34818-56-9Relevant academic research and scientific papers
Discovery of a Dual Function Cytochrome P450 that Catalyzes Enyne Formation in Cyclohexanoid Terpenoid Biosynthesis
Chein, Rong-Jie,Chen, Yu-Rong,Liang, Suh-Yuen,Lin, Chun-Hung,Lin, Hsiao-Ching,Naresh, Annavareddi
supporting information, p. 13537 - 13541 (2020/06/05)
The 1,3-enyne moiety is commonly found in cyclohexanoid natural products produced by endophytic and plant pathogenic fungi. Asperpentyn (1) is a 1,3-enyne-containing cyclohexanoid terpenoid isolated from Aspergillus and Pestalotiopsis. The genetic basis and biochemical mechanism of 1,3-enyne biosynthesis in 1, and other natural products containing this motif, has remained enigmatic despite their potential ecological roles. Identified here is the biosynthetic gene cluster and characterization of two crucial enzymes in the biosynthesis of 1. A P450 monooxygenase that has a dual function, to first catalyze dehydrogenation of the prenyl chain to generate a cis-diene intermediate and then serve as an acetylenase to yield an alkyne moiety, and thus the 1,3-enyne, was discovered. A UbiA prenyltransferase was also characterized and it is unusual in that it favors transferring a five-carbon prenyl chain, rather than a polyprenyl chain, to a p-hydroxybenzoic acid acceptor.
Synthesis and structure - Phytotoxicity relationships of acetylenic phenols and chromene metabolites, and their analogues, from the grapevine pathogen Eutypa lata
Smith, Leverett R.,Mahoney, Noreen,Molyneux, Russell J.
, p. 169 - 176 (2007/10/03)
Eutypa lata, the fungus responsible for dying-arm disease in grapevines, produces a number of structurally related secondary metabolites, of which eutypine (1) has been implicated as the principal phytotoxin. However, analysis of an E. lata strain from California known to be pathogenic to grapevines showed that eutypine was not present, suggesting that other metabolites could be phytotoxic. Investigation of the relative phytotoxicities of individual metabolites has been limited by insufficient material and lack of a reliable bioassay. Metabolites of particular interest and their precursors were therefore synthesized, and a rapid, quantitative bioassay via topical application of individual compounds to disks of grape leaves and measurement of chlorophyll loss was developed to provide a relative measure of tissue damage. The recently reported metabolite eulatachromene (2) was found to have phytotoxicity greater than that of eutypine (1). The cyclization product, 5-formyl-2-methylvinyl[1]benzofuran (3), also showed significant activity, whereas the reduction product, eutypinol (4), was inactive, as was the quinol, siccayne (5). These results indicate that before strains of Eutypa are incriminated as pathogenic they must be analyzed for the presence or absence of specific constituents for which the phytotoxicity has been unequivocally established.
Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans
Nicolaou,Pfefferkorn,Roecker,Cao,Barluenga,Mitchell
, p. 9939 - 9953 (2007/10/03)
Herein we report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran moiety is selected as an inaugural template for the construction of natural product-like libraries via this strategy. Initially, a novel solid-phase synthesis of the benzopyran motif is developed employing a unique cycloloading strategy that relies on the use of a new, polystyrene-based selenenyl bromide resin. Once the loading, elaboration, and cleavage of these benzopyrans was established, this new solid-phase method was then thoroughly validated through the construction of six focused combinatorial libraries designed around natural and designed molecules of recent biological interest.
Cardioselective antiischemic ATP-sensitive potassium channel (K(ATP)) openers. 6. Effect of modifications at C6 of benzopyranyl cyanoguanidines
Ding, Charles Z.,Rovnyak, George C.,Misra, Raj N.,Grover, Gary J.,Miller, Arthur V.,Ahmed, Syed Z.,Kelly, Yolanda,Normandin, Diane E.,Sleph, Paul G.,Atwal, Karnail S.
, p. 3711 - 3717 (2007/10/03)
The effect on potency and selectivity of modification at the C6 position of the cardioprotective K(ATP) opener BMS-180448 (2) is described. Structure- activity studies show that a variety of electron-withdrawing groups (ketone, sulfone, sulfonamide, etc.)
BENZOPYRANES AS POTASSIUM CHANNEL OPENERS
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, (2008/06/13)
The present invention relates to compounds of formula (I) and the pharmaceutically acceptable salts thereof, wherein the dashed line represents an optional covalent bond; X is O, NH, S or a direct link; R. sup.3 is hydroxy when the dashed line does not represent a covalent bond and R 3 is absent when the dashed line represents a covalent bond; R. sup.4 is (a), when X is O, a group of formula (i), (b), when X is O, NH or S, optionally substituted hydroxyphenyl, (c) an optionally substituted 4-to 7-membered heterocyclic ring, or (d), when X is NH, a group of formula (ii). The compounds are useful for the treatment of disease associated with the altered tone or motility of smooth muscle. STR1
HALOGENATED 2H-1-BENZOPYRANS: SYNTHESES AND REACTIVITY TOWARD ALUMINIUM, MAGNESIUM, AND LITHIUM ORGANOMETALLICS
Alberola, Angel,Calvo, Blanca,Gonzalez-Ortega, Alfonso,Lopez, Cristina,Villafane, Fernando
, p. 819 - 832 (2007/10/02)
3-, 4-, or 6-Halo-2H-1-benzopyrans are prepared by reacting the halogenated coumarins with lithium, magnesium or aluminium organometallics, and further thermal cyclization of the resulting o-hydroxycinnamyl alcohols.The method is not applicable for 3-halo
Acylation of 2,2-Dimathyl-2H-chromenes
Yamaguchi, Seiji,Yamamoto, Satoru,Abe, Shoichi,Kawase, Yoshiyuki
, p. 442 - 445 (2007/10/02)
Orientation in acylation reactions of 2,2-dimethyl-2H-chromenes was studied.Five acetylchromenes were obtained with two methods and six formylchromenes were obtained with a third method.Demethylation of four acyl-methoxy-substituted chromenes gave the corresponding acylchromenols. 2,2-Dimethyl-2H-chromene-6-carboxylic acid (anofinic acid) was also obtained by oxidation of 6-formylchromene.
