- Acylated serine derivatives: A unique class of arthropod pheromones of the Australian redback spider, Latrodectus hasselti
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(Figure Presented) Irresistible: Amino acid derivatives are very rarely used as pheromones by arthropods. The widow spider Latrodectus hasselti (see picture) uses a unique compound (see formula) to lure its males. The molecular configuration plays an impo
- Jerhot, Elena,Stoltz, Jeffrey A.,Andrade, Maydianne C. B.,Schulz, Stefan
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- Structural Revision of Pseudocerosine and Validation of a Biosynthetic Proposal for E-ring Formation in Pyridoacridine Alkaloids
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Pseudocerosine is the pigment responsible for the bright blue color of the rim on the marine flatworm Pseudoceros indicus. Compelling evidence is provided herein that pseudocerosine is actually a pyridoacridine, not an azepinoindole as initially proposed. This study also validates a biosynthesis proposal for E-ring formation in this revered class of alkaloids, and pseudocerosine (along with its intermediates described herein) is a new branch on the pyridoacridine family tree.
- Kim, Se Hun,S?hnel, Tilo,Sperry, Jonathan
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- The chemical reactivities of DOPA and dopamine derivatives and their regioselectivities upon oxidative nucleophilic trapping
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The chemical reactivities of four catecholamines, N-acetyl dopamine (NADA) and its dehydro derivative (NAΔDA), N-acetyl 3,4-dihydroxy-phenylalanine methyl ester (NADOPAME) and its dehydro derivative (NAΔDOPAME), under oxidative nucleophilic trapping and p
- Cheah, Yong Shung,Santhanakrishnan, Sridhar,Sullivan, Michael B.,Neoh, Koon Gee,Chai, Christina L.L.
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- Model insect cuticle sclerotization: Reactions of catecholamine quinones with the nitrogen-centered nucleophiles imidazole and N-acetylhistidine
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The catecholamines N-acetyldopamine (NADA) and N-β-alanyldopamine (NBAD) are two precursors for quinonoios used as sclerotizing agents in insect cuticle. This study focused on the reaction pathways of the quinones of NADA and NBAD by using two nitrogencen
- Huang, Xin,Xu, Rongda,Hawley, M. Dale,Kramer, Karl J.
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- Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity
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The use of arene/Ru/TsDPEN catalysts bearing a heterocyclic group on the TsDPEN in the asymmetric transfer hydrogenation (ATH) of dihydroisoquinolines (DHIQs) containing meta- or para-substituted aromatic groups at the 1-position results in the formation of products of high enantiomeric excess. Previously, only 1-(ortho-substituted)aryl DHIQs, or with an electron-rich fused ring gave products with high enantioselectivity; therefore, this approach solves a long-standing challenge for imine ATH.
- Barrios-Rivera, Jonathan,Xu, Yingjian,Wills, Martin
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supporting information
p. 6283 - 6287
(2020/09/02)
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- Synthesis, DNA binding and antitumor evaluation of styelsamine and cystodytin analogues
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A series of N-14 sidechain substituted analogues of styelsamine (pyrido[4,3,2-mn]acridine) and cystodytin (pyrido[4,3,2-mn]acridin-4-one) alkaloids have been prepared and evaluated for their DNA binding affinity and antiproliferative activity towards a pa
- Fong, Hugo K.H.,Copp, Brent R.
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p. 274 - 299
(2013/05/21)
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- Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles
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The enzymatic (tyrosinase) and chemical (NaIO4, Ag2O or Fremys's salt) oxidation of biologically relevant catecholamines, such as dopamine (DA), N-acetyldopamine (NADA) and the Ecstasy metabolites (α-MeDA and N-Me-α-MeDA) generates t
- Siopa, Filipa,Pereira, Alice S.,Ferreira, Luisa M.,Matilde Marques,Branco, Paula S.
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supporting information
p. 19 - 24
(2012/11/13)
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- Boronate derivatives of functionally diverse catechols: Stability studies
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Benzeneboronate of catecholic carboxyl methyl esters, N-acetyldopamine, coumarin and catechol estrogens were prepared as crystalline derivatives in high yield. Related catechol compounds with extra polar functional group(s) (OH, NH2) do not for
- Ketuly, Kamal Aziz,Hadi, A. Hamid A.
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experimental part
p. 2347 - 2356
(2010/08/04)
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- Benzene and dopamine catechol quinones could initiate cancer or neurogenic disease
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Catechol quinones of estrogens react with DNA by 1,4-Michael addition to form depurinating N3Ade and N7Gua adducts. Loss of these adducts from DNA creates apurinic sites that can generate mutations leading to cancer initiation. We compared the reactions o
- Zahid, Muhammad,Saeed, Muhammad,Rogan, Eleanor G.,Cavalieri, Ercole L.
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experimental part
p. 318 - 324
(2011/01/03)
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- Attempts to mimic key bond-forming events associated with the proposed biogenesis of the pentacyclic lamellarins
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The pyrrole-tethered veratroles 16 and 27 each engage in PIFA-induced oxidative cyclization reactions to give compounds 22 and 29, respectively, which incorporate a key tricyclic fragment associated with the title natural products. In contrast, the corresponding catechols 11 and 12 only produce polymeric materials on subjection to analogous reaction conditions. Efforts to study lactone ring formation by the oxidative cyclization of catechol 30 and veratrole 38 have been thwarted by an inability to prepare the former substrate and decomposition of the latter. The reported conversions 44 ? 45 and 46 ? 47 suggest that a C2-carboxy group attached to the pyrrole ring can ?direct' the oxidative cyclization of N-tethered aryl groups. The acquisition of compound 22 by the means described herein provides an adventitious and concise route to the racemic modification of the pyrrolo[2,1-a]isoquinoline alkaloid crispine A (52). CSIRO 2008.
- Axford, Lorraine C.,Holden, Kate E.,Hasse, Katrin,Banwell, Martin G.,Steglich, Wolfgang,Wagler, Joerg,Willis, Anthony C.
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- Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide
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Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide- stimulated BV-2 microglial cells was determined. While NAMDA at 100 μM inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by >50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH 4-dependent dimerization of the newly synthesized iNOS monomer.
- Jai, Woong Seo,Srisook, Ekaruth,Hyo, Jin Son,Hwang, Onyou,Cha, Young-Nam,Dae, Yoon Chi
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p. 3369 - 3373
(2007/10/03)
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- Towards the synthesis of aminodibenzo[b,e][1,4]dioxin derivatives via cationic ruthenium complexes
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Double nucleophilic aromatic substitution reactions between N-substituted (η6-1,2-dichlorobenzene)RuCp+ salts and substituted 1,2-benzenediols have been carried out under mild conditions to prepare N-substituted (η6-dibenzo[b,e][1,4]dioxin)ruthenium(II) complexes. The dibenzodioxin ligands were subsequently liberated by photolysis, with radiation from a sunlamp or from a medium pressure Hg lamp (300 nm).
- Cambie, Richard C.,Clark, George R.,Coombe, Sheryl L.,Coulson, Sally A.,Rutledge, Peter S.,Woodgate, Paul D.
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- N-docosahexaenoyl, 3 hydroxytyramine: A dopaminergic compound that penetrates the blood-brain barrier and suppresses appetite
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Fatty acids with varying chain lengths (2-22 carbon atoms long) and degrees of unsaturation (0-6 double bonds) were used to synthesize dopaminergic compounds for a study of the carrier mediated transport of dopamine (DA) to the brain. The most active carrier was the all cis C22:6 fatty acid [docosahexaenoic acid,( DHA)]which increased DA uptake through the blood-brain barrier by greater than 7.5 fold. The DHA-DA compound, NMI 8739, depressed the general locomotor activity of mice in a dose dependent manner. It also suppressed the appetite of Balb c mice and Charles River rats by 50% and 95% respectively at a dose of 10 mg/kg. Daily administration of NMI-8739 for a three week period did not induce tolerance. These results demonstrate DHA's potential for the carrier mediated transport of small molecules to the brain.
- Shashoua, Victor E.,Hesse, Gary W.
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p. 1347 - 1357
(2007/10/03)
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- N-Acylcatecholamines and 3,4-Dihydro-6,7-isoquinolinediols from N-Acyl-3,4-dimethoxyphenethylamines
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The N-acetamides 2a and 2e are cleaved with boron tribromide to yield as expected the catechols 3a and 3e whereas, under the same conditions, mixtures of the catechols 3b, 3c, 3f, or 3g and 1-(haloalkyl)dihydroisoquinolines 4
- Niederstein, Yvonne,Peter, Martin G.
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p. 1189 - 1194
(2007/10/02)
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- Synthesis and Antitumor activity of Cysteinyl-3,4-dihydroxyphenylalanines and Related Compounds
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The natural catecholic amino acid 5-S-cysteinyl-3,4-dihydroxyphenylalanine (1) was selectively toxic to a variety of human tumor cell lines in culture and exhibited antitumor activity against L1210 leukemia and B-16 melanoma in mice at doses which were not toxic to the host.Structural analogues of 5-S-cysteinyl-3,4-dihydroxyphenylalanine, including several new compounds, were synthesized and tested for growth inhibition of cultured cells of human neuroblastoma YT-nu and Chinese hamster fibroblast Don-6.Some were also examined for antitumor activity against L1210 and B-16 in vivo. 4-S-Cysteinylcatechols and 2- and 4-S-cysteinylphenols, which cannot be prepared by conventional methods, were synthesized by the reaction of catechols and phenols with cystine in boiling aqueous HBr. 5-S-Cysteinyl and 2-S-cysteinyl-3,4-dihydroxyphenylalanine (1 and 2), L-3,4-dihydroxyphenylalanine (L-Dopa), and 2- and 4-S-cysteinylphenol (14 and 15) were toxic to the YT-nu cell line only, while 4-S-cysteinylcatechol (6), 3-S-cysteinyl-5-methylcatechol (8), 5-S-cysteaminyldopamine (9), and 4-methylcatechol were strongly toxic to both cell lines.Compounds 1 (1000 mg/kg), 6 (500 mg/kg), and 8 (400 mg/kg) increased the life span of L1210-bearing mice by 50, 50, and 43percent, respectively, and compounds 1 and 8 were marginally effective against B-16 melanoma as well.Compound 9 was too toxic to show any activity.There was good correlation between the cytotoxicity and the in vivo activity.
- Ito, Shosuke,Inoue, Shigeki,Yamamoto, Yoshinobu,Fujita, Keisuke
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p. 673 - 677
(2007/10/02)
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