17407-56-6Relevant academic research and scientific papers
IDENTIFICATION, SYNTHESIS, AND BIOACTIVITY OF A MALE-PRODUCED AGGREGATION PHEROMONE IN ASSASSIN BUG, Pristhesancus Plagipennis (HEMIPTERA: REDUVIIDAE)
James, David G.,Moore, Christopher J.,Aldrich, Jeffrey R.
, p. 3281 - 3296 (1994)
Pristhesancus plagipennis, a large Australian assassin bug, possesses three pairs abdominal glands (DSGs). In the male, the anterior and posterior glands are hypertrophied and secrete an attractant pheromone. Gas chromatography-mass spectrometry (GC-MS) analyses of male DAG extracts and airborne volatiles emitted from calling males showed the pheromone signature to be dominated by the novel component. Subsequent chemical manipulations, GC-MS, and chiral-column analyses established its identity as (Z)-3-hexenyl (R)-2-hydroxy-3-methylbutyrate. Minor components included 3-methylbutanol, 2-phenylethanol, (Z)-3-hexenol, decanal, (E)-2-hexenoic acid, and three minor hexenyl esters. Bioactivity studies using laboratory olfactometers and outdoor flight cages demonstrated attraction by female P. plagipennis to calling males, heptane extracts of male posterior DAGs and a synthetic formulation of the (Z)R enantiomer of the major ester, alone or in combination with other components of male anterior and posterior DAGs. Males were also attracted to the major ester. The racemate and S enantiomer of the ester were not attractive. Contamination of the (Z)R enantiomer with 30-60 percent of the E isomer also made the compound nonattractive. This is the first report of an aggregation pheromone in the Reduviidae. The prospects for pheromonal manipulation of P. plagipennis populations to enhance the value of this predator in horticultural ecosystems, are discussed. - Keywords: Pristhesancus plagipennis; assassian bug; Hemiptera; Reduviidae; dorsal abdominal glands; (Z)-3-hexenyl (R)-2-hydroxy-3-methylbutyrate; aggregation pheromone
Cyclohexadepsipeptides from Acremonium sp. BCC 28424
Isaka, Masahiko,Yangchum, Arunrat,Sappan, Malipan,Suvannakad, Rapheephat,Srikitikulchai, Prasert
, p. 7929 - 7935 (2011)
Six new cyclohexadepsipeptides, beauvenniatins A-E (1-5), and beauvericin J (6), together with the known beauvericin (7) and enniatin B (8), were isolated from the fungus Acremonium sp. BCC 28424. The productions of minor derivatives 3-6, possessing an N-
(3R,6R)-4-methyl-6-(1 -methylethyl)-3-phenylmethyl-perhydro-1,4-oxazine-2,5-dione: An apoptosis-inducer from the fruiting bodies of Isaria japonica
Oh, Hyuncheol,Kim, Taewan,Oh, Gi-Su,Pae, Hyun-Ock,Hong, Kyung-Hwan,Chai, Kyu-Yun,Kwon, Tae-Oh,Chung, Hun-Taeg,Lee, Ho-Sub
, p. 345 - 348 (2002)
(3R,6R)-4-Methyl-6-(1-methylethyl)-3-phenylmethylperhydro1,4-oxazine-2,5- dione (1) was isolated from the fruiting bodies of Isaria japonica as an apoptosis-inducing agent. The complete structural assignment of the compound was accomplished on the basis of spectroscopic methods and chemical transformations. Compound 1 induced apoptotic cell death of the human leukemia cells (HL-60) in a dose-dependent manner, ranging from 5.0 μg/ml to 100.0 μg/ml.
Synthetic Indolactam V Analogues as Inhibitors of PAR2-Induced Calcium Mobilization in Triple-Negative Breast Cancer Cells
Stein, Jan,Stahn, Sonja,Neud?rfl, J?rg-M.,Sperlich, Julia,Schmalz, Hans-Günther,Teusch, Nicole
supporting information, p. 147 - 154 (2018/02/06)
Human proteinase-activated receptor 2 (PAR2), a transmembrane G-protein-coupled receptor (GPCR), is an attractive target for a novel anticancer therapy, as it plays a critical role in cell migration and invasion. Selective PAR2 inhibitors therefore have potential as anti-metastatic drugs. Knowing that the natural product teleocidin A2 is able to inhibit PAR2 in tumor cells, the goal of the present study was to elaborate structure–activity relationships and to identify potent PAR2 inhibitors with lower activity against the adverse target, protein kinase C (PKC). For this purpose, an efficient gram-scale total synthesis of indolactam V (i.e., the parent structure of all teleocidins) was developed, and a library of derivatives was prepared. Some compounds were indeed found to exhibit high potency as PAR2 inhibitors at low nanomolar concentrations with improved selectivity (relative to teleocidin A2). The pseudopeptidic fragment bridging the C3 and C4 positions of the indole core proved to be essential for target binding, whereas activity and target selectivity depends on the substituents at N1 or C7. This study revealed novel derivatives that show high efficacy in PAR2 antagonism combined with increased selectivity.
Synthesis of Natural and Unnatural Cyclooligomeric Depsipeptides Enabled by Flow Chemistry
Lücke, Daniel,Dalton, Toryn,Ley, Steven V.,Wilson, Zoe E.
supporting information, p. 4206 - 4217 (2016/03/16)
Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin (1 a), bassianolide (2 b) and enniatin C (1 b). A reliable flow chemistry protocol was established for the coupling and macrocyclisation to form challenging N-methylated amides. This flexible approach has allowed the rapid synthesis of both natural and unnatural depsipeptides in high yields, enabling further exploration of their promising biological activity. Harnessing technology: Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin (1 a), bassianolide (2 b) and enniatin C (1 b), resulting in increased overall yields, while decreasing the effort required for the researcher.
Urumamide, a novel chymotrypsin inhibitor with a β-amino acid from a marine cyanobacterium Okeania sp.
Kanamori, Yuki,Iwasaki, Arihiro,Sumimoto, Shinpei,Suenaga, Kiyotake
supporting information, p. 4213 - 4216 (2016/08/25)
Urumamide, a novel cyclic depsipeptide that contains a β-amino acid, was isolated from a marine cyanobacterium Okeania sp. Its gross structure was determined by spectroscopic analyses, and the absolute configuration was established based on Marfey's analyses and chiral HPLC analyses of hydrolysis products. Biologically, urumamide inhibited the growth of human cancer cells. In addition, urumamide inhibited chymotrypsin.
2-Bromo-6-isocyanopyridine as a Universal Convertible Isocyanide for Multicomponent Chemistry
Van Der Heijden, Gydo,Jong,Ruijter, Eelco,Orru, Romano V. A.
supporting information, p. 984 - 987 (2016/03/15)
The development of 2-isocyanopyridines as novel convertible isocyanides for multicomponent chemistry is reported. Comparison of 12 representatives of this class revealed 2-bromo-6-isocyanopyridine as the optimal reagent in terms of stability and synthetic efficiency. It combines sufficient nucleophilicity with good leaving group capacity of the resulting amide moiety under both basic and acidic conditions. To demonstrate the practical utility of this reagent, an efficient two-step synthesis of the potent opioid carfentanil is presented.
PHENOXYETHOXY COMPOUNDS
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Paragraph 0025-0028, (2014/09/03)
The present invention provides a compound of the Formula I: or a pharmaceutically acceptable salt thereof.
Solid-phase synthesis of tetrahydropyridazinedione-constrained peptides
Kang, Chang Won,Ranatunga, Sujeewa,Sarnowski, Matthew P.,Del Valle, Juan R.
supporting information, p. 5434 - 5437 (2015/02/19)
The design and solid-phase synthesis of tetrahydropyridazine-3,6-dione (Tpd) peptidomimetics derived from backbone-aminated peptides is reported. The described protocol features the synthesis of chiral α-hydrazino acids suitable for chemoselective incorporation into growing peptide chains. Acid-catalyzed cyclization to form the Tpd ring during cleavage affords the target peptidomimetics in good yield and purity. The scope of Tpd incorporation is demonstrated through the synthesis of constrained peptides featuring nucleophilic/electrophilic side chains and sterically encumbered α-substituted hydrazino acid residues. (Chemical Equation Presented).
Chiral propargylic cations as intermediates in SN1-type reactions: Substitution pattern, nuclear magnetic resonance studies, and origin of the diastereoselectivity
Nitsch, Dominik,Huber, Stefan M.,Poethig, Alexander,Narayanan, Arjun,Olah, George A.,Prakash, G. K. Surya,Bach, Thorsten
supporting information, p. 2851 - 2857 (2014/03/21)
Nine propargylic acetates, bearing a stereogenic center (-C*HXR 2) adjacent to the electrophilic carbon atom, were prepared and subjected to SN1-type substitution reactions with various silyl nucleophiles employing bismuth trifluoromethanesulfonate [Bi(OTf)3] as the Lewis acid. The diastereoselectivity of the reactions was high when the alkyl group R2 was tertiary (tert-butyl), irrespective of the substituent X. Products were formed consistently with a diastereomeric ratio larger than 95:5 in favor of the anti-diastereoisomer. If the alkyl substitutent R2 was secondary, the diastereoselectivity decreased to 80:20. The reaction was shown to proceed stereoconvergently, and the relative product configuration was elucidated. The reaction outcome is explained by invoking a chiral propargylic cation as an intermediate, which is preferentially attacked by the nucleophile from one of its two diastereotopic faces. Density functional theory (DFT) calculations suggest a preferred conformation in which the group R2 is almost perpendicular to the plane defined by the three substituents at the cationic center, with the nucleophile approaching the electrophilic center opposite to R2. Transition states calculated for the reaction of allyltrimethylsilane with two representative cations support this hypothesis. Tertiary propargylic cations with a stereogenic center (-C* HXR2) in the α position were generated by ionization of the respective alcohol precursors with FSO3H in SO2ClF at -80 C. Nuclear magnetic resonance (NMR) spectra were obtained for five cations, and the chemical shifts could be unambiguously assigned. The preferred conformation of the cations as extracted from nuclear Overhauser experiments is in line with the preferred conformation responsible for the reaction of the secondary propargylic cations.
