6039-59-4Relevant articles and documents
Synthesis of novel naphthoquinone aliphatic amides and esters and their anticancer evaluation
Kongkathip, Boonsong,Akkarasamiyo, Sunisa,Hasitapan, Komkrit,Sittikul, Pichamon,Boonyalai, Nonlawat,Kongkathip, Ngampong
, p. 271 - 284 (2013)
Fourteen new naphthoquinone aliphatic amides and seventeen naphthoquinone aliphatic esters were synthesized in nine to ten steps from 1-hydroxy-2- naphthoic acid with 9-25% overall yield for the amides, and 16-21% overall yield for the esters. The key step of the amide synthesis is a coupling reaction between amine and various aliphatic acids using 4-(4,6-dimethoxy-1,3,5-triazin- 2-yl)-4-methylmorpholinium chloride (DMTMM) as a coupling agent while for the ester synthesis, DCC/DMAP or CDI was used as the coupling reagent between aliphatic acids and naphthoquinone alcohol. Both naphthoquinone amides and esters were evaluated for their anticancer activity against KB cells. It was found that naphthoquinone aliphatic amides showed stronger anticancer activity than those of the esters when the chains are longer than 7-carbon atoms. The optimum chain of amides is expected to be 16-carbon atoms. In addition, naphthoquinone aliphatic esters with α-methyl on the ester moiety possessed much stronger anticancer activity than the straight chains. Decatenation assay revealed that naphthoquinone amide with 16-carbon atoms chain at 15 μM and 20 μM can completely inhibit hTopoIIα activity while at 10 μM the enzyme activity was moderately inhibited. Molecular docking result also showed the same trend as the cytotoxicity and decatenation assay.
Synthesis of 3,3′-(4H,4′H)-spirobi(2H-naphtho[1,2-b]pyran)-6, 6′-dicarboxylic acid and its optical resolution
Tojo, Kenta,Arisawa, Tatsuya,Yasutake, Mikio,Aoki, Yoshio,Teninuma, Daiyo
, p. 930 - 931 (2008)
The synthesis and optical resolution of 3,3′-(4H,4′H)- spirobi(2H-naphtho[1,2-b]pyran)-6,6′-dicarboxylic acid were successfully accomplished. The formation of the spiro skeleton and the bromination of the aromatic ring were easily achieved in the presence of bromine. Optical resolution was achieved by amidation with L-valinol (2-amino-3-methyl-1-butanol) . Copyright
TARGETED RADIOPHARMACEUTICALS FOR THE DIAGNOSIS AND TREATMENT OF PROSTATE CANCER
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Page/Page column 266; 267, (2021/01/29)
A compound of general formula (I): wherein: n is 1, 2 or 3; R1, R2, R3 and R4, independently represent OH or Q; and 20 Q represents a tissue-targeting moeity selected from the group consisting of or a stereoisomer, a hydrate, a solvate, or a salt thereof, or a mixture of same, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said 25 compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of soft tissue diseases, as a sole agent or in combination with other active ingredients.
Axially Chiral 1,1'-Binaphthyl-2-Carboxylic Acid (BINA-Cox) as Ligands for Titanium-Catalyzed Asymmetric Hydroalkoxylation
Blazejak, Max,Helmbrecht, Sebastian L.,Hintermann, Lukas,Schlüter, Johannes
supporting information, (2020/04/15)
Axially chiral, enantiopure 1,1'-binaphthyl-2-carboxylic acids (BINA-Cox) have recently been introduced as chiral ligands for transition metal catalysis. Together with equimolar, co-catalytic amounts of Ti(OiPr)4 and water they form an in situ catalyst that performs the asymmetric catalytic hydroalkoxylation of 2-allylphenols to 2-methylcoumarans at high temperature (240 °C, microwave heating). The synthesis of reference ligand 2'-MeO-BINA-Cox (L1) has been optimized and performed at molar scale. Synthetic routes have been developed to access a variety of substituted BINA-Cox ligands (>30 examples), which have been tested for ligand effects on the reference asymmetric cyclization of 2-allylphenol. The substrate range of asymmetric catalytic hydroalkoxylation has been explored through systematic substrate structure variations to define scope and limitations of the titanium-catalyzed process. The new substrates 2-(1-vinylcycloalkyl)phenols (1j, 1k), 2-(2-vinylphenyl)propan-2-ol (1t), and 2'-vinyl-[1,1'-biphenyl]-2-ol (1u) are shown to undergo asymmetric catalytic cyclization to benzodihydrofurans and benzo[c]chromene, respectively.
Aryl sulfamide compound, preparation method, pharmaceutical composition and uses thereof
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Paragraph 0377-0380, (2020/04/02)
The invention relates to the field of medicinal chemistry and pharmacotherapeutics, particularly to a compound represented by a general formula (I), a pharmaceutically acceptable salt, a prodrug molecule and a mixture thereof, a preparation method of the compound, a pharmaceutical composition containing the compound, and applications as an FABP4/FABP5 double-targeting inhibitor. The invention relates to applications of an aryl sulfamide compound in treatment of metabolic diseases and autoimmune diseases.
Organometallic complex with benzazole derivatives as a ligand and organic electroluminescent device including the same
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Paragraph 0182-0184, (2019/06/04)
Provided is an organometallic complex with benzazole derivatives represented by chemical formula 1 as a ligand. A novel organometallic complex according to the present invention can be used as an organic layer material of an organic electroluminescent dev
Design, Synthesis, and Characterization of Binaphthalene Precursors as Photoactivated DNA Interstrand Cross-Linkers
Lin, Zechao,Fan, Heli,Zhang, Qi,Peng, Xiaohua
, p. 8815 - 8826 (2018/07/05)
Most recently, alkylation via photogenerated carbocations has been identified as a novel mechanism for photoinduced DNA interstrand cross-link (ICL) formation by bifunctional aryl compounds. However, most compounds showed a low efficiency for DNA cross-linking. Here, we have developed a series of new 1,1′-binaphthalene analogues that efficiently form DNA ICLs upon 350 nm irradiation via generated 2-naphthalenylmethyl cations. The DNA cross-linking efficiency depends on the substituents at position 4 of the naphthalene moiety as well as the leaving groups. Compounds with NO2, Ph, H, Br, or OMe substituents led to 2-4 times higher DNA ICL yields than those with a boronate ester group. Compounds with trimethylammonium salt as a leaving group showed slightly better cross-linking efficiency than those with bromo as a leaving group. Some of these compounds showed a better cross-linking efficiency than that of traditional alkylating agents, such as nitrogen mustard analogues or quinone methide precursors. These highly efficient photoactivated carbocation precursors allow determination and characterization of the adducts formed between the photogenerated naphthalenyl cations and four natural nucleosides, indicating that the alkylation sites for these naphthalene analogues are dG, dA, and dC.
Selective fluorescence sensing of Cu(II) and Zn(II) using a simple Schiff base ligand: Naked eye detection and elucidation of photoinduced electron transfer (PET) mechanism
Ganguly, Aniruddha,Ghosh, Soumen,Kar, Samiran,Guchhait, Nikhil
supporting information, p. 72 - 80 (2015/05/19)
A simple Schiff base compound 2-((cyclohexylmethylimino)-methyl)-naphthalen-1-ol (2CMIMN1O) has been synthesized and characterized by 1H NMR, 13C NMR and FT-IR spectroscopic techniques. A significantly low emission yield of the compound has been rationalized in anticipation with photo-induced electron transfer (PET) from the imine receptor moiety to the naphthalene fluorophore unit. Consequently, an evaluation of the transition metal ion-induced modification of the fluorophore-receptor communication reveals the promising prospect of the title compound to function as a chemosensor for Cu2+ and Zn2+ ions selectively, through remarkable fluorescence enhancement as well as visual changes. While perturbation of the PET process has been argued to be the plausible mechanism behind the fluorescence enhancement, the selectivity for these two metal ions has been interpreted on the grounds of an appreciably strong binding interaction. Particularly notable aspects regarding the chemosensory activity of the compound is its ability to detect the aforesaid transition metal ions down to the level of micromolar concentration (detection limit being 2.74 and 2.27 ppm respectively), along with a simple and efficient synthetic procedure.
Direct displacement of alkoxy groups of vinylogous esters by grignard reagents
Brockway, Anthony J.,González-López, Marcos,Fettinger, James C.,Shaw, Jared T.
supporting information; experimental part, p. 3515 - 3518 (2011/06/24)
The direct displacement of alkoxy groups from the β position of aromatic and unsaturated esters and ketones is described. The reaction is chemo- and regioselective, displaying wide substrate scope.
Transforming rhinacanthin analogues from potent anticancer agents into potent antimalarial agents
Kongkathip, Ngampong,Pradidphol, Narathip,Hasitapan, Komkrit,Grigg, Ronald,Kao, Wei-Chun,Hunte, Carola,Fisher, Nicholas,Warman, Ashley J.,Biagini, Giancarlo A.,Kongsaeree, Palangpon,Chuawong, Pitak,Kongkathip, Boonsong
scheme or table, p. 1211 - 1221 (2010/08/07)
Twenty-six novel naphthoquinone aliphatic esters were synthesized by esterification of 1,4-naphthoquinone alcohols with various aliphatic acids. The 1,4-naphthoquinone alcohols were prepared from 1-hydroxy-2-naphthoic acid in nine steps with excellent yields. Twenty-four of the novel synthetic naphthoquinone esters showed significant antimalarial activity with IC 50 values in the range of 0.03-16.63 μM. The length of the aliphatic chain and the presence of C-2′ substituents on the propyl chain affected the activity. Interestingly, compounds 31 and 37 showed very good antimalarial activity and were not toxic to normal Vero cells, and the PTI values of 31 (> 1990.38) and 37 (1825.94) are excellent. Both 31 and 37 showed potent inhibition against P. falciparum 3D7 cyt bc1 and no inhibition on rat cyt bc1. They showed IC50 values in the nanomolar range, providing full inhibition of cyt bc1 with one molecule inhibitor bound per cyt bc1 monomer at the Qo site.
