2494-12-4Relevant articles and documents
Acylated serine derivatives: A unique class of arthropod pheromones of the Australian redback spider, Latrodectus hasselti
Jerhot, Elena,Stoltz, Jeffrey A.,Andrade, Maydianne C. B.,Schulz, Stefan
, p. 2037 - 2040 (2010)
(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
Structural Revision of Pseudocerosine and Validation of a Biosynthetic Proposal for E-ring Formation in Pyridoacridine Alkaloids
Kim, Se Hun,S?hnel, Tilo,Sperry, Jonathan
, p. 3495 - 3498 (2020)
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.
The chemical reactivities of DOPA and dopamine derivatives and their regioselectivities upon oxidative nucleophilic trapping
Cheah, Yong Shung,Santhanakrishnan, Sridhar,Sullivan, Michael B.,Neoh, Koon Gee,Chai, Christina L.L.
, p. 6543 - 6550 (2016)
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
Model insect cuticle sclerotization: Reactions of catecholamine quinones with the nitrogen-centered nucleophiles imidazole and N-acetylhistidine
Huang, Xin,Xu, Rongda,Hawley, M. Dale,Kramer, Karl J.
, p. 179 - 202 (1997)
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
Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity
Barrios-Rivera, Jonathan,Xu, Yingjian,Wills, Martin
supporting information, p. 6283 - 6287 (2020/09/02)
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.
Synthesis, DNA binding and antitumor evaluation of styelsamine and cystodytin analogues
Fong, Hugo K.H.,Copp, Brent R.
, p. 274 - 299 (2013/05/21)
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
Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles
Siopa, Filipa,Pereira, Alice S.,Ferreira, Luisa M.,Matilde Marques,Branco, Paula S.
supporting information, p. 19 - 24 (2012/11/13)
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
Boronate derivatives of functionally diverse catechols: Stability studies
Ketuly, Kamal Aziz,Hadi, A. Hamid A.
experimental part, p. 2347 - 2356 (2010/08/04)
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
Benzene and dopamine catechol quinones could initiate cancer or neurogenic disease
Zahid, Muhammad,Saeed, Muhammad,Rogan, Eleanor G.,Cavalieri, Ercole L.
experimental part, p. 318 - 324 (2011/01/03)
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
Attempts to mimic key bond-forming events associated with the proposed biogenesis of the pentacyclic lamellarins
Axford, Lorraine C.,Holden, Kate E.,Hasse, Katrin,Banwell, Martin G.,Steglich, Wolfgang,Wagler, Joerg,Willis, Anthony C.
, p. 80 - 93 (2008/04/04)
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.
