- Synthesis and thermal evaluation of novel mono- and bis-adamantylated resorcinol-based phthalonitrile resins with enhanced solubility
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Phthalonitrile (PN) resins are high-temperature-resistant thermosetting polymers which find applications in military as well as aerospace owing to their outstanding performance. At present, most of the PN resins are melt-processed and cured at high temper
- Mishra, Preeti,Pandey, A. K.,Shukla, S. K.,Singh, Ajit Shankar
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- Synthesis, biological evaluation and molecular docking studies of indeno [1, 2-c] pyrazol derivatives as inhibitors of mitochondrial malate dehydrogenase 2 (MDH2)
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Hypoxia inducible factor-1 (HIF-1) is a pivotal transcription factor, which is strongly correlated with the induction of angiogenesis, tumor survival, metastasis, and cell proliferation, making it a pivotal therapeutic target for solid tumor therapeutic agents. Herein, a new series of multi-functional chemical probes were designed including principal groups, viz. adamantyl and indene, at various locations of the parent compound LW6. Molecular docking studies were performed on the designed compounds and their relationship with HIF-1α and malate dehydrogenase 2 (MDH2). Inhibition of MDH2 by our compounds was expected to decrease the NADH level. Indeed, treatment of the breast cancer cell line 4T1 led to a strong reduction of the NADH concentration. The greatest reduction in NADH production in mitochondria was observed with (E)-3-(4-((3r, 5r, 7r)-adamantan-1-yl) phenoxy)-N-(5-(piperidine-1-carbonyl)-1, 4-dihydroindeno [1, 2-c] pyrazol-3-yl) acrylamide (18: IC50 = 59 nM), and has the best inhibitory potential under hypoxic conditions (MCF-7: IC50 = 57 nM). This compound also gave one of the highest docking “higher than the score obtained with LW6 in parallel (?31.63 kcal/mol) in the initial docking runs (PDB Code: 4WLO). Other related compounds with good yields were also synthesized from docking results, and all the synthesized compounds (14, 18, 22, 26, 29, 30) were evaluated in vitro on human adenocarcinoma cell lines.
- Ahmadi, Farzaneh,Engel, Matthias,Baradarani, Mehdi M.
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- Synthesis of 1,8-di(1-adamantyl)naphthalenes as single enantiomers stable at ambient temperatures
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Single enantiomers of 1,8-di(1-adamantyl)naphthalenes were synthesized by the [4+2]cycloaddition reaction of 6-adamantylbenzyne and 2-adamantylfuran. The enantiomers were resolved by conversion into diastereomeric ketopinic acid esters. The absolute confi
- Aikawa, Haruo,Takahira, Yusuke,Yamaguchi, Masahiko
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supporting information; scheme or table
p. 1479 - 1481
(2011/03/22)
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- Method of synthesizing adamantyl-substituted phenols based on 1,3-dehydroadamantane
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The possibility of obtaining adamantyl-substituted phenols by the reaction of 1,3-dehydroadamantane with phenols in the presence of catalytic amounts of sulfuric acid was studied.
- Butov,Mokhov,Saad,Kamneva
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experimental part
p. 691 - 692
(2011/06/09)
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- Studies on depigmenting activities of dihydroxyl benzamide derivatives containing adamantane moiety
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Six diphenolic compounds containing adamantane moiety were synthesized and evaluated as potent inhibitors on tyrosinase activity and melanin formation in melan-a cells. The inhibitory activity of 4-adamantyl resorcinol 1 was similar to that of 4-n-butyl resorcinol in both assays. However, dihydroxyl benzamide derivatives 6a-e showed different inhibitory patterns. All derivatives significantly suppressed the cellular melanin formation without tyrosinase inhibitory activities. These behaviors indicated that the introduction of amide bond changes the binding mode of dihydroxyl groups to tyrosinase. Among derivatives, 6d (3,4-dihydroxyl compound) and 6e (2,3-dihydroxyl compound) showed stronger inhibitory activities (IC50 = 1.25 μM and 0.73 μM, respectively) as compared to 4-n-butyl resorcinol (IC50 = 21.64 μM) and hydroquinone (IC50 = 3.97 μM). This study showed that the position of dihydroxyl substituent at aromatic ring is important for the intercellular inhibition of melanin formation, and also amide linkage and adamantane moiety enhance the inhibition.
- Rho, Ho Sik,Baek, Heung Soo,Ahn, Soo Mi,Yoo, Jae Won,Kim, Duck Hee,Kim, Han Gon
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scheme or table
p. 1532 - 1533
(2009/12/01)
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- ADAMANTANE DERIVATIVE, RESIN COMPOSITION CONTAINING SAME, AND OPTOELECTRONIC MEMBER AND SEALING AGENT FOR ELECTRONIC CIRCUIT USING THOSE
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Disclosed is an adamantane derivative which provides a cured product excellent in optical characteristics such as transparency and light resistance, long-term heat resistance, electrical characteristics such as and dielectric constant, and low water absorption. Also disclosed are a resin composition containing the adamantane derivative, a sealing agent for electronic circuits, optical electronic member, semiconductor device and copper-clad laminate all using the resin composition, and a radiation-sensitive resin composition which contains the above-mentioned adamantane derivative as a crosslinking agent. Specifically disclosed are an adamantane derivative represented by the formula (I-1) below, a resin composition containing the adamantane derivative, a sealing agent for electronic circuits, optical electronic member, semiconductor device and copper-clad laminate, all using the resin composition, and a radiation-sensitive resin composition which contains the above-mentioned adamantane derivative as a crosslinking agent.
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Page/Page column 17
(2008/12/04)
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- Alkylation of aromatic compounds with adamantan-1-ol
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Reactions of substituted benzenes, naphthalenes, and 2- and 3-phenyl-1-benzofurans with adamantan-1-ol in trifluoroacetic acid lead to the formation of the corresponding mono-and diadamantylsubstituted aromatic compounds. Nauka/Interperiodica 2007.
- Stepakov,Molchanov,Kostikov
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p. 538 - 543
(2008/02/02)
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