10313-60-7Relevant articles and documents
Practical Decagram-Scale Synthesis of a Lamellarin Analogue and Deprotection of Lamellarin Isopropyl Ethers
Klintworth, Robin,de Koning, Charles B.,Michael, Joseph P.
, p. 3860 - 3871 (2020)
Modular syntheses of naturally occurring lamellarin ε (5) and the synthetic analogue dehydrolamellarin J (6), both of them promising lead candidates for anticancer activity, were accomplished in high overall yields. Key steps in these routes are a late-st
2-Benzopyrilium Salts. 30. Synthesis and Properties of 2-Benzopyrilium Salts with the 2,6-Di-t-butylphenyl Substituent in Position 3
Shcherbakova, I. V.,Ukhin, L. Yu.,Komissarov, V. N.,Kuznetsov, E. V.,Polyakov, A. V.,et al.
, p. 824 - 829 (1987)
We achieved the synthesis of 2-benzopyrilium salts with a 2,6-di-t-butylphenyl substituent in position 3 by acylation of 3,5-di-t-butyl-4-hydroxy-3',4'-dimethoxydesoxybenzoin.We carried out a comparison of the concurrent deprotonation of 1-methylene and h
Oxidative route to pyrroloisoquinoline-2,3-dione
Kadam, Hari K.,Tilve, Santosh G.
, p. 184 - 190 (2018)
We herein report an efficient constructive method for synthesis of structurally important Pyrroloisoquinoline-2,3-dione from dihydroisoquinoline through oxidative cyclisation. Process is optimised to give best efficiency at gram scale and laborious purification techniques such as column chromatography or recrystallisation were avoided in all steps further featuring uniqueness of this method as compared to the available literature.
Synthesis of ortho-arylated/benzylated arylacetamide derivatives: Pd(OAc)2-catalyzed bidentate ligand-aided arylation and benzylation of the γ-C[sbnd]H bond of arylacetamides
Bisht, Narendra,Babu, Srinivasarao Arulananda
, p. 5886 - 5897 (2016)
In this paper, we report the Pd(OAc)2/AgOAc, bidentate ligand-directed C[sbnd]H functionalization of the sp2γ-C[sbnd]H bond of arylacetamides. While, the bidentate ligand-directed site selective functionalization of the β-C[sbnd]H bond of aromatic carboxylic acid derivatives is well known, we herein, report our attempts on the Pd(II)-catalyzed, bidentate ligand-directed arylation, benzylation, alkylation, acetoxylation and hydroxylation of the sp2γ-C[sbnd]H bond of the arylacetamide systems. The arylation and benzylation of arylacetamides were successful; however, the alkylation and acetoxylation/hydroxylation of arylacetamides were not successful. Various ligands were screened to substantiate the need for the bidentate ligand in the arylation/benzylation of arylacetamides, and 8-aminoquinoline was found to be the best bidentate ligand. Several substituted aryl-/heteroaryl iodides, 4-nitrobenzyl bromide and arylacetamide substrates were used to examine their reactivity pattern and accomplish the substrate scope/generality. In general, the bidentate ligand 8-aminoquinoline-directed arylation of arylacetamides gave the corresponding ortho-diarylated arylacetamides and benzylation of arylacetamides gave the corresponding ortho-mono benzylated arylacetamides as the predominant compounds. Overall, this method has led to the synthesis of new ortho-substituted arylacetamides in good to high yields.
Structure-based optimization of non-peptidic Cathepsin D inhibitors
Gr?dler, Ulrich,Czodrowski, Paul,Tsaklakidis, Christos,Klein, Markus,Werkmann, Daniela,Lindemann, Sven,Maskos, Klaus,Leuthner, Birgitta
, p. 4141 - 4150 (2014)
We discovered a novel series of non-peptidic acylguanidine inhibitors of Cathepsin D as target for osteoarthritis. The initial HTS-hits were optimized by structure-based design using CatD X-ray structures resulting in single digit nanomolar potency in the
A convergent and enantioselective synthesis of (+)-amurensinine via selective C-H and C-C bond insertion reactions
Tambar, Uttam K.,Ebner, David C.,Stoltz, Brian M.
, p. 11752 - 11753 (2006)
A convergent and enantioselective synthesis of the natural product amurensinine is described. The synthetic strategy takes advantage of mild and selective C-H and C-C bond insertion reactions, in addition to the palladium-catalyzed aerobic oxidative kinet
Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles
Morimoto, Naoki,Morioku, Kumika,Suzuki, Hideyuki,Takeuchi, Yasuo,Nishina, Yuta
, p. 2020 - 2023 (2016)
Indole readily undergoes nucleophilic substitution at the C3 site, and many indole derivatives have been functionalized using this property. Indole also forms indolium, which allows electrophilic addition in acidic conditions, but current examples have been limited to intramolecular reactions. C2 site-selective nucleophilic addition to indole derivatives using fluoroalcohol and a Lewis acid was developed.
Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives
Higginson, Cody J.,Malollari, Katerina G.,Xu, Yunqi,Kelleghan, Andrew V.,Ricapito, Nicole G.,Messersmith, Phillip B.
, p. 12271 - 12279 (2019)
A synthetic strategy to incorporate catechol functional groups into benzoxazine thermoset monomers was developed, leading to a family of bioinspired small-molecule resins and main-chain polybenzoxazines derived from biologically available phenols. Lap-she
A Simple and Efficient Synthesis of Fused Benzo[ b ]thiophene Derivatives
Ulyankin, Evgeny B.,Kostyuchenko, Anastasia S.,Chernenko, Sergey A.,Bystrushkin, Mikhail O.,Samsonenko, Anna L.,Shatsauskas, Anton L.,Fisyuk, Alexander S.
, p. 2422 - 2434 (2021/04/21)
A new approach to the synthesis of fused benzothiophene derivatives was developed based on iodine-promoted photocyclization of 4,5-diaryl-substituted thiophenes obtained in three steps from commercially available compounds. Comparative analysis showed that photochemical cyclization is a more efficient method for the preparation of fused benzo[ b ]thiophene derivatives, compared to oxidative coupling of 4,5-diaryl-substituted thiophenes in the presence of iron(III) chloride and palladium-catalyzed intramolecular arylation. This new approach provides an efficient synthesis of functionally substituted naphtho[2,1- b:3,4- b ′]dithiophenes, phenanthro[9,10- b ]thiophenes, benzo[1,2- b:3,4- b ′:6,5- b ′′]trithiophenes, as well as new fused heterocycles containing a pyridine ring and/or a carbazole moiety.
Design, synthesis, biological evaluation and silico prediction of novel sinomenine derivatives
Cui, Dongmei,Gao, Mingjie,Li, Jinjie,Li, Shoujie,Nian, Xin,Zhang, Chen,Zhang, Liyu,Zhao, Changqi
, (2021/06/25)
Sinomenine is a morphinan alkaloid with a variety of biological activities. Its derivatives have shown significant cytotoxic activity against different cancer cell lines in many studies. In this study, two series of sinomenine derivatives were designed and synthesized by modifying the active positions C1 and C4 on the A ring of sinomenine. Twenty‐three compounds were synthesized and characterized by spectroscopy (IR,1H‐NMR,13C‐NMR, and HRMS). They were further evaluated for their cytotoxic activity against five cancer cell lines, MCF‐7, Hela, HepG2, SW480 and A549, and a normal cell line, Hek293, using MTT and CCK8 methods. The chlorine‐containing compounds exhibited significant cytotoxic activity compared to the nucleus structure of sinomenine. Furthermore, we searched for cancer‐related core targets and verified their interaction with derivatives through molecular docking. The chlorine‐containing compounds 5g, 5i, 5j, 6a, 6d, 6e, and 6g exhibited the best against four core targets AKT1, EGFR, HARS and KARS. The molecular docking results were consistent with the cytotoxic results. Overall, results indicate that chlorine‐containing derivatives might be a promising lead for the development of new anticancer agents.
