aldehyde residues as synthetic handles for protein modification and purification
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Aldehydes are widely recognized as valuable synthetic handles for the chemoselective manipulation of peptides and proteins. In this report, we show that peptides and small proteins containing the aspartic acid semialdehyde (Asa) side chain can be easily p
- Murar, Claudia E.,Thuaud, Frdric,Bode, Jeffrey W.
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p. 18140 - 18148
(2015/03/04)
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- Selective oxidations of activated alcohols in water at room temperature
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Allylic and benzylic alcohols can be selectively oxidized to their corresponding aldehydes or ketones in water containing nanoreactors composed of the designer surfactant TPGS-750-M. The oxidation relies on catalytic amounts of CuBr, bpy, and TEMPO, with N-methyl-imidazole; air is the stoichiometric oxidant. the Partner Organisations 2014.
- Lipshutz,Hageman,Fennewald,Linstadt,Slack,Voigtritter
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supporting information
p. 11378 - 11381
(2014/11/08)
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- Design, synthesis and computational validation of novel benzimidazole/indole-based PPARα and PPAR? partial agonists
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The design and synthesis of benzimidazolyl and indolyl linked α-alkoxy phenylpropanoic acid derivatives and the β-keto ester analogues in an effort to develop novel peroxisome proliferator activated receptors ligands expected to exhibit PPARα and PPAR? pa
- Verma, Raman K.,Ghosh, Prithwish,Kumar, Vijay,Wadhwa, Lalit K.
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p. 1555 - 1571
(2014/04/03)
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- Regio- and stereospecific uncatalyzed reactions of electron-rich arenes and olefins at organomolybdenum enantiomeric scaffolds
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A novel uncatalyzed reaction between TpMo(CO)2(5- trifluoroacetoxy-η3-5,6-dihydropyranyl/dihydropyridinyl) complexes and electron-rich arenes/olefins is reported. The reaction proceeds under mild reaction conditions so that a variety of functional groups are tolerated. Combined with a stereospecific annulative demetalation, the new reaction provides a rapid access to polycyclic alkaloid structures. The sequential protocol was used to prepare analogues of the antimalarial agent isofebrifugine.
- Chen, Wenyong,Sana, Kasinath,Jiang, Yi,Meyer, Esmerelda V. S.,Lapp, Stacey,Galinski, Mary R.,Liebeskind, Lanny S.
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p. 7594 - 7611
(2014/04/03)
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- Heterocyclyl linked anilines and benzaldehydes as precursors for biologically significant new chemical entities
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Benzylidene and benzyl thiazolidinediones, oxazolidinediones, isoxazolidinediones and their acyclic analogs like alpha alkylthio/alkoxy phenylpropanoic acids, beta-keto esters and tyrosine-based compounds possess broad therapeutic potential in general and as Peroxisome Proliferator Activated Receptors (PPARs) agonists in particular in the management of hyperglycemia and hyperlipidaemia for the treatment of Type 2 Diabetes (T2D). We have synthesised and characterized some novel and suitably substituted heterocyclyl linked benzaldehydes and anilines, which can be easily and very readily derivatized to all the above mentioned classes to generate new chemical entities of broader biological significance. Synthesis of their benzylidene thiazolidinedione and diethyl malonate and also benzyl diethyl malonate and alpha-bromoesters derivatives is reported in some of the cases in the present work. Indian Academy of Sciences.
- Verma, Raman K.,Kumar, Vijay,Ghosh, Prithwish,Wadhwa, Lalit K.
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p. 1063 - 1069
(2013/03/13)
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- Synthesis of carbazoles by gold(I)-catalyzed carbocyclization of 2-(enynyl)indoles
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A new synthetic protocol for carbazoles through gold(I)-catalyzed intramolecular hydroarylation of (Z)-2-(enynyl)indoles was achieved in good yields. The requisite (Z)-2-(enynyl)indoles were synthesized stereoselectively by trimethylgallium-promoted, Z-selective Wittig olefination of N-alkylindole-2-carboxaldehydes with propargyl ylides. Substrates possessing both alkyl as well as aromatic groups are well tolerated under these reaction conditions. Georg Thieme Verlag Stuttgart.
- Praveen, Chandrasekaran,Perumal, Paramasivan Thirumalai
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p. 521 - 524
(2011/04/17)
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- Rhodium carbenoid approach for introduction of 4-substituted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles
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Chemical Equation Presentation An unusual rhodium carbenoid approach for introduction of 4-substltuted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles is described. These studies show that (Z)-vinylcarbenoids have a greater tendency than (E)-vinylcarbenoids to react at the vinylogous position of the carbenoid rather than at the carbenoid center
- Lian, Yajing Lian,Davies, Huw M. L.
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supporting information; experimental part
p. 924 - 927
(2010/06/16)
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- 3-O and 2-C Alkylation of L-ascorbates with benzyl halides and N-substituted indolemethanol derivatives
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Coupling of alkali metal ascorbates with benzyl halides and 2and 3-hydroxymethylindole methanesulfonates resulted in L-ascorbic acid 3-Oand 2-C-derivatives. In contrast to 3-Obenzyl L-ascorbate, its indole analogs are unstable compounds, which underwent decomposition or rearrangement during isolation to give thermodynamically stable 2-C-isomers.
- Korolev,Luzikov,Reznikova,Preobrazhenskaya
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experimental part
p. 457 - 462
(2011/02/17)
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- Synthesis of indolocyclotriveratrylenes
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Indolocyclotriveratrylenes linked through C2 and C3 can be prepared by acid-catalysed reactions of indole-2- or -3-methanols. The initial example, compound 1 has been confirmed, and an X-ray crystal structure is reported. Seven new examples of indolocyclo
- Santoso, Mardi,Somphol, Kittiya,Kumar, Naresh,Black, David StC.
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experimental part
p. 5977 - 5983
(2011/03/19)
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- Enantioselective organocatalytic intramolecular ring-closing Friedel-Crafts-type alkylation of indoles
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An enantioselective organocatalytic intramolecular ring-closing Friedel-Crafts-type alkylation of indolyl α,β-unsaturated aldehydes has been developed. This powerful new strategy allows enantioselective access to THPIs and THBCs in a straightforward and a
- Li, Chang-Feng,Liu, Hiu,Liao, Jie,Cao, Yi-Ju,Liu, Xiao-Peng,Xiao, Wen-Jing
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p. 1847 - 1850
(2008/02/02)
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- New versatile route to the synthesis of tetrahydro-β-carbolines and tetrahydro-pyrano[3,4-b]indoles via an intramolecular Michael addition catalyzed by InBr3
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A simple multistep synthetic strategy to 4-sub-stituted 1,2,3,4-tetrahydro-β-carboline and 1,3,4,9-tetrahydro-pyrano[3,4-b]indole derivatives starting from commercially available indole 2-carboxylic acid (5) is described. The final intramolecular Michael addition promoted by catalytic amount of InBr3 (5-10 mol %) provided the expected polycyclic compounds in excellent yields (up to 97%) both in anhydrous organic and aqueous media.
- Agnusdei, Marianna,Bandini, Marco,Melloni, Alfonso,Umani-Ronchi, Achille
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p. 7126 - 7129
(2007/10/03)
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- Heterocyclic compounds having anti-diabetic activity and their use
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Compounds of formula (I): STR1 [wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5] have hypoglycemic and anti-diabetic activities.
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