- A Versatile and Highly Selective Colorimetric Sensor for the Detection of Amines
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The utility of Meldrum's activated furan (MAF) for the colorimetric detection of sub ppm levels of amines in solution, on solid supports, and as vapors is reported. MAF is synthesized in one step from inexpensive and commercially available starting materials and exhibits high selectivity for primary and secondary amines in the presence of competing nucleophiles. The reaction between activated furans and amines results in a distinct color change, discernable by the naked eye. UV/Vis absorption spectroscopy was utilized to monitor reactions in solution and determine detection limits. Additionally, solutions of MAF were useful as stains for thin layer chromatography and for monitoring solid-phase synthesis of peptides and peptidomimetics. Finally, MAF was used to detect volatile amines released from fish samples, demonstrating potential for food spoilage applications.
- Diaz, Yvonne J.,Page, Zachariah A.,Knight, Abigail S.,Treat, Nicolas J.,Hemmer, James R.,Hawker, Craig J.,Read de Alaniz, Javier
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- New fascaplysin-based CDK4-specific inhibitors: Design, synthesis and biological activity
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The first biologically active non-planar analogues of the toxic anti-cancer agent, fascaplysin, have been produced; we present the design, synthesis and biological activity of three tryptamine derivatives.
- Aubry, Carine,Jenkins, Paul R.,Mahale, Sachin,Chaudhuri, Bhabatosh,Marechal, Jean-Didier,Sutcliffe, Michael J.
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- Antibacterial activity of (-)-deoxypseudophrynaminol versus its racemate and derivatives
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(-)-Deoxypseudophrynaminol 1 possesses 43-fold greater antibacterial potency than the racemate toward Staphylococcus aureus, indicating that the (-)-enantiomer is the biologically active isomer in this assay. Comparison of the percent growth inhibition by derivatives of 1 indicates that prenylation of N8 and replacement of N1-methyl by methyl carbamate are detrimental to antibacterial potency. (-)-1 is a promising lead structure for the development of the novel hexahydropyrrolo[2,3-b]indole class of antibacterial agents.
- Dix, Andrew V.,Meseck, Carly M.,Lowe, Adam J.,Mitchell, Miguel O.
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- Biphenyl-4-carboxylic acid [2-(1 H -indol-3-yl)-ethyl]-methylamide (CA224), a nonplanar analogue of fascaplysin, inhibits cdk4 and tubulin polymerization: Evaluation of in vitro and in vivo anticancer activity
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Biphenyl-4-carboxylic acid-[2-(1H-indol-3-yl)-ethyl]-methylamide 1 (CA224) is a nonplanar analogue of fascaplysin (2) that specifically inhibits Cdk4-cyclin D1 in vitro. Compound 1 blocks the growth of cancer cells at G0/G1 phase of the cell cycle. It also blocks the cell cycle at G2/M phase, which is explained by the fact that it inhibits tubulin polymerization. Additionally, it acts as an enhancer of depolymerization for taxol-stabilized tubulin. Western blot analyses of p53-positive cancer cells treated with compound 1 indicated upregulation of p53, p21, and p27 proteins together with downregulation of cyclin B1 and Cdk1. Compound 1 selectively induces apoptosis of SV40 large T-antigen transformed cells and significantly reduces colony formation efficiency, in a dose-dependent manner, of lung cancer cells. It is efficacious at 1/10th of the MTD against human tumors derived from HCT-116 and NCI-H460 cells in SCID mouse models. The promising efficacy of compound 1 in human xenograft models as well as its excellent therapeutic window indicates its potential for clinical development.
- Mahale, Sachin,Bharate, Sandip B.,Manda, Sudhakar,Joshi, Prashant,Bharate, Sonali S.,Jenkins, Paul R.,Vishwakarma, Ram A.,Chaudhuri, Bhabatosh
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- Catalytic enantioselective total synthesis of hodgkinsine B
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The power of palladium: The total synthesis of the alkaloid hodgkinsine B has been achieved with just six isolated intermediates and only four chromatographic operations. The route involves a palladium-catalyzed enantioselective desymmetrizing N-allylation of meso- chimonanthine to establish the absolute configuration and elaboration of the desymmetrized core by a diastereoselective palladium-catalyzed α-oxindole arylation. Copyright
- Snell, Robert H.,Woodward, Robert L.,Willis, Michael C.
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- Aromatic heterocyclic derivative and application thereof in medicine
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The invention provides aromatic heterocyclic derivatives or stereoisomers, tautomers, nitrogen oxides, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof, which are used for treating Alzheimer's disease. The invention also discloses pharmaceutical compositions containing the compounds and a method for treating Alzheimer's disease by using the compounds or the pharmaceutical compositions provided by the invention.
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Paragraph 0390; 0396-0399
(2020/02/08)
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- Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones
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The Pd/Cu cocatalyzed oxidative tandem C-H aminocarbonylation and dehydrogenation was developed, affording carbolinones with molecular oxygen as the terminal oxidant. Natural product strychnocarpine and its derivatives were prepared conveniently using this strategy.
- Han, Hui,Xia, Ji-Bao,Yang, Shang-Dong
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p. 3357 - 3369
(2019/04/06)
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- Use of novel haptens in the production of antibodies for the detection of tryptamines
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Tryptamines are a group of hallucinogenic drugs whose detection in body fluids could be simplified by immunochemical assay kits. Antibodies for these assays are obtained by the immunization of laboratory animals with conjugates of a hapten similar to the target analyte and a suitable protein. Therefore we synthesized novel haptens derived from tryptamine-based drugs, with N,N-dimethyltryptamine (DMT), 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) and N,N-diisopropyltryptamine (DiPT) selected as the target analytes. Their structures were modified with a short linker ended with a carboxylic group. The haptens were conjugated with bovine serum albumin (BSA) and rabbits were immunized with the conjugates. The obtained polyclonal antibodies showed good reactivity and the LOD of the constructed ELISAs was in the range 0.006-0.254 ng mL-1. Thus, they are suitable for the development of immunochemical assay kits.
- Mary?ka, Michal,Fojtíková, Lucie,Jurok, Radek,Holubová, Barbora,Lap?ík, Old?ich,Kucha?, Martin
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p. 16243 - 16250
(2018/05/22)
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- Unified Approach to the Spiro(pyrrolidinyl-oxindole) and Hexahydropyrrolo[2,3-b]indole Alkaloids: Total Syntheses of Pseudophrynamines 270 and 272A
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The first enantioselective total syntheses of architecturally interesting prenylated pyrroloindole alkaloids, (-)-pseudophrynamines 272A (3d) and 270 (3b), have been achieved starting from enantioenriched 2-oxindoles having all-carbon quaternary stereocenters. A common strategy involving a thio-urea catalyzed aldol reaction is employed for the total synthesis of both spiro(pyrrolidinyl-oxindole) and hexahydropyrrolo[2,3-b]indole alkaloids.
- De, Subhadip,Das, Mrinal Kanti,Bhunia, Subhajit,Bisai, Alakesh
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supporting information
p. 5922 - 5925
(2015/12/11)
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- Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy
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A concise and practical strategy to obtain C3 reverse-prenylated pyrrolidinoindoline scaffold has been executed in 28.8% overall yield. The key conjugative step involved a Booker-Milburn-Feudoloff reaction involving an NCS-mediated activation of indole, followed by coupling to C5 dimethylallylalcohol. This linchpin step proceeded in 74% yield. The overall sequence proceeded in five steps from commercially available N-methyltryptamine with a single protection-deprotection operation and a single redox manipulation. Mechanistic insights of NCS activation, and an ensuing rearrangement of the isoprene unit were gained by rationally varying the C3 substituent.
- Ignatenko, Vasily A.,Zhang, Ping,Viswanathan, Rajesh
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supporting information; experimental part
p. 1269 - 1272
(2011/04/17)
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- Intercepting bacterial indole signaling with flustramine derivatives
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Indole signaling is one of the putative universal signaling networks in bacteria. We have investigated the use of desformylflustrabromine (dFBr) derivatives for the inhibition of biofilm formation through modulation of the indole-signaling network in Escherichia coli and Staphylococcus aureus. We have found dFBr derivatives that are 10-1000 times more active than indole itself, demonstrating that the flustramine family of indolic natural products represent a privileged scaffold for the design of molecules to control pathogenic bacterial behavior.
- Bunders, Cynthia A.,Minvielle, Marine J.,Worthington, Roberta J.,Ortiz, Minoshka,Cavanagh, John,Melander, Christian
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supporting information; scheme or table
p. 20160 - 20163
(2012/01/15)
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- FASCAPLYSIN DERIVATIVES AND THEIR USE IN THE TREATMENT OF CANCER
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A method of treating cancer comprising administering a compound of Formula (I), (II) or (III) to a patient.
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Page/Page column 121-122
(2009/04/25)
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- Design, synthesis and biological evaluation of new tryptamine and tetrahydro-β-carboline-based selective inhibitors of CDK4
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We present the design, synthesis and biological activity of a library of substituted (biphenylcarbonyl)-tryptamine and (biphenylcarbonyl)-tetrahydro-β-carboline compounds related to the natural product fascaplysin, as novel inhibitors of CDK4/cyclin D1. We show all these molecules, prepared using the Suzuki-Miyaura reaction, being selective inhibitors of CDK4 over CDK2. The most active compounds have a CDK4 IC50 in the range 9-11 μM, three of them containing the para-biphenyl plus para-substituents supporting the existence of a π-stacking pocket within the active site of CDK4.
- Jenkins, Paul R.,Wilson, James,Emmerson, Daniel,Garcia, Marcos D.,Smith, Matthew R.,Gray, Stephen J.,Britton, Robert G.,Mahale, Sachin,Chaudhuri, Bhabatosh
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p. 7728 - 7739
(2008/12/23)
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- Design, synthesis and biological activity of new CDK4-specific inhibitors, based on fascaplysin
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We present the design, synthesis, and biological activity of three classes of tryptamine derivatives, which are non-planar analogues of the toxic anti-cancer agent fascaplysin. We show these compounds to be selective inhibitors of CDK4 over CDK2, the most active compound 9q has an IC50 for the inhibition of CDK4 of 6 M. The Royal Society of Chemistry 2006.
- Aubry, Carine,Wilson, A. James,Jenkins, Paul R.,Mahale, Sachin,Chaudhuri, Bhabatosh,Marechal, Jean-Didier,Sutcliffe, Michael J.
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p. 787 - 801
(2007/10/03)
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- Dimerization of indole derivatives with hypervalent iodines(III): A new entry for the concise total synthesis of rac- and meso-chimonanthines
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Hypervalent iodine(III)-induced dimerization of indole derivatives, mitragynine, tetrahydrocarbazole, and Nb-carbomethoxytryptamine, was investigated. By applying this procedure, the concise total synthesis of rac- and meso-chimonanthines was accomplished.
- Ishikawa, Hayato,Takayama, Hiromitsu,Aimi, Norio
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p. 5637 - 5639
(2007/10/03)
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- The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry
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Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.
- Somei,Yamada,Kurauchi,Nagahama,Hasegawa,Yamada,Teranishi,Sato,Kaneko
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- Intramolecular inverse electron demand Diels-Alder reactions of tryptamine with tethered heteroaromatic azadienes
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1,2,4,5-Tetrazines and 1,2,4-triazines tethered to tryptamine via the ethylamine side chain undergo intramolecular inverse electron demand cycloadditions to produce adducts with the [ABazaCE]-ring skeleton of the Aspidosperma alkaloids. (C) 2000 Elsevier Science Ltd.
- Benson, Scott C.,Lee, Lily,Yang, Lydie,Snyder, John K.
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p. 1165 - 1180
(2007/10/03)
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- Scavenger assisted combinatorial process for preparing libraries of amides, carbamates and sulfonamides
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This invention relates to a novel solution phase process for the preparation of amide, carbamate, and sulfonamide combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.
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- Synthesis of the brominated marine alkaloids (±)-arborescidine A, B and C
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A straightforward synthesis of the brominated marine alkaloids arborescidine A (1), B (2) and C (3), starting from 6-bromo-(N-methyl) trypatamine is described. An equilibrium, under both basic and acidic conditions was found to exist between the trans- and cis-isomers 3 and 4. Spectral data indicated that the structure of isomer 4 does not correspond with the compound identified as arborescidine D recently isolated from the marine tunicate Pseudodistoma arborescens.
- Burm, Brigitte E.A.,Meijler, Michael M.,Korver, Jacco,Wanner, Martin J.,Koomen, Gerrit-Jan
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p. 6135 - 6146
(2007/10/03)
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- Syntheses of Serotonin, N-Methylserotonin, Bufotenine, and Melatonin, and the First Total Synthesis of N-(Indol-3-yl)methyl-N-methyl-5-methoxytryptamine from Tryptamine through a Common Intermediate, 1-Hydroxytryptamine
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Simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), and melatonin (2), and the first total synthesis of N-(indol-3-yl)methyl-N-methyl-5-methoxytryptamine (3) from tryptamine (4a) are reported through acid catalyzed nucleophilic substitution reaction of 1-hydroxytryptamines.
- Somei, Masanori,Yamada, Fumio,Morikawa, Harunobu
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- Indole derivatives with antimycobacterial activity
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1,3-Dinitro-2-(indol-3'-yl)-propanes 3 are synthesized by Michael reaction of nitromethane with the indolylnitroethenes 2. - Reaction of the aldehydes 4 and 10 with the benzylamines 12 as well as the reaction of the indolylalkylamines 6a and 9a with the benzaldehydes 11 lead to Schiff bases which are reduced to N-benzyl-(indol-3-ylmethyl)-amines 13 and N-benzyl-(indol-3-ylethyl)-amines 14, respectively; tert amines 16 are synthesized via the formamides 15, amines 18 are prepared according to Mannich. - Inhibitory effects on Mycobacterium tuberculosis H 37 Ra are investigated, a structure-activity relationship is discussed.
- Mahboobi,Grothus,Meindl
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p. 105 - 114
(2007/10/02)
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- Diastereoselective Pictet-Spengler Reactions of L-(Boc)Phenylalaninal and L-(Boc)Prolinal: Biomimetic Syntheses of Eudistomin T and (-)-Woodinine
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The diastereoselective Pictet-Spengler reaction of L-(Boc)phenylalaninal with tryptamine and the elaboration of this intermediate to the antibacterial compound eudistomin T and analogues of the antileukaemic compound eudistomidin B are described.We also report an efficient synthesis of the naturally occuring alkaloid (-)-woodinine from L-(Boc)prolinal and 5-bromotryptamine in three steps, using a diastereoselective Pictet-Spengler reaction.This approach affords, in addition, formal synthesis of the marine alkaloids eudistomins H and I.
- McNulty, James,Still, Ian W. J.
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p. 1329 - 1338
(2007/10/02)
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- Psychotomimetic N-Methyl-N-isopropyltryptamines. Effects of Variation of Aromatic Oxygen Substituents
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Eight N-methyl-N-isopropyltryptamines (MIPTs) possessing various aromatic oxygen substituents were prepared, characterized, and evaluated for hallucinogenic activity in man.In at least two instances (the Ar H and the Ar 5-OCH3, 1 and 4) the unsymmetrical nitrogen substitution led to a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues.Qualitatively, 4-hydroxy-N-methyl-N-isopropyltryptamine (2) was the most interesting in overall effect, producing a classic hallucinogenic profile.The 5-methoxy congeger 4 resulted in a state characterized by heightened conceptual stimulation lacking in visual phenomena.Other members of the series exhibited diminished effects.
- Repke, David B.,Grotjahn, Douglas B.,Shulgin, Alexander T.
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p. 892 - 896
(2007/10/02)
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