61-49-4Relevant academic research and scientific papers
A Versatile and Highly Selective Colorimetric Sensor for the Detection of Amines
Diaz, Yvonne J.,Page, Zachariah A.,Knight, Abigail S.,Treat, Nicolas J.,Hemmer, James R.,Hawker, Craig J.,Read de Alaniz, Javier
, p. 3562 - 3566 (2017)
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.
New fascaplysin-based CDK4-specific inhibitors: Design, synthesis and biological activity
Aubry, Carine,Jenkins, Paul R.,Mahale, Sachin,Chaudhuri, Bhabatosh,Marechal, Jean-Didier,Sutcliffe, Michael J.
, p. 1696 - 1697 (2004)
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.
Antibacterial activity of (-)-deoxypseudophrynaminol versus its racemate and derivatives
Dix, Andrew V.,Meseck, Carly M.,Lowe, Adam J.,Mitchell, Miguel O.
, p. 2522 - 2524 (2006)
(-)-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.
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
Mahale, Sachin,Bharate, Sandip B.,Manda, Sudhakar,Joshi, Prashant,Bharate, Sonali S.,Jenkins, Paul R.,Vishwakarma, Ram A.,Chaudhuri, Bhabatosh
, p. 9658 - 9672 (2014)
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.
Catalytic enantioselective total synthesis of hodgkinsine B
Snell, Robert H.,Woodward, Robert L.,Willis, Michael C.
, p. 9116 - 9119 (2011)
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
Aromatic heterocyclic derivative and application thereof in medicine
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Paragraph 0390; 0396-0399, (2020/02/08)
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.
Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones
Han, Hui,Xia, Ji-Bao,Yang, Shang-Dong
, p. 3357 - 3369 (2019/04/06)
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.
Use of novel haptens in the production of antibodies for the detection of tryptamines
Mary?ka, Michal,Fojtíková, Lucie,Jurok, Radek,Holubová, Barbora,Lap?ík, Old?ich,Kucha?, Martin
, p. 16243 - 16250 (2018/05/22)
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.
Unified Approach to the Spiro(pyrrolidinyl-oxindole) and Hexahydropyrrolo[2,3-b]indole Alkaloids: Total Syntheses of Pseudophrynamines 270 and 272A
De, Subhadip,Das, Mrinal Kanti,Bhunia, Subhajit,Bisai, Alakesh
supporting information, p. 5922 - 5925 (2015/12/11)
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.
Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy
Ignatenko, Vasily A.,Zhang, Ping,Viswanathan, Rajesh
supporting information; experimental part, p. 1269 - 1272 (2011/04/17)
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.
