34225-11-1Relevant articles and documents
Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents
Freijo, Mónica Blanco,López-Arencibia, Atteneri,Pi?ero, José E.,McNaughton-Smith, Grant,Abad-Grillo, Teresa
, p. 1312 - 1324 (2017/11/13)
Screening of a designed collection of mono-substituted amino-1H-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure-activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices >100.
Evaluation of synthetic naphthalene derivatives as novel chemical chaperones that mimic 4-phenylbutyric acid
Mimori, Seisuke,Koshikawa, Yukari,Mashima, Yu,Mitsunaga, Katsuyoshi,Kawada, Koichi,Kaneko, Masayuki,Okuma, Yasunobu,Nomura, Yasuyuki,Murakami, Yasuoki,Kanzaki, Tetsuto,Hamana, Hiroshi
, p. 811 - 814 (2015/02/19)
The chemical chaperone 4-phenylbutyric acid (4-PBA) has potential as an agent for the treatment of neurodegenerative diseases. However, the requirement of high concentrations warrants chemical optimization for clinical use. In this study, novel naphthalene derivatives with a greater chemical chaperone activity than 4-PBA were synthesized with analogy to the benzene ring. All novel compounds showed chemical chaperone activity, and 2 and 5 possessed high activity. In subsequent experiments, the protective effects of the compounds were examined in Parkinson's disease model cells, and low toxicity of 9 and 11 was related to amphiphilic substitution with naphthalene.
Radical scavenging capacity of 2,4-dihydroxy-9-phenyl-1 H -phenalen-1-one: A functional group exclusion approach
Duque, Luisa,Zapata, Carolina,Rojano, Benjamin,Schneider, Bernd,Otalvaro, Felipe
, p. 3542 - 3545 (2013/08/23)
2,4-Dihydroxy-9-phenyl-1H-phenalen-1-one (4-hydroxyanigorufone, 1), a compound isolated from Anigozanthos flavidus and Monochoria elata, displayed a high radical scavenging capacity in the ORAC assay. A systematic approach was adopted in order to explore
Synthesis of musafluorone: A naphthoxanthenone isolated from Musa acuminata
Duque, Luisa,Restrepo, Catalina,Sáez, Jairo,Gil, Jesús,Schneider, Bernd,Otálvaro, Felipe
experimental part, p. 4640 - 4643 (2010/09/10)
5-Methoxy-3H-naphtho[2,1,8-mna]xanthen-3-one (musafluorone, 1), the only naphthoxanthenone reported so far from Musaceae, was synthesized starting from 2-naphthol in nine steps and resulted in an overall yield of 3%. Grignard addition of phenylmagnesium b
Synthesis of 4-methoxy-1H-phenalen-1-one: a subunit related to natural phenalenone-type compounds
Nanclares, Juliana,Gil, Jesús,Rojano, Benjamín,Saez, Jairo,Schneider, Bernd,Otálvaro, Felipe
, p. 3844 - 3847 (2008/09/21)
4-Methoxy-1H-phenalen-1-one (4-methoxyperinaphthenone, 1), a subunit found in some Musa phytoalexins and related natural products from the Haemodoraceae, was synthesized starting from 2-methoxynaphthalene in five steps and an overall yield of 36%. A Heck-Fujiwara coupling between ethyl acrylate and 1-bromonaphthalene afforded the corresponding (E)-naphthylpropanoic acid which, after hydrogenolysis, was subjected to a one-pot Friedel-Crafts acylation-DDQ dehydrogenation procedure to furnish 1.
Tricyclic compounds, preparation method and pharmaceutical compositions containing same
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, (2008/06/13)
The invention concerns compounds of formula (I) in which: A forms a tricyclic system of formula A1, A2, A3or A4; R1represents a hydrogen atom, an alkyl, hydroxy, alkoxy or oxo group; (R2)mand (R3)m′are such as defined in the description; n represents an integer such that 0≦n≦3; p represents an integer such as defined in the description; B represents a group (a) or (b). The invention is useful for preparing medicines.
Rhodium(II)-Catalyzed Decomposition of 1-Diazo-4-(1- or 2-naphthyl)-2-butanones as a New Route to Rearranged Pimarane and Abietane Skeleta. Synthesis of Umbrosone
Manitto, Paolo,Monti, Diego,Zanzola, Simona,Speranza, Giovanna
, p. 6658 - 6665 (2007/10/03)
The Rh2(OAc)4catalyzed intramolecular Buchner reaction of 1-diazo-4-(1- or 2-naphthyl)butan-2-ones was examined as a potential route to abietane and rearranged abietane derivatives. Treatment of the α-diazo ketone 26 with catalytic amount of dirhodium tetraacetate in CH2Cl2 at 0 °C furnished the tetracyclic derivative 27 in good yield. Addition of TFA to 27 (in CH2Cl2) resulted in an acid-induced opening of the cyclopropane ring to give the 4a- and 10a-methyldihydrophenanthrenones 28 and 29 in nearly equal amounts. These compounds and their analogs appear to be suitable intermediates for the synthesis of diterpenoids containing aromatic A or C rings. When the diazo ketone 34 was decomposed under Rh(II) catalysis, a 10-methyldihydroanthracenone (i.e., 36) was obtained as the main product, besides minor amounts of the expected tetracyclic ketone 35. The extension of this result to the preparation of the methoxy-substituted dihydroanthracenone 39 (52% yield) was exploited in a new total synthesis of umbrosone (6), an unusual diterpenoid possessing a rearranged linear skeleton.
