18523-76-7Relevant academic research and scientific papers
A Mixed-Ligand Chiral Rhodium(II) Catalyst Enables the Enantioselective Total Synthesis of Piperarborenine B
Panish, Robert A.,Chintala, Srinivasa R.,Fox, Joseph M.
, p. 4983 - 4987 (2016)
A novel, mixed-ligand chiral rhodium(II) catalyst, Rh2(S-NTTL)3(dCPA), has enabled the first enantioselective total synthesis of the natural product piperarborenine B. A crystal structure of Rh2(S-NTTL)3(dCPA) r
Design and synthesis of dual active neovibsanin derivatives based on a chemical structure merging method
Fukuyama, Yoshiyasu,Imagawa, Hiroshi,Kasai, Yusuke,Kishimoto, Suguru,Kubo, Miwa,Matsui, Nobuaki,Yamamoto, Hirofumi,Yanagimoto, Tsuyoshi
, (2020)
A hybrid compound consisting of neovibsanin and trans-banglene was designed according to a structure merging method and synthesized via a sequence of key steps including a Diels–Alder cycloaddition, stereoselective alkynylation, and intramolecular oxa-Mic
NEW PHENOLIC ETHERS FROM ESSENTIAL OILS OF SOME RUTACEAE
Campbell, William E.,George, Peter
, p. 1455 - 1456 (1982)
Two phenolic ethers were isolated from the essential oils of some Agathosma species.Structures elucidated by spectral analysis and synthesis were trans-1,2-methylenedioxy-4-(3'-methoxy-1'-propenyl)benzene and trans-1,2-dimethoxy-4-(3'-methoxy-1'-propenyl)
Antimutagenic Activity of Phenylpropanoids from Clove (Syzygium aromaticum)
Miyazawa, Mitsuo,Hisama, Masayoshi
, p. 6413 - 6422 (2003)
Phenylpropanoids that possess antimutagenic activity were isolated from the buds of clove (Syzygium aromaticum). The isolated compounds suppressed the expression of the umu gene following the induction of SOS response in the Salmonella typhimurium TA1535/pSK1002 that have been treated with various mutagens. The suppressive compounds were mainly localized in the ethyl acetate extract fraction of the processed clove. This ethyl acetate fraction was further fractionated by silica gel column chromatography, which resulted in the purification and subsequent identification of the suppressive compounds. Electron impact mass spectrometry, IR, and 1H and 136 NMR spectroscopy were then used to delineate the structures of the compounds that confer the observed antimutagenic activity. The secondary suppressive compounds were identified as dehydrodieugenol (1) and trans-coniferyl aldehyde (2). When using 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide) as the mutagen, compound 1 suppressed 58% of the umu gene expression as compared to the controls at a concentration of 0.60 μmol/mL, with an ID50 (50% inhibitory dose) value of 0.48 μmol/mL, and compound 2 suppressed 63% of the umu gene expression as compared to the controls at a concentration of 1.20 μmol/mL, with an ID50 value of 0.76 μmol/mL. Additionally, compounds 1 and 2 were tested for their ability to suppress the mutagenic activity of other well-known mutagens such as 4-nitroquinolin 1-oxide (4NQO) and N-methyl-N′-nitro-N-nitrosoguanidine (MNNG), which do not require liver metabolizing enzymes, and aflatoxin B1 (AfB1) and 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1), which require liver metabolizing enzymes and activated Trp-P-1 and UV irradiation. Compounds 1 and 2 showed dramatic reductions in their mutagenic potential of all of the aforementioned chemicals or treatment. For the search of the structure-activity relationship, the derivatives of 1 and 2 (1a and 2a-c) were also assayed with all mutagens. Finally, the antimutagenic activities of compounds 1, 1a, 2, and 2a-c against furylfuramide, Trp-P-1, and activated Trp-P-1 were assayed by the Ames test using the S. typhimurium TA100 strain.
Acquisition of female-attracting fragrance by males of oriental fruit fly from a Hawaiian lei flower, Fagraea berteriana
Nishida, Ritsuo
, p. 2275 - 2285 (1997)
Males of the Oriental fruit fly, Bactrocera dorsalis, are strongly attracted to and compulsively feed on a fragrant let flower, Fagraea berteriana. A series of phenylpropanoid components, trans-3,4-dimethoxycinnamyl alcohol, its acetate, and trans-3,4-dim
A new lead compound for abscisic acid biosynthesis inhibitors targeting 9-cis-epoxycarotenoid dioxygenase
Han, Sun-Young,Kitahata, Nobutaka,Saito, Tamio,Kobayashi, Masatomo,Shinozaki, Kazuo,Yoshida, Shigeo,Asami, Tadao
, p. 3033 - 3036 (2004)
9-cis-Epoxycarotenoid dioxygenase (NCED), a key enzyme in abscisic acid (ABA) biosynthesis, cleaves the olefinic double bond of 9-cis-epoxycarotenoid. Several analogues of nordihydroguaiaretic acid (NDGA) were designed and synthesized, and their efficacy
Laccase-catalyzed oxidation of allylbenzene derivatives: Towards a green equivalent of ozonolysis
Antoniotti, Sylvain,Blerot, Bernard,Chietera, Giorgiana,Lecourt, Mathilde
supporting information, (2021/10/19)
Laccase-based biocatalytic reactions have been tested with and without mediators and optimized in the oxidation of allylbenzene derivatives, such as methyl eugenol taken as a model substrate. The reaction primarily consisted in the hydroxylation of the propenyl side chain, either upon isomerization of the double bond or not. Two pathways were then observed; oxidation of both allylic alcohol intermediates could either lead to the corresponding α,β-unsaturated carbonyl com-pound, or the corresponding benzaldehyde derivative by oxidative cleavage. Such a process consti-tutes a green equivalent of ozonolysis or other dangerous or waste-generating oxidation reactions. The conversion rate was sensitive to the substitution patterns of the benzenic ring and subsequent electronic effects.
Incorporation of catechyl monomers into lignins: Lignification from the non-phenolic end: Via Diels-Alder cycloaddition?
Ando, Daisuke,Boerjan, Wout,Elder, Thomas J.,Eugene, Alexis,Kim, Hoon,Lu, Fachuang,Ralph, John,Tobimatsu, Yuki,Vanholme, Ruben
, p. 8995 - 9013 (2021/11/27)
Canonical lignification occurs via the coupling of phenolic radicals, in which chain extension can occur only from phenolic ends of growing polymer chains. Radical coupling of catechyl monomers, including caffeyl and 5-hydroxyconiferyl alcohols, gives ris
(±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis
Bernal, Freddy A.,Gerhards, Marcel,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
, (2020/08/06)
Leishmaniasis, a neglected tropical disease caused by parasites of the genus Leishmania, causes a serious burden of disease around the world, represents a threat to the life of millions of people, and therefore is a major public health problem. More effective and non-toxic new treatments are required, especially for visceral leishmaniasis, the most severe form of the disease. On the backdrop that dihydrobenzofurans have previously shown antileishmanial activity, we present here the synthesis of a set of seventy trans-2-phenyl-2,3-dihydrobenzofurans and evaluation of their in vitro activity against Leishmania donovani as well as a discussion of structure-activity relationships. Compounds 8m-o and 8r displayed the highest potency (IC50 4.6). Nonetheless, structural optimization as further requirement was inferred from the high clearance of the most potent compound (8m) observed during determination in vitro of its metabolic stability. On the other hand, chiral separation of 8m and subsequent biological evaluation of its enantiomers demonstrated no effect of chirality on activity and cytotoxicity. Holistic analysis of in silico ADME-like properties and ligand efficiency metrics by a simple scoring function estimating druglikeness highlighted compounds 16c, 18 and 23 as promising candidates for further development. Overall, the potential of trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents was confirmed.
SCAPHOPETALONE ANALOGS AND THEIR USES
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Page/Page column 24-25, (2017/05/10)
The present disclosure relates to scaphopetalone analogs, methods of making the analogs, and their medicinal uses.
