25054-53-9Relevant articles and documents
Novel synthesis of graveoline and graveolinine
Bandatmakuru, Sreenivasula Reddy,Arava, Veera Reddy
, p. 2635 - 2641 (2018)
Cyclization of 2-aryl amides with base lead to quinolone derivatives. Both graveoline and graveolinine were synthesized.GRAPHICAL ABSTRACT (Figure presented.).
Influence of structure of benzodioxole derivatives on photoinitiation efficiency of benzophenone
Yang, Jinliang,Xu, Fei,Shi, Suqing,Nie, Jun
, p. 1377 - 1382 (2012)
To investigate the influence of the substituents at the 5-position of the phenyl ring of benzodioxole on the reactivity of a benzophenone (BP)/benzodioxole-based photoinitiator system, three benzodioxole-based compounds were synthesized in this study. The structure was characterized by FT-IR, 1H NMR and 13C NMR. The kinetics were monitored by a real-time Fourier Transform near-IR (FT-NIR) spectrometer. The results showed that the introduction of the electron-donating substituents in the 5-position of the phenyl ring contributed to the increase in the reactivity of the BP/benzodioxole-based system. On the contrary, the electron-drawn substituents at the 5-position of the phenyl ring caused the opposite effect. Compared with the BP/ethyldimethylaminobenzoate (EDAB) photoinitiating system, the combination of BP/5-methoxy-1,3-benzodioxole (BDOOMe) led to almost the same Rp max and final double bond conversions. It indicated that BDOOMe had the potential to be used as a coinitiator in the place of an amine in current BP/amine initiating systems for practical applications to decrease cytotoxicity and yellowing.
Synthesis and biological evaluation of novel piperidine-benzodioxole derivatives designed as potential leishmanicidal drug candidates
Fernandes, ítalo A.,De Almeida, Letícia,Ferreira, Patrícia Espuri,Marques, Marcos J.,Rocha, Raíssa P.,Coelho, Luiz F.L.,Carvalho, Diogo T.,Viegas, Claudio
, p. 3346 - 3349 (2015)
Abstract A novel series of ester and carbamate derivatives was synthesized and evaluated its activities against Leishmania amazonensis. All compounds exhibited weaker leishmanicidal activity than amphotericin B. However, results indicated that substituents on the aryl-acyl subunit are important for modulation of the leishmanicidal effect. The nitro derivative showed the highest activity of the series with an IC50 = 17.24 μM, and comparable potency to the 3,4-benzodioxole ester and n-hexyl carbamate derivatives. All compounds showed low toxicity against human cells. These results revealed interesting novel piperine-like molecular pattern for exploitation in search and development of effective and low toxic antileishmanial drug candidates.
Hybrids of aurantiamide acetate and isopropylated genipin as potential anti-inflammatory agents: The design, synthesis, and biological evaluation
Wang, Hongwei,Gao, Sufan,Li, Jiaming,Ma, Xiaodong,Liu, Wandong,Qian, Shihu
, p. 797 - 808 (2020/12/03)
A novel series of hybrids designed on the basis of aurantiamide acetate and isopropylated genipin were synthesized and biologically evaluated as anti-inflammatory agents. Among them, compound 7o exhibited the best inhibitory activity against TNF-α secretion (IC50?=?16.90?μM) and was selected for further in vitro and in vivo functional study. The results demonstrated that 7o was capable of suppressing the expression of LPS-induced iNOS and COX-2, as well as reducing the production of NO at the concentration of 5?μM, which may be resulted from its regulation of NF-κB signaling and MAPK signaling. Moreover, compound 7o exhibited favorable in vivo anti-inflammatory activity with an inhibition rate of 53.32% against xylene-induced ear swelling in mice at the dose of 5?mg/kg.
Pd(II)-catalyzed annulation reactions of epoxides with benzamides to synthesize isoquinolones
Wang, Huihong,Cao, Fei,Gao, Weiwei,Wang, Xiaodong,Yang, Yuhang,Shi, Tao,Wang, Zhen
supporting information, p. 863 - 868 (2021/02/06)
Epoxides as alkylating reagents are unprecedentedly applied in Pd(II)-catalyzed C?H alkylation and oxidative annulation of substituted benzamides to synthesize isoquinolones rather than isochromans, which is accomplished through alerting the previously reported reaction mechanism by the addition of oxidant and TEA. Under these conditions, various isoquinolones have been prepared with yields up to 92%. In addition, this methodology has been successfully employed in the total syntheses of rupreschstyril, siamine, and cassiarin A in an expedient fashion.
Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole -Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
G?bel, Dominik,Rusch, Pascal,Duvinage, Daniel,Stauch, Tim,Bigall, Nadja-C.,Nachtsheim, Boris J.
supporting information, p. 14333 - 14355 (2021/10/20)
Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.
Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**
Brauer, Jan,Quraishi, Elisabeth,Kammer, Lisa Marie,Opatz, Till
supporting information, p. 18168 - 18174 (2021/11/30)
A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1°,2°, benzylic, α-oxy & α-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.
Electrochemical intramolecular C-H/N-H functionalization for the synthesis of isoxazolidine-fused isoquinolin-1(2: H)-ones
Zhang, Lin-Bao,Geng, Rui-Sen,Wang, Zi-Chen,Ren, Guang-Yi,Wen, Li-Rong,Li, Ming
supporting information, p. 16 - 21 (2020/01/13)
A general and practical protocol for the construction of isoxazolidine-fused isoquinolin-1(2H)-ones has been described by electrochemical-oxidation-induced intramolecular annulation via amidyl radicals. In an undivided cell, isoquinolinones could be easily generated from various available amides bearing CONHOR groups under metal-free, additive-free and external oxidant-free conditions. Moreover, this transformation proceeded smoothly by using cheap 95% ethanol as the green solvent and could be extended to the gram scale.
Photoredox Catalyst Free, Visible Light-Promoted C3?H Acylation of Quinoxalin-2(1H)-ones in Water
Lu, Juan,He, Xiang-Kui,Cheng, Xiao,Zhang, Ai-Jun,Xu, Guo-Yong,Xuan, Jun
supporting information, p. 2178 - 2182 (2020/03/19)
A method for the synthesis of 3-acyl quinoxalin-2(1H)-ones through visible-light promoted decarboxylative acylation of α-oxo-carboxylic acids with quinoxalin-2(1H)-ones was developed. The reaction was performed in aqueous phase and photoredox catalyst was not required to run the process. (Figure presented.).
Rhodium-Catalyzed Electrooxidative C?H Olefination of Benzamides
Ackermann, Lutz,Struwe, Julia,Zhang, Yan
supporting information, p. 15076 - 15080 (2020/06/20)
Metal-catalyzed chelation-assisted C?H olefinations have emerged as powerful tools for the construction of functionalized alkenes. Herein, we describe the rhoda-electrocatalyzed C?H activation/alkenylation of arenes. The olefinations of challenging electron-poor benzamides were thus accomplished in a fully dehydrogenative fashion under electrochemical conditions, avoiding stoichiometric chemical oxidants, and with H2 as the only byproduct. This versatile alkenylation reaction also features broad substrate scope and used electricity as a green oxidant.
